We curate a Chicago weekend itinerary of the city’s best concerts, culture and cuisine, every week, just for you.
Friday
Taste of Chicago in Grant Park
The granddaddy of Chicago food festivals runs through Sunday evening. If you're willing to brave the crowds (and the sun), you can trade tickets for a taste of Chicago's street fare, including Rainbow Cones and Billy Goat Tavern cheezborgers. Check out our favorite new dishes at the fest.
Jimmy Buffet at Wrigley Field
Parrotheads take over Wrigleyville for a day as Hawaiian shirt-clad “Margaritaville” singer Buffet returns to headline the home of the Cubs.
Black Star at Petrillo Music Shell in Grant Park
Hip-hop heavyweights Yasiin Bey (formerly Mos Def) and Talib Kweli join forces as Black Star at this free Taste of Chicago concert.
Windy City Smokeout at 560 W Grand St
Country acts Brett Young and Midland headline the opening night of this twangy barbecue festival, which features pitmasters from across the U.S. and music from the likes of Brett Eldredge and Brothers Osborne throughout the weekend.
Square Roots Festival in Lincoln Square
Head to Lincoln Square to see Matthew Sweet perform on the first night of this eclectic three-day street fest, which also features alt-country pioneers the Jayhawks, Americana explorer Pokey LaFarge and Appalachian folk duo the Handsome Family.
Saturday
The Flaming Lips at Petrillo Music Shell in Grant Park
Oklahoma weirdos the Flaming Lips bring psychedelia, streamers and costumed dancers to a free Taste of Chicago show.
Volleywood at North Avenue Beach
Hit the sand, grab a drink and see sets from DJs Matoma and Thomas Jack at this sun-soaked beach party and volleyball tournament.
Southport Art Festival at Southport Ave and Addison St
The Southport Corridor hosts its annual two-day art festival, where attendees can find deals at local businesses and shop for items from a variety of makers and local vendors.
Michael Che at Vic Theatre
The Weekend Update co-host gets out from behind the desk and onto the stage for a pair of stand-up sets featuring a barrage of witty observations.
Sunday
Roscoe Village Burger Fest at Belmont and Damen Aves
Loosen your belt and prepare to taste grilled creations from local restaurants, such as Kuma's Corner and Bareburger, while enjoying live music and ample libations.
World Cup Final Viewing Party at Thalia Hall
Get up early to watch Croatia and France face off in the final game of the World Cup on Thalia Hall's gigantic screen. You can also test your soccer skills, enjoy music from a DJ and have a few morning cocktails.
Chinatown Summer Fair at 2200 S Wentworth Ave
Chinatown celebrates the arrival of summer at this annual event, featuring food, art, music and a traditional Lion Dance Procession.
George Clinton and Parliament Funkadelic at Petrillo Music Shell in Grant Park
Before the Godfather of Funk retires next year, catch his band closing out Taste of Chicago in the grooviest way possible. As usual, lawn seating is free.