With the weekends affording many of us time to take a break from our work lives, we must fill them with memories. Whether exploring the parks, spending valuable time with friends and family, or enjoying an event somewhere in Chicago, weekends are designed to be enjoyed! Luckily, in such a sensational city like Chicago, options are abundant. To ensure you can make your weekend fun, we’ve rounded up some of the best things to do in Chicago this weekend, March 14 through March 16.
Check out this Bingo Loco party
Go for the bingo, stay for the party! The ultimate Bingo Loco party is coming to Chicago this weekend! Don’t miss epic lip-sync battles, dance-offs, CO2 cannon madness, hilarious comedian MCs, and BINGO! You could win epic gifts like an epic trip to Vegas or a cruise or random gifts like a giant inflatable flamingo, a microwave, a lawnmower, and much more! Grab final tickets here!
📍 Location: Morgan MFG
🗓️ Dates: February 28 – April 25, 2025
Head to Milk Bar’s in Chicago’s Fulton Market
Dessert lovers, rejoice! The viral New York-based sweets shop Milk Bar is opening its first Chicago location in Fulton Market on February 8. Founded by acclaimed pastry Chef Christina Tosi, Milk Bar has gained a cult following for its creative baked goods and unmistakable hot pink branding. Visitors can expect the full menu of cookies, cake truffles, and ice cream, along with special Chicago-inspired treats like a “Hotdog Bomb” bagel and a Portillo’s Chocolate Cake-inspired cookie.
📍 Location: 200 N. Green Street, Chicago
🗓️ Date: Opening February 8, 2025
Sip cocktails at a speakeasy in a secluded lounge
We love the allure of a cool, hidden gem. While there are many spots in Chicago, you should check out upstairs at Nisos this weekend in Chicago/ The Lounge is an alluring, hidden cocktail lounge (hint: look for the bookshelf) tucked away on the second floor of Nisos Prime. The 2,000-square-foot room offers a wondrous, carefree late-night speakeasy full of animation and melody Wednesdays—Saturdays while transporting guests to the nightlife of the Mediterranean.
Check out the Hamptons of the Midwest
Chicago actually has its own romantic and bucolic destination: Harbor Country, haphazardly labeled “The Hamptons of the Midwest.” Harbor Country is a region in Southwestern Michigan. It’s a favored weekend getaway destination for those looking to relish in a tranquil retreat with beaches, bed and breakfasts, and wineries.
Grab Bottomless Brunch
Chicago food is seriously on another level, and nothing makes that more apparent than the city’s endlessly delicious list of bottomless brunch options. This popular weekend activity typically involves breakfast delicacies, bottomless mimosas, and perhaps endless Bloody Marys if you feel extra spicy.
It’s one of the best things to do in Chicago this weekend, centered around festivity and fun. With this in mind, we’ve rounded up a few of the best spots to enjoy an exciting bottomless brunch in Chicago!
Escape the city to a charming town for a weekend getaway
The small town is a storybook setting with historic 1800s architecture that is dazzling as you stroll Main Street, coined “Helluva Half Mile,” which sprawls with more than 125 independently owned business shops. It will make you feel as if you have fallen straight into the scene of an Emily Henry novel.
Dine at one of the best new restaurants
Deciding where to dine on a Friday or Saturday night can be daunting. Whether you’re with a group of friends or having a date night, everyone is opinionated when selecting a restaurant. From arbitrary TikTok recommendations to Instagram reels, narrowing down the Chicago dining scene is easier said than done. That’s why we’ve done it for you with this unequivocal list of the best new restaurants in Chicago you need to try this weekend! Now, let’s hope there is a reservation open.
Discover Chicago’s Best Indoor Pickleball Courts
Chicago’s pickleball scene is thriving, even in the winter months. Indoor pickleball courts across the city offer enthusiasts the chance to play year-round. From Big City Pickle’s beginner-friendly sessions to the luxurious facilities at Social Pickleball Fun, there’s a court for every skill level. With options like Jackson Park Fieldhouse and Lakeshore Sport and Fitness, Chicagoans can enjoy this popular sport regardless of the weather.
📍 Location: Various locations across Chicago, IL
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