Spending Columbus Day weekend in Chicago? Here are the best things to do in Chicago for Columbus Day weekend (October 9-12, 2026) from the top Chicago attractions to best Columbus Day weekend events and fall and Halloween activities.
Chicago Columbus Day Weekend
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Columbus Day weekend is a great time to visit Chicago. There are tons of fun things to do in Chicago on Columbus Day (October 12, 2026) and even more during Columbus Day weekend.
For out of town visitors, please note that the weather in Chicago during Columbus Day weekend is very unpredictable and temperatures can vary greatly. Be prepared for either cooler fall or hot and humid summer like temperatures (sometimes all in one day!) as well as rain. Make sure to pack layers, a travel umbrella and check the weather right before your visit to know what to expect.
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
Chicago Columbus Day Weekend Events
Here are the best things Columbus Day weekend events.
Watch the Chicago Marathon
Cheer runners on during the Chicago Marathon on Sunday morning (October 11, 2026). Even if you are not interested in the marathon, take a look at the route map for street closures.
Watch the Columbus Day Parade
Attend the annual Columbus Day Parade (Monday, October 12, 2026) in downtown Chicago.
More Chicago Columbus Day Weekend 2026 Events
In addition to the events and activities mentioned above, other events taking place on Columbus Day weekend include: Oktoberfestiversary (October 10-11, 2026), Chicago Fashion Week (October 8-18, 2026), Chicago Art Fair (October 7-10, 2026), Lincoln Park Wine Fest (October 9-11, 2026), Chicago Vampire Ball (October 9, 2026), TenderFest at Navy Pier (October 10, 2026) and Lincoln Brunch Fest (October 10, 2026).
For more Columbus Day weekend events, bookmark this post about the best weekend events which is updated every week.
More Things to do in Chicago during Columbus Day Weekend
Here are more of the best things to do in Chicago on Columbus Day weekend.
Smithsonian Starstruck: An Immersive Experience
Launching in Chicago, and created in collaboration with the Smithsonian Astrophysical Observatory, Smithsonian Starstruck: An Immersive Experience is a fully interactive, 3D virtual reality experience that takes visitors on a breathtaking journey through the cosmos, from dazzling galaxies to the edge of a black hole.
Where: 108 West Germania Place, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
Drunk Dracula
Step into a darkly enchanting adult-only adventure at Drunk Dracula where laughter, tipsy thrills, and the legend of Dracula collide. Each 90-minute session invites you to sip, shiver, and revel in the mischievous antics of a vampire gone delightfully rogue. Mingle with fellow thrill-seekers in a mysterious, adult-only setting. Must be 21+ with valid ID.
Where: 182 North Wabash Avenue, Chicago, IL 60601
Cost: Prices start at $29 per person. Click here to purchase tickets.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful indoor venues bathed in candlelight. Some of the concerts taking place Columbus Day weekend include:
Tribute to Ariana Grande
Vivaldi’s Four Seasons (Oak Park)
Neo-Soul Favorites ft. Songs by Prince, Childish Gambino & More
You can find the full list of candlelight concerts in Chicago here.
AirOtic BITE
AirOtic BITE is a dark and seductive Halloween burlesque and contemporary circus experience taking place only for a few weeks this October. 21+ with valid ID.
Where: Experience 868, 868 N Franklin St, Chicago, IL 60610
Cost: Prices vary. Click here to purchase tickets.
Serial Killer: The Exhibition World Tour
Serial Killer: The Exhibition World Tour is a gripping, immersive true-crime experience featuring the world’s first and only collection of authentic artifacts connected to history’s most notorious serial killers. Following its massive success in London, Paris, and Berlin, and fresh off its U.S. premiere in Atlanta, Chicago is officially the second stop of this blockbuster American tour. Built on ten years of research and collaboration with over sixty global collectors, this expanded landmark exhibition features over 2,100 authentic artifacts while introducing exclusive Chicago content exploring the city’s dark criminal history, including dedicated sections on H.H. Holmes and John Wayne Gacy. Recommended for ages 14+ (not suitable for sensitive audiences).
Where: Cinespace Chicago Film Studios, 2428 W 15th St, Chicago, IL 60608
Cost: Prices vary. Click here to purchase tickets.
Take an Architecture River Cruise
An architecture river cruise is a must do Chicago experience.
Hang Out on the Riverwalk
The Chicago Riverwalk along the south bank of the Chicago River is one of the best spots in Chicago for people watching. There are restaurants, bars, shops and places to sit along the way – see a map here.
Island Party Hut, a bar and grill on the Riverwalk, will be hosting its annual Fall Fest on the Riverwalk on Saturday with live music, hayrides on the river, pumpkin patch, fall cocktails & beer, apple cider donuts and other fall themed fun.
Take a Haunted History or 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.
Have Fun at Navy Pier
A ride on the large Ferris wheel offers paranoramic skyline views of Chicago and is another great way to see the fall colors from above. (Click here to purchase a fast pass ticket and skip the long line).
Check out Flyover, an immersive flyover experience.
Other fun attractions at Navy Pier include rides and games, restaurants, shops and the Chicago Children’s Museum. Navy Pier is a must do if you are visiting Chicago with toddlers or kids. Navy Pier is also the starting point for many boat rides and lake cruises.
Kayak in the River or Lake
If the temperatures are pleasant, a fun way to explore the city is to go kayaking in the Chicago River or the lake. You can rent a kayak in the Chicago River here and Ohio Street beach here.
You can also join a guided kayaking tour in the downtown portion of the Chicago River including this history and architecture kayak tour and this sunset kayak tour.
Please note that you will get a little wet when kayaking so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Walk or Bike the Lakefront Trail
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. During Columbus Day weekend, the lakefront will be 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 the 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
Looking for a unique thing to do for Columbus Day weekend? Walk around Chicago looking for street art.
One of the most famous 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 well known tourist attractions.
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 Lincoln Park Zoo During Fall Fest
Visit Lincoln Park Zoo during its annual Fall Fest. This family-friendly celebration offers free fun fall activities including a pumpkin patch, professional pumpkin carvers, free musical entertainment, story times and more.
When: 10 a.m.-5 p.m during Columbus Day Weekend
Address: 2400 N. Cannon Drive
Cost: Admission to the zoo is FREE but some fall fest attractions are paid.
Take 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.
Where: 1465 N Elston Ave, Chicago, IL 60642
Cost: Prices vary by date.
Visit a Pumpkin Patch
There are many pumpkin patches you can visit in Chicago and the suburbs during Columbus Day weekend. 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.
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.
Minecraft Experience: Villager Rescue
Minecraft Experience: Villager Rescue is an immersive adventure that lets you and your friends become heroes, fighting spiders, creepers, and skeletons on your quest to rescue villagers from a zombie attack. Explore eight interactive Minecraft rooms and gather resources for your quest in these interactive biomes. Practice your Minecrafting skills with a handheld Orb to chop down trees, collect resources, and fight mobs.
Where: 9900 Berwyn Ave, in the Pearl District, Rosemont, IL 60018
Cost: Prices vary. Click here to purchase tickets.
Wondra: Immerse yourself in the magic of nature
Looking for a fun activity for kids? Head to the suburbs for Wondra, where each space invites curious minds to discover hidden details, dazzling colors, and natural awe-scapes that spark imagination and evoke wonder. Experience nature’s wonders in a whole new light with this immersive journey.
Where: 5 Woodfield Mall, Schaumburg, IL 60173
Cost: Prices vary. Click here to see prices and purchase tickets in advance.
As you can see there are many things to do in Chicago on Columbus Day weekend. If you are looking for things to do during the week, here are the best things to do in Chicago this October.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
