‘Tis the season of falling leaves, spooky haunts and pumpkin spice. With autumn just beginning and Halloween around the corner, every weekend in Chicago is full of fun activities sure to get you ready for sweater weather. I thought I’d share some that caught my eye – the lineup is frighteningly good!
Seasonal
Fall Festival & Bulb Sale | 10/4
There’s no rest for a gardener! Even though the warm season is wrapping up, now is a great time to get your hands on spring bulbs, and the Chicago Botanic Garden is here to help. Friday is exclusive to members, but the sale and festival are open to the public for the rest of the weekend! Peruse an extensive selection of over 200 bulb varieties, enjoy a caramel apple, and be sure to explore the straw maze.
Oktoberfestiversary | 10/12 – 10/13
Begyle Brewing and Dovetail Brewery’s celebration returns for its twelfth year in 2024. Donations at entry are sent to The Friendship Center and provide meals to those in hunger within the community. There will be food trucks, live music on two stages, beer from the brewery and even activities for the kiddos. Bring your family, dogs included, and support a good cause!
Arts in the Dark Upside Down Parade | 10/26
This marks the tenth anniversary of the parade, setting out to celebrate Halloween as the “artist’s holiday” in a street display of performance and creation. Typically hosting 50,000 viewers, the parade consists of floats and performances put together by cultural organizations, city youth programs, and artists of all sorts. For more Arts in the Dark events and news this month, check out their website!
Haunted Halsted Halloween Night Parade | 10/31
Northalsted boasts one of the largest Halloween parades in the city, with Fodor’s Travel ranking it one of the top ten in the country. This year’s celebration is hosted by Batty Davis and The Dancing Diva. Not only do viewers get to witness live drag performers and musicians amidst the parade, there will also be a costume contest with some pretty killer prizes! The parade concludes with an awards ceremony and afterparty for those who want even more fun.
Haunted Hues at the Color Factory | All Month
Step into a world where Halloween meets art at Haunted Hues in the Color Factory! From interactive installations to photo-worthy backdrops, this experience is all about vibrant colors with a spooky twist. Take the kiddos or make it a fun date night—either way, you’ll leave feeling inspired by the creative vibes and the playful surprises lurking around every corner. Halloween has never looked so bright!
Jack’s Pumpkin Pop-Up | All Month
It’s not officially fall in Chicago until you’ve visited Jack’s Pumpkin Pop-Up! With its sprawling pumpkin patch, corn maze, and Insta-perfect setups, this spot screams autumn fun. Whether you’re chasing after little ones or enjoying a night out with friends, Jack’s has something for everyone—food trucks, photo ops, and all the pumpkin spice your heart desires. Pro tip: go after dark for an extra magical vibe with twinkling lights that turn the place into a fall wonderland.
Autumn Fest at Gallagher Way | All Month
Fridays | 4-9pm
Saturdays | 11am-9pm
Sundays | 11am-7pm
Get ready for fall fun at Autumn Fest at Gallagher Way! This family-friendly celebration is packed with festive activities all season long. Kick off the fall vibes at Harvest Hangout with carnival games and a petting zoo, then mark your calendar for Boos & Brews—an adults-only night of drinks, live music, and spooky mingling. Fall Movie Nights are back, perfect for an evening out with the family, while the bravest can tackle the Fright Night Fall Movie, if you dare! For those looking to celebrate Oktoberfest, Gallagher Way is bringing Munich to Chicago with cold brews and hearty bites. And don’t miss the Wicked Halloween Party where costumes are highly encouraged for a night of tricks and treats. Pumpkin Party is also making a comeback, so there’s truly something for everyone at Gallagher Way this fall. It’s the ultimate autumn destination! Visit their website for all the details!
Family Fun
Boo! at the Zoo | 10/5 – 10/20
For the first few weekends in October, the Brookfield Zoo transforms itself into an all-ages Halloween hang. Costumes are strongly encouraged for kids (there will be so many great photo ops!), but everyone over thirteen is asked not to enter with full body costumes and/or head coverings. In between capturing memories and visiting the animals, guests can decorate pumpkins, enjoy a variety of goodies, join the daily costume parade, board a ride, see a magician… the list goes on!
Spooky Zoo | 10/19
Comer Children’s Hospital and Lincoln Park Zoo are working together to throw a trick-or-treat extravaganza!. Take the kids to get their treats and watch an interactive storyteller or musician, get hands-on in the craft zone and enjoy riding the carousel free of charge until 1:00 pm.
Lincoln Park Spooktacular | 10/26
Lincoln Avenue transforms itself into the perfect trick-or-treat street from Wrightwood to Webster! For three haunted hours, business along the Avenue become trick or treat spots just for you and the family.
Lincoln Scared + Ravenswoooood | 10/27
On the Sunday before Halloween, the business districts of Lincoln Square and Ravenswood rebrand themselves for even more safe, daytime trick-or-treating. The event is free and takes place between 11:00 am and 1:00 pm.
Trick or Treat on Southport | 10/28
For those with other plans over the weekend, Southport is throwing a neighborhood tick-or-treat fest on Monday from 4-7! Along with goodies for the kids, families can find fun themed activities, a pumpkin patch, local craft beer and wine, crafts, inflatables and music. Get spooky on Southport between Roscoe and Grace, rain or shine!
Bubbleween at Bubbles Academy | 10/20, 10/26, 10/27
For the tiniest Halloween fans, Bubbleween at Bubbles Academy is the perfect festive treat. This family-friendly event brings together music, movement, and a little spooky fun designed especially for the littles. Costumes are encouraged, and you’ll definitely want to capture the cuteness as your kiddos dance, sing, and explore interactive Halloween-themed stations. It’s a gentle way to introduce them to the magic of Halloween without the scares! Don’t forget to register!
Bubbleween Bucktown: 10/26 from 4-6pm
Bubbleween Highland Park: 10/20 from 10am-12pm
Bubbleween 900 Shops: 10/27 from 1-4pm
Night of 1,000 Jack-o’-Lanterns | 10/16-20 & 23-27
Enjoy a frightfully fun fall evening. Dare to experience the Garden after hours. This year’s professionally carved pumpkins feature recreations of popular album covers, haunted tales from Chicago, eerie cartoons, and more to get you in the Halloween spirit. You’ll find costumed entertainers and live pumpkin-carving demos along our paved outdoor path, as well as seasonal fare and drinks available for purchase. It’s (slightly) sinister fun for all.
Arts
West Town Art Walk | 10/4 – 10/6
The local shops in West Town turn into showcases for artists of all kinds over the weekend, boasting displays of fashion, music, cuisine, and visual arts. The walk is set up so that attendees can begin at any location they choose, and free pedicabs are offered for those needing assistance walking. Garden and home retail shops participate as well as the galleries, with some offering specials and presentations of their own!
Andersonville Arts Weekend | 10/4 – 10/6
It’s the 20th anniversary of this arts extravaganza, and Andersonville is showing up in style! For three days, the neighborhood becomes a walkable gallery of theatre, dance, music, makers, food, public installations and beyond. Take a self guided tour through the expositions or join a free guided tour – and if you’re looking to pair some tastings with your art, Sunday’s schedule includes a Fall Wine Walk!
Chicago International Film Festival | 10/16 – 10/27
The longest-running competitive film festival in North America belongs to our city, now on its sixtieth year! Chicago will be welcoming screenings of nearly 200 films from all over the globe, and showing them across seven local venues over twelve days. There are multiple ticket packages available for sale, and you can purchase tickets to individual movies starting an hour before screenings. CIFF’s programs span across several genres, including LGBTQ+ media, horror, new directors, shorts, documentaries and more, so there’s bound to be something to match your taste!
Chicago Fashion Week | 10/9 – 10/20
For the first time ever, the Windy City is launching its own fashion week! Many events will be free to the public with advanced registration, allowing the whole city to participate in this historic moment. Fifty events are taking place at different locations, presenting a curated selections of shows, retail events, educational panels, exhibitions and more. Local artists and industry stars alike will show their work, and existing awards within the industry have been incorporated into the celebrations to make it an unmissable twelve days!
Chicago Zine Fest | 10/5
Gather to celebrate local small press and independent publishers with a plethora of workshops and over seventy zine vendors selling and trading their works. All events are free to the public and take place during the day at the Columbia College Student Center – check out the list of exhibitors on their site or go in and see what draws your eye! Creatives should be sure to swing by one of the workshops and discussions, where they can learn about paper engineering, learn about making their own zines, and even hear about how zines are being innovated into DIY gaming. This year the organizers are joined by the Midwest Perzine Fest!
Food and Drink
Lincoln Square Ravenswood Apple Fest | 10/5 -10/6
It’s harvest season! From Lawrence to Sunnyside, Lincoln Avenue turns into an apple-lover’s haven, making it the perfect way to welcome autumn. Vendors will be selling any and all apple products – candy apples, freshly baked apple pies, apple bushels, hot apple cider, and original dishes. Children can hang out in the Kids Zone, and the music can be heard from the Giddings Plaza while you enjoy your sweet treats.
Chicago Beer Festival | 10/5
65 breweries are setting up shop in the Field Museum for a whole evening! Get samples of local seasonal beers for autumn, and browse the open exhibits with your fellow beer lovers.
Lincoln Park Wine Fest | 10/4 – 10/6
Jonquil Park’s tranquil setting is the perfect backdrop to this open-air wine market. Ticketed wine tastings will bring showings of several varietals, and food pavilions are located throughout the market in case you’re hungry. GA tickets include tastings and a commemorative wine glass, but if you go with the VIP ticket you also get additional specialty tastings, a private area to sip (and private restrooms), and a separate entrance to get around the lines.
Meals on Wheels Chicago Celebrity Chef Ball | 10/25
Dozens of Chicago’s top chefs are coming together at The Geraghty to create a completely unique evening for each table, presented by Meals on Wheels. Teams will be preparing, presenting and serving six courses before your eyes, and throughout the experience there are opportunities to win prizes and experiences during the cause-supporting auction. The ball will start off with a cocktail reception before commencing the culinary show, with charitable proceeds benefitting Chicagoans enduring food insecurity.
Windy City Events
Bucktown 5K and Kids Run | 10/6
It should be the perfect time of year for a run throughout this beloved Chicago neighborhood. The planned course is flat and kid-friendly, aiming to highlight Bucktown’s beautiful and historic architecture before ending with a block party. Winners will even have a chance to win prizes! This run is perfect for beginner and experienced marathoners alike, and little athletes will absolutely love the Kids Dash – and the donuts.
Bank of America Chicago Marathon | 10/13
More practiced runners may have their eyes on this iconic course, spanning an impressive 26.2 miles. The Bank of America Chicago Marathon is known as one of the most prestigious marathons in the world, claiming one of six World Marathon Major spots. Participants are estimated to be around 45,000, and nearly two million people will gather to watch and cheer. Athletes completing the course will see the sights of over two dozen neighborhoods, several of which will have their own special way of showing support!
Historic Pullman House Tour | 10/12 – 10/13
Long-time locals are surely familiar with this long-running house tour, which is celebrating its half-centennial anniversary this fall. Visitors will have a chance to take self-guided tours of iconic historic buildings found in Pullman, with many containing architectural features unlike any in the area. See homes of all sorts, from massive mansions to small personal homes, or head to participating visitor centers and buildings for even bigger sights. Additional highlights include live music and a classic car show!
Open House Chicago | 10/19 – 10/20
Chicago Architecture Center is throwing a free public festival to give us all access to incredible local gems, while also putting on over 40 talks, events, and demonstrations. Individual buildings, themed itineraries, event schedules and more are listed online, giving you every opportunity to tailor the festival to your specific interests. Open House Chicago is a part of Open House Worldwide and is one of the largest events of its kind in existence.
Fall Color 5K Run and Walk | 10/26
If you enjoy a run amidst a more natural kind of beauty, Morton Arboretum invites you to “unearth your inner tree champion” in this race! Breathe the fresh air and smell the fallen leaves as you make your way through the Arboretum’s East Side, providing the perfect escape from urban life. Afterwards, racers spectators both have the option of attending the postrace party to enjoy tunes, food and a complimentary beverage!
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