George's Cocktail Lounge

If you’re headed to Lollapalooza, you’ve committed to a weekend’s worth of braving quarter-mile bathroom lines and dodging sweaty adolescents who look like they were bussed through time from a high school in 1992. If you’re older than 21, you’re gonna need a drink. And something to eat too since you’re a responsible(ish) grownup (unlike some people). Whether you’re looking to pregame or postgame, Grant Park is situated near plenty of watering holes and places to grab a bite. We’ve chosen some of the best bars and restaurants in the vicinity of the park, so you can match the booze to your mood and escape the flower-crowned masses.

“I want as big a vessel for my alcohol as possible.”

The Berghoff
This revamped Loop institution complements its pricey German fare with some of the better happy hour deals in the area. House beer is served by the stein, and the express bar sandwich menu (Mon-Fri 11 AM-2 PM) includes hearty prefest options like roast beef, rahmschnitzel, and bratwurst. Might be the place if you don’t want to be tempted by the overpriced fare in Grant Park.
17 W. Adams, Fri 11 AM-9 PM, Sat 11:30 AM-9 PM, Closed Sun

“Let’s go to a place that’s probably too classy for us.”

The Gage
With such sophisticated menu items as bison tartare and green curry tofu, the Gage might not exactly fit the vibe of Lolla, but its tendency to draw crowds means festgoers could feel at home this weekend (to be fair, they also offer a $13 burger, called “The Regular Burger”—please). There’s a nice array of draft beers as well, with some classier cocktail choices to complement.
24 S. Michigan, Fri 11 AM-midnight, Sat 10 AM-midnight, Sun 10 AM-10 PM

“Guys, I have an idea: we after-party . . . the after-party.”

George’s Lounge
If your day-to-day Lolla routine involves too-loose tank tops, misplacing things you’ll only care about later, and dipping into something you refer to as “your stash,” this throwback cash-only dive bar is going to be your spot. It’s a no-frills establishment that just wants to give you booze. No nonsense.
646 S. Wabash, Fri 11 AM-4 AM, Sat 11 AM-5 AM, Sun 11 AM-4 AM

“What’s the best thing aside from, ya know, actually going to Lolla?”

Sometimes, FOMO can be pretty real. No one wants to be that person shut out of the festival while all of their friends—literally, every single one (even Rachel, and you don’t even like her that much)—enter the gates and have the “best weekend of the whole summer, man.” This bar, on the 27th floor of the Wit Hotel, is definitely crowded, but you’ll have a distant bird’s-eye view of all the fun you’re maybe secretly glad you’re not having.
201 N. State, Fri 2 PM-2 AM, Sat 2 PM-3 AM, Sun 2 PM-8 PM

“Hey, isn’t this the place with the SNL people or whatever?”

Billy Goat Tavern
An outpost of the famed skit-inspired grease joint sits just a 20-minute walk up Michigan Ave from the festival grounds. Despite being one of the more touristy options in the area, this might be the cheapest spot on our list, with their classic double-cheezborgers barely above five bucks. Wash down the beef with a beer or some headache-cure OJ, which they sell for 30 cents a glass.
60 E. Lake, Fri-Sat 7 AM-midnight, Sun 10 AM-midnight

“I just want to go someplace where we can feel clean for an hour.”

Seven Lions
It’s at the upper end of the price range, sure, but considering all your other money this weekend is going toward a glorified romp in a musical mud pit, the bump in cost might be worth the level of class you have here. The extensive bar menu includes an array of whiskeys, plenty of local draft beers, and signature cocktails. Going before the fest is probably prudent.
130 S. Michigan, Fri 11 AM-close, Sat-Sun 10 AM-close

“I’m young, entitled, and I demand choices.”

Chicago Athletic Club Hotel
Hey, that’s cool. We understand. Fortunately for your inflated ego, this establishment features five diverse choices for you to find respite from Lolla. Cindy’s is an upscale open-aired terrace, the Game Room is speakeasy-esque, the Milk Room is a whiskey bar, Shake Shack remains a capstone, and we were quite pleased with the quality of the Cherry Circle Room. But hey, don’t let us restrict your spirit—do whatever.
12 S. Michigan, times vary; see website