Nightlife & Entertainment in Chicago
Comedy and theater
From big name shows previewing before their Broadway runs to local theater groups and quirky offbeat sketches, Chicago’s long been known as a bastion for live theater and comedy.
The Second City
A spring board for some of the country’s best loved comedians – think Tina Fey, Bill Murray and Steve Carrell – The Second City’s the perfect spot to catch some side-splitting, hard-hitting sketches. Tucked in the heart of Chicago’s Old Town, it hosts nightly revues on love, life and politics, and some fast-paced improv, too.
1616 N Wells Street, Chicago IL 60614. Tel: +1 312 337 3992
The Second City website
Dive bars, tap rooms, old-timey speakeasies – Chicago’s awash with cool hangout spots where you can sup on a beer with the city’s locals. And if you’re dressed up for a glitzy night on the town, swanky cocktail bars and gleaming Champagne joints will have you feeling giddy on bubbles in no time.
The Signature Lounge
Whizz on up to the 96th floor of the towering Hancock Building to enjoy a cooling glass of your favorite tipple while watching the twinkly amber lights of the city streets below. If you’re in need of a snack after one too many cocktails, choose from a gourmet menu of appetizers.
875 N Michigan Avenue, Chicago IL 60611. Tel: +1 787 312 9596
The Signature Lounge website
With 2 venues to choose from – its grungy original in Lakeview and an industrial alternative in River North – Headquarters Beercade is quickly becoming a Chicago institution. Remember to put aside your craft beer or cocktail to test your skills against one of the bleeping old-school arcade games.
213 W Institute Place, Chicago IL 60610. Tel: +1 312 291 8735
Headquarters Beercade website
Jazz and blues venues
Let's face it, you can’t visit the Windy City without tapping your foot to some blues or jazz tunes in one of its Rat Pack-inspired music clubs.
Buddy Guy’s Legends
Home of blues icon Buddy Guy, this hub for impossibly good local and national musicians is a no-brainer night out hotspot. Small enough to feel cozy, this legendary club has a consistently impressive show calendar.
700 S Wabash Avenue, Chicago IL 60605. Tel: +1 312 427 1190
Buddy Guy’s Legends website
Check out the big name weekend acts at Chicago’s oldest jazz club – showcasing sax-playing piano-tapping cats since 1947. If you’re around in the week you’ll be treated to low-key performances from local names.
806 S Plymouth Court, Chicago IL 60605. Tel: +1 312 360 0234
Jazz Showcase website
It’s not just blues and jazz in Chicago. The city’s huge auditoriums and venues pull in chart-topping pop and rock stars, while small theatres, pubs, and bars are host to indie bands, up-and-coming musicians, and guitar-strumming locals.The Chicago Theatre
With its retro-cool neon signs flashing out from the heart of downtown, chandelier-swathed Chicago Theatre’s an iconic concert venue, home to big name musicals, comedy revues, and pop concerts.
175 N State Street, Chicago IL 60601. Tel: +1 312 462 6300
The Chicago Theatre website
Find your perfect holiday in Chicago
From 780 hotels.