Lollapalooza Weekend Is Now the Super Bowl for Chicago Celebrity Sightings

Lollapalooza has become the Super Bowl of A-list downtown Chicago celebrity sightings.

These celebrity “moments” captured on social media aren’t always organic — publicists dip into whisper networks banked with lists of preferred restaurants, ones with experience accommodating high-profile customers in affording them the privacy they may need after a late-night gig. Restaurants know celebrities talk among themselves and to ensure they themselves remain A-listed, general managers and servers have become more responsive to the needs of these rarefied clientele, helping them orchestrate meals — and occasionally stunts — that drive up social media impressions.

Victoria Shapow

Victoria Shapow

Victoria Shapow

Beabadoobee was at Sushi-San, Maisie Peters was at Miru, and Linda Lindas dined at RPM Seafood.

Still, restaurant workers say they do it for the love of hospitality and Lettuce Entertain You Enterprises’ restaurants have earned a reputation for creating celebrity safe spaces. Last month it was Drake sipping malört at Miru. Two years ago, it was Dave Matthews eating a family meal at RPM Seafood celebrating a special anniversary.

During this year’s festival, diners saw Diplo at the Oakville in Fulton Market, and The Red Hot Chili Peppers at RPM Italian. Filipino English singer Beabadoobee visited Sushi-San. The importance of these moments can be debated. The older crowd can be cynical — who are the Linda Lindas and why would I care if they sat by the river at RPM Seafood? The younger crowd can also have doubt — why would I care about Chris Rock at the same stuffy River North spot?

Wieners Circle

Ensuring customers have a good time, even if they’re famous, is the responsibility of folks like Adam Biolchin, who’s the general manager at RPM Italian. He’s worked for Lettuce’s RPM restaurants across the country. At the Washington, D.C. location, he notes, there’s an entrance through a parking garage that goes straight to elevators that brings guests to a private dining room. VIPs use that entrance so they aren’t seen (as opposed to Flea, who preferred to waltz through the main entrance during his band’s Chicago visit).

Biolchin says celebrities are drawn to Chicago: “There’s no paparazzi,” he says “They feel like in Chicago they can let their hair down a little bit and be themselves a little more.”

And while there might be a temptation for a restaurant to send out a special dish just as a band sits down, Biolchin says they always check in with a rep about allergies or stop at the table to figure out the vibe first. The staff doesn’t want to define the experience for the customer. For example, if an NHL player from Europe is in, they might want to sit at the bar and talk to the bartender — they may not have friends or family in Chicago; they’re searching for a conversation. “They want a social experience, to be a normal person for a little while,” Biolchin says.

Though Chicago’s largest restaurant company seemingly has a monopoly on celebrity dining, they aren’t don’t have a monopoly on star sightings.

Ed Sheeran’s reps recently arranged an appearance at the Wiener’s Circle, the Chicago hot dog stand known for its charming work staff, mostly Black women, who hurl insults at belligerent customers in Lincoln Park, one of Chicago’s whitest neighborhoods. Sheeran did not know the Lincoln Park landmark’s history when he got behind the counter with Cheyenne Ford and the rest of the circle’s staff. Sheeran did not engage in insults, and neither did customers.

“No one wanted to curse him out — they tried to tell him stories,” Ford says, pausing briefly before displaying the raw candor fans of the hot dog stand relish. “One girl was telling him about dancing to his song during her wedding. We don’t give a fuck, bitch. Get the fuck out of there!”

Thanks to a social media post that went live when he was 30 minutes from the restaurant, Sheeran’s fans flooded the space. While organizers initially planned to hand out 100 hot dogs, Sheeran, being a solid dude, ultimately handed out 300 dogs, Ford says.

Despite the overall enthusiasm behind the Sheeran appearance, Bon Appetit took a shot at Sheeran, Lana Del Rey, and other celebrities who have posed as restaurant workers for stunts: “In an industry and time in which most servers are overworked and underpaid […] it’s a decidedly un-cute look to try out a little bit of hourly labor as a treat,” writes Sam Stone.

Nevertheless, some restaurants aren’t as cynical and benefit from the free advertising of a celebrity dining moment. Just a week prior, another music megastar visited Chicago’s Black-owned Bronzeville Soul. As Beyonce performed for two nights at Solider Field, Jay-Z posed for a photo with restaurant co-owner Mario Coleman after a friend recommended he pay them a visit. Coleman says he couldn’t believe that Jay-Z knew exactly what to order and walked out with pound back and beef short ribs.

Since the visit, Coleman has renamed those short ribs the “Jigga Man Short Ribs” and seen business surge 200 percent. Coleman says he grew up listening to Jay Z’s music, saying he prefers his first album, Reasonable Doubt, so he was awestruck when he saw his hip-hop hero come through the door. He also left the interaction with greater respect for Jay-Z as a community activist and entrepreneur, noting that when he requested a photo, Jay-Z insisted that Coleman come around the counter and pose right next to him for a photo worth showing off on Instagram.

“Jay-Z understood the assignment,” Coleman says. “He knew exactly what he was doing and the power he possesses.”

Coleman and his partner, Angie Price, are first-time restaurant owners who opened their doors in summer 2022 with the help of six-member staff. While Coleman says he’s confident in his food, he knows it’s a competitive world out there and he worries about what happens to the business after the Jay-Z bump — or even if Bronzeville Soul is worthy of the attention Jay-Z has brought to his restaurant. But unlike some celebrity restaurant sightings, there’s something special about this appearance. It wasn’t purely transactional and he hope he gets a chance to say thank you.

“I would just like to look Jay in the face and say ‘I appreciate who you are and what you do and how you go about handling who you are,’” he says.