Chicago’s October calendar includes Halloween parties at parks, art events, and Open House Chicago.
Things to Do in October in Chicago:
Table of Contents
Ravenswood Apple Fest
When: October 1-2, 2022
Neighborhood: Ravenswood
Address: Lincoln Avenue between Lawrence and Wilson
An October festival that welcomes autumn with live music, kid’s activities, farm stands, and a variety of apple-inspired food and drink.
Wing Out Chicago
When: October 1-2, 2022
Neighborhood: Old Town
Address: St. Michael’s Church Parking Lot, 456 West Eugenie Street
Sample over 20 varieties of wings at this event which also has a live music stage.
Lincoln Roscoe Art & Craft Fair
When: October 1-2, 2022
Neighborhood: Roscoe Village
Address: Roscoe Street to School Street
A new festival taking place on Lincoln Avenue from Roscoe Street to School Street highlighting over 60 local artists, makers, and independent shops.
Metroberfest
When: TBD
Neighborhood: Avondale
Address: Metropolitan Brewing, 3057 North Rockwell Street
A one-day event that takes place at Metropolitan Brewery early in October to celebrate Oktoberfest.
Lincoln Park Wine Fest
When: October 7-9, 2022
Neighborhood: Lincoln Park
Address: Jonquil Park
Cost: $40 and up
This event has wine tastings and a food pavilion. General admission tickets are $40 in advance and include 12 standard tastings. *This is a 21+ event.
Chicago Marathon
When: October 9, 2022
Throughout Chicago
One of the largest marathons in the world, the Chicago Marathon is known for its flat and fast course that weaves through 29 neighborhoods. The race starts and finishes in Grant Park. (There are a variety of road closures on marathon day).
Greektown hosts a special cheer event from 8 am until 2 pm at the corner of Gladys and Halsted Streets. There will be a sign making station, complimentary coffee, Greek pastries, and a DJ.
Joffrey Ballet’s Beyond Borders
When: October 12 -23
Neighborhood: The Loop
Address: Lyric Opera
The Joffrey Ballet is opening it’s 2022-2023 season with a program that features three works, including the world premiere of a powerful new work by in-demand choreographer Chanel DaSilva that explores good and evil through bold color and emotion.
Chicago International Film Festival
When: October 13-24, 2022
Various locations
Over 80 films are screened at this annual event that takes place at theaters, drive-ins, and virtually.
Open House Chicago
When: October 15-16, 2022
Neighborhood: Throughout Chicago
An annual event hosted by the Chicago Architecture Center each October. During this event, significant architectural, historical, and cultural sites are open to the public for free – including some spaces that usually aren’t open to the public.
18th Street Pilsen Open Studios
When: October 16-17, 2022
Neighborhood: Pilsen
Address: 18th Street between Western and Halsted
An October event that includes gallery tours, open studios, workshops, mural tours, and live painting.
Lincoln Roscoe Beer Stroll
When: October 22, 2022
Neighborhood: Roscoe Village
Address: along Roscoe Street and Lincoln Avenue
This event celebrates local breweries and businesses. Shop at locally owned businesses while tasting Chicago craft beer.
Día de los Muertos Xicágo
When: TBD
Neighborhood: Pilsen
Address: Harrison Park
Hosted by the National Museum of Mexican Art at Harrison Park, this annual event takes place at the end of October and features ofrendas created by the community, art activities, and performances.
Oktoberfestiversary
When: TBD
Neighborhood: Ravenswood
Address: Ravenswood and Belle Plaine Ave
A collaboration between Begyle Brewing and Dovetail Brewery that celebrates Begyle’s birthday and allows Chicagoans to soak up the last of the warm weather. Special beers are tapped for the event and Oktoberfest-inspired food is served. The event benefits The Friendship Center. The event takes place in October, check Begyle’s Facebook page for details.
Halloween Events
Boo Palooza
When: TDB
Neighborhood: Wicker Park
Address: Wicker Park
An annual one-day event hosted by Mr. Dave’s Music at Wicker Park that combines live kid’s music, activities, and a costume parade.
Loyola Park Halloween Pet Parade
When: October 1, 2022, 9 am – 11 am
Neighborhood: Rogers Park
Address: Loyola Park
Awards for Best Costume, Best Trick, Cutest, and Best in Show will be handed out at this event.
Ghouly Park Halloween
When: TBD
Neighborhood: Gold Coast
Address: Goudy Park
An annual Halloween event for families that takes place in Goudy Park.
Upside Down Halloween Parade
When: TBD
Neighborhood: Washington Park
Location: Washington Park
Both the Upside Down Halloween Parade and the Arts in the Dark Halloween Parade celebrate Halloween as a holiday for artists and creativity. Cultural organizations and artists from throughout Chicago participate. The Upside Down Halloween Parade is a daytime event.
Arts in the Dark Halloween Parade
When: TBD
Neighborhood: The Loop
Address: State Street from Lake to Van Buren
The Arts in the Dark Halloween Parade shares the same mission and inspiration as the Upside Down Halloween Parade, but it takes place after the sun has set giving participants the opportunity to add lighted elements to their costumes.
Northalsted Halloween Parade
When: TBD
Neighborhood: Lakeview/Northalsted
Address: Halsted Street from Aldine to Waveland
A parade and costume contest that ends with a live music performance. This is one of Chicago’s best Halloween events.
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