Amazing Things to Do In Chicago This October (Family Friendly/Kid Friendly Events Included)

Oct 2, 2025

October is the perfect time to head out for a day in the city with your family and friends. All month long during October, there are numerous events to celebrate Autumn and Halloween in Chicago! From games and rides, pumpkin picking and jack-o-lantern carving and costume contests, and even nature strolls and haunted walking tours, we’re sure you’ll have a blast! Check out our picks for amazing things to do in Chicago this October on today’s blog.

Jack’s Pumpkin Pop-Up is Chicago’s largest fall pumpkin patch featuring larger than life outdoor displays and over-the-top festive fun! This immersive exhibit engages visitors with all their senses. Enjoy carnival games, axe throwing, a giant corn maze, seasonal food and drink, photo ops, and more during the day. At night, the venue is transformed into an adult-oriented Halloween haunt; enjoy “BOO-zy” cocktails, food and drink under the lights, and a veritable all out fall festival party atmosphere. With two acres of fun, you’ll find something for everyone! Purchase tickets in advance so you don’t miss out. The event runs now through November 2nd; you must be 21+ to drink, 18+ to do axe throwing, but all ages are welcomed to the event as a whole.

Night of 1000 Jack O‘Lanterns at the Chicago Botanic Garden features an abundance of artist-carved pumpkins featuring Chicago Sports Teams, PLant inspired monsters, famous vampires, pets in costumes, and more. It features 75 giant pumpkins weighing in at more than 150lbs each! Plus, watch artists carve pumpkins live, enjoy costumed character walkarounds, and spooky fun frights around every corner. This family-friendly event is only here for a limited time: October 8th through the 12th, 15th through the 19th, 22nd through the 26th, each from 6:30PM to 10:30PM.

Lincoln Park Zoo Fall Fest is in operation through October 26th and is free admission for all ages. This event features family-friendly fall celebrations with pumpkin picking, s’mores roasting over the fire, games and rides, and entertainment. Each weekend there will be new and exciting things to explore. And feel free to stroll the seasonally decorated gardens and free musical entertainment while you’re there! Attractions in the zoo are ticketed entry.

The Feminist Bird Club Chicago Fall Bird Walk is hosting a free walk with Kelly Ballantyne at LaBagh Woods on October 4th starting at 9AM. This accessible and inclusive nature walk will detail the patterns of fall migration for birds, and help you learn about native species as well. Families are welcome, and children need not RSVP. Register in advance and request a pair of binoculars on loan if you’ve not already got a pair.

Chicago Botanic Garden Bird Walk Fall Migration events will take place on October 4th and 18th from 8AM to 9:30AM. On the first bird walk, visitors can expect to see warblers, vireos, and flycatchers; on the second walk, it may be more common to spot ducks, sparrows, and hawks. The event costs $24-$30 per person, and pre registration is required.

Femmes and Thems Bike Chicago will be hosting an 8-mile bike ride on October 5th culminating with a dance performance by Comedy Dance Chicago. The group is meeting at 1PM at the Welles PArk Gazebo and pedaling 10-12mph pace/ All wheels are encouraged from e-bikes to scooters to cargo bikes. Children and pets are welcome passengers! The event is free, register in advance.

Enjoy a one-of-a-kind, limited time only engagement by native Chicagoan Tim Ramirez this month at Wild Mile. With his Hydrosonic Light Show, the artist creates visuals in real time utilizing overhead and slive projects, liquids, handmade creations, and other experimental forms of visual media. This 2-hour performance experience is free and is soundracked to a unique playlist of music. Performances of the Hydrosonic Light Show will be from 8:30PM to 10:30PM on October 7th and 14th.

The Morton Arboretum is hosting the 15th annual Glass Pumpkin Patch, in which thousands of one-of-a-kind glass pumpkins will be on display. Each work is handcrafted by glass artists who will display their works on the West Lawn next to the Visitor Center. The Glass Pumpkin Patch will be on view from October 10th through the 12th, and admission is included with a GA ticket to the arboretum.

On October 18th from 10AM to 1PM at Steelworkers Park, join in the festivities for South Chicago Dia de Los Muertos Workshops and Ofrenda Walk. Explore cultural and spiritual connection through art making workshops. The event includes free workshops during the community climb at Steelworker Park Climbing Wall, and a lecture on the meaning and significance of Ofrendas.

We always love a good walking tour, but bonus points for the spooky atmosphere and ghost hunting that comes with October! The “Shadows on the Street: Haunted Tours of HIstoric Prairie Avenue” is a walking tour after dark starting at the Glessner House. Learn about the mysterious deaths and unexplained sightings on the grounds, and other haunting bits of Chicago history! Cost is $16-$20 per person, registration is required. Shadows on the Street Tours take place on October 25th from 6:30-9:30PM.