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Are you ready to embrace the spooky season in Chicago? Fall is the perfect time to experience the Windy City, with events ranging from festive hayrides to vibrant Halloween bar crawls. I have explored some of the best fall activities in Chicago, and I am thrilled to share my experience. Here are my top ten must-do activities for the season!
1. Fall Fest On The Riverwalk
The Fall Fest On The Riverwalk is a cozy fall escape with stunning river views, hayrides, and everything pumpkin spice. Imagine strolling along the Riverwalk, wrapped up in your favorite sweater, sipping on warm apple cider while taking in the autumn colors reflected in the water. With hayrides on the river, live music from 1 to 4 and 5 to 8, a pumpkin patch, apple cider donuts, fall cocktails and beer, photo ops, and games, it is the perfect fall festivity to enjoy with friends and family. It runs every Saturday through October 31, noon to 8 PM, at Island Party Hut, 355 Chicago Riverwalk. Early bird tickets start at $5, and tickets include a welcome shot for those 21+ or a fall drink for kids and non-drinkers. Mark October 31 on your calendar: the finale is the DOG HOWL-O-WEEN dog costume party and parade, with parades at 2, 3:30, and 5 PM. Do not forget to use code TWTR for a discount when purchasing your tickets!
2. Night of 1,000 Jack-o’-Lanterns
There is nothing more worth the trip than a fall night glowing with more than 1,000 hand-carved pumpkins. Night of 1,000 Jack-o’-Lanterns lights up the Chicago Botanic Garden in Glencoe on select nights: October 7 to 11, 14 to 18, and 21 to 25, 2026, from 6:30 to 10:30 PM. Some of the pumpkins weigh up to 150 pounds, and along the trail you will find live carving demonstrations, costumed entertainers, and seasonal treats. Advance tickets start at $24 for adults and $17 for kids ages 3 to 12, and popular nights sell out, so grab yours early.
3. Boo! at the Zoo
Photo: Kris Nelson
Boo! at the Zoo is Brookfield Zoo Chicago’s family-friendly fall tradition, running October 3 through 25, 2026. Think festive decor, not-so-scary surprises, trick-or-treating on the weekends, costume parades, inflatables, and Halloween-themed photo ops, all included with general zoo admission ($32.95 adults, $23.95 kids ages 3 to 11, free for kids under 2 and zoo members). Zoo hours are 10 AM to 5 PM on weekdays and 10 AM to 6 PM on weekends during the event. Costumes are encouraged, so bring the little ghosts and ghouls and make a whole day of it.
4. Trick or Drink Chicago Halloween Bar Crawl (3 Days)
If you are looking for an adult-only Halloween celebration, the Trick or Drink Halloween Bar Crawl is an epic choice. This year it runs three days: Saturday, October 24, Friday, October 30, and Saturday, October 31. You will experience Chicago’s most lively bars decked out with Halloween decor. I had a blast trying themed drinks, dancing to live DJ sets, and meeting other partygoers. Check in at Headquarters Beercade (213 W Institute Pl) to grab your wristband and map, then enjoy no cover and drink specials at more than a dozen participating bars, from Billy Goat Tavern to the RIU Rooftop. Whether you are a ghost, ghoul, or goblin, this bar crawl is the place to be. 21+ with valid ID.
5. The Boos & Booze Chicago Halloween Bar Crawl (2 Days)
For a two-night Halloween extravaganza, check out The Boos & Booze Chicago Halloween Bar Crawl in River North. One ticket covers both days: Friday, October 30 from 4 to 11 PM and Saturday, October 31 from 2 to 10 PM. Start at Headquarters Beercade and follow the music through River North, with no cover at participating bars, drink specials, 5+ complimentary shots, and admission to the official after party at Fame. Tickets start at $10, and costumes are a must. The lively atmosphere makes it feel like the entire city is celebrating with you. This event is the ultimate way to make unforgettable Halloween memories. 21+ with valid ID.
6. Dining in the Dark Chicago at About Last Knife
Dining in the Dark is an experience like no other. With a blindfold on, you are led to your table at About Last Knife in Arlo Chicago, and the rest is a surprise! This immersive dining experience heightened my senses and brought out a whole new appreciation for food. You pick a Red (meat), Blue (seafood), or Green (vegan) menu and discover the secret three-course menu one bite at a time. Tickets run about $67 per person, plus a $10 food gratuity, with various fall dates available. Perfect for a date night or a night out with friends, this unique experience adds a bit of mystery to your fall festivities.
7. BITE! by AirOtic Soiree
A little sultry, a little spooky, and a lot of fun: BITE! by AirOtic was one of the most thrilling nights of my fall season. This Halloween-themed cirque-burlesque cabaret blends spine-tingling burlesque with high-flying circus acts: seductive vampires, aerial acrobats, and haunting visual surprises in a dark, shadow-drenched atmosphere. It returns to Experience 868 (868 N Franklin St) for a strictly limited run, October 9 through 31, 2026: shows nightly at 7 PM (doors 6 PM), plus two shows on Halloween itself at 4 PM and 6 PM. Tickets start at $65. It is sexy, spooky, and spectacularly unhinged, and a bold way to celebrate the season. 21+ with valid ID.
8. Gangsters and Ghosts Tour in Chicago
Explore the darker side of Chicago with the Gangsters and Ghosts Tour. Walking through the city’s historic streets, I learned about notorious gangsters and legendary ghost stories. The guide was fantastic, weaving together true crime and the supernatural. This two-hour walking tour runs daily at 11 AM, 1 PM, 4 PM, and 8 PM, departing from the Loop. Perfect for history buffs and Halloween enthusiasts alike, this tour gives you a glimpse of Chicago’s haunted past, and past guests rate it 4.7 out of 5. Do not forget to use code THERUSSELLS10 for a discount on your ticket!
9. Neon Brush Chicago: Sip & Paint
This Neon Brush Sip & Paint night is a colorful way to unleash your creativity! With a glass of wine in hand, I painted under blacklights, creating neon masterpieces in a fun and relaxing atmosphere. This 90-minute glow-in-the-dark painting experience is all about great tunes, good company, and drinks available to keep the creativity flowing. Whether you are a seasoned artist or a beginner, it is a fantastic evening activity to do with friends. Check the ticket page for this fall’s venue. 21+ with valid ID.
10. Illumination: A Halloween Gala
Nothing says Halloween like a grand gala, and the Illumination Gala is back for its tenth and final year. This is your last chance to experience Chicago’s most vibrant Halloween party: Saturday, October 24, 2026, from 9 PM to 2 AM at Vertiport Chicago (1339 S. Wood St.). Expect immersive illuminated art installations, live performances, prominent DJs, costumed servers, floating dessert tables, seven full-service bars, and even helicopter rides over the city and lake. General admission is $150, and every ticket supports a great cause: the event has raised over $14 million to fund research for treating rare diseases. Dress to impress, because this final encore is all about stepping up your Halloween game in the most chic way possible.
Plan Your Chicago Fall Adventure!
Chicago in the fall is full of vibrant colors, incredible activities, and Halloween spirit! From riverwalk festivals to spooky tours, there is something for everyone. These events are just the tip of the iceberg when it comes to fall things to do in Chicago, so grab your tickets and get ready for an unforgettable season.
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