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Lollapalooza Guide

Lollapalooza is happening this weekend, August 1-4, in Grant Park. There will be headliners including The Strokes, Chainsmokers, Twenty One Pilots, Childish Gambino, Tame Impala, Flume, and our queen, Ariana Grande, along with so many more.

Whether you are a regular Lolla-er, going for the first time, or just enjoying the shows from afar – we are here to give you the low down on how to eat and drink your way through this four-day festival.

Skip trying (and failing) to sneak booze into Lolla, and pregame beforehand with a boozy brunch instead. We have a roundup of where to eat, drink, and cool off during the festival.

SX Sky Bar Brunch

SX Sky Bar

Get ready to enjoy booze and views at SX Sky Bar — and most importantly, it’s a short walk to the festival. This restaurant overlooks Grant Park and offers a great bottomless deal. SX offers bottomless mimosas, Bloody Marys, and Bellinis for $25. Read our review here.

SX Sky Bar, 808 S Michigan Ave., Chicago, (773) 633-0214

Whisk 1


Grab a few bottles of Champagne, and head to Whisk in Ukrainian Village. This BYOB restaurant has a hearty, Ron Swanson-approved menu. While you don’t have to worry about making a reservation, you will need to get there early because tables fill up fast! Read our full review here.

Whisk, 2018 W. Chicago Ave., Chicago, (773) 252-9060


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Z Bar

Festival fun doesn’t have to wait until you enter the gates. Z Bar is hosting a pre-Lolla brunch from 11:30 a.m. to 3 p.m. on Saturday and Sunday. Enjoy themed cocktails like the “Ariana Grande,” a frozen drink with rum, coffee, Amaretto, and cinnamon, or “The Chainsmokers,” a mescal Bloody Mary with burnt sage. DJs will be spinning from noon to 3 p.m. to get the party started.

Z Bar, 108 E Superior St., Chicago, (312) 573-6888



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Schubas Tavern

By Sunday, you’re going to be tired of fighting the commute and wrangling all of your friends to make a decision on where to eat beforehand. Get ready to solve two problems at once. For $20, you can enjoy a brunch, two cocktails, and a music-bumping, party bus ride to the show at Schubas Tavern. The shuttle will leave promptly at 3 p.m and tickets are required.

Schubas Tavern, 3159 N Southport Ave., Chicago, (773) 525-2508



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Castaway’s Bar and Grill

Beat the heat with a “frozen Lolla lemonade” at Castaway’s. This vodka lemonade is available for $9 from noon to 11 p.m. You can also grab a bite to eat and enjoy the patio views while waiting for the next act.

Castaways, 1603 N Lake Shore Dr., Chicago, (773) 281-1200

Steingold’s Chicago

At Lolla, wristbands = money, but at Steingold’s, they equal a free meal. The deli is offering free mini bagels with a purchase to those with Lollapalooza wristbands from July 29 to August 9. Grab breakfast and head on down to Grant Park to enjoy the shows!

Steingold’s, multiple locations

Kirsten Ballard

Chicago Food Editor & Social Manager

Kirsten is our Chicago Food Editor & Social Manager. From 9-5, she works at a Great Lakes nonprofit, but after hours she loves exploring Chicago, looking for dog-friendly bars and good Southern biscuits.

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