BEST Things to Do in Chicago Next Weekend (September 29-October 1, 2023)

Searching for what to do next weekend in Chicago? Below are the top things to do in Chicago next weekend (September 29 – October 1, 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.

view from Photographers Point North Avenue beach in Chicago

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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 next weekend:

Lincoln Square Ravenswood Apple Fest

Usher in the fall with the Lincoln Square Ravenswood Chamber of Commerce’s Annual Apple Fest (September 30 -October 1, 2023). Apple Fest is a long standing tradition in Lincoln Square, bringing the neighborhood together to celebrate the beginning of autumn. Enjoy on ciders and apple inspired dishes and stock up on your fall essentials from local vendors while listening to local musicians.

More Chicago Weekend Festivals

Other festivals taking place in Chicago next weekend include:

Lakeview East Oktoberfest – September 29- October 1, 2023

St. Benedict’s OktoberFest – September 29- October 1, 2023

Best Weekend Events in Chicago

In addition to the festivals mentioned above, below are the best weekend events in Chicago:

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: Friday, September 29–Sunday, October 1, 2023

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.

More Chicago Weekend Events

Other weekend events and activities taking place in Chicago next weekend include:

Chi Food Truck Fest – Friday, September 29, 2023 from 11:00 am to 3:00 pm

The Market by the River – Friday, September 29, 2023 from 3-7 pm

Maxwell Street Market – Sunday, October 1, 2023, 9am–3pm

More Things to Do in Chicago Next Weekend

In addition to the weekend festivals and events listed above, below are more of the best outdoor things to do in Chicago next weekend:

Take an Architecture River Cruise

weekend in chicago bucket list

Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.

Take a Lake Cruise

skyline from lake cruise in Chicago in the summer
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

rides at Navy Pier Chicago

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

best things to do chicago travel blog

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.

July is one of the best times of the year to visit Chicago

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.

Explore the Lakefront Trail

Chicago lakefront

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

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

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 next 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 next weekend. If you are looking for things to do during the week, here are the best things to do in Chicago this fall.


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