Five Things To Do in Chicago: Oct. 31–Nov 2, 2025

From orchard visits to neighborhood fests, fall is full of reasons to get outside and soak it all in. We've rounded up a few local happenings to add to your list this weekend.

Trick-or-treat at Montrose Monster Mash.

Montrose Avenue gets a spooky makeover for the inaugural Montrose Monster Mash, a new family-friendly Halloween event hosted by the Greater Ravenswood Chamber of Commerce. Local shops and restaurants will open their doors with candy, specials, and plenty of Halloween cheer. Expect familiar favorites like Margie's Candies, Farm Bar, and Hazel joining in on the fun.

Date: Oct. 31
Time: 4–7 p.m.
Cost: Free
Location: 2000 W. Montrose Ave.
More Info: ravenswoodchicago.org

  
Head to the Pigmented Black Fine Art Faire.

The Pigmented Black Fine Art Faire showcases the power and perspective of Black artists across the Midwest. This Black-run fine art fair highlights galleries, creators, and cultural organizations dedicated to elevating representation in the arts. Expect transformative exhibitions, thought-provoking discussions, and a celebration of innovation rooted in community.

Date: Oct. 31–Nov. 2
Time: Fri 5–10 p.m.; Sat 11 a.m.–7 p.m.; Sun 11 a.m.–5 p.m
Cost: $24+
Location: Zhou B Art Center, 1029 W. 35th St.
More Info: pigmentintl.com

Celebrate at the Haunted Halsted Halloween Parade.

Chicago's most dazzling Halloween parade returns to Northalsted for another night of costumed chaos. This event brings out thousands of spectators for an evening of over-the-top outfits, fierce drag performances, and high-energy fun in the heart of Boystown. Expect everything from ghoulish glamour to campy creatures parading down Halsted Street.

Date: Oct. 31
Time: 7:30–10 p.m.
Cost: Free
Location: Halsted St. from Addison St. to Grace St.
More Info: northalsted.com 

Honor loved ones at Día de los Muertos on Camino Clark.

Camino Clark businesses will transform into a corridor of remembrance and celebration during Día de los Muertos. Visitors can view altars honoring loved ones, learn about the holiday's roots, and enjoy special promotions from local spots. Marigolds, art, and storytelling line the way, making this an immersive experience that blends history, culture, and community spirit.

Date: Nov. 1–2
Time: Various Times
Cost: Free
Location: Various Locations
More Info: business.rpba.org 

Have a little friendly competition at Pumpkins & Pickleball Fall Fest.

SPF Chicago hosts its first-ever Pumpkins & Pickleball Family Fall Fest, a free community event packed with family-friendly fun. Guests can enjoy pumpkin decorating, fall crafts, and face painting—plus open-play pickleball and cider for all ages. Adults can sip seasonal cocktails while kids snack on treats from Honey Butter Beach Club. Costumes are encouraged, and the fun continues with live music from South City Revival after hours.

Date: Nov. 1
Time: 12–5 p.m.
Cost: Free
Location: SPF Pickleball, 2121 N. Clybourn Ave.
More Info: www.facebook.com