BEST Things to Do in Chicago in October, 2021 (From a Local!)

Wandering what to do in Chicago this October? Here are the best things to do in Chicago in October (from a local).

October is a great month to visit Chicago. Temperatures are typically pleasant but popular attractions are less crowded than they are in the summer.  October also brings beautiful fall foliage as well as new fall and Halloween themed activities like visiting pumpkin patches and corn mazes.

For out of town visitors, please note that the weather in Chicago in October is very unpredictable and temperatures can vary greatly. Be prepared for fall, winter, or summer like temperatures (sometimes all in one day!) as well as rain.  Make sure to pack a travel umbrella, layers and check the weather right before your visit to know what to expect.

I suggest bookmarking this blog post as I plan to update it regularly with current information and any new activities and events.

Things to Do in Chicago in October

fall foliage is one of the best things to do in Chicago in October

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.

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 when the water is frozen in the winter), they tend to be less crowded and the weather tends to be more pleasant in October. If the temperature is still warm you might enjoy a combination river and lake cruise.


Open House Chicago

Every October, the Chicago Architecture Center hosts Open House Chicago, a free, two-day public festival that offers behind-the-scenes access to architecturally, historically and culturally significant sites across the city.

When: October 16-17, 2021

Cost: Free

Look for Street Art

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

October is a great month to walk around Chicago looking for street art while also enjoying fall 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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

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 is a great time to visit as you can see fall colors from above.

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


Visit Lincoln Park Zoo During Fall Fest

The fall season is one of the most beautiful times to visit Lincoln Park Zoo. During select days in October, enjoy fall activities during Lincoln Park Zoo’s annual Fall Fest. During this free, family-friendly celebration, enjoy a pumpkin walk, live pumpkin carvers, a festive pop-up bar, animal chats, musical entertainment and more!

Where: 2400 N. Cannon Drive

When: The zoo is open every day from 10 a.m.–5 p.m. Fall Fest is on Fridays–Sundays from October 8–October 31 and Monday October 11. Select Fall Fest attractions will remain open during the week.

Cost: FREE. There are also paid experiences including AT&T Endangered Species carousel rides, Lionel Train Adventure rides, pumpkin walk, pumpkin patch, caricatures & face painting, caramel apple & S’mores station and a festive pop-up bar.

Enjoy the Pier Pumpkin Lights at Navy Pier

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

During the entire month of October, Navy Pier will transform into an insta-worthy fall spectacle with nearly 1,000 pumpkins. There will be a variety of pumpkin pop-up installations and other Halloween festivities throughout the month as well as pier-wide deals.

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


Experience the Marvel: Universe of Super Heroes Exhibit at Museum of Science and Industry

The Marvel: Universe of Super Heroes exhibit at the Museum of Science and Industry ends October 24. Marvel: Universe of Super Heroes celebrates Marvel history with more than 300 artifacts including original comic book pages, sculptures, interactive displays and costumes and props from Marvel’s blockbuster films. Guests can examine the origins of iconic characters such as Spider-Man, Black Panther, Hulk, and Captain Marvel and see how they have evolved alongside society over the past 80 years, making these characters a pop culture mainstay.

When: Through October 24, 2021

Where: 5700 S Lake Shore Drive, Chicago, IL 60637

Hours: Wednesday through Sunday from 9:30 a.m. to 5:30 p.m. Closed Mondays and Tuesdays.

Cost: Not included in Museum Entry. Requires an additional, timed-entry ticket: Adults $18, Children (3-11) $14, Members $9.

Visit the Neon and Light Museum

The new Museum of Neon and Light pop-up opened in September for limited eight-week run. Stand in, under and around 70 professional neon and light-based sculptures in a dazzling and dramatic immersive exhibition. The Neon and Light Museum is an expansion of the successful On Neon show presented here in 2020 by the Ken Saunders Gallery, which, since 1995, has exhibited important and innovative artists working with glass in the world.

When: Ends October 31, 2021.

Hours: Thursday-Friday: 4pm-10pm, Saturday: 11am–10pm, Sunday: 11am–6pm

Where: 325 West Huron, Chicago

Cost:  $40 per person. Online reservations are required.

See the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris (one of my favorite travel shows on Netflix), the Immersive Van Gogh Exhibit, is a massive indoor digital presentation of Vincent Van Gogh’s artwork. Tickets must be purchased online in advance and they are selling quickly! There are also yoga sessions which include a 35 minute Yoga class + 45 minutes thereafter to enjoy the exhibit. The Chicago show is ending in November, 2021 so there is not much time left to see it.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago, IL

Cost:  Tickets start at $39.99 plus fees for off peak times. See https://www.vangoghchicago.com/ for full prices and to purchase tickets in advance.

Immerse Yourself in The Office Experience

The Office Experience pop-up opens October 15 in Chicago for a three month run. Visit Schrute Farms, walk through the Dunder Mifflin set, and relive Jim and Pam’s iconic romance. The world of The Office will come to life with iconic set recreations, original show costumes and props, and opportunities for fans to engage with the show in new ways. Timed tickets are now on sale online.

When: Opens October 15, 2021

Where: 540 N Michigan Ave on the Mag Mile.

Cost: General admission is $37.50 plus taxes + fees for off-peak times or $45 plus taxes and fees for peak times. Children 3 and younger are free. Groups can also purchase private access tickets or book the space for a private party.

See The Art of Banksy Exhibit

“The Art of Banksy” Exhibit is the largest touring exhibition of authentic Banksy artworks in the world. The exhibit will feature over 80 original works from private collectors across the globe, offering a rare opportunity to view authenticated and certified Banksy artworks rarely seen by the general public including iconic works such as ‘Girl and Balloon’, ‘Flower Thrower’ and ‘Rude Copper’ alongside some of Banksy’s lesser known masterpieces. On display are prints, canvasses, screenprints, sculptures, unique works and limited-edition pieces mainly dated between the years 1997 to 2008, the period which resulted in Banksy’s most recognisable and well-known works.

This exhibition is not authorized by Banksy nor is it curated in collaboration with the artist but sourced from private collections allowing the public to see works that would otherwise stay hidden in private homes or warehouses.

When: Exhibit ends October 31, 2021

Where: 360 N. State St, Chicago, IL 60654

Cost:  Tickets prices range from $39.99 to $99.99 for adults and $29.99 for children 6-16 years old (plus $6.85 service fee). See https://banksyexhibit.com/chicago/buy-tickets for full prices and to purchase tickets in advance.

Immerse Yourself in the Dr. Seuss Experience

The Dr. Seuss Experience is an imaginative and interactive immersion into the wondrous world of Dr. Seuss. This Seuss-tacular sensory spectacle takes each guest on an awe-inspiring journey through nine different Dr. Seuss books, allowing each visitor a chance to magically step into the pages of each of the books.

When: Opens October 8, 2021

Where: Water Tower Place, 835 N. Michigan Avenue, Ste 100, Chicago, IL 60611

Cost:  Prices vary. Tickets prices start from $29.00 for adults and $18.00 for children (1-13 years old) for non-peak hours. Visit their website to purchase tickets in advance.

Visit the Museum of Illusions Chicago


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Experience mind-bending illusions in a festive Halloween go-to destination. Museum of Illusions Chicago has completely transformed into the Museum of Spooky Illusions during the month of October. The museum offers an interactive, immersive and fun experience for both adults and kids with exhibits that will teach you about vision, perception, the human brain and science.

Where: 25 E Washington St., Chicago, Illinois

Cost:  Prices vary. Tickets prices start from $21.00 for adults and $15.00 for children (5-12) for non-peak hours. Visit their website for full details on hours and prices.

Watch Scary Movies Outdoors or at a Drive-In

You can watch scary movies to get you in the Halloween spirit either outside or at a drive-in theatre.

Movies at Gallagher Way

Enjoy free movies outside at Gallagher Way next to Wrigley Field. Gallagher Way has teamed up with the Music Box Theatre to show free outdoor movie screenings in October. Attendees can to bring their own food, or grab a meal from the food truck or nearby restaurants. The movie schedule is as follows:
October 6: Casper
October 13: The Addams Family
October 20: Ghostbusters
October 27: The Nightmare Before Christmas

When: Wednesdays, October 6, 13, 20 & 27. Gates open at 6 p.m. and movies start at 7:00 p.m.

Where: Gallagher Way Chicago, 3635 N Clark St, Chicago, IL 60613

Cost: FREE. VIP seating is available for $25.

Music Box of Horrors at the Drive-In

The Music Box of Horrors: Dawn of the Drive-In will once again take over the Chi-Town Movies Drive-In for late shows Sunday-Thursday, and double-features every Friday and Saturday night. This years themes include Nü-Metal Mondays, Thirsty Thursdays, Friday Night Double Features, Rip-Off Saturdays, and Serial Killer Sundays. With mind-melting visuals and high body counts, this year’s lineup is perfectly in line with the Music Box’s eclectic taste in horror offerings and events—a combination of audience favorites and rarely screened titles, specialized intros, pre-show content, filmmaker Q&As, nightly trivia with fantastic prizes, and of course, some surprises. Every element will be presented safely & responsibly in the Drive-In setting.

If you don’t have a car, you can select Row A when making your ticket purchase and come with a chair for you and your friends to watch the movie.

When: October 1-31, 2021

Where: Chi-Town Movies Drive-In, 2343 S Throop St, Chicago, IL 60608

Cost: Single Feature – $30 per car / $25 Music Box Members Double Feature – $40 per car / $35 Music Box Members

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.

Some of the best farmers markets in Chicago include the Green City Market, the Logan Square Farmers Market and the Wicker Park Farmers Market.

Have a Pumpkin Patch Shake at Jojo’s Shake Bar

Pumpkin Patch Shake
Instead of a Pumpkin Spice Latte why not try a Pumpkin Patch Shake? At Jojo’s Shake Bar you can have Pumpkin Patch Shake, which is topped with a whole pumpkin pie slice, taffy apple, roasted marshmallow, and toffee pretzel.

Jojo’s Shake Bar has 2 locations in Chicago: Water Tower Place (835 N. Michigan Ave) and River North (23 W Hubbard St). They have created a pumpkin patch on their 5,000 sq ft patio in River North with over 600 pumpkins, a 1954 Red Ford truck, Hay Bales, and a bathtub filled with corn to satisfy your perfect fall photo needs.

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 in 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 corn mazes open sometime in September and stay open 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.

Go Apple Picking

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 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.

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.

This haunted segway tour and Halloween bike tour are only offered in October.

This ghosts and gangsters tour is available year round and also covers Chicago’s history of organized crime.

Admire Fall Colors

There are many places in and near Chicago to admire the beautiful autumn leaves. The peak time for the best fall colors in Chicago is usually mid October to late 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”), 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. Some of the best spots 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 including the Fall Color 5K Run and Walk (October 2, 2021), Annual Glass Pumpkin Patch (October 13 -17, 2021) and Cider and Ale Festival (October 23, 2021). Don’t miss Human+Nature, an outdoor art installation by renowned South African artist Daniel Popper which features five 15- to 26-foot-tall sculptures.

• 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. Their website has a recommended fall color-tree walk for the best viewing. Every October, they host the popular Night of 1,000 Jack-o’-Lanterns (October 13 – 17 and 20 – 24, 2021) with more than 1,000 hand-carved pumpkins—some as large as 150 pounds—will light up the night.

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

October 2021 Events

In addition to the activities mentioned above, other October events include: Chicago Pride Fest (October 1-3, 2021), St. Benedict’s Oktoberfest (October 1-3, 2021), Lincoln Square Greek-tober Fest (October 1-3, 2021), Chicago Wine Fest (October 2, 2021), WingOut Chicago (October 2-3, 2021), Lincoln Square Ravenswood Apple Fest (October 2-3, 2021), Lincoln Park Wine Fest (October 8-10, 2021), Chicago Beer Festival (October 9, 2021), Chicago Marathon (October 10, 2021), 57th Chicago International Film Festival (October 13-24, 2021), Illumination (October 23, 2021), Meet Me on The Mile (October 24, 2021), Logan Square Halloween Parade (October 24, 2021), Pumpkin Party (October 28, 2021), Arts in the Dark Halloween Parade (October 30, 2021), Haunted Halloween Ball Chicago (October 30, 2021) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2021).

As you can see there are many things to do in Chicago in October.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



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