Searching for what to do this weekend in Chicago? Below are the top things to do in Chicago this weekend (September 27-29, 2024). (If you are planning ahead, you can also find the best things to do next weekend here.)
I suggest bookmarking this blog post as it is updated regularly with new events and activities.
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.
Best Weekend Events in Chicago
Below are the best weekend events in Chicago:
World Music Festival Chicago – September 20-29, 2024
Chicago Gourmet – September 21-29, 2024
Brick Convention: LEGO® Fan Event – September 28-29, 2024
Oktoberfest Chicago at St. Alphonsus – September 27-29, 2024
Chicago Horror Film Festival at the Logan Theatre – September 27-29, 2024
Midnight Circus in the Parks at Welles Park – September 27-29, 2024
Hyde Park Jazz Festival – September 28-29, 2024
Randolph Street Market Festival – September 28-29, 2024
St. Helen Carnival (Ukrainian Village) – September 27-29, 2024
ECOS: A Chicago Latine Poetry Festival – September 26-28, 2024
Reeling Film Festival – Through September 29, 2024
11th Annual Beverly Art Walk – Saturday, September 28, 2024, 12pm – 5pm
St. Pauls’ Oktoberfest – Saturday, September 28, 2024, 1–8pm
The Massacre Horror Movie Marathon at the Davis Theater – Saturday, September 28, 2024
Candlelight Concert: A Tribute to Coldplay on Strings – Saturday, September 28, 2024
Sinatra Under the Stars – Sunday, September 29, 2024
More Weekend Events in Chicago
Below are more events taking place this weekend in Chicago:
Chi Food Truck Fest – Friday, September 27, 2024 from 11:00 am to 3:00 pm
Navy Pier Open Air: Vintage Culture (Ages 18+ Only) – Friday, September 27, 2024, 4pm
Island Party Hut Fall Fest on the Riverwalk – Saturday, September 28, 2024
Live on the Lake (at Navy Pier) – Saturday, September 28, 2024, 2:00 – 11:10 pm | FREE
Sky Blue Music and Culture Fest (Southside YMCA Field) – Sunday, September 29, 2024, 11am – 6pm | FREE
World Music Festival Chicago Global Peach Party (at Navy Pier Beer Garden) – Sunday, September 29, 2024, 2-8 pm | FREE
More Things to Do in Chicago This Weekend
In addition to the weekend events listed above, below are more of the best things to do in Chicago this weekend:
Take a Ghost Tour
Explore Chicago while learning about its haunted past and visiting the sites of some of the most gruesome disasters and murders in Chicago’s history.
If you enjoy guided tours, this haunted segway tour and this Halloween bike tour are fun fall themed tours.
This ghosts and gangsters tour is available year round and also covers Chicago’s history of organized crime.
Visit Lincoln Park Zoo During Fall Fest
Visit Lincoln Park Zoo during its annual Fall Fest. This family-friendly celebration will offer free fun fall activities including a pumpkin patch, professional pumpkin carvers, free musical entertainment, story times and more. Every weekend will offer something new.
When: Fridays-Sundays, September 27–October 27, 2024
Hours: 10 a.m.-5 p.m.
Address: 2400 N. Cannon Drive
Cost: Admission to the zoo is FREE but some fall fest attractions are paid.
Take an Architecture River Cruise
Chicago has amazing architecture and the best way to enjoy it is joining an architecture river cruise.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is a fun activity whether in the day, around sunset and in the evening. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views and a refreshing cool lake breeze. If your time is short, you can do a combination river and lake cruise. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.
Look for Street Art
Chicago is full of street art and there are always new murals popping up. One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts located at 33 E. Ida B. Wells Drive. It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other tourist attractions.
Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave. You can see this mural and other street art on this street art tour.
Check Out the New Flyover Chicago at Navy Pier
Flyover Chicago, an immersive flyover experience, is Chicago’s newest attraction.
Other fun attractions at Navy Pier include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line) and other rides and games.
Navy Pier is also home to the Chicago Children’s Museum which is perfect for toddlers and younger kids.
Titanic: The Exhibition
Titanic: The Exhibition is ending its limited time run in the Chicago area in a few weeks. This interactive experience allows you to step inside recreations of the Titanic’s interior. Immerse yourself in the stories of its passengers, see hundreds of artifacts, and discover the tale of the design, creation, launch, maiden voyage, and tragedy of the historic ship.
Where: 4963 Old Orchard Shopping Center, Skokie, IL 60077 (about 17 miles from downtown Chicago)
Cost: Price varies. Click here for full prices and to purchase tickets in advance.
Visit a Pumpkin Patch
Looking for a fun fall themed activity? There are many pumpkin patches you can visit in Chicago and the suburbs.
Pumpkin patches usually open to the public sometime in September and stay open until the end of October. Here is a list of the best pumpkin patches in and near Chicago.
Get Lost in a Corn Maze
There are many corn mazes in the Chicago area – from large intricate mazes perfect for adults and older children to small kid-friendly corn mazes. Most mazes open sometime in September until the end of October.
Richardson Adventure Farm located in Spring Grove, Illinois (about an hour north of the city) claims to be world’s largest most intricate corn maze. Here are more corn mazes near Chicago to visit this fall.
As you can see there are many things to do in Chicago this weekend. If you are looking for more things to do in the Chicago area, you can find the best things to do in the suburbs here. If you are looking for things to do during the week, you can find more things to do in Chicago in September here.