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, May 9 through May 11.
SAUCED Spring Night Market
SAUCED shoppers can enjoy bites from local eateries, brews, and music from DJ Johnny Walker while shopping from local vendors at this night market. The event will feature a variety of items, ranging from ceramics and screen prints to small-batch hot sauce and vintage home goods.
📍Location: Half Acre Beer Co., 2050 W. Balmoral Ave.
🗓️ Dates: May 8-9
Wicker Park’s Only Rooftop Pool Escape at Solana
Solana at The Robey Hotel invites everyone to enjoy a private beach club vibe with skyline views, street-style tacos, and frozen cocktails at Wicker Park’s only public rooftop pool.
📍 Location: The Robey Hotel, Wicker Park
🗓️ Dates: Opening party Saturday, May 10, 2:00–6:00 PM; pool open for the season from May 5
Illinois Craft Beer Week At Begyle Brewing
Head to the Begyle for the kickoff of Illinois Craft Beer Week! Enjoy the special “Keep The Pint,” Happy Hour deals, and delicious Neapolitan-style pizza from Limoni Belli. Illinois Craft Beer Week runs from May 9 to May 16.
📍 Location: 1800 W Cuyler Ave, Chicago, IL 60613
🗓️ Dates: May 9-16
Civic String Quartet At Indian Boundary Park
Enjoy a free concert in the park featuring members of the Civic Orchestra of Chicago. The performers include Jonah Kartman and Sean His on violin, Darren Carter on viola, and Sam Day on cello.
📍 Location: 2500 W Lunt Ave, Chicago, IL 60645
🗓️ Dates: May 10
Cafetón: Coffee & Latin Beats Party at Mima’s Taste of Cuba
Cafetón is bringing its high-energy Latin beats and coffee-fueled celebration to Mima’s Taste of Cuba this weekend. The event promises a lively morning with DJs, dancing, and Cuban flavors, all for free—just RSVP in advance! Expect a unique blend of music, culture, and caffeine that’s perfect for kicking off your weekend with a twist.
📍 Location: Mima’s Taste of Cuba, 2925 W Irving Park Rd, Chicago
🗓️ Dates: May 10th, 10 AM–2 PM
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. 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.
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.
Get Early Access To Tickets For The LIV Golf Event Coming To Chicago Later This Year
LIV Golf is returning to the Bolingbrook Golf Club August 8-10, but you can start preparing for the world-class event this weekend! First, the event: it’s a three-day festival-style tournament where 54 of the world’s top golfers compete in a team-based format. Kids get in free, and there are plenty of options for food, drinks, live music, and interactive activities. There’s something for everyone, and the waitlist for early access to tickets just went live. Click here to get your tickets before everyone else! Kids under 12 get in free with a ticketed adult.
📍 Location: Bolingbrook Golf Club – 2001 Rodeo Dr, Bolingbrook, IL 60490
🗓️Dates: August 8-10, 2025
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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