Posted 3 days ago
5 MIN READ -- Crisp air, cozy sweaters, and vibrant colors mean one thing—fall has arrived in Chicago! From festive riverfront celebrations and pumpkin patches to colorful Halloween experiences and seasonal treats, the city is buzzing with ways to soak in the season. This guide is your go-to for the best fall happenings in the Chicago Loop—perfect for family outings, date nights, or a fun day with friends.
skeletons On State
Twenty monstrous skeletons line State Street and pay tribute to local Loop and Chicago institutions. Experience this skeleton takeover and snap a pic with these bone-chilling displays. These skeletons will be dressed to the bones from October 1 through November 3. Learn more here.
sundays on state
Sundays on State, Chicago Loop Alliance’s internationally acclaimed event series, returns October 5! Neighbors from every Chicago community and beyond unite for a free, interactive block party, while safely enjoying art, culture, active recreation, food, drinks, shopping, and local attractions in the heart of everyone’s neighborhood – the Loop. Learn more here.
creepy cruise
Cruise the Chicago River amidst twilight tales of the city you never knew existed. From mysterious sightings to creepy haunts, mobsters and more, guests will hear stories of Chicago’s darker side on First Lady’s newest nighttime tour. Learn more here.
Haunted hues at Color factory
Experience Halloween like never before at Color Factory with a colorful celebration filled with seasonal treats, playful photo ops, and a brand-new all-ages scavenger hunt. Tickets (starting at $29) include fall-flavored bites and entry to immersive exhibits, from the fan-favorite pumpkin and Gradient Remix ghosts to a Haunted Hues room and a ball pit crawling with whimsical spiders. Gather your ghouls and goblins for a Halloween event that’s as vibrant as it is spooky. Book your visit here.
Howl-o-ween canine cruise
Celebrate October with furry friends dressed in their best costumes. During the first two weekends of the month, enjoy pumpkin dog treats, a doggie costume contest, and plenty of photo-worthy moments as you and your pup soak up the season together. Guests can also enjoy a non-themed Canine Cruise on other weekends which welcome leashed pups aboard for a narrated tour filled with architecture, history,
and dog-friendly highlights. Learn more here.
lurking in the loop
Chicago Loop Alliance is thrilled to present the first-ever spooky bar crawl through the Loop! Grab a date or rally your friends and get ready to explore 13 unique bars scattered throughout the heart of the Loop. The only requirement? Come dressed in your Halloween best!
This one-of-a-kind event is free and open to the public, taking place October 25 from 8 p.m. to midnight. If you’re ready to sip, stroll, discover special drink and food deals, and spook your way through the city, be sure to RSVP here.
fall fest on the riverwalk
Throw on your favorite sweater and head to Fall Fest on the Riverwalk at Island Party Tiki Hut, where autumn fun goes far beyond pumpkin spice. Enjoy live music, hayrides on the river, seasonal cocktails and cider donuts, plus a pumpkin patch, games, photo ops, and more—all set against the backdrop of the Chicago Riverwalk. Tickets include admission, a welcome drink (for both kids and adults), and access to all the festive activities, making it the perfect spot for family outings or a day with friends. Learn more here.
