Searching for what to do this weekend in Chicago? Below are the top things to do in Chicago this weekend (September 22-24, 2023) including the best festivals and other weekend events.
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
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Chicago Weekend Festivals
Do you enjoy live music, food, drinking and people watching? There are several festivals taking place in Chicago this weekend:
Chicago Gourmet – September 21-24, 2023
Oktoberfest at St. Alphonsus – September 23-24, 2023
Hyde Park Jazz Festival – September 23-24, 2023
Chicago Live! Festival – September 23-24, 2023
Randolph Street Market – September 23-24, 2023
Best Weekend Events in Chicago
In addition to the festivals mentioned above, below are the best weekend events in Chicago:
Concert Under The Stars: Sinatra Under the Stars at AIRE – Sunday, September 24, 2023
10th Anniversary Beverly Art Walk – Saturday, September 23, 2023
Water Lantern Festival – Saturday, September 23, 2023
More Chicago Weekend Events
Other weekend events and activities taking place in Chicago this weekend include:
Chi Food Truck Fest – Friday, September 22, 2023 from 11:00 am to 3:00 pm
The Market by the River – Friday, September 22, 2023 from 3-7 pm
Maxwell Street Market – Sunday, September 24, 2023, 9am–3pm
Life Time Chicago Half Marathon & 5k – September 24, 2023
More Things to Do in Chicago This Weekend
In addition to the weekend festivals and events listed above, below are more of the best outdoor things to do in Chicago this weekend:
Take an Architecture River Cruise
Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is also a fun activity. 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 enjoy the cool breeze on the water.
If your time is short, you can do a combination river and lake cruise.
Have Fun at Navy Pier
Navy Pier is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), restaurants, shops and the Chicago Children’s Museum.
Navy Pier is the starting point for various sightseeing tours and cruises.
Hang Out on the Riverwalk
The Chicago Riverwalk is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars, shops and spots to sit and relax along the way.
Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map of attractions on the Riverwalk here.
Watch Digital Art at Art on the Mart
If you are on or near the Chicago Riverwalk in the evening, you might want to check out Art on theMART, the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. The programming changes every few months and you can see current projections here.
When: 30-minute program of projections are displayed twice nightly
Where: The Merchandise Mart, 222 W Merchandise Mart Plaza, Chicago, IL 60654. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
Cost: Free.
Take a Kayak Tour in the River
A fun way to explore the city is to go kayaking in the Chicago River. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.
Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Watch a Baseball Game
The Chicago Cubs are playing the Colorado Rockies at historic Wrigley Field all weekend. See the schedule and purchase tickets here.
Explore the Lakefront Trail
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. In the summer and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to see Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.
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 which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here.
Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour.
Visit a Farmers Market
Visit a farmer’s market to to buy healthy, local, farm-fresh foods from local farms. Some of the best farmers markets in Chicago this weekend include: Green City Market in Lincoln Park and the Logan Square Farmers Market.
You can see the list and schedule of all Chicago farmers markets here.
As you can see there are many things to do in Chicago this weekend. If you are looking for things to do during the week, here are the best things to do in Chicago this September.
