Chicago | August 6, 2021 7:54 am

What Are the Chicago Hotspots Where You’re Most Likely to Run Into a Celeb?

We consulted the Instagram gossip lords at DeuxMoi to try to track down some famous Chicagoans in the wild

The bar at Gibson's
The bar at Gibson's
Gibson's Steakhouse

Oprah split for the coast and we’re still waiting for Real Housewives of Chicago — but that doesn’t mean that our beloved Windy City is a celebrity-less wasteland.

While celebrities in New York and Los Angeles spend their days dodging paparazzi, here in Chicago, we put our celebrities to work. Joan Cusack runs the popular gift shop Judy Maxwell Home, Giuliana and Bill Rancic manage the ever-growing RPM restaurant family and Brian Urlacher’s busy hawking hair growth products on every billboard in the greater Chicagoland area. 

That said, it’s arguably more challenging to casually rub shoulders with the powerful and beautiful here than it is on the coasts at reliable celeb spots like Little Dom’s (L.A.) or Via Carota (NYC). Nonetheless, I resolved to find them, and to help me get there, I consulted the ultimate 2021 celebrity almanac: pro-level gossip Instagram account DeuxMoi, which recently solicited suggestions for the top celebrity hangouts in Chicago. We put those recs to the test one recent weekend, with a trip to the top four locations — where we got the inside scoop from bartenders, copied some of the city’s most famous visitors’ drink orders, and tried to fit in with the glitterati for a night. 

Let’s dive in. 

Stop One: Hugo’s Frog Bar 

The Celebrity: Scott Weiland, the late lead singer of the Stone Temple Pilots 
The Drink: Gin Martini 

Our first stop was Hugo’s Frog Bar, a wood-paneled Chicago favorite that feels like the kind of place Al Capone would have liked. (Well, if Hugo’s hadn’t opened in 1997.) 

Even on a Thursday night, Hugo’s Frog Bar was bustling. A quick survey of the place revealed no celebrities on hand, so I shifted to reportorial mode and asked the bartender to name the biggest celebrity he’d ever served at Hugo’s. 

He pointed to a stool in front of him. “Scott Weiland used to sit right there, wearing a big poncho and sunglasses, until his bandmate showed up to drag him away to his show.” 

I told him that I’d have whatever it was that Scott Weiland drank during his visit. 

“Are you sure?” he asked kindly. “He drank gin martinis.” 

I winced, although I shouldn’t have been surprised that the guy who wrote a song called “Dead and Bloated” had an intense drink order. To drown out the taste of gin (sorry, gin-lovers), I ordered a side basket of Hugo’s hand cut french fries — the perfect chaser. 

Stop Two: Gibson’s Steakhouse

The Celebrity: Jack Nicholson 
The Drink: Bloody Mary 
Another Celebrity: Ric Flair 
Another Drink: Citron and 7-Up 

Stomach sloshing with gin, I headed to the famous Gibson’s Steakhouse, miraculously finding a seat at the bar across from Mark, the restaurant’s bartender. Mark has been serving Gibson’s customers for 30+ years, and he rates as a Chicago celebrity in his own right. He has a knack for remembering the name of every person who’s ever walked into Gibson’s, famous or not. 

“Is Jack Nicholson famous enough?” he asks when I request the drink of the biggest celebrity he’s ever served. (Again: no celebrities on hand.) 

Mark starts making Jack Nicholson’s favorite Bloody Mary (I do a silent thank you to Jack for not being a gin guy) as he rehashes the visit.  

“I had my head down, washing glasses,” Mark said. “This guy comes up to me and asks ‘Make a good Bloody Mary?’ And I knew that voice. I look up, awe-struck. Of course, I’m not giving Jack Nicholson the pre-made stuff so I go in the back — grinding pepper, the whole thing.”

The Bloody Mary was so good that Jack came back the next day. 

“The next day, Jack Nicholson comes back to the bar, asking for me — ‘the tall guy with the slicked-back hair,’” Mark continues. “When they tell him I’m in the service bar, he walks in like he owns the place. He says, ‘Hey, remember me?’ and I say, ‘Yeah, hi, Jeff!’”

My entire section of the bar is now hanging on Mark’s every word. 

“Jack starts talking to the cooks, asking if they make a good steak,” Mark says. “He asks for a reservation for the night, so the hostess saves him two of the best tables we have — one in the section for people who want to be seen, and one that’s more hidden. Jack picks the section where he can be seen.”

Mark says that later that night, the owner of the Admiral Gentleman’s Club came in with some of the dancers. 

“They’re all waiting in the hall, and a dancer spots Jack,” Mark says. “Suddenly 25 strippers start going up to him. I try to stop them from bothering Jack when he turns to me and says, ‘Mark, let ‘em through.’ So Gibson’s is the place where even Jack Nicholson wants to be seen.” 

It’s the ideal Chicago celebrity story. In the hearty Midwestern city known for pragmatism and openness, it’s these kinds of interactions that stand out. Jack Nickelson isn’t some aloof celebrity dashing into a VIP booth — he’s just one of the gang, already on a first-name basis with the whole staff. Time and time again throughout the night, I’m told this is the definition of the ideal Chicago celebrity: someone who meets Chicagoans where they’re at, instead of wanting special treatment.

Mark follows up with another story — and another drink — from a different celebrity, WWE icon Ric Flair. We can’t print the story here, but trust us: Go to Gibson’s and get Mark to share it. It’s worth it.

Stop Three: Tavern on Rush

The Celebrity: Ellen Pompeo (we think)
The Drink: Rosè 

Plopping down at a high top at the bar on Tavern on Rush, the kind waitress seemed surprised to hear that the restaurant was high on the list of Chicago celebrity hotspots. 

“Uh, the girl from Grey’s Anatomy ordered a rosè once?” she offered up. (We agreed that the actress was probably Ellen Pompeo, but neither of us were 100 percent positive.) 

As I sat sipping my $14 glass of maybe-Ellen’s wine, I noticed two beautiful girls at the bar, flanked by older men. Emboldened by the gin (and the Bloody Mary) (and the citron and 7-Up), I sidled up to ask them — were they themselves celebrities?

The blonder of the two leaned in and whispered, “We’re kind of celebrities. I won’t tell you my real name, but I’m a sugar baby. And tonight, I’m looking for a new daddy.” 

She added that the pandemic had been rough on many industries — including sugar babies. Now that the world was opening up, she’d recruited her friend to play wing woman to line up her docket again. 

“Tavern on Rush is the place for sugar babies,” she assured me. “If you’re a pretty young girl, you’re gonna get swooped up in a second here.” She added that she’s paid upwards of $1,000 per night, just for dinner. 

A potential daddy leans over and buys the girls their drink of choice: tequila on the rocks. While they may not have been Hollywood famous, I was excited to get a quick glimpse into their world — so they were close enough to a celebrity for the night. 

Stop Four: Bub City

The Celebrity: Kameron Marlowe
The Drink: No Shirt, No Shoes Cocktail

One of the most common answers for where to spot celebrities on the DeuxMoi poll was Bub City, a country bar that I thought was mostly just known for cover bands and finance bros. But I was assured throughout the night that it was the spot for celebrities to let loose, with several people telling me in hushed tones that the “Jonas Brothers are always going there.” 

The place was packed at 11:30 p.m. on a Thursday. When I asked the bartender who the biggest celebrity he’d served was, he looked at me like I told him country music sucked. 

“I have no idea,” he said.

A sweet server I ran into later said she didn’t know what the Jonas Brothers got, but she’d recently served country singer Kameron Marlowe, and he and his crew were drinking the tropical No Shirt, No Shoes cocktail all night. 

Moral of the evening: If you can’t hang out with celebrities, you can absolutely drink like one. The drink tasted like juice — I could have had 100 more. As I licked the last drops off the tropical garnishes, I thought I spotted billionaire Jeff Bezos behind me. 

“Isn’t he in space?” my friend asked me. “But we can tell people we saw him anyway.” 

Maybe that’s another lesson from celebrity spotting in Chicago.