Greater Grand Crossing Family-Friendly Fall Activities 2026

Chicago Free

Community trunk or treat gathering featuring candy and a costume contest.

Illustration of a giant pumpkin float rolling down a town street past costumed figures, with orange balloons and confetti (Haunted Halsted Halloween Parade)

Haunted Halsted Halloween Parade

Chicago 7 mi Free

Chicago's Halloween night parade featuring a costume contest with cash prizes.

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (West Chicago Halloween Festivities)

West Chicago Halloween Festivities

West Chicago 8 mi

Family trick-or-treating and fall activities in downtown West Chicago.

Illustration of a child in a witch costume holding a pumpkin bucket on a leafy sidewalk lined with glowing houses at dusk (Spooktacular Trick or Treat)

Spooktacular Trick or Treat

Sun, Oct 25

Berwyn 11 mi

Family Halloween trick-or-treating celebration at Proksa Park

BOO-seum Bash

Sun, Oct 25

Chicago 11 mi $$

Family Halloween fun featuring animal encounters, owl pellet dissection, and crafts.

Jack's Pumpkin Pop-Up

Sep 19 – Nov 1

Chicago 10 mi

Features downtown Chicago's only corn maze and over 10,000 pumpkins.

Lincoln Park Zoo Fall Fest

Sep 25 – Nov 1

Chicago 11 mi Free

Free harvest festival featuring animal enrichment, rides, and pumpkin carving.

Illustration of striped market booths and pumpkin displays on a street with small clay figures under orange autumn trees (BooPalooza and BarkPalooza)

BooPalooza and BarkPalooza

Chicago 11 mi Free

Community festival featuring all-ages and dog costume parades, music, and games.

Spooktacular Trunk-or-Treat

Oct 24 – Oct 25

Chicago 11 mi

Neighborhood trick-or-treating at local businesses across Lincoln Park.

Illustration of a clay altar with candles and marigolds, skull decorations and small dancing figures under paper banners (Slightly Spooky Saturday)

Slightly Spooky Saturday

Chicago 9 mi Free

Trick-or-treating, live entertainment, and free workshops at Navy Pier.

Fall Fest at Oak Park

Sun, Sep 27

Oak Park 12 mi Free

Carnival rides, live bats and skunks, and pumpkin carving demonstrations.

Monster Madness

Lisle 24 mi $$

Festive autumn fun fair for children with games, inflatables, and hayrides.

Hull-o-ween Open House

Chicago 8 mi Free

Folklore storytelling, 1920s silent films, and custom spooky poetry on-site.

IPH's Fall Fest on The Riverwalk

Sep 19 – Oct 31

Chicago 8 mi $

Riverwalk festival featuring boat hayrides on the Chicago River and pumpkin patch.

The Great Pumpkin Party

Sat, Oct 3

Orland Park 17 mi

Family fall festival with pony rides, hayrides, and costume contests.

Illustration of two small costumed children and a witch among pumpkins, hay bales and autumn trees on a sunny lawn (Monster Fun Halloween Wristband)

Monster Fun Halloween Wristband

Lombard 22 mi $$

Unlimited indoor attractions and free parkwide trick-or-treating in costume.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (Howl-O-Ween at Wolfe Wildlife)

Howl-O-Ween at Wolfe Wildlife

Oak Lawn 8 mi $

Halloween games and activities along the Wolfe Wildlife walking path.

Halloween Hoot and Howl

Fri, Oct 2

River Forest 14 mi Free

Family event featuring pumpkin painting and live music.

Illustration of costumed figures mingling among striped festival booths, pumpkins, and orange autumn trees at dusk (Nightmare on Grounds St. Market)

Nightmare on Grounds St. Market

Chicago 8 mi Free

Chicago Halloween and horror market featuring local vendors, tattoos, and oddities.

Illustration of glowing jack-o'-lanterns, candles and scattered seeds on a wooden table under string lights at dusk (Pumpkin Carving & Painting at Midwest Coast Brewing Company)

Pumpkin Carving & Painting at Midwest Coast Brewing Company

Thu, Oct 29

Chicago 9 mi $$$

Includes a pumpkin, carving supplies, paint, and your first drink.

Illustration of small costumed figures and a witch playing on a sunny lawn with pumpkins, hay bales, a tent and orange trees (Hands-On Family Spooky Snacks and Sweet Treats)

Hands-On Family Spooky Snacks and Sweet Treats

Chicago 14 mi $$$

Kids and adults cook festive savory bites and sweet treats together.

Illustration of small costumed figures and a witch playing on a sunny lawn with pumpkins, hay bales, a tent and orange trees (Spooktacular Fun Night)

Spooktacular Fun Night

Fri, Oct 30

Westmont 19 mi Free

Free family games, crafts, and silly fun with Wacky Drac.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (Trick or Treat @ Woodson Branch)

Trick or Treat @ Woodson Branch

Trick-or-treating for children in Pre-K through eighth grade.

Pumpkin Fun @ Woodson

Thu, Oct 22

Bring your own pumpkin to decorate using library-supplied materials.

Pumpkin Painting

Summit 10 mi $

Hands-on pumpkin decorating session designed for kids and families.

Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees (Halloween and Fall Story Hour @ Children’s Services)

Halloween and Fall Story Hour @ Children’s Services

Mon, Oct 19

Gary 18 mi

Seasonal story hour hosted at the library's Children's Services department.

Illustration of two small costumed children and a witch among pumpkins, hay bales and autumn trees on a sunny lawn (Scarecrow Craft @ Kennedy Branch)

Scarecrow Craft @ Kennedy Branch

Tue, Oct 20

Children's scarecrow craft session at the Kennedy Branch library.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (Halloween Story Time & Craft @ Woodson)

Halloween Story Time & Craft @ Woodson

Mon, Oct 26

Halloween story session and craft activity held at the library branch.

Pumpkin Fest at Cosley Zoo

Oct 1 – Oct 31

Wheaton 27 mi $

Thousands of pumpkins line the zoo lawn alongside daily scavenger hunts.

Family Fall Fest 2026

Mon, Oct 12

Lockport 27 mi $

Fall festival featuring hayrides, a petting zoo, inflatables, and Scarecrow Lane.

Harvest Fest

Sat, Oct 3

Medinah 27 mi Free

Annual community festival featuring live music, hayrides, games, and food trucks.

Family Spooktacular

Oct 24 – Oct 25

Naperville 28 mi $

Not-so-scary Halloween fun with Disney tribute concerts and historic trick-or-treating.

Illustration of small costumed figures and a witch playing on a sunny lawn with pumpkins, hay bales, a tent and orange trees (10/16: Spooktacular Halloween Stroll)

10/16: Spooktacular Halloween Stroll

Fri, Oct 16

Wheaton 27 mi $

Evening zoo stroll featuring seasonal decorations and pumpkin decorating.

Trick or Treat Trail