Chicago entertainment

Top Choice Jazz in Andersonville & Uptown

Green Mill

The timeless – and notorious – Green Mill was Al Capone's favorite speakeasy (a trap door behind the bar accessed tunnels for running booze and escaping the feds). Sit in one of the curved booths and feel his ghost …
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 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…
Top Choice Theater in Andersonville & Uptown

Neo-Futurist Theater

The Neo-Futurists are best known for their show The Infinite Wrench, in which the hyper troupe makes a manic attempt to perform 30 original plays in 60 minutes. Admission costs $10 to $15 – you pay $9 plus the roll …
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 with nightly shows. The Mainstage and ETC stage host sketch revues (with an improv scene thrown in); they're similar in price and q…
Top Choice Live Music in Lincoln Square & Ravenswood

Old Town School of Folk Music

You can hear the call of the banjos from the street outside this venerable institution, where major national and international acts such as Richard Thompson and Joan Baez play when they come to town. Old Town also h…
Top Choice Live Music in Wicker Park, Bucktown & Ukrainian Village

Hideout

Hidden behind a factory past 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 gra…
Top Choice Blues in The Loop

Buddy Guy's Legends

Top local and national acts wail on the stage of local icon Buddy Guy. The man himself usually plays a series of shows in January; tickets go on sale in October. Free, all-ages acoustic shows are staged at lunch and…
Top Choice Live Music in Logan Square & Humboldt Park

Whistler

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 schmuck if you didn’t order at least one of the swanky cocktails or craft beers to keep the…
Top Choice Live Music in Lake View & Wrigleyville

Constellation

The producer of Pitchfork Music Festival opened this intimate club, which actually breaks down into two small venues inside. The city's hepcats come out of the woodwork for the progressive jazz and improvisational m…