Chicago knows how to throw a weekend. The skyline glitters, the neighborhoods hum with activity, and the options are endless. Whether the vibe calls for laughter, music, great eats, or something completely unexpected, this city knows how to deliver. Here are some of the best fun things to do in Chicago this weekend that can turn an ordinary couple of days into a highlight reel.

Chicago Events That Steal the Spotlight

There’s always something new popping up on the calendar. From art fairs in Millennium Park to food truck gatherings on the lakefront, Chicago events keep the city buzzing. This weekend, check out Randolph Street Market, a treasure trove of vintage finds and artisan goods. Over in Grant Park, there’s often a festival or pop-up that pairs perfectly with a stroll through the lakefront paths.

Rock Out With Live Music

The city has a rhythm all its own, and it comes alive every weekend with live music. Catch a show at Metro Chicago, a legendary venue where everyone from Smashing Pumpkins to Chance the Rapper has graced the stage. For jazz lovers, The Green Mill is a must, complete with Prohibition-era vibes. Or, if an outdoor concert calls your name, Navy Pier’s Live on the Lake! series brings the tunes to the water’s edge.

Laugh It Off at Comedy Shows

Chicago is the birthplace of improv comedy, and the tradition is alive and well. Comedy shows at The Second City guarantee big laughs, and many performers here go on to become household names. For edgier stand-up, Zanies Comedy Club is a Chicago institution, serving up cocktails and punchlines in equal measure. There’s no better way to wrap up a weekend night than with sore cheeks from laughing too hard.

Taste the City at Food Festivals

Few cities celebrate food quite like Chicago. This weekend, wander through Chicago Gourmet or a neighborhood street fest, where the smells of deep-dish pizza, hot dogs, and international bites mingle in the air. Smaller local food festivals pop up all the time, from taco tastings in Pilsen to BBQ block parties in Wrigleyville. It’s the ultimate way to savor the weekend.

Step Into the Action With a Murder Mystery

For something completely unique, swap out the usual bar crawl for a night of intrigue. Hosting a murder mystery party with The Murder Mystery Company turns friends into suspects and detectives in a laugh-out-loud whodunnit. Or, for a more effortless option, grab tickets to a Chicago dinner theater show where a three-course meal meets an interactive mystery. It’s part game night, part live theater, and completely unforgettable.

The Grand Finale

Every weekend in Chicago holds something new—whether it’s shopping local markets, catching a band, laughing through improv, feasting at a festival, or cracking clues at a murder mystery dinner. The only challenge is choosing what to do first.For a truly one-of-a-kind night, contact The Murder Mystery Company to host your own private event or grab seats at a public show. Call 888-643-2583 or fill out the contact form on their website to book an evening packed with food, fun, and mystery.