BEST Things to Do in Chicago in the Fall 2023 (From a Local!)

The best things to do in Chicago in the fall 2023 with family, friends or romantic date ideas. From pumpkin patches and apple picking to fall foliage and fun activities and events, there is something for both adults and families with kids to do in late September, October and November in the city and suburbs.

I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.

Chicago in the Fall

Fall is my favorite season and one of the best times to visit Chicago. It has the best weather (not too hot or too cold) which makes it a perfect time to be outdoors.

There are many fun activities and events that take place in Chicago in the fall. September brings the start of unique fall activities like apple picking, visiting pumpkin patches and corn mazes. October brings beautiful fall colors and fun Halloween themed activities, while November brings the start of Christmas holiday events and activities and Thanksgiving.

Best Chicago Fall Activities in 2023

top Chicago fall activities include fall foliage

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Whether you live in the Chicagoland area or are planning a visit, here are the best things to do in and around Chicago in the fall including the best Chicago fall 2023 events.

Take an Architecture Cruise

Taking an architecture river cruise is a must when visiting Chicago. While you can go on an architecture cruise most of the year (except during winter), they tend to be less crowded and the weather tends to be more pleasant in the fall.

Take a Lake Cruise

skyline from lake cruise in Chicago in the summer
Early fall is your last chance for a lake cruise before it gets too cold and lake cruises stop running (usually end of October). While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. Just a warning it is much colder on water than on land especially in the evening.

If your time is short, consider a combination river and lake cruise.

Lake cruises depart from Navy Pier or the Michigan Avenue bridge.

Enjoy the Views from 360 CHICAGO Observation Deck

360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan. October and November are great months to visit as you can see fall colors from above.

(Click here to buy a skip the line ticket).

Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611

Steve McCurry: ICONS: An Extraordinary Photography Exhibition

The Steve McCurry. ICONS: An Extraordinary Photography Exhibition is in Chicago only for a limited time after touring Sydney, Lisbon, Madrid and Mexico City. ICONS is an international photography exhibition showcasing the work of Steve McCurry, one of the greatest travel photographers. Discover over 80 large-format photographs, such as the iconic “Afghan Girl,” who captivated the world on the cover of 1985’s National Geographic magazine. Access audio descriptions from 42 selected photographs to hear the story behind the photo, in Steve McCurry’s own words.

Where: Loyola University Museum of Art (LUMA), 820 North Michigan Avenue, Chicago, IL 60611

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

Disney100: The Exhibition

The Disney100: The Exhibition is coming to Chicago for a few weeks this fall. The Walt Disney Archives opens its vault of historical and special treasures, works of art, artifacts, costumes, and memorabilia with the launch of Disney100: The Exhibition. This exhibition celebrates the magic of Disney, which is capturing the hearts of audiences of all ages around the globe. Wonder at more than 250 artifacts and props, see costumes from some of your favorite Disney classics, and explore enchanting galleries that bring the magic of Disney to life. Featuring the latest members of the Disney family (Pixar, Star Wars, and MARVEL) along with renowned classics like Snow White and the Seven Dwarfs (1937) and recent releases such as Encanto.

When: Opens November 18, 2023

Where: Exhibition Hub Art Center Chicago, 2367 W Logan Blvd, Chicago, IL 60647

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

Look for Street Art

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

Fall is a great time to walk around Chicago looking for street art while also enjoying the beautiful full colors.

One of the most well known Chicago murals is “Moose Bubblegum Bubble” by Jacob Watts which located at 33 E. Congress (South Wall).  This famous mural is part of the Wabash Arts Corridor and 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.

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 through October 29, 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.

Attend a Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this fall include:

Candlelight: A Tribute to Taylor Swift
Candlelight: A Tribute to Adele
Candlelight: 1990s Unplugged: A Tribute to Nirvana and More
Candlelight: The Best of Hans Zimmer at Music Box Theatre

You can find the full list of candlelight concerts in Chicago here.

Have Fun at Navy Pier

Navy Pier is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include restaurants, shops, the Chicago Children’s Museum, rides and games and a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line).

On select Saturdays afternoons this fall visitors can enjoy free dynamic performances celebrating local artists, musicians and cultural organizations showcasing their talents.

Navy Pier is also the starting point for many boat rides and lake cruises.

Take Instagram Photos at Jack’s Pumpkin Patch Pop-Up

Jack’s Pumpkin Patch Pop-Up is an outdoor fall experience located on over 2 acres in Goose Island. You will find the largest corn maze in downtown Chicago, hidden boozy bar, axe throwing, carnival games, music, fortune telling, three full-service bars and several picture back drops to take instagrammable fall photos. Pre-purchased access is required.

When: September 21-November 5, 2023

Where: 1465 N Elston Ave, Chicago, IL 60642

Cost: Prices vary by date.

Visit a Pumpkin Patch

pumpkin patch by Chicago

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.

Go Apple Picking

apple picking orchards near Chicago

You might not associate apple picking with a big city like Chicago, but there are many apple orchards located nearby. The closest apple orchards are located in the Chicago suburbs about an hour or less from downtown.

Some apple orchards are small and only offer apple picking for an affordable price while other farms offer fresh apple cider donuts and kid friendly attractions and activities like pumpkin patches, corn mazes, kid farms, animals, playgrounds and more.

Apple picking season starts mid to late August and lasts until mid to end of October but different types of apples are available for picking throughout the season.  Here is a list of apple orchards near Chicago for apple picking with locations, dates, hours, prices and all the information you need to plan your visit.

Enjoy Fall Foliage

There are many places in and near Chicago to admire the beautiful autumn leaves. The peak time for the best fall foliage in Chicago is usually mid October. For exact dates, this weekly fall color report keeps track of fall foliage times across Illinois and this fall foliage map by weather.com shows the progress of fall foliage in all of the United States.

You can see fall colors at some of Chicago’s most popular attractions including Cloud Gate (aka “The Bean”) in Millennium Park, Lurie Garden, Chicago Riverwalk and Lincoln Park.

If you are willing to leave the city, you can find even more spectacular fall foliage in the suburbs of Chicago. Some of the best spots to see fall colors in the suburbs include:

Morton Arboretum (in Lisle about 26 miles west of downtown) is home to more than 4,000 different types of trees among 1,700 acres. They publish a weekly fall color report every Friday on their website. The arboretum hosts fall events and activities including the Fall Color 5K Run and Walk (October 7, 2023), Annual Glass Pumpkin Patch (October 13-15, 2023), Cider and Ale Festival (October 21, 2023) and the Scarecrow Trail.

• The Chicago Botanic Garden (in suburban Glencoe about 24 miles north of downtown) is one of the world’s great living museums and conservation science centers with 27 gardens and four natural areas, situated on 385 acres on and around nine islands, with six miles of lake shoreline. Every October, they host the Night of 1,000 Pumpkins (October 11 – 15 & 18 – 22, 2023) which is very popular and sells out quickly! Their website has a recommended fall color-tree walk for the best viewing.

Here are more places to see fall colors in and around Chicago.

Visit Local Farmers Markets

You can find many farmers markets around Chicago until the end of October. These markets are a great place to buy healthy farm-fresh foods from local farms.

Two of the best farmers markets in Chicago include the 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.

Best Chicago Fall Events

Open House Chicago

The Chicago Architecture Center hosts Open House Chicago – a free event which gives you behind-the-scenes access into hundreds of buildings across Chicago every year in October. They will have virtual events all month but in-person site visits will take place on October 14-15, 2023.

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 Fall 2023 Events

In addition to the activities mentioned above, other Chicago fall themed events in 2023 include: Chicago Gourmet (September 21-24, 2023), Oktoberfest St. Alphonsus (September 22-24, 2023), Lakeview East Oktoberfest (September 29- October 1, 2023), St. Benedict’s OktoberFest (September 29- October 1, 2023), Lincoln Park Wine Fest (October 6-8, 2023), Chicago Marathon (October 8, 2023), 57th Chicago International Film Festival (October 11-22, 2023), Arts in the Dark Halloween Parade (October 21, 2023), Sauced – Fall Night Market (November 3-4, 2023) and Bingo Loco: The Ultimate Bingo Rave (November 22, 2023).

These are some of the best things to do in Chicago during the fall.

Visiting Chicago for the first time? Check out my Chicago travel guides:

Best Things to Do in Chicago in the Fall



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