25 Fun Things to Do in Chicago This Fall
As the vibrant city of Chicago begins to transform into a colourful autumn wonderland, there's no shortage of exciting activities to enjoy this fall. Whether you're a local or just passing through, Chicago, Illinois offers a range of fun experiences that capture the essence of the Chicago fall season. Ruby Travels has you covered with a list of 25 fun things to do in Chicago this fall. From foliage-filled parks to cultural festivals and delectable dining, there's something fun for everyone.
25 Things to Do in Chicago This Fall
1. Frolic in Chicago Fall Foilage: You don’t need to escape to the mountains to enjoy the colours of Fall foliage. Whether you are wandering through one of Chicago’s parks or just strolling the leaf-strewn streets, you’ll find fall foliage wherever you go.
2. Pumpkin Patch Fun: Embrace the season by visiting a local pumpkin patch. Many offer not only pumpkins but also hayrides and apple-picking. Don’t want to leave Chicago? Luckily you don’t have to with Jack’s Pumpkin Pop Up, Chicago’s only pumpkin patch, and home to the largest Halloween festival in Chicago.
3. Go Apple Picking Near Chicago: Apple picking is always one of my favourite fall activities. Within an hour's drive of Chicago, you have plenty of options for apple-picking orchards that let you pick your own apples. Many offer hot apple cider and apple cider donuts so you can fully indulge in the fall flavours.
4. Take a Hike Near Chicago: Wanting to trade the city for some nature? Thankfully, you don't need to go far because there's no shortage of great hiking spots near Chicago. Whether you decide to stay in Illinois and explore the likes of Starved Rock State Park, or cross state borders to the Indiana Dunes State Park, you’ll be hitting the trails in no time.
5. Wander Lincoln Park Zoo: Fall is a fun time to visit Lincoln Park Zoo. The animals are still active, and the zoo often hosts Halloween-themed events. Bundle up and don’t forget to bring a thermos with something warm to sip while you marvel at this inner city zoo.
6. Lincoln Square Apple Fest: Indulge in the flavours of fall at the Lincoln Square Apple Fest. Enjoy apple cider, apple pie, and more apple-inspired treats at this annual festival that celebrates the beginning of autumn.
7. Take a Haunted Tour: Get your scare on with Chicago's many haunted houses and Halloween-themed attractions. Popular choices include HellsGate Haunted House and 13th Floor Haunted House. Stay spooky!
8. Board a Fall Boat Cruise: Explore the city's unique architecture by taking a boat tour along the Chicago River. Many of Chicago’s boat tours are still setting sail through the fall season, like the Chicago Architecture Center River Cruise aboard Chicago’s First Lady through late fall (weather permitting).
9. Dive into Deep Dish: As the weather cools down, it’s the perfect opportunity to dive into some Chicago deep-dish pizza. My favourite deep dish is Pequod’s Pizza in Lincoln Park with its caramelized crust. BRB, drooling just thinking about it…
10. Attend a Bears Game: Football season is among us. Why not take advantage of the weather before the snow begins and attend a Chicago Bears game at Solider Field? Not just for the sports enthusiasts, Soldier Field has in-stadium game day activities for all ages.
11. Chicago Gourmet: Foodies, rejoice! The Chicago Gourmet Festival showcases the city's culinary prowess with food tastings, wine pairings, and cooking demonstrations.
12. Get Haunted at Haunted Halsted Halloween Parade: Watch on in awe at one of the top ten Halloween parades in the USA. Set within Chicago’s landmark LGBTQ Northalsted neighbourhood, the annual Haunted Halsted Halloween Parade is free to watch and happens rain or shine.
13. Cheer on the Chicago Blackhawks: Get your ice hockey on and cheer on the Chicago Blackhawks at Chicago’s United Center. The NHL season usually starts mid-October and runs until April.
14. Catch a Film Fest: Fall in Chicago is an excellent time for movie lovers. In October, the city hosts the longest-running competitive film festival in North America. Chicago International Film Festival is an esteemed event featuring films from around the world.
15. Chicago Ghost Tour: Walk with Chicago Ghost Tour as the sun sets through downtown Chicago and hear first-hand about some of the most gruesome and creepy Chicago stories. Leave the kiddos at home because this is one for the adults.
16. Art Institute of Chicago: Delve into Chicago's cultural side by visiting the Art Institute. Marvel at world-renowned artworks and enjoy the warmth of the museum's interiors.
17. Chicago Farmers Markets: Visit local farmers' markets, such as the Green City Market or the Logan Square Farmers Market, to savour fresh produce and artisanal products. Enjoy its final few weeks before the season ends, usually around the end of October.
18. Night of 1,000 Jack-o'-Lanterns: Monstrous vibes meet crisp fall evenings at Night of 1,000 Jack-o'-Lanterns, where artist-carved pumpkins light your way through the Garden after dark. You'll find costumed entertainers and live carving demos along the paved path, as well as seasonal light fare and drinks for purchase. Enjoy this slightly sinister fun for all.
19. Take a Riverwalk: Enjoy the crisp autumn air with a leisurely walk along the Chicago Riverwalk. The scenery is breathtaking as the trees along the riverbanks turn various shades of red and gold. Enjoy it before it turns to ice.
20. Catch Fall Favourite Movies at the Drive-In: Enjoy your favourite movies under the stars at ChiTown Movies Drive-In. Movies rotate every week at their Pilsen location, thankfully this is one you can enjoy year-round.
21. Get Lost In The Richardson Corn Maze: Did you know the largest corn maze in the world is in Illinois? Richardson Adventure Farm Corn Maze boasts up to 10 miles of trails winding through 28 acres of live corn. At this corn maze, you’re in for a challenge and a treat!
22. Sip Some PSL (Pumpkin Spice Latte): It wouldn’t be fall without drinking down a pumpkin spice latte. You’re in luck in Chicago as most coffee shops around Chicago will offer their own version of the PSL. My favourite pumpkin drink will forever be Starbucks’s Pumpkin Cream Cold Brew.
23. Face Your Fears at Nightmare on Clark Street: Get your thrills and chills on at Nightmare of Clark Street’s Haunted House.
24. JoJo’s Pumpkin Patch: JoJo’s bringing fall to all. Get into the fall spirit with their pumpkin patch shakes, specialty cocktails, caramel apples and more. Enjoy their fally decked-out patio where they host pumpkin painting mixology classes and more.
25. Halloween Bar Crawl: Trick or drink your way through one of Chicago’s many Halloween bar crawls. Most bar crawls will include drink specials and entrance to some of the best bars in Chicago.
Fall in Chicago
Chicago is a city that truly comes alive in the fall. With an abundance of cultural events, natural beauty, and seasonal festivities, there's no shortage of things to do this autumn. Whether you're captivated by the city's architecture, craving delicious fall treats, or looking for family-friendly fun, Chicago has something for everyone. Make the most of this wonderful season in Chicago, Illinois and create unFALLgettable memories.
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