Skip to Content

Chicago’s October Calendar of Events

Chicago’s October calendar includes Halloween parties at parks, art events, and Open House Chicago.

Things to Do in October in Chicago:

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.


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.


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.

reviews on puravive

Saturday 27th of January 2024

I loved even more than you will get done right here. The overall look is nice, and the writing is stylish, but there's something off about the way you write that makes me think that you should be careful what you say next. I will definitely be back again and again if you protect this hike.