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, September 20th to September 22nd.
1. Riotfest
Chicago’s largest rock music festival, Riot Fest, is back this weekend at North Lawndale’s Douglass Park, following months of uncertainty and location changes. This year’s lineup features big-name acts, including Fall Out Boy, St. Vincent, Slayer, and The Offspring.
2. Englewood Jazz Festival
The 25th Anniversary Englewood Jazz Festival will take place on September 19—21, 2024, at Hamilton Park and Cultural Center, 513 W 72nd St., Chicago. This year features Nicole Mitchell, Jeremiah Collier, Corey Wilkes, Junius Paul, Greg Ward Quartet, Jahari Stampley, The Young Masters, and an encore performance of Paul Robeson: Man of the People. The festival is FREE and will be held indoors on Sep 19-20 and outdoors on September 21, rain or shine. In case of bad weather, the event will move indoors.
3. World Music Festival
The World Music Festival Chicago is celebrating its 24th year and will feature performances in 11 indoor and outdoor venues across the city. The 10-day festival offers music enthusiasts the chance to explore diverse musical genres from countries such as Colombia, Italy, Pakistan, Sweden, and more. All performances are free, and seating is available on a first-come, first-served basis. Please note that some venues have limited capacity, so arriving early is best to secure a spot.
4. World Dumpling Fest
Celebrate the deliciousness of the dumplings at World Dumpling Fest. The event, located just off the Logan Square Blue Line Station, will feature cultural performances, live music, interactive crafts, drinks, and, of course, dumplings. This is a free event, and dumplings can be purchased using Tasting Tickets—$1 per ticket, $18 for 20 tickets, or $45 for 50 tickets.
When: September 21st
5. 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.
6. See ‘Harry Potter And The Cursed Child’
Potterheads rejoice! The world’s most famous wizard will be heading to a Chicago Broadway theater today!
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.
7. 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.
8. 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.
9. 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.
10. 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!
11. 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.
12. 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.
13. 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!
14. 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.
15. 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.
16. 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.
17. 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.
18. Check out a beach bar
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 beach 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.
19. 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!
20. Check out the Converse pop-up store
The brand’s newest storefront is right in the heart of the Magnificent Mile; the new door not only showcases Converse’s bestselling, full-price footwear and apparel but also features an elevated Converse By You customization experience, encouraging customers to show off their own creative self-expression through unique takes on the brand’s classic styles.
21. Go rooftop glamping
Chicago’s award-winning Gwen Hotel is offering the city’s first and only urban glamping experience on the private terrace of its stunning Gwen Lux Suite. Perched up on the 16th floor of the landmark McGraw-Hill building, guests can enjoy over 1,000 square feet of private terrace and sensational sweeping views over Michigan Avenue all to themselves.