17 Great Chicago Fall Date Ideas


17 Great Chicago Fall Date Ideas
You don't have to be in Chicago to enjoy the list of great fall date ideas!

So you met a great date at one of our Nut & Bolts Singles Parties last month and now you need to impress them with a great an unique date? Easy! It’s fall in Chicago- here are the best things to do in fall in Chicago. Surprise your date with one of these top fall date ideas and you’ll be cozied up with them all winter!


  • Hop on your bike and head to a bike trail. The crisp (but still warm) air is something us Chicagoans will be missing in a few months.
  • Have a bonfire in the backyard.  It doesn’t have to be huge or anything- roast some marshmallows and make out like high school kids.
  • Attend your old high school football game; show your date around your home town.
  • Check out Pumpkin Festival in Dekalb County. It has a parade, pie eating contests, carnival rides and 1,000’s of decorated pumpkins.
  • Head out to Oktoberfest in Naperville for some live music, beer and brats.
  • Get terrorized on the lake front. Take your date to a haunted house just off of Lake Shore Drive and Fullerton. If it’s nice out, head over to Lincoln Park Zoo afterwards.
  • Hayrides and pumpkin picking! Drive down to Tinley Park and enjoy fall!
  • Seasonal beer sampling and the fall foliage is a great way to get a little boozy while enjoying the fall colors. The Chicago Botanic Garden offers both and is a great date idea!
  • A little bit of a drive, but well worth the trip. Head out early on a Saturday with a group, or just the two of you and enjoy some fall hiking and outdoor sports at Starved Rock State Park.
  • Freebies in October- Saturdays in October: Free admission to the Art Institute of Chicago from 5-8pm Thursdays in October: Free admission to the Museum of Contemporary Art
  • FRIGHT FEST! What better way to get her to curl up next to you? Maybe skip the cockroach eating contest if you’re looking to get frisky later on.
  • If roller coasters aren’t your thing but you still want that fear based adrenalie rush, check out the list o Illinois haunted houses here.
  • Sticking with the haunted and scary theme- and staying in Chicago- check out Weird Chicago Bus Tours for a scary tour of Chicago. Learn our haunted history.
  • Want to get a little more animalistic? The cooler fall weather brings out the animals, and you’ll love seeing them! Brookfield Zoo’s got a special fall or Halloween theme going on this month too!
  • Do you have Columbus day off? Ask your date to the parade! Grab a bite downtown and enjoy the loop in the fall.
  • Downtown Chicago has “Chicagoween” every year and can be fun to check out the vendors. A great daytime date and can be followed up with a romantic dinner at one of my favorites, Rosebud.
  • What’s more romantic than getting lost in a corn field? How about zorbing in a giant bubble ball down a hill, or zip lining over Illinois corn fields! Check out Richardson Adventure Farm for a ton of fall adventures.

Are you still looking for a great guy or gal to date? Mingle Around has events every week in Chicago and the suburbs- come out and mingle with us, I’m sure you’ll find someone great to invite to one of these fall date ideas. Visit us online at

This article was originally published at . Reprinted with permission from the author.

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