How to Escape Lollapolooza Weekend in Chicago

Eater

4 days ago

It's that time of year, Chicago — when [insert event name here] takes place and draws hundreds of tourists downtown, crowding our beloved CTA trains, providing locals with a (perhaps unwanted) crash course in fashion trends, and seeing our parks and public resources plundered by outsiders.
Got an appointment downtown this weekend? Good luck — it's Lollapolooza time from Thursday, July 31 through Sunday, August 3 in Grant Park. Yes, we know — it's good practice to squeeze sales and tax dollars out of tourists. Crowded bars and restaurants are great for the Loop and Mag Mile, especially after the pandemic wreaked havoc. The festival gives a handful of local restaurants exposure while part of Chow Town, its lineup of food vendors.
But that doesn't mean you have to be happy about ceding the city to a legion of confused suburban kids. Yes, we might be curmudgeons, but at least we're aware of our limitations as we yell at clouds while our grays whistle in the wind. Even our pals at the Chicago Reader laid out their grievances, including this gem of a line: 'No one should have to pay — or slog through Lollapalooza — to see a beautiful August sunset through the city skyline from Grant Park.'
At least Taste of Chicago was a celebration for the city's residents. (Taste of Chicago is, indeed, happening this year from September 5 through September 7 in Grant Park, in case anyone still cares – do you?).
Surely, there's plenty of space in and around Chicago to survive the inconvenience of Lollapalooza. While the easy answer is to stay away from downtown, we're going to do better than that and share some of our best suggestions on how to escape the festival.
Middle Brow has consistently delivered quality with its beer, food, and wines since the Logan Square brewpub debuted in 2019. The long and narrow space is comfy and has become a community beacon with pastries and coffee in the morning, easy-drinking beers all day, and pizza at night. The patio is welcoming, and there's even a basketball hoop to practice your jump shot. The crew also recently unveiled soft-serve ice cream, which has received a lot of attention. It's made with dairy from Kilgus Farms, and there's one flavor — charred vanilla. — Ashok Selvam, lead editor for Eater's Midwestern Region
This seafood market and restaurant on the Northwest Side has been around for almost eight decades and is one of only two remaining natural hardwood smokehouses in Chicago — South Deering institution Calumet Fisheries being the other. Smoked fish, from salmon to sable to trout, is the main attraction, but there's also a variety of fried seafood and a stellar crispy pollock sandwich. What makes Hagen's really worth a visit, though, is its smoking service; customers can bring their own fish and the shop will clean and smoke it for them. There's no indoor seating and only a few tables outside, so be prepared to take the food to go. — Jeffy Mai, associate editor for Eater's Midwestern Region
For some Chicagoans, Lolla weekend is the ideal time to go on a vacation to a faraway place. While River Grove, located 15 miles west of the Loop, doesn't quite fit the bill, it does offer an escape by way of Hala Kahiki. The tropical bar has been a suburban institution since 1964, and is the standard bearer in the Chicago area for Polynesian-style drinks. The menu is massive, featuring over 130 cocktails as well as rum flights, and the space feels like a charming time warp that erases all memories of the Lolla crowds. There's also a small menu of snacks, but the suggested move is to grab a pre- or post-drink hot dog at Gene & Jude's, which is located just down the street. — J.M.
In February, I chatted with superstar baker Christina Tosi of Milk Bar about the talented Maya-Camille Broussard, who appeared on Tosi's reality baking show, Bake Squad. Broussard, a Chicago native, is known for her sweet pies, but I felt her mastery of savory was underrated. Tosi started snapping her fingers in agreement, having seen Broussard's skills in action. Justice of the Pies is a love letter to Chicago. There's not a lot of seating, but the pastries and quiches are out of this world. Broussard puts a lot of care into her craft, and we tend to take her bakery for granted, especially in 2025 when new bakeries are debuting seemingly every month with customers lining up and waiting for hours. You want to escape the big, dumb line? Head out to Marynook. — A.S.
One of my favorite places in Chicago is Loyola Park because it's a rare public park with a playground along the lakefront. If you have young children, this is truly one of the most serene spots in town with gorgeous views of the skyline. It's so spectacular you'll be able to filter out any commotion a child may produce. Blue Jay Cafe has great coffee drinks and hot dogs at the park, but if you want a sit-down meal and a new setting, Khmai — one of two Cambodian restaurants in Chicago (the other being the brilliant Hermosa) — is less than a mile south of the park. The more casual side, Kaun Khmai, takes reservations, and the dips and egg rolls provide a special kind of fuel to make you forget all your worries. You can always just forget the park and go directly to Khmai if the weather is threatening. — A.S.
Most of Chicago's hottest rooftops are located in downtown skyscrapers — near Grant Park. For a more laid-back experience, free of festgoers, take the CTA Blue Line to the Damen stop and walk over to the Robey. On the hotel's 13th floor sits the Up Room, an intimate cocktail lounge offering sweeping views of the city. The drinks are great — try the spicy Oaxacan on Broken Glass (mezcal, chile poblano, hellfire bitters) — and there are both indoor and outdoor seating areas so guests can enjoy a breeze or get away from scorching temps. Yes, Up Room is located atop a bustling intersection in one of the trendiest neighborhoods, but it somehow still manages to feel like a hideaway. — J.M.
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