October is just around the corner, and Chicago is gearing up for a season of family‑friendly Halloween celebrations. Block Club has compiled a list of over 70 events across the city, ranging from free parades and pumpkin patches to ticketed bar crawls and craft fairs. Below is a curated guide to help Chicagoans plan a safe, enjoyable holiday.

Signature Parades and Public Festivities

Arts in the Dark Halloween Parade – 6‑8 p.m., Oct. 24
Columbus Drive, Loop (Balbo to Monroe)
The 12th annual parade returns to its original route, expecting more than 100,000 spectators. Costumed participants and live performances will light up the skyline and Buckingham Fountain. Admission is free.

Haunted Halsted Parade – 11 a.m.–10 p.m., Oct. 31
North Halsted Street, Northalsted
Celebrating its 30th year, this day‑long event features food, music, vendors and a kids’ zone. A costume contest offers a $4,000 grand prize. Free admission.

Upside Down Parade – Noon‑2 p.m., Oct. 31
Russell Drive, Washington Park
The 7th annual parade invites families to walk the route in costume while enjoying performances from dance teams, musicians, acrobats and sports mascots. Free candy will be handed out by Mars and Ferrara Candy Company.

Neighborhood Bar Crawls and Adult‑Oriented Fun

Ravenswood Bar Crawl – 5:30 p.m., Oct. 28
Various locations, Ravenswood
Participants check in in costume, receive a wristband, swag bag and map, then visit 15 local businesses, including Margie’s Candies and the Ravenswood Tavern. The after‑party at KOVAL Distillery includes a costume contest. Tickets start at $35.98.

West Loop Bar Crawl – 4‑10 p.m., Oct. 31
Various locations, West Loop
Self‑guided crawl with stops at Esco and Bandit, offering exclusive drink specials for wristband holders. Costumes are encouraged. Tickets are $7.23.

Wrigleyville Crawl – 5 p.m., Oct. 31
Various locations, Wrigleyville
More than 20 venues, including the Cubby Bear and Murphy’s Bleachers, provide a free dinner buffet and festive drinks. Early‑bird tickets start at $15.97.

North Side Bar Crawl – Oct. 31
Lincoln Park, Gold Coast, Old Town
Sixteen bars waive cover fees and offer welcome shots, drink deals and “adult trick‑or‑treating.” Tickets are $12.85.

Family‑Focused Festivals and Activities

Lincoln Park Zoo Fall Festival – Through Nov. 1
2400 N. Cannon Drive, Lincoln Park
Free family fun includes s’mores, professional pumpkin carving, a pumpkin‑picking station, rotating animal enrichment, a Ferris wheel and photo opportunities.

Jack’s Pumpkin Pop‑Up – Through Nov. 1
1625 W. Le Moyne St., Goose Island
A month‑long pop‑up featuring corn mazes, carnival games, photo ops, food and full‑service bars.

Three Avenues Bookshop Spooky Book Fair – 6 p.m., Oct. 2
3009 N. Southport Ave., Lakeview
A BYOB, open‑house event with cider, sweet treats and book promotions. Costumes are encouraged; admission is free.

Idea Box Integrated Arts Costume Sale – Oct. 2‑4
5419 N. Lincoln Ave., Lincoln Square
A free event with a suggested donation, offering gently used costumes, props, jewelry and vintage clothing for Halloween.

Somerset Pumpkin Patch – 2‑5 p.m., Oct. 10
1118 N. State St., Near North Side
Patio pumpkin patch with decorating stations, face painting, a kids’ costume contest and fall food and drinks. Reservations recommended.

Jefferson Park Family Festival – 11 a.m.–2 p.m., Oct. 11
4822 N. Long Ave., Jefferson Park
Features a pumpkin patch, pumpkin decorating, petting zoo, costume exchange and the Jefferson Park Sunday Market. Free admission.

Wicker Park Family Day – 10 a.m.–2 p.m., Oct. 17
1425 N. Damen Ave., Wicker Park
Live performances, an all‑ages costume parade, a dog parade and costume contest. Suggested donation of $10 per family.

Nightmare Grounds Vendor Market – 2‑8 p.m., Oct. 17
747 S. Western Ave., Near West Side
Horror‑themed coffee shop hosts local artists, oddities, tarot readers and tattoo artists. Free admission with required RSVP.

Chicago Vintage Festival – Noon‑6 p.m., Oct. 17‑18
2 N. Riverside Plaza, West Loop
A Halloween market with 20 vendors, free tote bag giveaways on Saturday and mini pumpkins on Sunday. Free admission.

Unity Park Festival – 10 a.m.–2 p.m., Oct. 24
2636 N. Kimball Ave., Logan Square
Family‑friendly festival with a free pumpkin patch, DJ, costume parade, face painting, pumpkin decorating and a Día de los Muertos ofrenda. Free admission.

Unique Seasonal Experiences

JoJo’s ShakeBAR Pumpkin Paint Party – Through Oct. 31
23 W. Hubbard St., River North
River North patio transformed into a pumpkin patch with painting stations, signature desserts, festive cocktails and food.

Uni Uni and Haibay Pop‑Up – 3‑8 p.m., Oct. 25
1132 W. Argyle St., Uptown
A pop‑up featuring specialty drinks and Halloween‑themed treats.

With so many options, Chicago families can enjoy a safe, community‑focused Halloween season without missing out on the city’s vibrant cultural scene. Whether you prefer a free parade, a pumpkin‑filled zoo day, or an adult‑oriented bar crawl, there’s an event for every taste and age group.

Original reporting: Block Club Chicago — read the source article.