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, October 25th to October 27th.
1. Attend Joffrey Ballet’s Atonement
The Joffrey Ballet is back! The first show of the 2024-25 season will open the highly anticipated North American premiere of Cathy Marston’s interpretation of Ian McEwan’s 2001 novel-turned-Academy Award®-winning film Atonement. The full-length narrative ballet follows Briony Tallis, who is portrayed as a celebrated choreographer, as she grapples with the haunting echoes of her past through a breathtaking dance of redemption.
📍 Location: Lyric Opera House
🗓️ Dates: October 17-27
🎟️ Grab tickets here
2. Chicago International Film Festival Returns for Its 60th Edition
The Chicago International Film Festival is back for its 60th edition, running from October 16-27. This year’s event showcases an impressive lineup of 122 feature films and 71 shorts from over 60 countries. The festival spans multiple theaters across the city, including AMC New City 14, Gene Siskel Film Center, and Music Box Theater. Notably, five locally produced feature films will compete for the coveted Chicago Award, highlighting the city’s vibrant filmmaking scene.
📍 Location: Various theaters across Chicago
🗓️ Dates: October 16-27, 2024
3. Spooktacular Hotel Transylvania Brunch at Wonderverse
Experience a ghoulishly delightful brunch with your favorite Hotel Transylvania characters at Wonderverse’s Restaurant this October. Indulge in spooky-themed dishes like sausage fingers and “scream”bled eggs while interacting with Dracula, Mavis, and the gang. Don’t miss the waffle station featuring Crunchy Boo Berry Waffles and Fright Toast Sticks with various toppings.
📍 Location: Wonderverse’s Restaurant in Oak Brook
🗓️ Dates: October 26-27, 2024
4. Jack’s Pumpkin Patch
One of the best of these can be found on Goose Island, where a roster of exciting seasonal popups offer something new with every changing season, and now the popular fall experience ‘Jack’s Pumpkin Pop-Up’ has returned in Chicago. Spanning more than 2 acres of land down in Goose Island, guests will once again find Chicago’s largest corn maze, carnival games, photo opportunities, axe throwing, various bars, food trucks, and over ten thousand pumpkins all within the over-the-top outdoor pop-up.
5. See ‘Harry Potter And The Cursed Child’
The Tony Award-winning play Harry Potter and the Cursed Child will embark on its first-ever North American tour, debuting in Chicago from September to February 2025. The play debuted at London’s Palace Theatre in 2016 and on Broadway in April 2018.
6. Shop at a 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.
7. 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!
8. 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.
9. 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.
10. 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!
11. 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.
12. 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.
13. 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.
14. 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.
15. 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!
16. 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.
17. Check out MSI’s 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.