Searching for fall activities in Chicago? There are endless annual and seasonal options throughout the city worth discovering. From autumn-themed festivals to spooky attractions and natural foliage landscapes, it’s truly one of the best times to visit the Windy City.
If you don’t know what to do in Chicago in the fall, here are our top recommendations for locals and visitors alike.
Explore the Top 10 Fall Activities in Chicago: What to Do & See During the Autumn Season
Below are the 10 best things to do in Chicago in the fall, with public transit directions and why they’re worth checking out.
1. Haunted Halsted Halloween Parade
Source: Northalsted
The Haunted Halsted Halloween Parade isn’t your average parade. It’s a top-ranking fall event in Chicago for its exuberant costumes, larger-than-life floats, and fire-breathing street performers. There’s a costume contest where winners get a combined $4,000 in prizes and a sweepstakes for gift cards from local Northalsted businesses. You can also keep the night going at their after-party and awards show.
The annual parade is free to watch, taking place on Halloween night from Halsted & Belmont to Halsted & Brompton. The Belmont train station is only a five-minute walk via the Brown, Purple, and Red Lines. It starts at 6:30 pm and ends at 10:00 pm in the historic Northalsted neighborhood in East Lakeview.
2. Jack’s Pumpkin Pop-Up
Source: Jack’s Pumpkin Pop-Up
The Jack’s Pumpkin Pop-Up is the largest fall festival in Chicago, with the biggest pumpkin patch and corn maze in the city.
It features so many onsite activities for all ages, including:
•Photo ops with over 10,000 pumpkins
•Axe-throwing
•Carnival games
•Gem mining
•Fortune tellers
•Mechanical pig racing
•Dueling mechanical bulls
There are even four full bars with specialty fall-themed drinks like Hocus Pocus fireball-infused vodka cocktails, seasonal beers, and spiked apple cider. Ticket prices start at $30, with add-on attractions and group packages available.
It’s an outdoor seasonal event taking place from mid-September to the first week of November at Goose Island. The North/Clybourn train station is a 15-minute walk via the Red Line.
3. Printers Row Lit Fest
Source: Axios Chicago
The Printers Row Lit Fest is the largest free literary showcase in the Midwest and one of the biggest Chicago fall festivals. The annual two-day event has over 200 authors, over 100 booksellers, and attracts more than 100,000 people from all over to attend. There are also six indoor and outdoor stages for author panel discussions, open mic storytelling, children’s read-alongs, and more. You’ll find so many vendors lining the streets, from booksellers, literary podcasters, and authors. It’s a bookworm’s dream and perfect for all ages.
The Printers Row Lit Fest takes place in the second week of September on the streets of South Dearborn, from Ida B Wells to Polk in the Printers Row neighborhood. The LaSalle St station is a five-minute walk via the Blue Line.
4. Lincoln Park Zoo Fall Fest
Source: Lincoln Park Zoo
Another popular Chicago fall festival is the Lincoln Park Zoo’s Fall Fest. It’s free to attend with pumpkin patches, fall-themed animal feedings, and fire pit s’mores. There are also ticketed attractions, including a Ferris wheel, haunted history tours in the zoo’s cemetery, and penguin encounters. There’s even an adults-only costume-themed night with a live DJ and free face painting.
The Fall Fest takes place throughout late September into October in the Lincoln Park neighborhood. The Fullerton station is a 20-minute walk away via the Brown Line.
5. Night of 1,000 Jack-o’-Lanterns
Source: Chicago Botanic Garden
The Chicago Botanic Garden gets completely transformed to celebrate Halloween at their annual Night of 10,000 Jack-o’-Lanterns. Explore 385 acres of trails with thousands of artist-carved glowing pumpkins featuring monsters, celebrities, Chicago sports teams, and more.
It’s one of the largest jack-o’-lantern festivals in the world, where you can watch live pumpkin carving, see 150-pound giants, and experience the beautiful botanic gardens after dark. Costumes are encouraged, and you can enjoy fall season flavors, like butternut squash soup, homemade caramel apples, and pumpkin-spiced bourbon cocktails.
The Night of 1,000 Jack-o’-Lanterns runs throughout October. Adult tickets are $22 for members and $25 for non-members. Tickets for children ages 3 to 12 are $15 for members and $17 for non-members, and free for ages 2 and under. Ticket prices slightly increase if you buy them the day of the event, with VIP and group bundles also available.
The Chicago Botanic Garden is about a 40-minute train ride from the Ogilvie Transportation Center (OTC) to the Braeside station via the Union Pacific North (UP-N) Line. While not in the city itself, Glencoe is one of the surrounding Chicago suburbs worth travelling to.
6. Chicago Architecture Biennial
Source: Chicago Architecture Biennial
If you’re looking for non-spooky fall activities in Chicago, the Chicago Architecture Biennial is the largest architecture and design exhibition in North America. Absorb over 400 contemporary exhibitions and global artists from 40 countries.
It’s free and open to the public with many things to do, including:
•Film screenings
•Architectural tours and open houses
•Youth educational programs
•Public lectures
•Design workshops
The sites are scattered throughout downtown Chicago, but most are hosted in the Chicago Cultural Center in the Loop neighborhood. You can start there by travelling from the State/Lake station, which is a seven-minute walk away. The event runs from mid-September to the end of February.
7. Lakefront Trail
Source: City of Chicago
Soak in the stunning Chicago autumn season at the Lakefront Trail. It’s an 18.5-mile trail where you’ll see lakeside and cityscape views of changing foliage, connecting Lake Michigan beaches, and recreational activities along the way. From biking to rollerblading and onsite dining, it’s one of the most scenic places to visit this time of year.
The Lakefront Trail stretches from Ardmore Ave to 71st St. The Millennium Station is less than a 20-minute walk via the Metra Electric (ME) Line or the South Shore Line (SSL).
8. Chicago International Film Festival
Source: The Chicago International Film Festival
Looking for more Chicago fall festivals? Add the Chicago International Film Festival to your bucket list. It’s the longest-running international competitive film festival in North America and is held every year. Founded in 1964, it celebrates Chicago cinema with famous directors over the years, like Steven Spielberg and Quentin Tarantino.
Discover the best of cinematic storytellers from around the world with over 100 feature films and over 70 short films across various genres. From documentaries to comedy and animation, you’ll get immersed on the silver screen. There’s also red carpet galas, filmmaker Q&A panels, and an award ceremony.
Single-day tickets range from $17 to $50, depending on the ticket type, such as general screenings and closing nights. Festival passes range from $180 to $400, depending on membership, to access multiple screenings throughout the festival duration. You even share these passport passes with friends!
It’s an annual event taking place from mid to the end of October, with several venues across the city.
9. Wind & Souls Ghost Tour
Source: Ghost City Tours
If you want more scary fall activities in Chicago, the Wind & Souls Ghost Tour is an adults-only attraction. You must be 16 and older to attend due to its graphic tours, mature language, and disturbing themes. Learn about Chicago’s haunted history with unsolved true crime scenes, paranormal tales, and ghost stories that are sure to spook you.
Tickets cost $34.99 with group rates available. It’s a 90-minute tour starting at 9:00 pm at The Chicago Theatre on 175 N State St. The State/Lake train station is only a one-minute walk via the Brown, Green, Orange, Pink, and Purple Lines.
10. Chicago Architecture Center River Cruise
Source: Chicago Architecture Center
While this may seem like a summer attraction, the Chicago Architecture Center’s river cruise tours are a great fall activity because it’s not too hot or cold when on the water. It’s a highly rated 90-minute experience where you’ll learn about the city’s architectural history along the Chicago River on a luxury cruising vessel, called the First Lady.
Enjoy amenities, including a full-service bar, climate-controlled cabins, and outdoor seating on an open-air deck for picturesque photos. Tours run from March to November with tickets starting at $56, depending on group or private tour options. The Grand train station is a 15-minute walk via the Red Line.
Call Chicago Your New Apartment Home This Fall Season
Want to find your dream city apartment before the fall season kicks off? We can help.
At TLC Management Co., we have over 30 properties within the Chicagoland area with the local expertise to find you the perfect place to live. We also manage our own properties, offering our residents a better renting experience—as it should be.
Our convenient and luxury amenities include:
•Lakefront communities with exclusive access to a private beach and Lake Michigan
•Oversized windows and high ceilings in newly renovated apartments
•Resident Bark Parks with agility equipment and tree-lined trails
Browse our Chicago properties or contact us at info@chicagorentals.com to start scheduling tours today!
