35 Fun Things to Do in Chicago in October

It doesn’t get better than October in Chicago. Whether you’re in for late summer sunshine or crisp fall days, it’s a beautiful time to explore the city. The arts and culture calendars are booming, the sports teams are in town, and the weather is perfect for getting out and about. Whether you’re looking for fall activities or spooky season events, October is a great time to enjoy autumn in Chicago. 

I’ve lived in Chicago for nearly two decades, and I’ve written two books about Chicago. October is always one of my favorite times in the city. Whether you’re visiting Chicago in October or you live in Chicagoland, here are 35 fun things to do in Chicago in the fall.

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Fun Things to Do in Chicago in October

1. Play Mini Golf in a Funeral Home

If you thought you couldn’t have fun at a funeral home, you’re dead wrong. Beneath Ahlgrim Family Funeral Services in Palatine, you’ll find arcade games, shuffleboard, ping pong, pool tables, and Ahlgrim Acres, a 9-hole miniature golf course. Read my interview with the owners.

2. Set Sail on Chicago Creepy Cruise

Get ready to experience Chicago’s darker side as you sail the Chicago River on a Creepy Cruise. Learn about mysterious sightings, creepy haunts, mobsters, and other dark tales from Chicago’s history.

3. Get Lost in the World’s Largest Corn Maze

Richardson’s Adventure Farm in Spring Grove boasts 28-acre corn maze with ten miles of trails to explore and games to play. With a pumpkin patch, petting zoo, donuts and cider, pig races, wagon rides, and a zipline, it’s a great way to spend a fall day.

4. Chicago International Latino Theater Festival – October 1-November 2, 2025

Destinos: Chicago Latino Theater Festival promotes Chicago’s local Latino theater community. Expect a diverse lineup of 13 performances from musicals to sketch across 13 venues citywide and in Northwest Indiana.

5. Homo Homecoming at Dorothy – October 3, 2025

Reclaim homecoming at Chicago’s lesbian bar, Dorothy. Homo Homecoming goes down at the West Town cocktail bar, complete with performances by The Chicago Spirit Brigade, Cut-Cuz, and CHATA.

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

6. Lincoln Square Ravenswood Apple Fest – October 3-5, 2025

Fall fun returns to the North Side with the Lincoln Square Ravenswood Apple Fest. Get your fill of apples with food, cider, live music, and autumn activities. 

7. West Town Art Walk – October 3-5, 2025

Explore the creative neighborhood’s galleries, shops, and restaurants at the West Town Art Walk. The 49 participating locations welcome artists and visitors and offer special discounts for attendees.

8. Admire Chicago’s Fall Colors

October is one of the most beautiful times to take in Chicago’s changing leaves and scenic views. From the Osaka Garden to Grant Park and Graceland Cemetery, don’t miss the opportunity to soak in autumn in Chicago.

9. Lincoln Park Wine Fest –  October 3-5, 2025

Spend an autumn afternoon tasting wine with your friends in Jonquil Park at the Lincoln Park Wine Fest. Choose a two-hour tasting session, stroll the market, and take home a commemorative tasting glass.

10. Andersonville Arts Weekend – October 3-5, 2025

Celebrate Andersonville’s creative community at the 21st annual Andersonville Arts Weekend. Admire the work of local artists across the neighborhood, take an art walk, and indulge in a wine walk at local businesses.

11. Visit the Grave of a Bride Who Communicated from Beyond the Grave

Did a young bride send messages from beyond the grave? Visit a supposedly haunted grave at Mount Carmel Cemetery in Hillside where a woman’s family had her exhumed. Read Julia Buccola’s story.

12. Chicago Beer Fest – October 4, 2025

How often do you have the opportunity to drink beer among the dinosaurs? The Chicago Beer Fest features 65+ breweries to sample at the stunning Field Museum in the South Loop.

13. Taylor Swift Listening Party – October 4

Strap on your friendship bracelet, sing along to Taylor favorites, and listen to her newest album at Streeterville Social at Loews Chicago Hotel. In Our Showgirl Era: An Exclusive Fan Listening Party features a red carpet, bites and sips, a live sketch artist, giveaways, and more. 

14. Night of 1,000 Jack-o’-Lanterns – October 8-26, 2025

Light up spooky season at the Chicago Botanic Garden’s Night of 1,000 Jack-o’-Lanterns. Be dazzled by 1,000 real pumpkins lit by LED that line the pathways that lead to entertainment and seasonal snacks.

15. Haunted Chicago Booze and Boos Ghost Walking Tour

Explore the city’s spooky corners on a haunted Chicago pub crawl. The mile-long journey will lead you through spooky stories of cemeteries and spirits as you raise a glass at three bars.

16. Chicago Fashion Week – October 9-19, 2025

Creativity spans the city at a variety of more than 50 events and runway shows. Chicago Fashion Week spotlights the city’s fashion history and cutting-edge design.

17. Glass Pumpkin Patch at Morton Arboretum – October 10-12, 2025

Take home a pumpkin that will last beyond Thanksgiving at Morton Arboretum’s Glass Pumpkin Patch. Choose from more than 8,000 hand-blown glass pumpkins and meet the artists behind the dazzling work.

18. The Monster Mosh III at Cobra Lounge – October 11, 2025

The annual horror-fueled fest returns to Cobra Lounge in West Town for the Monster Mosh III. Rock out to two stages of music, including headliner Action/Adventure. Wear your finest to win prizes in the costume contest and enter the pit if you dare.

19. Historic Pullman House Tour – October 11-12, 2025

Step into history and into your neighbors’ homes during the Historic Pullman House Tour. Eight restored homes in the historic neighborhood are open to the public, allowing you to see the storied architecture up close.

20. Black Girl Art Show – October 12, 2025

Celebrate the work of Black women artists with more than 100 talented women at the Black Girl Art Show. Head to Navy Pier for art displays, installations, live performances, and more.

21. Cheer the Chicago Marathon – October 12, 2025

You don’t need to be a runner to get into the Chicago Marathon spirit. Cheer on global athletes in neighborhoods from the Loop to Greektown to Chinatown in a celebration of the city.

22. Dive into True Crime on a Chicago Mobs and Haunts Walking Tour

Take a two-hour walking tour into Chicago’s dark history on a Mobs and Haunts Walking Tour. Trace the stories of mobsters, ghosts, and criminals as you take to the Chicago streets in search of the spooky and mysterious.

23. Chicago International Film Festival – Oct 15-Oct 26, 2025

Tune in to more than 100 films from 70 countries during the Chicago International Film Festival. The longest-running film festival in the country features shorts to documentaries and more.

24. Shop for Unique Gifts at Sauced Night Market – October 17-18, 2025

The free night market is back in Lincoln Square at Half Acre Beer Co. from 5-10 p.m. Raise a glass, sample bites from local restaurants, and stock up on unique gifts at Sauced.

25. Spooky Zoo – October 18, 2025

Get into the fall spirit at Spooky Zoo, a free event for 15,000 families and children. The event at Lincoln Park Zoo includes spooky chats, carousel rides, kid entertainment, and free trick-or-treating.

26. Arts in the Dark Parade – October 18, 2025

A spectacular parade lights up the Loop during the annual Arts in the Dark celebration. The free festival welcomes spectators to line the streets from State to Lake to Van Buren while costumed merrymakers parade.

27. Rosehill Cemetery ‘Crypt’ 5K – October 18, 2025

Burn off all that Halloween candy with a 5K in Rosehill Cemetery on a candlelit course. Ghost sightings aren’t guaranteed, but a long-sleeve T-shirt, medal, and post-race party are at the Crypt 5K.

28. Open House Chicago – October 18-19, 2025

Chicago is an architecture city, and Open House Chicago is like Christmas for fans of history and design. More than 200 sites across 24 neighborhoods will be open to the public for the weekend to explore. Check out past Open House Chicago events. 

29. The Other Art Fair – October 30-November 2, 2025

This touring art fair hits Chicago at Artifact Events in Ravenswood. The Other Art Fair features more than 115 artists with affordable works to purchase.

30. Haunted Halsted Halloween Parade – October 31, 2025

If you’re looking for a Halloween spectacular like none other, head to Northalsted for the Haunted Halsted Halloween Parade. It’s free to watch the grand costumes, Chicago Full Moon Fire Jam performers, and more. 

33. Visit an Apple Orchard

Chicago is surrounded by lovely apple orchards to stock up for fall. Prairie Sky Orchard, an hour outside Chicago, offers 15 delicious apple varieties to fill a bag. Treat yourself to pie, coffee, cider, and more.

32. Drunk Dracula – Through November 2

I love Drunk Shakespeare, but it’s no match for Drunk Dracula at the Lion Theater. What will happen to the townspeople when Dracula gets drunk? There’s only one way to find out.

33. Jack’s Pumpkin Pop-up – Through November 2nd, 2025

A patch of West Town is once again transformed into a two-acre Halloween wonderland at Jack’s Pumpkin Pop-Up. Wander a huge corn maze, play carnival games, snap seasonal selfies, throw axes, chow down on food trucks, surrounded by pumpkins.

34. Color Factory’s Haunted Hues – Through November 3

This fall, Color Factory adds a vibrant twist to Halloween with its Haunted Hues exhibit. Visit for frightfully fun photo opportunities, fall treats, and a seasonal scavenger hunt. 

35. Día de Muertos at the National Museum of Mexican Art – Through December 14, 2025

The free National Museum of Mexican Art’s annual Día de Muertos celebration includes an outdoor installation created by youth artists and “Día de Muertos: A Celebration of Remembrance”, an exhibit dedicated to Texans and New Mexicans flood victims. Add a memory of a lost loved one to the community ofrenda.

Visiting Chicago in October FAQ

Is October a good time to visit Chicago?

Autumn in Chicago might be my favorite time of year in the city. Cooler temperatures and changing leaves make fall in Chicago a beautiful time to get outside. There is a full calendar of festivals, cultural events, concerts, sporting events, and fall activities across Chicago. The city is still lively, but you can find cheaper flights and hotel deals than other times of year. I recommend booking ahead for popular restaurant reservations and tickets to Chicago’s top attractions like the Field Museum, 360 Chicago Observation Deck, or the Art Institute, to skip the lines.

What is Chicago Weather like in October?

October in Chicago is a mix of warm, sunny days and cooler evenings. According to the National Weather Service, the average temperatures in Chicago in October range from a high of 62 degrees to a low of 45 degrees. You might experience hot summer-like days or even snow at the end of the month. The weather can shift rapidly, so be sure to check the forecast before you visit Chicago in the fall so you can pack accordingly.

What Should I Wear to Chicago in October?

If you’re wondering what clothes to wear to Chicago in October, I recommend packing light layers. The days are typically warm and sunny, but you might experience a cool lake breeze off Lake Michigan. Check the weather before you visit Chicago in October so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the fall.

• Chicago is a walking town, so pack comfortable shoes like sneakers or boots.
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. Merino wool makes a great base layer for men and women. You may want to layer with a women’s flannel or a men’s flannel.
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped Breton shirt that I didn’t like.
• In the fall, I typically layer a lighter trench coat, leather jacket, or bomber jacket over my outfit.
• It doesn’t hurt to pack a windproof travel umbrella for rainy days and a beanie in case it gets chilly at night.

Where to Stay in Chicago in October

Wondering where to stay overnight in Chicago in the fall? I love the views of Grant Park from the Blackstone Hotel and the iconic pool at the InterContinental. The Chicago Athletic Association has great views of Millennium Park’s fall foliage and a rooftop fire pit, while the LondonHouse boasts beautiful views of the Chicago River from its rooftop bar.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you prepare to visit Chicago in October!

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things to Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May
• What to Do in Chicago in June
• Fun Things to Do in Chicago in July
• What to Do in Chicago in August
• Fun Things to Do in Chicago in September
• What to Do in Chicago in October
• Fun Things to Do in Chicago in November
• What to do in Chicago in December

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