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.
1. Chicago Pride Kick-Off Urban Queer Art Show & Market
This market runs for five nights and features artwork and handmade goods by local queer artists. Explore unique creations and support the urban LGBTQ+ art scene.
Date: Wed, June 5 – Sun, June 9
Address: 4139 N Broadway, Chicago, IL 60613
2. Andersonville Midsommarfest
This Swedish tradition has become a summertime staple in Chicago. It features food, vendors, and five entertainment stages, including the Balmoral Pride stage, which showcases DJs, drag performances, and more.
Date: Fri, June 7 – Sun, June 9
Address: 5200 N Clark St, Chicago, IL 60640
3. Head to BUMP
The monthly party series is back, featuring “RuPaul’s Drag Race” S14 cast member Kornbread as the main attraction. The theme is “Sex on the Beach,” so organizers encourage attendees to wear their “hottest swimwear looks.”
Date: Saturday, June 8, 11 p.m.
Address: 2247 N Lincoln Ave, Chicago, IL 60614
4. Pride Pop Culture Trivia With Mash Potato
Head to Hald Acre Beer for a night of hard-hitting questions about queer LGBTQIA+ pop culture with the beloved Masha Potato!
Date: Sunday, June 9, 4-6 pm
Address: 2050 W Balmoral Ave, Chicago, IL 60625
5. Head to the largest waterpark in Illinois
Luckily for Chicagoans, Illinois’ largest waterpark, Raging Waves, will reopen for summer this weekend, celebrating its 17th year in business!
6. See the fireworks at Navy Pier
The arrival of summer in Chicago is synonymous with Navy Pier’s glittering summer program of events. In particular, the Navy Pier fireworks shows return every May to signal that it’s time to start looking up again.
This year, the first fireworks show will take place on Saturday, May 25th, at 10 p.m., followed by the first Wednesday show on May 29th at 9 p.m. Shows will then continue every Saturday and Wednesday in June, July, and August, with the final fireworks show at 10 p.m. on Saturday, August 31st.
7. Check out Castaways
After closing in June 2023 to undergo an extensive $3 million renovation, the popular 22,000-square-foot Castaways will reopen this coming weekend with a new look, name, menu, and vibe.
The revamped boat-shaped bar and restaurant will reopen as “Castaways Beach Club” on Memorial Day weekend. It will feature a new layout with additional dining decks, bar areas, and cabanas available for rent with bottle service.
8. Wicker Park Farmers Market
The Wicker Park Farmers Market is now open for its 24th summer season starting Sunday, May 5, in Wicker Park. The market is a local favorite, with more than 50 vendors offering a variety of fresh produce, including meat, cheese, dairy, vegetables, fruit, flowers, baked goods, coffee, fresh-pressed juice, and ready-to-eat meals. The market is held every Sunday, from 8 a.m. to 2 p.m., until October 27, and is open rain or shine.
9. Kayak in the Chicago River
Chicago’s iconic kayaking returns to the Riverwalk this weekend in Chicago! After shutting down for the winter season, Urban Kayaks has announced that it will open on Saturday, April 20th, kicking off the spring and summer kayaking seasons in just a few weeks!
10. Watch Merchandise Mart’s Art Projections
The world’s largest permanent digital art projection is illuminating Chicago’s riverwalk again. For its Spring 2024 Program, the MART will fire up all 34 digital projectors and once again breathe life into the 25-story-tall face of the Merchandise Mart.
11. Have elegant high tea at Bar Pendry
Be pampered for the day and have an elegant tea experience at a luxury boutique hotel. Chicago’s Bar Pendry will add a seasonal touch to its Sunday tea service offerings, perfect for welcoming in the warmer weather.
12. Don’t miss this thrilling card cheating experience
Learn the ins and outs of card cheating at this theatrical experience in Chicago! The Unfair Advantage takes you into deception with sleight-of-hand expert Harry Milas at Steppenwolf Theatre’s Merle Reskin Garage Space from March 26 – April 21, 2024! Get your tickets here!
13. Ride on Navy Pier’s FlyOver
Calling all adventure-seekers! If you were among the few people who missed this news on your timeline, we’re here to tell you that a new thrilling ride is now open at Navy Pier. The Chicago Flyover offers a brand-new adventure that will suspend riders above the city’s incredible skyline. Immerse yourself in Chicago surrounded by a massive 65-foot spherical screen and take flight as your motion seats soar.
The exciting 48,000-square-foot FlyOver experience dropped its first trailer at the start of the month is one of the best things to do in Chicago this weekend.
14. Check out MSI’s new James Bond exhibit
Chicago’s beloved Museum of Science and Industry has opened a temporary new James Bond exhibit adding to the wonderful array of exhibitions already taking place across the city.
The new exhibit, titled 007 Science: Inventing the World of James Bond showcases the science and technology behind the world’s longest-running movie franchise. Opened on Thursday, March 7th, it is now the first-ever official exhibition to focus on the world of history’s most famous fictional spy.
Read more about the Museum of Science and Industry’s James Bond exhibit.
15. 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!
16. Grab tickets to a Newport peek-easy burlesque show
Catch some of Chicago’s finest burlesque, belly dance, drag, and variety entertainers and screenings of incredible digital content played live in this hour-long show. Specialty cocktails, intimate tables, and a true speakeasy feel make this one of the best things to do in Chicago this weekend. Grab tickets to the show here!
17. 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.
18. 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.
19. Head to a Broadway Show
Everyone who thinks of NYC as the place to see Broadway shows should think again. Chicago is home to magnificent theaters and acclaimed Broadway shows that are constantly rotating. To simplify it, we’ve compiled a list of productions happening right now!
20. Get a little tipsy at Drunk Shakespeare
For one of the best things to do in Chicago this weekend, join The Drunk Shakespeare Society for an unforgettable evening of Shakespearean revelry, where cocktails meet the classics. Set within a speakeasy located behind The Chicago Theater, five fearless actors take on the classics after downing shots of various alcohols.
21. Visit “Titanic: The Exhibition”
One of the best things to do in Chicago this weekend is transport yourself onto the Titanic. You can walk across the promenade deck of the most famous ship to sail the seas. Titanic: The Exhibition dives 2 ½ miles below the Atlantic’s surface to uncover the liner’s captivating story like never before.
The exhibit follows the ship’s journey from its design in 1908 to its recovery in 1985. You’ll see hundreds of real artifacts from the Titanic, her sister ships, and films capturing the emotional tale. As you touch a take in stunning photography of the Titanic and step across the ocean floor strewn with relics, you’ll feel like you’re walking through history.
22. 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.
23. 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.