Chicago October events bring some of the most exciting things to do all year. From fashion week and film festivals to seasonal food celebrations, Halloween happenings, and neighborhood cultural events.
Personally, I think I do some of my best exploring this month. Between art shows, fall activities, and everything in between, October in Chicago always feels stacked. Maybe it’s because everyone is trying to squeeze in the best events before the holidays—but honestly, I don’t mind.
Explore what the city has to offer with this ultimate guide to events and things to do in Chicago this October.
The Best Things to Do in Chicago This October
Use the navigation below to explore can’t-miss events, recurring city favorites, and editor-curated picks. Bookmark this guide—we’ll be updating it throughout the month with new Chicago October festivals, activities, and last-minute finds.
Top Events: Must-attend events of the month.
Recurring Chicago Events & Activities: Regular events worth adding to your calendar.
The Curated List: Personal recommendations for unique Chicago experiences.
Top October Festivals & Things to Do in Chicago
Discover the biggest summer festivals and street fairs happening throughout the city.
October Chicago Art Fairs & Exhibitions
October is a big month for Chicago’s art scene, with expos, fairs, and open studios happening across the city. Highlights include:
- October 3, 2025: Huge Art Show & Open House at Hubbard Street Lofts
- October 3–5, 2025: 21st Annual Arts Weekend
- October 12, 2025: Black Girl Art Show Chicago
- October 17, 2025: Marwen Art Fair
- October 17–19, 2025: The Fall West Loop Contemporary Fine Art Expo
- October 18–19, 2025: Festival del Arte Popular
- October 25, 2025: Pancakes and Booze Art Show
- October 30 – November 2, 2025: The Other Art Fair Chicago
- October 2025 (TBA): BUTTER Fine Art Fair
World Music Festival Chicago
October 1–5, 2025 | Citywide, including Chicago Cultural Center
The World Music Festival Chicago celebrates diverse music from nations across the globe. All performances are free, and seating is first-come, first-served. Some venues have limited capacity, so early arrival is encouraged.
Lincoln Park Wine Fest
October 3–5, 2025 | Jonquil Park, Lincoln Park
Sample wines from around the world at Lincoln Park Wine Fest, a neighborhood festival that transforms Jonquil Park into an open-air tasting pavilion. Enjoy global varietals, live music, and food pairings—a relaxed fall outing perfect for wine lovers.
Chicago Beer Fest
October 4, 2025 | The Field Museum, Museum Campus
Sip seasonal brews inside one of Chicago’s most iconic venues. The Chicago Beer Fest features more than 65 breweries pouring fall favorites in the grand setting of the Field Museum. Early entry includes an exclusive hour with specialty pours.
Apple Fest
October 4–5, 2025 | Lincoln Square, Ravenswood
Kick off the season at Lincoln Square’s Apple Fest, a family-friendly tradition featuring apple-inspired treats, local cider, baked goods, and seasonal goods. With live music and neighborhood vendors, this is one of Chicago’s most beloved fall festivals.
Chicago Fashion Week® 2025
October 9–19, 2025 | Multiple Venues, Downtown & Beyond
Chicago Fashion Week® returns with runway shows, designer showcases, and citywide programming that celebrates the city’s role in global style. From intimate shopping experiences like Marché Privé: Fashion Edition to thought-provoking conversations such as The Business of Fashion: Assessing Now, Looking to the Future, alongside bold runway presentations and creative pop-ups, CHI✶FW spotlights both emerging talent and established names shaping fashion today.
The 61st Chicago International Film Festival
October 15–26, 2025 | Multiple Theaters & Venues
Now in its 61st year, the Chicago International Film Festival is North America’s longest-running competitive film festival, bringing global cinema to the heart of the city. Expect an extraordinary lineup of dramas, thrillers, documentaries, comedies, and more, with programs like Black Perspectives, OutLook, International Comedy, After Dark, and City & State spotlighting Illinois filmmakers.
Arts in the Dark
October 18, 2025 | State Street, Downtown
Celebrate Halloween in Chicago with Arts in the Dark, a spectacular nighttime parade featuring illuminated floats, giant puppets, dancers, and live music. This family-friendly event brings together artists and performers for one of the city’s most magical October traditions.
Open House Chicago
October 18–19, 2025 | Citywide, Various Neighborhoods
Explore over 150 architectural treasures and cultural landmarks during Open House Chicago, a free citywide festival that gives behind-the-scenes access to historic and iconic spaces. Perfect for design enthusiasts and curious explorers alike.
Journey Chicago
October 2025 | Citywide, Various Neighborhoods
Journey Chicago is a citywide, intercultural festival of art, ideas, and performance. With dozens of partner organizations, the family-friendly festival highlights the cultural diversity of Chicago through talks, exhibitions, and live performances across neighborhoods throughout October. Many events are free or low-cost.
Chicago Farmers Markets
October | Various Locations
Now through the fall, you can find fresh fruit, vegetables, flowers, baked goods, and more at various neighborhood farmers’ markets in the city of Chicago.
Maxwell Street Market
October | West Maxwell Street &, S Halsted St
On select Sundays, enjoy this free event in Chicago. The Maxwell Street Market will open, featuring an eclectic mix of foods and finds. This year’s edition will also feature live entertainment and programming from cultural partners, incorporating nearby businesses and restaurants, including several “Maxwell Street originals” with longstanding ties to the neighborhood.
Looking for Chicago events and things to do in Chicago this weekend? Check out the events calendar.
Ongoing Things to Experience in Chicago in Chicago
Looking for things to do in Chicago in Chicago that are available all month long? Here’s a round-up of ongoing attractions and seasonal experiences to check out this month.
- Architecture Boat Tour: Experience Chicago’s stunning skyline on a Chicago boat tour,before it gets too cold in Chicago.
- Flyover in Chicago: Marvel at Chicago’s skyline and lakefront from a thrilling 30-minute immersive ride. Located at Navy Pier.
- Chicago Crime & Mob Bus Tour: Step into the city’s darker history and discover infamous crime spots.
- 360 CHICAGO Observation Deck Admission: Tower above Chicago from the 94th floor of 875 N. Michigan Avenue, enjoying panoramic views, grab a cocktail at CloudBar, or try the exhilarating TILT experience.
- Museum Free Days: Take advantage of free or discounted admission at museums.
- Interactive Museums: Capture Insta-worthy photos in interactive museums like the Museum of Ice Cream or the colorful Color Factory.
- Weekday Events: Break your routine with free movies in the park, neighborhood festivals, happy hour specials, and concerts happening Monday through Thursday.
The Curated List of Chicago Events in October
Here’s The Haute Seeker’s curated list of the best events, activities, and coolest events to check out during October.
What’s Out There® Weekend Chicago
What: Free expert-led tours of parks, gardens, and designed landscapes across Chicago (TCLF)—discover the stories of places like the Lily Pool, Jackson Park, and The Wild Mile. Registration required.
When: October 4–5, 2025 | Tour times vary
Where: Location Varies Link for more information: TCLF – What’s Out There Weekend Chicago
Simone’s Sweet 16 Block Party
What: Simone’s Bar in Pilsen turns 16 and is celebrating with a weekend-long block party. Expect food trucks, DJs, live music, raffles, and karaoke with host Pablo Serrano. Free to attend, this community celebration is all about music, food, and neighborhood love.
When: October 4–5, 2025
Where: Simone’s Bar, 960 W. 18th St, Chicago, IL
Link for more information: Simone’s Bar Event Page
Sundays on State
What: Sundays on State, transforms Chicago’s most iconic street into a community block party that features food, drinks, shopping, and local attractions in the heart of everyone’s neighborhood – the Loop
When: October 5, 2025 | 11:00 a.m. – 6:00 p.m.
Where: State Street from Randolph to Jackson
Link for more information: Chicago Loop Alliance
Slow & Low: Chicago Lowrider Festival
What: The city’s largest Lowrider culture gathering with custom cars, music, live performances, art, and community programming.
When: October 11, 2025 | Times vary by schedule
Where: Festival Hall, Navy Pier, 600 E. Grand Ave, Chicago, IL
Link for more information: Chicago Lowrider Festival
Begyle Brewing & Dovetail Brewery Oktoberfestiversary
What: Begyle’s 13th anniversary + the 10th Oktoberfestiversary with food trucks, live music, kids’ activities, and a fundraiser supporting The Friendship Center (suggested donation).
When: October 11–12, 2025 | Sat 11 a.m.–9 p.m.; Sun 11 a.m.–8 p.m.
Where: Between Begyle & Dovetail (Ravenswood Corridor), Ravenswood, Chicago, IL
Link for more information: Begyle Oktoberfestiversary
Indigenous Peoples’ Day at the Field Museum
What: Cultural performances, hoop dance, Danza Azteca, family workshops, and the Indigi-Fair celebrating Indigenous knowledge and traditions. Admission included with museum entry.
When: October 13, 2025 | 11:00 a.m.–2:00 p.m.
Where: Field Museum, 1400 S. DuSable Lake Shore Dr, Chicago, IL
Link for more information: Field Museum – Indigenous Peoples’ Day
AFRORHYTHMIC: A Felabration
What: A Felabration-style night curated by DJ Duane Powell honoring Fela Kuti with Afrobeat, AfroHouse, live percussion, and community dance — bring percussion and energy.
When: October 16, 2025 | 8:00 p.m.–1:00 a.m.
Where: Room 43, 1401 E. 43rd St (Bronzeville area), Chicago, IL
Link for more information: AFRORHYTHMIC — Room 43
RuPaul (DJ Set)
What: The legendary entertainer, TV host, and global drag icon RuPaul brings the energy to Chicago with a special late-night DJ set. Expect fierce beats, iconic vibes, and an unforgettable night on the dance floor. Ages 18+.
When: October 18, 2025 | 10:00 p.m. (Doors 10:00 p.m.)
Where: Radius
Link for more information: Rupaul Dj Set
The Rocky Horror Picture Show — 50th Anniversary Spectacular
What: An interactive screening with original cast members Barry Bostwick, Nell Campbell, and Patricia Quinn — includes live shadow cast, memorabilia displays, costume contest, and VIP meet & greets. R-rated; audience participation expected (no outside props).
When: October 19, 2025 | 7:30 p.m. (Doors 6:30 p.m.)
Where: The Chicago Theatre, 175 N. State St, Chicago, IL
Purchase Tickets: Rocky Horror
Adam Sandler: You’re My Best Friend Tour
What: Comedy icon Adam Sandler brings new stand-up, music, and signature humor to Chicago following sold-out runs — recommended for older teens/adults.
When: October 20, 2025 | 7:30 p.m. (Doors 6:00 p.m.)
Where: United Center, 1901 W. Madison St, Chicago, IL
Purchase Tickets: Adam Sandler Chicago
Penn & Teller — 50th Anniversary Tour
What: The legendary duo performs a milestone show of magic, comedy, and audience interaction — a rare anniversary tour stop.
When: October 24, 2025 | 8:00 p.m. (Doors 7:00 p.m.)
Where: The Chicago Theatre, 175 N. State St, Chicago, IL
Purchase Tickets: Penn & Teller
G Herbo Presents: Swerv & Friends Birthday Bash
What: G Herbo headlines a star-studded birthday concert featuring top hip-hop acts and surprise guests — a major one-night-only show.
When: October 26, 2025 | Time TBA
Where: Wintrust Arena, 200 E. Cermak Rd, Chicago, IL
Purchase Tickets: Swerv & Friends Tickets
October in Chicago: Everything You Need to Know
What’s October weather in Chicago like?
Should I visit Chicago in October?
Should I visit Chicago in October?
Absolutely! October is a great time to visit the city. If you love the arts, think plays, musicals, the opera, this month is one of the best times to visit as the new season for theater begins. one of the most dynamic months in the city. Fall foliage is in full swing, many neighborhoods host Oktoberfest celebrations and harvest festivals, and Halloween events—including haunted houses, costume parties, and themed pop-ups—make it an exciting time for visitors and locals alike.
What should I wear in Chicago in October?
What should I wear in Chicago in October?
Layering is key. Bring long-sleeve shirts, sweaters, and a warm jacket for evenings. Comfortable shoes are essential for walking city streets and festival grounds. Don’t forget scarves and gloves for cooler mornings.
What to Look Forward to in October
Expect harvest festivals, pumpkin patches, outdoor markets, arts and culture events, haunted attractions, and the city’s best fall-themed activities. From neighborhood street fairs to immersive theater experiences, October in Chicago offers a mix of family-friendly fun, foodie adventures, and spooky seasonal thrills that all can enjoy.
