Former President Donald Trump is owed a tax refund of $1 million for his Chicago skyscraper, but local officials are trying to stop it from being issued.
An Illinois tax agency ruled last month that Trump paid too much on his 2011 tax bill after the value of Trump International Hotel and Tower’s rooms and retail space was over-assessed by the Cook County Board of Review, the Chicago Sun-Times reported.
The ruling by the Illinois Property Tax Appeal Board means Trump is owed $1.03 million, which would come from property taxes due to the city and other government agencies. Chicago Public Schools would lose out on about $540,000, according to the Sun-Times.
The Cook County State’s Attorney’s has since filed a lawsuit to block the refund. When reached by Insider, the State’s Attorney’s office said it was unable to comment on pending litigation.
The dispute is the latest development in the story of Trump’s taxes in Chicago. Alderman Ed Burke, the longest-serving member of Chicago’s City Council in history, served as Trump’s lawyer for more than a decade. His firm originally filed the tax appeal arguing the value of Trump’s building had been overestimated.
Burke, a Democrat, helped Trump secure $14 million in tax breaks on his Chicago skyscraper before parting ways with Trump’s company in 2018, The Chicago Tribune reported.
Later that year, the FBI raided Burke’s City Hall office and he was later charged with racketeering, bribery, and extortion, among other charges.
Prosecutors say Burke used the power of his office to drive business to his law firm, including blocking permits for people who did not hire them. He has pled not guilty to all charges, WTTW reported.
A man who works as a driver for rideshare apps like Lyft and Uber in Chicago last week filed a lawsuit against the CDC over its federal mask mandate, saying it was unconstitutional.
Justin Mahwikizi said in his complaint that the mask mandate limited both his freedom of religion and freedom of speech. He said that’s because he’s had to refuse service to unmasked passengers.
“It’s against my Christian beliefs to refuse service to someone in need, referring to the Good Samaritan parable of Jesus Christ and the Bible,” he told Insider in a phone interview on Saturday. “And so I’m arguing that the CDC is infringing on my religious practice rights that’s forcing me to deny service to someone in need.”
The lawsuit came amid a broader discussion about whether the CDC should update its stance on mask-wearing for fully vaccinated travellers. The CDC’s guidance from January 29 ordered all travellers to cover their faces when on public transit, including planes, buses, and rideshares.
Sen. Ted Cruz late last month led a group of senators in announcing a bill that sought an end to federal mask mandates for those who’ve had their shots.
Others have called for travellers to continue wearings masks. Transportation secretary Pete Buttigeig in late May said wearing a mask was a “matter of safety, but it’s also a matter of respect.”
Mahwikizi in his lawsuit sought a preliminary injunction and temporary restraining order to stop the CDC and the Dept. of Health & Human Services from enforcing mask mandates.
“The [mandate] is arbitrary, irrational, and capricious because the Federal Defendants failed to reasonably explain why other measures are insufficient to tackle the rapidly declining COVID-19 infection and death rates,” he wrote.
Insider has reached out to the CDC for comment.
Mahwikizi, who’s representing himself, said he mostly works in the Chicago area, but sometimes takes passengers into Indiana or Wisconsin. He said he’s found himself in a few situations where he had to leave potential customers behind because they didn’t have their faces covered.
“The acceptance of service is a form of free speech,” he wrote in his complaint, filed Monday in US District Court in the Northern District of Illinois.
He started drafting his complaint a few months ago. When Lucas Wall last month sued seven airlines, Mahwikizi followed the news coverage.
He said he reached out to Wall for some advice on handling federal rules and procedures, since Wall was also representing himself.
Narrator: In 2016, Toronto spent $31 million to fend off a raccoon invasion. The masked critters were everywhere, pooping on porches, stopping traffic, and infesting attics, and they’re not just taking over Toronto. Reports of raccoon vandalism have plagued cities like Portland, Chicago, and New York City, and as raccoon-ridden cities know, we can’t seem to stop them.
Between the 1930s and 1980s, the US raccoon population increased twentyfold, and it’s still going strong. From 2014 to 2015, raccoon complaints in Brooklyn nearly doubled, so how are these masked bandits making it in big cities?
Well, for starters, they can digest just about anything from fish and acorns in the forest to dog food and pizza on the street, and just like humans, raccoons usually prefer the pizza, which is why they flock from woodland to city in the first place.
In Brooklyn, for example, captured raccoons sometimes get relocated to Prospect Park and nearby forests, but wildlife biologists report they often head right back to the dumpster-packed city streets.
It’s just about impossible to stop them, as Toronto discovered after it spend millions on raccoon-proof waste bins. Unlike traditional bins, the lids had special gravity locks, which open when a garbage truck arm turns the bin upside down. The idea was that if you cut off their major food source, they would skip town, but that didn’t happen. In fact, one year later, a wildlife-control business reported that raccoon-related work had doubled.
Finally, a clever raccoon was caught on camera jailbreaking the new bin. How did she outwit an entire city? Well, study after study has revealed that raccoons are considerably smarter than your average medium-sized critter. Turns out raccoon brains have more neurons packed into their brains than other animals of the same size.
In fact, they have the same neuron density as primates, who are notoriously smart, and their clever brains help explain why raccoons can open complex locks, solve puzzles with ease, and even come up with solutions to problems that scientists didn’t think of. Add to that their ultrasensitive hands, er, paws, which have four times as many sensory receptors as their feet. This helps them to feel subtle textures like special trashcan lids in Toronto and even open locks without looking.
And unfortunately for us, driving them away is a fool’s errand. Studies show that after mass removal, populations tend to rebound to their previous levels in a year. After all, females can start giving birth at just 1 year old and can have as many as eight kits in a single year. This quick breeding is also why experts say mass cullings aren’t a long-term solution.
And while they’re awfully cute, the damage they can cause is not. When raccoons nest in buildings, they can destroy insulation, chew up wires, and tear holes through walls, and it can cost you hundreds or even thousands of dollars to repair that kind of damage. One raccoon was even caught destroying over $3,000 worth of artwork, and just removing them can cost $300 to $500 a pop.
Plus, the poop they leave behind can contain roundworms and other parasites, which can enter your lungs when you breathe or get tracked into your home by your pets. Even worse, raccoons can transmit diseases like canine distemper and, in rare cases, rabies.
So it’s understandable that cities are trying to find some way, any way, to manage them.
Man on broadcast: Can’t do a thing about it, just chase them off. They come back.
Narrator: If nothing else, it’s a lesson learned. We may have built the cities, but we don’t necessarily rule them.
EDITOR’S NOTE: This video was originally published in May 2019.
When Lesley Campbell sued Citibank in March 2015 to get a portion of her law school debt forgiven in bankruptcy, everyone told her she was wasting her time. Conventional wisdom held that student debt is impossible to get rid of, even in bankruptcy.
Then, she got a text from an unknown number advising her that there was a legal way to discharge her debt – along with an offer to help do just that.
Campbell thought it was a joke.
It was Austin Smith, a newly-minted lawyer who had previously worked as a headline writer at The Onion. Except he wasn’t joking. Smith believed courts had systematically misinterpreted the federal bankruptcy code in favor of lenders over student borrowers. He was on the hunt for a client to test his legal theory.
A year later, Smith succeeded in convincing a federal judge that the unpaid portion of Campbell’s $15,900 bar exam study loan from Citibank could be cancelled in bankruptcy.
The victory marked the starting point for what’s become Smith’s raison d’être to help as many student loan borrowers as possible. At 39, Smith estimates that he has prevailed in about 75 cases, leading to the canceling of some portion of his clients’ student debts. Bankruptcy judges have cited the Campbell case at least 20 times, court records show.
Smith has also resorted to unconventional methods that blend hard-knuckle lawyering with public pressure campaigns, advocacy and a relentless stream of YouTube broadcasts that document his quest to help student loan borrowers find a lifeline. In the process, he’s borrowed hundreds of thousands of dollars to keep their legal fights alive while pursuing his own life-or-death struggle with cancer.
“This is not exactly a normal law firm,” Smith wrote in an email to his team last October. “We do not charge our clients an hourly rate, nor do we seek out the most profitable types of lawsuits such as medical malpractice or securities fraud. We seek out groups of people who are being tormented and we make it stop.”
Seth Frotman, former student loan ombudsman for the Consumer Financial Protection Bureau, says that Smith’s battle makes clear that America’s student loan system, in which obtaining relief for borrowers is difficult even when the law is on their side, is broken. “When you talk to Austin, you see the culmination of hearing from these borrowers day-in and day-out and the predatory practices they’ve been forced to endure,” Frotman says.
Smith’s legal victories upended years of case law that had steadily built up in lenders’ favor; one lawyer who has worked with Smith credits him with providing the “intellectual genesis” behind a whole line of cases that are now undoing that case law.
Yet even after five years of non-stop litigation, Smith’s goal seems as distant as ever. The niche area of bankruptcy law that he’s identified can only help some borrowers who took out privately-issued student loans – a small chunk of the total $1.7 trillion owed by Americans. And even for them, getting relief can sometimes take years. That hasn’t deterred Smith, who was once called the “Don Quixote of student debt,” by a federal bankruptcy judge, according to an attorney who witnessed the exchange.
It’s a moniker Smith readily accepts; he bought a Don Quixote print to hang over his desk, which he calls a “good reminder that you never know if what you’re about to do it quite stupid.”
Lenders have had more choice words for him. Lawyers for Navient Corp., the giant student loan servicer, have accused Smith of running a “media crusade riddled with falsehoods” and recently sought about $600,000 in costs and attorneys’ fees, a figure that could have potentially crushed his fledgling legal practice. A federal judge awarded Navient about one-tenth of the sum after it successfully fought off a bold attempt by Smith to push its loan-servicing arm into bankruptcy through an involuntary bankruptcy petition.
In mid-March, after confessing to his YouTube followers that the gambit had amounted to an “epic failure,” Smith decided to change tack: He filed paperwork to run for Congress in New York’s first House district, which includes the posh Hamptons getaways of the rich and famous, where he moved during the pandemic.
“If we are unsuccessful in the judicial branch then maybe there is a solution in the legislative branch,” Smith said in an interview, adding a touch of bravado that colors much of his legal briefs: “I can get that done.”
In some ways, Austin Connell Smith was an unlikely candidate to champion the cause of America’s overly-indebted student borrowers. Smith grew up in an affluent Chicago suburb, where his father worked as a corporate lawyer for Brunswick Corp. and other large companies. A trust fund worth around $100,000 awaited him should he ever decide to go to law school.
When Smith first turned his attention to law school in 2006, he wondered if then-FBI director Robert Mueller might write a letter of recommendation for him, according to an email exchange with his father. Smith’s father had gone to law school with Mueller and Mueller’s wife is godmother to one of Smith’s sisters. His dad wrote back that Mueller was not the right person to ask for a recommendation. Mueller didn’t respond to a request for comment.
When Smith got passed up for a full-time job at The Onion, he finally turned to law school. He enrolled at the University of Maine Law School, where he often spent his mornings at a coffee shop near campus writing a satirical novel and searching for a topic to dig into for a law review article. A chance encounter with another regular at the coffee shop, Bill Wilson, provided the spark he was looking for.
Wilson was the byproduct of a different era. A retired litigator, he attended Maine Law some 35 years before Smith, when tuition was so cheap that he could easily pay for law school by working a union job at a paper mill during the summers. By the time they met in 2014, tuition was so high that Smith still owes about $170,000 for his law degree.
Wilson was in the midst of examining bankruptcy rules surrounding student loans. He was surprised to learn that educational debt was exempt from discharge unless it met certain exceptions. He encouraged Smith to research them and see if they were as ironclad as everyone believed they were.
“Austin took it and ran with it,” Wilson recalls.
Thicket of confusion
Each year, about a quarter million student loan debtors file for bankruptcy. Of those, fewer than three hundred get their educational debt discharged in bankruptcy. That’s a success rate of 0.1%, according to calculations by Jason Iuliano, law professor at Villanova University who specializes in bankruptcy and student loan issues.
But those figures don’t tell the whole story. In 2017, for instance, only 447 out of the 241,000 student loan borrowers who filed for bankruptcy actually sought to have their educational loans discharged. The remaining 99.8% didn’t bother trying. But of those who did, around 60% managed to get a discharge of some portion of their student debt, Iuliano found.
“When you look at the people who bring these cases, they’re by and large very successful,” Iuliano says. But few borrowers bother trying to cancel their student loans when they file for bankruptcy because doing so requires an extra step – a lawsuit petitioning a judge to discharge the loans. And thanks to a widely-held belief that student debt is categorically exempt from discharge, few are willing to take that chance.
Until recently, a presentation titled “Bankruptcy Mythbusters” posted on the website of one of the nation’s most prominent bankruptcy courts, the Southern District of New York, said that student loans are not dischargeable in bankruptcy along with the mea culpa, “yeah, sorry about that.” But in Jan. 2020, the court’s chief judge, Cecelia Morris, made headlines when she canceled about $220,000 of student loans owed by a U.S. Navy veteran named Kevin Rosenberg.
“Most people (bankruptcy professionals as well as lay individuals) believe it impossible to discharge student loans,” Judge Morris wrote in her decision. “This Court will not participate in perpetuating these myths.”
The court updated the incorrect language in its presentation after Business Insider asked Morris about it. The truth is that there are exceptions. Borrowers can have their student debts canceled in bankruptcy if they can show that paying them off would impose an “undue hardship,” which is what Rosenberg proved in his case. Typically, that requires a borrower to demonstrate that they cannot maintain a minimal living standard, that their circumstances are unlikely to change, and that they’ve made good-faith efforts to repay their loans.
Rosenberg had kept current on his undergrad and law school loans even as the balance swelled from less than $200,000 to nearly $400,000 over the course of 14 years. After his camping and hiking gear store collapsed in 2017, he researched bankruptcy rules and decided to seek discharge of his private and federal student debts. His lenders either settled or lost in court; when one of them appealed, Smith stepped in to handle the appeal for free. Meanwhile, Rosenberg, freed from his debts, is getting ready to start a new life in Norway as a tour guide for Arctic and sub-Arctic expeditions. “I want people to know that this is a viable option,” he says.
Iuliano estimates that, of the more than 2.6 million student loan debtors who filed for bankruptcy between 2011 and 2019, at least 29% would have been able to prove “undue hardship” if they sought to do so in court. It’s the only way for bankruptcy filers to get rid of any student loans owned or backed by the federal government, which are projected to nearly double to $3 trillion by 2030.
But borrowers who owe privately-issued loans have even more exceptions they can rely on. That’s because “private” student debt isn’t defined anywhere in the U.S. bankruptcy code. Instead, the law refers to “qualified education loans” – those made for direct education expenses like tuition, books, room and board at accredited colleges and universities. Private student loans meeting that definition – such as a $20,000 loan that’s used to pay tuition at a four-year state university – can’t be cancelled in bankruptcy, absent a showing of “undue hardship.”
Smith noticed that over the last 20 years, banks originated various loans which resembled student debt but didn’t fit the qualified loan definition – like Campbell’s Citibank loan, which she used to cover rent and groceries while studying for her bar exam in 2009 (A spokeswoman said Citi has since exited the student loan business and declined further comment).
Even after Smith succeeded in getting Campbell’s bar exam loan cancelled, she still owes about $360,000 in federal student debt for her Pace University law degree. The amount has more than doubled over the years even as she continued to make payments since the interest is accruing faster than the payments she’s making – a phenomenon known as negative amortization. Some 60% of student loans owed by millennials are experiencing negative amortization, according to a recent study.
Campbell didn’t seek to have her federal loans discharged when she filed for bankruptcy. “I did not know about this case!!!!!!!” she said in a text message when informed of Judge Morris’s ruling.
A life’s cause
Smith noticed these discrepancies when he dug into the bankruptcy code at Wilson’s behest. Once he graduated law school and joined a corporate law firm, he published his findings in an article, arguing that “the common belief that all student loans are protected from discharge in bankruptcy is based on a misunderstanding” of federal bankruptcy law. The article helped him convince his higher-ups to let him test his legal theory by litigating the issue pro-bono, at no cost to his clients.
The permission slip set Smith off on a search for the perfect plaintiff. Smith often worked late into the night, digging through internet chat forums and court records for several months before finally stumbling across Campbell in May 2015. After prevailing in her case in the spring of 2016, Smith left his corporate law job to start representing borrowers like Campbell full-time. The search began for others like her.
Instead, prospective clients were soon finding him. Smith’s inbox filled up with emails from borrowers whose lives had been crushed by student debt. “I was so despondent that I considered suicide as the only viable way of getting out from under these loans,” one email reads. “I have $50k student debt, no degree, was a victim of attempted murder, out of work, and homeless,” reads another. “I’m so desperate. Please help. I make $65K a year. I can’t even afford the monthly interest that accrues on my loans (all federal),” reads a third from a borrower who owed about $225,000. Another borrower who owed $598,000 wrote about seeing no viable future for herself.
Such emails hit a nerve with Smith. Despite his upper-class upbringing, he had grown up with a sense of empathy for those less fortunate than him. When he was in junior high school, his mom got a call from another parent thanking Smith for helping her son when he saw him being bullied by older kids after school. Without being prompted, Smith had intervened to help put an end to it, she recalls.
But helping student loan borrowers is tricky – and costly. The best plaintiffs are often the ones least able to pay legal fees. Class-action lawsuits, while often more lucrative for lawyers, are hard to organize due to the intricacies of bankruptcy courts and student loan plaintiffs’ unique circumstances.
To help run the firm, Smith borrowed $100,000 from a bank, and another $125,000 from his father. He turned to litigation finance firms – which specialize in funding cases that hold out the promise of large payouts – to cover the rest.
As his practice grew, Smith won acclaim for making novel legal arguments to help borrowers discharge their student debts. Meredith Jury, a former California bankruptcy judge who has provided pro bono assistance to Smith in one of his cases, said Smith began making legal arguments that judges hadn’t heard before. “Very few lawyers understand the loans well enough to even raise them,” she said.
Then, life took an unexpected turn: In Jan. 2017, Smith was diagnosed with stage two testicular cancer. One doctor said he might have six months to live, though others gave him better odds. “I felt so ashamed at that moment,” he recalls, “like I had an expiration date.” He signed up for chemotherapy and lost all his hair. As he laid in bed, he said that he would often occupy his mind thinking about what he would do if he had a chance to live longer.
Eventually, he says, he vowed to make it his life’s cause to help the student loan borrowers. “The calls, the emails, the stories. I felt so responsible for it,” he thought. “You have to finish this or at least die trying.”
Navient provided Smith the challenge he was looking for.
While he was receiving treatment for cancer in 2017, Smith and his co-counsel sought class-action certification in a lawsuit against Navient centered on a Texas borrower in similar circumstances to Campbell. The complaint alleged that Navient had sought to collect on the borrower’s bar exam study loan even though the debt had been discharged in bankruptcy and was no longer owed. Navient countered that the borrower hadn’t been harmed by its collection efforts and couldn’t pursue a nationwide class action.
The case wended its way through the legal system for years, until it finally landed in court-approved mediation in late 2020. By then, Smith had Boies Schiller Flexner LLP, the powerhouse law firm led by David Boies, at his side. Even so, Smith saw little possibility of a quick resolution.
“We’ve just been going and going and going and going,” he told his potential class action clients in a December Zoom call streamed from the garage of the home he was renting in East Hampton, N.Y.
In February, Smith filed a new petition to try to force Navient’s loan collection arm into bankruptcy. He alleged the company should be considered insolvent and placed in bankruptcy. That would protect the interests of three plaintiffs who alleged that Navient had wrongfully collected $45,684 in debt that had been discharged in bankruptcy. If Smith prevailed, the move would have flipped the calculus in his student loan litigation, turning his clients from borrowers who owed Navient money into creditors in a bankruptcy proceeding.
It was by far the biggest gamble of Smith’s career. It meant withdrawing as counsel from the Texas case since other attorneys in that litigation didn’t back the move. Within hours of filing the petition, Smith resigned from the case and six others, waiving all rights to compensation in legal battles that held out the promise of a big potential payday even as he racked up debts to run his law practice.
“Navient may well dismiss this as the desperate act of a small-time plaintiff’s lawyer. In that they would not be entirely wrong; but it is desperation born of years of battling an adversary who . . . refuses to acknowledge the psychological toll its actions are having on people,” Smith wrote in the bankruptcy petition against Navient.
Navient’s attorneys logged over 630 hours on the case, according to a court filing. Meanwhile, Smith didn’t file a response to their motion to dismiss. And when the hearing on the dismissal started-on Feb. 25, he was nowhere to be found.
A petitioner who joined the hearing on Smith’s behalf explained that Smith had experienced a recurrence of his cancer and had flown to Chicago for treatment.
About thirty minutes after that exchange, the boldest case Smith had ever filed collapsed.
U.S. Bankruptcy Judge Martin Glenn dismissed the case, which he called an “ill informed” attempt by Smith to jump the queue in his other litigation. He also ruled that Smith had acted in bad faith and awarded Navient a small share of its attorney’s fees and costs after determining that its defense was “overstaffed with too many lawyers and paralegals from two law firms.”
Smith disputes filing the petition out of dishonest motives. A Navient spokesman said Smith “brought baseless but extremely serious claims against our company, so we mounted a serious defense” and “will continue to defend ourselves against any bad faith and baseless accusations in the future.”
When Smith re-emerged from his treatment a few weeks later, he apologized to his clients for getting their hopes up of winning relief from their debts.
“I had heard increasing irritation, I believed, from a number of judges that led me to believe that this was potentially, or likely, a sort of novel way to approach this problem. And I got it wrong. I got it very wrong,” he said in a March 12 YouTube video he labeled as a “somewhat overly bleak explanation of the events.”
Smith vowed to fight on, but admitted that he wasn’t quite sure how. “I still am trying to figure out exactly how to get this done in a way that doesn’t leave three-fourths or half of you out in the cold,” he added.
The same day, he launched his bid to run for Congress in 2022. He’s seeking to represent Long Island’s Eastern half as a Democrat, running on a platform of reforming student loan bankruptcy rules, increasing judicial oversight and demanding accountability for the January 6 attack on the Capitol.
The district has been in Republican hands since 2014. But its current congressman, Lee Zeldin, who voted to overturn the results of the last presidential election, announced last month that he plans to challenge Gov. Andrew Cuomo in 2022, opening up the seat.
When members of a Long Island Democratic group asked during a recent Zoom call why Smith wanted to go to Washington, he said one thing which no one should doubt: “I just want to be a footsoldier. I want to work twenty hours a day.”
Cezary Podkul is an award-winning freelance journalist. He was previously a reporter at the Wall Street Journal, ProPublica, and Reuters.
Do you have a story or a news tip about student debt? We’d like to hear from you. Studentdebt@insider.com
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Chicago’s architecture, dining scene, and lakefront location are longtime draws for tourists.
There are many hotels at all prices, from boutique stays to cheap hotels and 5-star properties.
We chose top hotels in Chicago with historic features, great rooftops, and COVID-19 safety policies.
Table of Contents: Masthead Sticky
As you might expect from one of the world’s greatest cities, Chicago is home to architectural marvels, an award-winning dining scene, innovative museums, and stunning lakefront scenery. Since I moved here more than 20 years ago, I’m constantly impressed by the rich cultural offerings the city provides.
The largest city in the Midwest has also grown to include numerous compelling hotel choices, from intimate boutiques to world-renowned opulence. There is an enormous selection of accommodations for business travelers, luxury seekers, families, and tourists of all sorts.
Minimal, yet modern and edgy, Ace Hotel Chicago speaks to hip business travelers and locals looking for a West Loop base with cool factor. It’s hard not to feel taken by the immersive vibe.
The West Loop is one of Chicago’s trendiest neighborhoods, and the whole hotel seems to channel that sentiment. Rooms are purposefully utilitarian (a hallmark aesthetic of the Ace brand) yet still very comfortable, and some even come with their own turntable or guitar. The restaurant, lobby bar (with outdoor patio and fire pits), and rooftop bar are all hotspots that attract locals as well. Weeks later, I’m still thinking about the heart-stealing views from my east-facing room and the rooftop.
Created by Sir Richard Branson, the very first of the Virgin Hotels opened in Chicago in 2015 inside the Old Dearborn Bank Building. Steps away from Michigan Avenue in Chicago’s Loop, the downtown boutique hotel offers a refreshed approach to modern luxury and comfort, catering to younger business types and tech-savvy travelers. An app is utilized for check-in, room service requests (which is actually handled through delivery services like Door Dash), and it also serves as your TV remote control.
Each room (they call them chambers) in the 26-story hotel is separated into two areas, with a large dressing area, closet space, and shower separated by a set of sliding privacy doors from the sleeping area. The vibe is cool and no-nonsense. I love the fact that Virgin has no hidden fees and they offer “street-level” pricing on minibar items and videos on demand, without the typical upcharge found at similarly elevated hotels.
The Loews Chicago Hotel is housed within a gleaming 52-story glass and steel tower and favored by business travelers who eschew stuffy or traditional hotels for one such as this that favors a clean, sleek approach. Unlike many of Chicago’s hotels set in rehabbed historical buildings, I love the newness of Loews. The spacious public spaces feel contemporary, and the rooms, while decently sized, still seem airy.
I’m also enamored by the enormous rooftop terrace (one of the largest in the city) and the 24-hour state-of-the-art fitness center and large indoor lap pool. Located one block from the Chicago River, the hotel is about a five-minute walk to Michigan Avenue.
Originally home to an elite men’s club, the Chicago Athletic Association hotel building is an architectural gem dating back to 1893. Converted to a boutique hotel in 2015, the lobby always gives me goosebumps with its Harvard meets Hogwarts aesthetic.
Rooms play into the vibe, but it’s comfortable rather than kitschy. I often bring out-of-towners up to Cindy’s Rooftop, an airy restaurant with a large outdoor terrace offering some of the city’s best views of Millennium Park and Lake Michigan.
After I stayed at the LondonHouse Chicago, I consider it one of my favorite hotels in the city. The hotel is located only steps from the corner of Michigan Avenue and Wacker Drive in a Chicago landmark building, the former London Guarantee and Accident Building.
Many of the plush rooms in this Hilton Curio Collection property overlook the Chicago River and I highly recommend my Vista Suite for the prime river views and comfortable accommodations. Though, the real scene-stealer is the rooftop bar, arguably the best in the city with 360 panoramic views and three levels, at the top of which is a columned cupola — expect to witness daily marriage proposals in the summer.
Packed in amidst the Loop’s skyscrapers, the Kimpton Gray Hotel is ideal for downtown business travelers but it’s a far cry from the bland cookie-cutter business hotels you might expect. Formally known as the New York Life Insurance building, the landmark edifice dates back to 1894. The hotel takes its name from the preserved Georgia Gray marble, which is found throughout much of the restored interiors.
The IHG property deftly combines such historic features with contemporary-styled guest rooms with crisp furnishings. Upgrade to the King Spa room for a walk-in shower and separate soaking tub, which is pretty nice after a long workday. We love the social vibe of the complimentary evening wine hour in the lobby, an IHG hallmark. Head upstairs to the lively Argentinian rooftop lounge with an enormous retractable roof. It’s a great after-work spot for entertaining clients.
Hotel EMC2, Autograph Collection (part of Marriott Bonvoy’s collection of hotels) is a truly one-of-a-kind boutique hotel in Chicago’s downtown Streeterville neighborhood. True to its name, it impressed me with a refreshingly different design concept mixing art with science. It’s far more interesting and immersive than it might initially sound.
Rooms feature sleek decor, hardwood floors, and dramatic artwork that feels experiential over traditional. My favorite part: the hotel “employs” two-room service robots, Leo and Cleo, who will deliver extra towels and such to your room. That was a first for me.
Dark and sophisticated, The Thompson Chicago (a World of Hyatt luxury property) immediately makes you feel cool with a stylish, loft-like urban edge that attracts a cosmopolitan crowd.
Reviewers love the luxury linens, Gold Coast location, and modern, state-of-the-art bathrooms and city views. Nico Osteria on the ground floor is well known in the neighborhood for its raw bar, house-made pasta, and tasty seafood.
Located right on iconic Michigan Avenue, The Gwen, a Luxury Collection Hotel from Marriott Bonvoy, is set in a 1920s Art Deco landmark building (yes, it’s a common theme in Chicago).
Bright and modern rooms come with ultra-luxe Frette linens and a plush bed. Amenities include excellent on-site restaurants from one of Chicago’s most celebrated chefs and the sleek rooftop terrace has fire pits and a unique “curling” rink in winter.
From the beautifully restored 1930s façade to the 30-foot lobby wall of quotes, the Viceroy is all about looks.
During a recent stay, I was quite impressed by the highly-designed rooms, which felt like a study in midcentury modern decor, and as if I was living in my own pied-à-terre rather than a standard hotel.
I also loved that Viceroy is located in the Gold Coast neighborhood with its great shopping and dining. Staying here gives visitors a taste of residential life, but with plenty to do nearby, and prime beach access. The hotel is very close to Lake Michigan.
Often named not only the best hotel in Chicago but also one of the best in the US, the five-star Peninsula Chicago earned a spot on our list for its winning combination of service and elegance.
We appreciate all the plush details found within rooms from the Pratesi linens to the TV above the soaking tub in the marble bathroom. It’s opulence at its finest. Although it’s pricey, sometimes they have special offers like a third night free.
Whenever you visit, try to stay over Friday or Saturday night so as not to miss the decadent, chocolate buffet of your dreams in the Lobby restaurant. This is also where the celebrated Peninsula Afternoon Tea takes place. And don’t miss the 1930s supper club decor and world-class dining at Shanghai Terrace or the views of Michigan Avenue from the rooftop terrace.
The five-star Langham Chicago is a classic example of luxury, consistently praised for its excellent service and posh appearance. The art-filled hotel resides in the landmark, 52-story IBM building designed by renowned architect Mies van der Rohe. It’s perched on the Chicago River, steps from Michigan Avenue, Millennium Park, and Chicago’s business district, offering one of the best locations in all of the city.
Large rooms all have floor-to-ceiling windows with stellar city views. Splurge on a Club Level room and you’ll receive a complimentary breakfast buffet, afternoon tea, cocktails and snacks all day and into the evening, and butler service, which offers tremendous value for the higher price tag. Oh, and don’t forget your swimsuit to do laps in one of Chicago’s nicest indoor pools.
More on our methodology for selecting the best hotels
In addition to the criteria previously outlined, we considered the following factors:
Experience: Every hotel on this list has been visited first-hand by one of our local Chicago writers, who confirmed that the overall experience delivers on design, value, location, and more.
Value: In fact, value matters a lot. We chose Chicago hotels that offered strong value through rooms that feel worth the money, as well as a combination of other important travel factors such as on-site amenities and a location that makes it easy to explore the city.
COVID-19 protocols: We only selected hotels that prioritize the health and safety of their guests with new strict new cleaning policies in light of COVID-19.
Price: We only accepted hotels with room rates that start under $400 in low season.
Guest profile: We chose hotels that would appeal to families, young professionals, solo travelers, couples, business travelers, friends, and more.
Reviews: We consulted past guest reviews and ratings on trusted traveler sites such as Trip Advisor, Hotels.com, Booking.com.
FAQ: Chicago hotels
What are the best hotels in Chicago?
The ones on this list, of course! As a self-proclaimed ambassador for Chicago who’s always encouraging friends to visit, I’m always asked for recommendations on where to stay. My answers typically depend on the person’s style preferences, location requirements, reasons for visiting, and of course, budget. These factors similarly fueled this very list, to highlight the hotels that best tick all those boxes: stylish, centrally located, near business and leisure, and are reasonably priced.
What is the best time of year to visit Chicago?
Chicago’s harsh winter means spring, summer, and fall are the ideal times to visit, though, summer can also be quite humid. However, the city is filled with fun outdoor things to do during these warmer months, from sunbathing on the beach at Lake Michigan, to sitting riverside at a restaurant on the Riverwalk, strolling through Millennium Park, hitting farmer’s markets, and more.
But because of cold weather, winter will also be the cheapest time of the year to visit. Expect to pay higher prices in summer and early fall.
Which is the best location to stay in Chicago?
If you’re visiting Chicago on business, you’ll probably want to be based downtown, otherwise known as The Loop, which is the city’s financial center. It’s also home to Millennium Park.
Foodie should head to West Loop, an emerging hotspot for chef-driven restaurants and swanky cocktail lounges.
If shopping is on the agenda look to areas in and around Magnificent Mile, such as Streeterville, which is also well-suited to first-time visitors, as is River North. To travel further afoot like a local, consider Wicker Park or Lincoln Park.
Is it safe to stay in hotels?
The CDC has said that fully vaccinated people can safely travel within the US. Experts also say hotels are safe if you are unvaccinated, so long as you take proper precautions.
Hotels are also implementing new cleaning policies to help guests rest easier. We’ve noted updated policies for each of the hotels on this list below.
Less than a second. That’s the time between when a Chicago police officer told Adam Toledo, 13, to “show me your f—ing hands,” and when that officer fatally shot the boy in his chest on March 29.
Police body-camera video of this event, the incident report, and the tactical response report were released to the public on Thursday by the Civilian Office of Police Accountability, a police watchdog agency in Chicago.
The officer, 34-year-old Eric Stillman, stated in an incident report on the March 29 incident, that the suspect was a John Doe, listed as an adult, between the ages of 18 and 25.
According to NPR, another person apprehended at the scene, 21-year-old Ruben Roman, gave a false name for Toledo, delaying his identification; authorities later identified Toledo by finding him in missing persons reports.
Police accuse Roman of firing a gun at a passing car, blaming him for the events that then unfolded.
But police also misstated events, Officer Stillman stating in a separate tactical response report that the deceased “did not follow verbal direction” – and that the officer faced an “imminent threat of battery with weapon” and said the subject “used force likely to cause death or great bodily arm.”
Those claims do not entirely match up with troubling footage, released on Thursday, from the body cam Officer Stillman was wearing.
Toledo in the video appears to have had a gun but dropped it before complying with the officer and raising his hands. The report lists the weapon as a “semi-auto pistol.”
An attorney for the family asserted during a press conference that Toledo complied with the officer’s request and was not holding a gun when he was shot.
The shooting occurred, police say, after officers responded to a “shots fired” call and reports of “two males in a nearby alley,” CNN reported.
Police initially claimed the shooting took place following an armed confrontation.
Police forces across the country are reportedly preparing for white supremacist rallies planned for this weekend.
White supremacist groups are organizing the rallies over encrypted messaging app Telegram, Newsweek first reported. There are also public event pages on Facebook suggesting there will be several rallies on Sunday, April 11.
“Patriots all over this nation are peacefully marching to raise awareness for whites being victims of massive interracial crime and also persecution by the government,” one Facebook event page reads.
“This is happening in every majority white nation on earth. Time to make a stand. Please join your brothers and sisters in this amazing event,” the event description continues.
Organizers have, for the most part, not disclosed the locations planned for these rallies. But Newsweek and local news outlets reported that police have identified numerous cities where the white supremacist rallies are expected. Among them are New York, Fort Worth, and Chicago.
The Facebook event page encourages people to organize a rally in their own city.
It’s unclear how many people these planned rallies will attract.
But officials who are aware of planned rallies this weekend in their cities are taking steps to prepare, news outlets reported.
Huntington Beach police in California, for example, are aware of an event to “unify White people against white hate” circulating on social media and planned for this Sunday.
Interim Police Chief Julian Harvey told the San Bernardino Sun that the police are preparing for large crowds in case the rally attracts a lot of people.
“Like any demonstration in the city, we are preparing and will continue to prepare until the day,” he said. “We do have a plan to ensure public safety – not just the safety of the participants and the attendees, but also residents, businesses and motorists.”
The Asheville Police Department in North Carolina told Newsweek its officers have been briefed on the “call for action around the country” coming from white supremacists. The department is tracking any action, Newsweek reported.
In response to the planned rallies, counterprotesters have also begun to organize.
The local Black Lives Matter chapter in Huntington Beach, for example, is assembling for a counterprotest a few hours ahead of the planned white supremacist rally, the San Bernardino Sun reported.
And in Albuquerque, New Mexico, counterprotesters are encouraging residents to “rally against white supremacy in all its forms.”
“On Sunday, April 11th – local Proud Boys and White Supremacists are planning on hosting a ‘White Lives Matter’ Event on the Albuquerque Civic Plaza alongside a national day of actions by far-right extremists across the United States – we refuse to let them bring their violence to our beautifully diverse city because white supremacy has no place here,” a Facebook event page for the counterprotest reads.
“Please wear your masks, bring creative signs, water, plan on being loud, and bring your friends – we have safety in numbers,” the page says.
A federal district court judge has ruled that three groups of restaurants operating in four US states should be able to move forward with legal action, which claims that business interruption insurance should cover their pandemic losses.
Restaurants being run by Valley Lodge in Illinois, Rising Dough in Illinois, and Big Onion Tavern Group in Wisconsin, Minnesota, and Tennessee all took action against Wisconsin-based insurer Society Insurance. The cases were initially filed separately before being combined into a multi-district bellwether case.
The insurance company tried to dismiss the cases – but the US District Court for the Northern District of Illinois turned this down, meaning that the restaurants will be able to take the issue to court.
“The case serves as an accountability mechanism,” Shannon McNulty of Clifford Law Offices, who is co-lead counsel in the case, told Insider.
The restaurants alleged that under their insurance policy with Society Insurance, they had coverage that should have been triggered last March when the pandemic started.
Society Insurance, in response, said that this pandemic coverage isn’t included in the language of the policy.
Society Insurance had told the restaurants in an email in March 2020 that “a quarantine of any size … would likely not trigger business income or extra expense coverages under our policies.” It also said “a widespread governmental imposed shutdown due to COVID-19 would likely not trigger the additional coverage of civil authority.”
The insurance company added that COVID-19 would be “unlikely” to trigger contamination coverage because it isn’t a foodborne illness, and that exposure that their food products had to COVID-19 would not count as a spoilage-covered cause of loss.
In a 31-page ruling viewed by Insider, the court found that the restaurants’ insurance policy “does not contain a specific exclusion of coverage for losses due to a virus or pandemic.” The restaurants said that is a standard exclusion in the insurance industry.
“The fundamental questions at stake in this litigation are how properly to classify the interruption that has happened here, and whether this particular interruption is covered under the policy,” Edmond Chang, the judge leading the ruling, wrote.
The court said that “exclusions are narrowly or strictly construed against the insurer if their effect is uncertain.”
“The decision is highly significant for businesses, particularly here in the Midwest, who have suffered financial losses due to the pandemic and paid insurance premiums to protect against those losses,” McNulty said.
“The court correctly found no coverage under the civil authority, contamination, and sue and labor provisions of Society’s policy,” Society Insurance told Insider. “But Society is disappointed that the court allowed the claims for business-interruption coverage to survive early motions to dismiss and for summary judgment.”
“This is an early, preliminary ruling, and does not resolve the merits,” it said. “Society will continue to vigorously defend its interests in the litigation.”
The court classed the multi-district case as a “bellwether” case, but it’s part of a much bigger wave of coronavirus-related litigation covering everything from individual businesses to industries, lawmakers, and even entire governments.
The last time Brianna Wolin stationed herself at the phone in the hopes of finally getting through, she was trying to win a radio contest in 2005.
Her latest phone calls have higher stakes. Wolin, a graduate student at Northwestern University, has been calling county COVID-19 vaccination sites in Chicago with the goal of booking appointments for elderly residents and frontline workers.
“You feel like you’ve won the lottery when you get an appointment,” Wolin told Insider. “It’s almost absurd, because we’re talking about booking vaccines for people to save them from a global pandemic.”
While the US is doing fairly well in the global vaccine distribution race – for its own citizens, at least – local sign-up processes have been mired in complications. Phone sign-up lines have been long, and competitive online registration doesn’t favor those who are high-risk due to old age, or people who are away from their computers all day at essential jobs.
Volunteers like Wolin have joined forces to make sure high-risk vaccine seekers don’t slip through the cracks, earning them the nickname “vaccine angels.” They make up one arm of a loose patchwork of “vaccine hunters,” or people who have banded together, mostly in online groups, to find extra shots.
They started out vaccine hunting for themselves, but some wanted to help others
The team of angels working in Chicago have booked appointments for 1,250 people and counting, Wolin said. Similar initiatives have emerged across the country, from Washington State to Massachusetts.
The vaccine angels formed a coalition within the larger Chicago Vaccine Hunters Facebook group, a community of more than 50,000 people hoping to get shots themselves or for loved ones.
Roger Naglewski created the group in early February after he came across similar online communities based in other cities. He started out by sharing tips he picked up from the NOLA Vaccine Hunters page, but soon the Chicago members were posting their own experiences and advice.
One day, Naglewski got a message from Ben Kagan, a kid he guessed to be college-aged, based on his profile picture. Kagan, who turned out to be 14, wanted to use his computer skills to book appointments for less tech-savvy Chicagoans. A couple of other members had been doing similar work, so Naglewski put them in touch.
The team grew from just a few volunteers to 55 “vaccine angels” in less than a month. They now have an official inbox for requests, and they’ve coordinated a schedule of volunteer shifts for around-the-clock coverage.
Vaccine hunting requires quick fingers and connections
After wrapping up her day job as a manager at a publishing company, Gisele Gover sits at her computer waiting for the telltale ping that means a vaccination site has updated their available appointments.
Heart pounding, she frantically exchanges messages with other volunteers and refreshes the relevant webpages, sometimes logging on as late as midnight to check for open spots.
“My husband thinks I’m nuts,” she told Insider, but the work has been a rewarding way to give back to her community during the pandemic.
Recently, she was looking for an appointment for a breast cancer survivor who was practically in tears after she struggled to find a spot. Gover was able to book her a shot, and the woman was overjoyed. “So freakin’ blessed that you crossed my path,” she wrote in a text to Gover.
Many of the tips and tricks used by vaccine hunters and angels alike require a combination of computer proficiency and insider knowledge. If a vaccine angel books an appointment for someone who later needs to cancel, the team tries to time it so a volunteer can snag the spot for another person in need.
“When you think about a senior citizen trying to do that – like, ‘okay, I’m cancelling this appointment, but I want you to have it’ – there’d be no way,” Gover said. “Really, what it’s all about is representing the people that can’t navigate this whole thing on their own.”
Booking appointments for those who can’t
Right now, the demand for vaccine angels exceeds their bandwidth. Group coordinators like Wolin are trying to balance fielding requests with training new volunteers, and every few days, they need to temporarily shut down the registration form to play catchup.
The team tries to turn around requests within three to five days, prioritizing people who qualified for the earliest phases of rollout but have struggled to book vaccine appointments themselves.
Some of the populations at the highest risk of getting severely ill or dying of COVID-19 are those who would have trouble booking an appointment, whether that’s due to lack of computer skills or Internet access, or because of busy work schedules.
That inequity is not lost on the vaccine angels, who are conscious of people trying to grab vaccine appointments designated for underserved communities, despite “never stepping foot on one of those streets in their lives,” Wolin said. They also have some Spanish speakers on the team, and Wolin said they’re seeking to partner with community organizations.
All of these efforts – the outreach, the late hours at the computer, the heart-pounding thrill of booking an appointment – are fueled by unpaid volunteers.
“It almost feels like finding a group of friends that you’ve never met, because it’s all people who have the same values and priorities,” Wolin said. “We’re not getting paid a penny; we’re not looking for money. We just want to make a difference in our community.”
As a result, companies are gearing up for this potential boom, including Southwest Airlines. In the last year, Southwest has dramatically expanded its flight offerings with new services to locations like Palm Springs, California, Cozumel, Mexico, and Miami.
Now, the airline has added additional flights to two travel hotspots: Florida and Bozeman, Montana.
Bozeman, Montana – known as “Boz Angeles” – has become a hot destination, especially for wealthier travelers looking to trade city life for a break in nature. Bozeman also been named one of the fastest-growing cities in the US and offers close access to hotspots like Yellowstone National Park.
This will be Southwest Airline’s first destination in Montana. Flights to Bozeman Yellowstone International Airport will take off from airports in Denver and Las Vegas starting at $40 beginning May 27.
On the opposite end of the climate spectrum, Florida has also emerged as a top travel destination during the COVID-19 pandemic due to its warm weather and more relaxed restrictions. Southwest already flies to 10 other airports in Florida but decided to expand its offerings in the state for “winter-weary families” looking to get away to warm destinations, Andrew Watterson, Southwest Airlines’ executive vice president and chief commercial officer, said in the press release.
Direct Southwest flights to Destin-Fort Walton Beach Airport can be taken starting May 6 from these four airports: Dallas Love Field, Baltimore/Washington, Nashville, and Chicago Midway, the latter starting June 6. These flights will start at $70.