27 Things to Do This Fall in Chicago

1. This fall, pumpkins are mandatory. We get ours at this Andersonville plant wonderland. The only question is whose big orange head will we carve into it. Hmmm.

2. Head over to Chicago Ideas Week (October 16 to 22), which goes beyond talks and lectures with one-of-a-kind interactives. That means everything from bicycle building at World Bicycle Relief to paint by numbers (with wine!) focused on the work of Jacob Lawrence.

3. Put on by the Chicago Architecture Foundation, this event (October 14 and 15) lets you take a rare look inside some of Chicago’s most gorgeous places (that you maybe hadn’t heard of).

4. Grand Geneva is only an hour from the city, but you’ll feel like you’re worlds away. Book a villa and spend your afternoon traipsing through the freshly fallen leaves at the Adventure Center. Make sure to pack a trusty pair of boots, like these riding boots from Lands’ End, and a slouchy turtleneck sweater.

5. The outdoor fire pits at this café-cum-bike-shop are so choice on a chilly fall day. Grab a latte (and maybe a new bicycle) inside, then park it with your best friend.

6. Surprise—Chicago is home to the longest-running competitive film festival, and its 53rd installment is happening October 12 to 26. Peep the schedule and buy your pass now.

7. Trendy yet tasteful styles for sizes 14 to 28? Praise. Eloquii brings its fab fashions to a one-year pop-up at the Shops at North Bridge. Get there...now.

8. Even if you’re tired of hearing about every other coworker’s and acquaintance’s training schedule for the Chicago Marathon, definitely show up and cheer them on from the sidelines. The sight of so many people running together is inspiring.

9. We’ll take any excuse to bask in the beauty of the Chicago Athletic Association Hotel, including this inaugural art book fair (November 16 to 19). With 150 independent publishers showcasing emerging artists and designers, you’ll be on beauty overload. 

10. Like chocolate-covered pretzels and, well, pretty much anything covered in chocolate, David Sedaris’s wry essays are one thing we can’t get enough of. Which is why we’ll be catching him when he hits the Auditorium Theatre on November 1.

11. Yeah, so it’s really never too early to think about Christmas, which is why you should witness the Millennium Park tree lighting on November 17. That’s also the day Christkindlmarket starts up.

12. Make supper last just a little longer with this sophisticated spin on the campfire treat. Bernie’s serves it up with butterscotch pudding, chocolate ganache, toasted marshmallows and graham crumble. Yum.

13. Rainy fall days were made for movie theater visits. What better movie than Manolo and what better theater than Music Box?

14. Volleyball and softball season may be over, but your love of league sports lives on thanks to The League. Every Monday night from September 11 to November 6, teams of at least four can battle it out at table tennis.

15. The Chicago Symphony Orchestra has some big (and surprising) names on its October calendar. On October 21, see jazz legend Herbie Hancock perform, while on October 10, Bill Murray teams up with German cellist Jan Vogler for an evening of music and literature.

16. We always treat fall as an excuse to stock up on cold-weather staples. The must-haves? A Lands’ End striped cotton sweater, dreamy camel peacoat and trusty pair of cords.

17. Skin Laundry’s 15-minute laser facials have already swept through L.A. and NYC, and now you can finally try them in Chicago. Head to the Michigan Avenue Ulta Beauty for the “Drybar of laser rejuvenation.”

18. Even at 50 years, MCA still manages to feel cutting-edge thanks to exhibitions from the likes of Jeff Koons and Kerry James Marshall. To celebrate the milestone, take advantage of the free admission, celebrity appearances, interactive artworks and beer garden (yes) on October 20 and 21.

19. Ipsento may have only two locations (unlike some other PSL makers), but trust us, it’s worth the trip to Bucktown or Humboldt Park for this award-winning drink.

20. Check into a haunted hotel. Sorry, but there’s no such thing as “too old” for Halloween. At least not while The Godfrey continues its annual party (October 28) with costumes, spooky cocktails and a haunted hotel floor.

21. If you’re more comfortable letting someone else dress up for Halloween, hit this family-friendly parade (October 21). Produced by LUMA8, it features costumed artists, giant puppets, fanciful floats and live music.

22. Experience one of ballet’s most tragic romances at one of Chicago’s most beautiful theaters(October 18 to 29)? Sign us up.

23. Walk, stand, eat, repeat. That’s our plan for this mobile smorgasbord (October 6 and 7), which runs alongside the West Town Art Walk.

24. The smoky flavor of wagyu beef back ribs feels just right this time of year, so we’re heading straight to Frontier for its new fall menu. Also on the agenda: blueberry and tarragon old-fashioned doughnuts with lemon curd ice cream.

25. Savor the last warm nights of Indian summer at Waydown, Ace Hotel Chicago’s top-floor bar. If things get chilly, enjoy the view from inside with one of mixologist Caitlin Laman’s sherry cocktails—it will warm you right up.

26. A powerful experience that can renew health and creativity, yoga nidra actually feels a lot like a really good nap. There’s no need to move during this two-and-a-half-hour session (October 13), but expect to be moved by spoken word, mantra and sound therapy.

27. Watch Dave Eggers, Natalie Moore and Margaret Atwood (swoon, swoon and swoon) as they are honored at the Carl Sandburg Literary Awards (October 11). Tickets are a hefty $1,000, but proceeds benefit the Chicago Public Library (worth it).