Chicago Event & Entertainment Guide
Chicago is a city that will fight you over a food opinion and then buy you a beer about it. Deep dish vs. tavern style isn't a preference here - it's a personality test.
Get Down
The live music scene runs deep. Subterranean in Wicker Park has that sweaty-upstairs-stage energy where you're three feet from the band. Kingston Mines in Lincoln Park does blues until 4 AM on weekends - two stages, no cover before 8, and the kind of guitar playing that makes you forget what day it is. Lollapalooza takes over Grant Park every August and turns the entire Loop into one big afterparty.
For comedy, it doesn't get more legit than The Second City. Tina Fey, Stephen Colbert, Bill Murray, Chris Farley, both Belushis - the list goes on and on! They all came through those stages. iO and The Annoyance are smaller and scrappier. Nate Bargatze plays the Chicago Theatre whenever he swings through, and that room is gorgeous.
Game Day
A Cubs game at Wrigley Field isn't just baseball - it's a full-day Wrigleyville experience. Pre-game at Murphy's Bleachers, sing "Go Cubs Go" after a W, and stumble down Clark Street. The Bears at Soldier Field with the lake behind you and the wind trying to kill you is football the way it was meant to be watched. And the White Sox - look, the South Side faithful are a different breed and Guaranteed Rate Field has underrated food.
Eat Up
Lou Malnati's (*cough*) for deep dish - get the buttercrust with sausage patty. Portillo's for a Chicago dog and an Italian beef dipped with hot giardiniera. Just make sure you don't put ketchup on your dog or the locals will give you dirty looks! Kuma's Corner in Avondale does a burger that weighs about a pound and is named after a metal band. For something fancier, Girl & The Goat on Randolph Street is worth the reservation hassle. Order the goat empanadas.
After Dark
The Riverwalk is gorgeous for a warm-weather drink. Boystown around Roscoe's goes off on weekends. If you want a quieter night, hit Myopic Books in Wicker Park (yes, a used bookstore, yes, it's cool) and then grab cocktails at The Violet Hour next door - no sign on the door, no phone policy, incredible drinks.
The United Center, the Chicago Theatre, Moulin Rouge at the Nederlander - this city stacks entertainment like it stacks Italian beef. Summer means rooftop bars and beach volleyball at North Avenue. Winter means hockey, comedy, and warming up with a cup from Intelligentsia. Grab what you need on Evil Tickets and layer up. You'll need it.
