Ready for a music-filled weekend in Chicago? While it’s impossible to fit all of Chicago’s legendary venues into just a few days, this jam-packed itinerary will give you a good primer on the city’s unforgettable music scene.
We’ll start with one of the city’s best neighborhoods for indie bands, then go for a spin around Chicago’s classic blues and jazz clubs — with a few gospel songs and dance parties in between.
Friday night: Find your indie spirit — and a little Chicago history
Spend your first night bar hopping in Wicker Park, one of Chicago’s hippest neighborhoods and a local music haven on the city’s northwest side.
Catch the Blue Line ‘L’ train to the Damen stop, and you’ll step out into the heart of Wicker Park. Just a few steps away, you’ll find Subterranean, a two-floor venue where locals hang out to see everything from live musicians to DJs to burlesque. A couple doors down, Chop Shop is a hybrid restaurant, butcher shop, and concert venue all housed in a 100-year-old former auto body shop. Come for the cool industrial vibes and eclectic musical line-up.
Before calling it a night, head north to Uptown for a dose of Chicago jazz history at the Green Mill. First opened in 1907, the Green Mill was a speakeasy during Prohibition and a favorite hangout of Al Capone. Expect the same sultry vibes from its speakeasy days, plus great live jazz well into the early morning hours.
Saturday: Sing the blues — and a few show tunes
After a late-night out, take some time to sleep in. When lunchtime rolls around, start your day off right with a blues legend — the one and only Buddy Guy. Grab some Louisiana-inspired grub at Buddy Guy’s Legends in the South Loop and enjoy a free acoustic session while you eat. Keep an eye on the bar — it’s where Buddy likes to hang out when he’s in town. If you’re around in January, you might even see him take the stage.
Next, hop in a cab and head to bustling River North, where you’ll find The Bassment. This underground speakeasy is hidden behind a secret door in The Hampton Social. Grab a cocktail, find a spot on the velvet couches, and enjoy live music with an emphasis on the blues.
In the mood to dance? Just walk a couple blocks north to SpyBar. Named one of the best dance clubs in America by Rolling Stone, this high-octane nightclub is all about house music, the electronic dance genre that was born in Chicago. Top DJs spin regularly, keeping the dance floor going till the early hours of the morning.
Heading east toward Lake Michigan, your next stop is casual, late-night hangout Blue Chicago, where you’ll hear some of the city’s finest live blues all evening long — including a little of Chicago’s distinct electrified blues.
End the night on a high note at The Redhead Piano Bar, where modern-day musicians pay homage to old-school crooners and lounge singers.
Sunday: Gospel brunch and all that jazz
Don’t make plans to leave early on Sunday. There’s still way too much to see (and hear).
Start your day at the World Famous Gospel Brunch at the House of Blues in River North that takes place every Sunday at 10 a.m. and 12:30 p.m. You can feast on an all-you-can-eat buffet while live traditional and contemporary gospel lifts your spirits.
After, catch a ride to iconic Navy Pier, where the Miller Lite Beer Garden hosts free live music on Saturdays and Sundays starting at 2 p.m. You’ll hear everything from reggae to R&B, with views of Lake Michigan as your backdrop.
End your weekend at Winter’s Jazz Club, just a 15-minute walk west of Navy Pier. This relaxed lounge is known for showcasing straight-ahead jazz, but you can find anything from gypsy jazz and swing to big band and Dixieland — not to mention Chicago-style jazz. This warm and welcoming spot is the perfect place to wind down your ultimate music weekend in Chicago.
Bonus! Plan your weekend around Chicago’s music festivals
Attention music lovers: If you’re wondering when’s the best time to visit Chicago, you might want to consider summer. That’s when weekends start to fill up with our famous music festivals, from free outdoor shows to intimate neighborhood fests to one of the biggest music festivals in the country.
Festival season opens with the Gospel Music Festival and Chicago Blues Festival. The best part? All the shows are free and held in Millennium Park, where you’ll get spectacular views of the surrounding city.
Looking for more free shows? From June through September, you can hit up the Grant Park Music Festival at Millennium Park for free classical music performances from the acclaimed Grant Park Orchestra. And don’t miss the world-renowned Chicago Jazz Festival in August and the World Music Festival in September.
Other headlining acts: In July, Pitchfork features the latest beats from alternative and indie bands, and Windy City Smokeout brings the beer, barbecue, and country stars. And in August, Lollapalooza takes over Grant Park for four days of blockbuster shows from some of music’s biggest acts.
Check out more Chicago music festivals here.
