Places In Chicago Where You're Most Likely To Spot Celebrities

Look, Chicago isn't Los Angeles or New York City, but that doesn't mean celebs don't visit the Windy City. Tons of famous folks have walked the streets of Chicago through the years. Many comedians started out at The Second City comedy club, made their name in music on the stages here, or paved their way to fame in Chicago's famed theater scene. There are many ways to fame, and Chicago is home to many.

Even if they aren't always here, some celebrities still have homes in Chicago or Chicagoland. Folks like Oprah Winfrey, Barack Obama, and John Cusack are known for being longtime Chicagoans. Of course, not every celeb who can be spotted in Chicago lives here. Since its one of the largest cities in the country, Chicago is frequently visited by celebrities, big and small.

You probably won't make a ton of run-ins here like you would in NYC or LA, though it isn't entirely impossible. Heck, this writer sat directly behind Oscar-winning, beloved Chicagoan Michael Shannon at the Jeff Awards. So you never know where you might spot a celeb.

The wealthy Gold Coast neighborhood of Chicago is a treasure trove of spots to spot the odd celeb. Full of stunning architecture, delicious eateries, and cocktail curators, celebrities flock to the Gold Coast when they're in the city. Not quite Downtown, the Gold Coast is where some of the most expensive homes are in the city, along with some of the most decadent eateries in town.

One such restaurant is Le Colonial. This French-Vietnamese cuisine eatery, flush with a unique tropical aesthetic, is where local and far-flung celebs spend time in the neighborhood. Both comedian D.L. Hughley and former Chicago mayor Rahm Emanuel have been spotted here.

When visiting celebs crave home-style Italian in Chicago, they head to Carmine's. Celebrities who have visited the Italian eatery in the past include Sammy Hagar and Sting, though they're far from the only ones in this restaurant's history. The rumor is even the Chicago mob loves this place.

Out-of-towners consider this Downtown adjacent northern neighborhood a part of downtown, but technically it's not. River North is its own neighborhood that is a celeb foodie paradise. Not quite as ritzy as the Gold Coast, River North is a tad more trendy. Spots like RPM Italian, Underground, and Chicago Cut are no strangers to celebrity diners.

At Chicago Cut, a River North steakhouse, celebrities like Barack Obama, Kristin Cavallari, and even Jay Cutler have been spotted here in the past. With such stunning views of downtown, it certainly makes sense why they would choose to spend time here.

It should be no surprise that RPM Italian is a haven for celebs. It's owned by Bill and Giuliana Rancic, both famous from E! News shows over the years. With the inclusion of a private dining area, it makes sense that so many famous folks have come here through the years. Several of them have made their way to RPM Italian, including Lady Gaga, Michelle Obama, Michael Jordan, Cindy Crawford, Hilary Swank, and Janet Jackson.

One of the newest restaurants in the Gold Coast has already become a bastien for celebrity sightings. It replaced the longtime eatery Tavern on Rush when it opened in May 2023. The tavern was once a spot where plenty of celebs like Bon Jovi and Michael Jordan gathered, so it makes sense that the newest eatery on the street is doing the same.

It's already been visited by surprise guest bartender Mark Wahlberg. Sure, he was there in part to promote his tequila brand Flecha Azul, but he still showed up to the surprise of patrons. It's not the first time Wahlberg has shown up unannounced in Chicago to promote his liquor brand, he was also spotted at a Binny's liquor store in the city.

Tina Fey and Amy Poehler even stopped by for dinner before their joint sold-out show at the Chicago Theatre. Bellevue didn't even need a year to become a place to spot celebrities. So even though it doesn't have the reputation behind it like Tavern on Rush did, it's already establishing itself as a glimmer of Hollywood in Chicago.

This spot will be no surprise to anyone familiar with Chicago's culinary scene. Alinea is widely considered one of the best restaurants in the city and certainly one of the most imaginative. As Chicago's only three Michelin-star location, Alinea is appreciated by run-of-the-mill diners and celebs alike. Justin Timberlake, for example, has been there though he didn't get the kind of celebrated visit that some "Game of Thrones" folks did in 2019.

According to the owner's Instagram, Kit Harrington and Gwendoline Christie's visit was made even more special by Alinea chef-owner Grant Achatz. As a big fan of "Game of Thrones," Achatz got to use one of his own fan objects to serve Harrington and Christie. Achatz's staff got him a replica of LongClaw, a sword from the show, and he proceeded to serve frozen aerated Meyer lemon on the nitro-frozen sword. After the gesture, Harrington even signed the sword for Achatz. What a sighting that would've been.

One of the top-grossing independent restaurants in the country and the top in Chicago, Gibson's food beckons to a range of appetites. Michael Jordan reportedly visits Gibson's after every Bulls home game. Even folks like Adam Sandler, Rob Schneider, and Jennifer Lopez have hung out here. And can't you imagine Billy Joel showing up and making himself cozy by the piano?

Jack Nicholson is a particular fan drawn to the spot for a Bloody Mary made just the way he wanted it. With over 30 years of experience at Gibson's, bartender Mark Wagner told InsideHook that Nicholson took him by surprise one day when he asked if Mark made a good Bloody Mary. Mark said he did and immediately got to work making one from scratch, not using the bar's mix. The drink was so good Nicholson came back for another the next day.

This trendy cocktail bar, Three Dots and a Dash, is a favorite for celebs for various reasons. One such reason is that it has a private back entrance perfect for anyone trying to sneak in unencumbered. And a fun fact for anyone who doesn't know, the name is also Morse Code for the letter V or victory. It is also a cocktail made famous after WWII that comes garnished with three cherries and a chunk of pineapple to represent the dots and dash.

Joey King celebrated her 23rd birthday at the bar. She even ordered a Shotstapus, a combination of rum, passionfruit, pomegranate, lemon, absinthe, and bitters. King is far from the only celeb who has cozied up at Three Dots. Some other folks who have stopped by include Mick Jagger, Lorde, the cast of Hamilton, David Arquette, and Bob Saget. You may have a more challenging time spotting celebs here since there's a back entrance, but just keep your eye out. Who knows who you may see!