Top Choice Theater in Lincoln Park & Old Town

Steppenwolf Theatre

Steppenwolf is Chicago’s top stage for quality, provocative theater productions. The Hollywood-heavy ensemble includes Gary Sinise, John Malkovich, Martha Plimpton, Gary Cole, Joan Allen and Tracy Letts. A money-sav…
Top Choice Blues in South Loop & Near South Side

Buddy Guy's Legends

Top local and national acts wail on the stage of local icon Buddy Guy. Tickets cost $20 Friday and Saturday, $10 on other evenings. The man himself usually plugs in his axe for a series of shows in January (tickets …
Top Choice Jazz in Andersonville & Uptown

Green Mill

The timeless Green Mill earned its notoriety as Al Capone's favorite speakeasy (the tunnels where he hid the booze are still underneath the bar). Sit in one of the curved velvet booths and feel his ghost urging you …
Top Choice Comedy in Lincoln Park & Old Town

Second City

Bill Murray, Stephen Colbert, Tina Fey and more honed their wit at this slick venue. Shows take place nightly. The Mainstage and ETC stage host sketch revues (with an improv scene thrown in); they're similar in pric…
Top Choice Live Music in Lake View & Wrigleyville


For more than three decades the Metro has been synonymous with loud rock. Sonic Youth and the Ramones in the '80s. Nirvana and Jane’s Addiction in the '90s. White Stripes and the Killers in the new millennium. Each …
Top Choice Live Music in Logan Square & Humboldt Park


Hometown indie bands, jazz combos and DJs rock this wee, arty bar most nights. There’s never a cover charge, but you’d be a shmuck if you didn’t order at least one of the swanky cocktails or craft beers to keep the …
Top Choice Live Music in Wicker Park, Bucktown & Ukrainian Village


Hidden behind a factory at the edge of Bucktown, this two-room lodge of indie rock and alt-country is well worth seeking out. The owners have nursed an outsider, underground vibe, and the place feels like your grand…
Top Choice Comedy in Lincoln Park & Old Town

iO Theater

One of Chicago's top-tier improv houses, iO is a bit edgier (and cheaper) than its competition, with four stages hosting bawdy shows nightly. Two bars and a beer garden add to the fun. The Improvised Shakespeare Com…
Top Choice Classical Music in The Loop

Grant Park Orchestra

It's a summertime must-do. The Grant Park Orchestra – composed of top-notch musicians from symphonies worldwide – puts on free classical concerts at Millennium Park's Pritzker Pavilion. Patrons bring lawn chairs, bl…
Live Music in Gold Coast

Zebra Lounge

The piano in this tiny, dark and mirrored room can get as scratchy as the voices of the crowd, which consists mainly of older folks who like to sing along. The ivory strokers here are veterans who know their stuff.