Autumn in Chicago from A-Z

Apple fests

This is the one time of the year where “apple-flavored anything” is a wholly acceptable lunch (or dinner or breakfast) option. Lincoln Square’s is among the best of the best! 


Chicago likes to play well into the fall these days. Whether your train stop is Addison or 35th, there’s nothing quite as exciting as the seventh inning stretch. Even your toddlers can enjoy a White Sox game!


Pros: Midnight Circus in the Parks brings a fantastic experience to the masses while providing a boon to the local city parks. Cons: At least one member of the family will be inspired to join the circus. (You’ve been warned.)

Día de los Muertos

If your Day of the Dead knowledge doesn’t go much further than sugar skulls, Pilsen’s National Museum of Mexican Art can fill in some details and beautifully at that with their free event.

Election Day

You don’t have to talk to your kids about politics, but it’s important to bring up some issues and how Americans can exercise their right to vote. Learn how to create meaningful conversations with your kids. 

Fall Playdate

Chicago Parent is back with their Fall Playdate! Head out to Naperville for the ultimate day of play for families with kids 2-14. This year, dress up with your family to participate in a costume parade and contest with fun prizes.


Namely, those stunning displays at the Chicago Botanic Garden. From the Fall Bulb Festival to the Spooky Pooch Parade, fun’s in bloom all season long.


Don’t you just love Halloween in Chicago? Find out all the best Halloween events for kids happening near you.

Indian summer

Temps are still balmy into October? Grab a picnic dinner to share at any of the Chicago Park Districts and stave off bedtime for a little while longer.

Jogging paths

Fall’s the clear winner for “working out conditions.” The Bloomingdale Trail (aka The 606) and the 1.2k acre’s worth of Lincoln Park paths and greenery are terrific places to pretend to run!

Lake Michigan

You can keep your early spring breezes; fall on the lake is an unparalleled experience. Don’t have a friend who docks in Belmont Harbor? That’s OK, you’ve got 18 miles of lakefront to play on.

Nature preserves

Hoodie weather is here at last! So it’s the absolute best time to explore the nature paths at LaBagh Woods and the North Park Village Nature Center


Oh, Midwest, how we love you and your abundance of pick/eat-as-you-go apple orchards. (And yes, sometimes Wisconsin and Indiana orchards count as “greater Chicagoland area.”) Find lots of fall fun at these local farms

Pumpkin patches

Choose carefully: Does your ideal patch feature a gigantic, metal, pumpkin-eating dinosaur a la Goebbert’s Pumpkin Patch? How about a Hootenanny Train through Pumpkin Junction like, for example, at Bengtson’s Pumpkin Farm?


Proof that peace can be found in a city: the quiet oasis of the Lurie Garden, the calm Alfred Caldwell Lily Pool and the stunning stained glass domes at the Chicago Cultural Center.

River cruise

The temps are finally ideal for (incredibly kid-friendly!) jaunts up and down the Chicago River, taking in world-famous architecture and filing away the kind of trivia you can wow visiting relatives with. 


Fewer tourists mean an excellent time to play tourist in your own town! The lines at the Willis’ SkyDeck and the Hancock will never again be this short, and you might even have a chance at nabbing last-minute “Hamilton” lottery tickets at the PrivateBank Theatre (…maybe).

Toy and Game Fair

Like you need an excuse to act like a kid: The 16th annual Chicago Toy and Game Fair (Nov. 15-18) is the largest of its kind, and features vendors, designers, inventors and every last hot toy on every last holiday list.


Navy Pier’s Centennial Wheel is the best way to get up close ‘n’ personal with that sparkling skyline.

Vivid colors

From the Morton Arboretum to Chicago Botanic Garden, this is nature’s season to show off (more than) a little with pretty fall colors.

Weekend plans

There’s so much to do on the weekend in the fall! Be sure to stay up-to-date with the latest events with Chicago Parent’s weekend picks.  

eXposure (To Artistic Excellence!) 

Fam-friendly performances have evolved way beyond clapping along to rhymes and, especially in a town like Chicago, it’s exceptionally easy to start a love of the theatrical arts early. Your tween and teens will love these upcoming fall shows

Y hiding in plain sight

History buffs: Did you know that the “y” is a Chicago symbol that predates the Chicago flag? Go hunt for representations of this branching of the Chicago River all over town during an excellent time of the year for self-guided tours! (Need a starting off point? Check out the marquee for the famed Chicago Theatre.)

Zoo fun

Both Brookfield Zoo and Lincoln Park offer non-stop this fun with Fall FestBoo! at the Zoo, Spooky Zoo Spectacular and more. 

This article was originally written on Sept. 22, 2017. It has been updated with the most recent information.

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