20 Things to Do in Chicago this Fall

August 28, 2023

Fall is quickly approaching, and the weather is perfect in Chicago! It’s time to get your Fall Bucket List together. I always tell people September/early October is really the best time to visit if you’re from out of town! The weather is some of the best we have all year, not too hot or too cold.

Here’s my guide to things to do this fall around the Chicagoland area! They range from free to ticketed events for families, date nights, or out with friends!

If you like any of these or go to any, tag me @thechicagogoodlife on Instagram!

Visit a Pop-Up

The Malibu Barbie Cafe pop-up has been extended until October 15! And I’m checking out the new experience by Fever, Clue: A Walking Mystery soon. They close on October 31, and the tour starts at Block 37.

National Museum of Mexican Art

I highly recommend visiting the beautiful altar at the National Museum of Mexican Art for their Día de Muertos exhibit. The museum is free, and we love going as a family! The museum will set up an altar inside starting September 22nd. During the last weekend in October, there is a celebration of life where people of the community set up their own altars in Harrison Park (right behind the museum), and it’s absolutely beautiful. I would definitely add this to your Fall Bucket List!

Nightmare on Clark Street

This popup at Bamboo Club has their Nightmare on Clark Street for the past few years now and it’s decorated really well for Halloween! This is more of a take photos and have some drinks, but it’s fun if you are looking for a bar decorated for Halloween. In years past, they allowed kids until 8pm, but I would check with them before heading there!

Hyde Park Jazz Festival

The Hyde Park Jazz Festival is September 23-24 this year. It’s free to attend (but it’s highly suggested to help out with this amazing event by providing a donation), and it’s so much fun! Grab some blankets, chairs, and food, and enjoy a relaxing night listening to live jazz!

Brewer’s Triangle Oktoberfest

The Brewer’s Triangle is a new collaboration between Maplewood Brewery & Distillery, Ravinia Brewing Co., and Metropolitan Brewing. They’re throwing an epic Oktoberfest at all three locations on September 23, 2023.

Fall Fest at the Lincoln Park Zoo

The Fall Fest at Lincoln Park Zoo is such a classic event. Running September 29–October 29, the event is free to attend, but most attractions (like the fun slide and harvest maze) need paid tickets. 

Open House Chicago

If you have never done Open House Chicago with the Chicago Architecture Center, you’re truly missing out.! It’s happening October 14-15 this year. This is your chance to explore buildings and parts of the city that are normally closed to the public and learn its history. It’s FREE and a really cool way to explore the city. Many of the sites will indicate if they are family-friendly, accessible, etc. This is awesome for tourists and residents to explore the city! Tickets are required just to reserve your spot because some locations fill up quickly.

We did the Lincoln Park tour two years ago as a family. We learned so much! The park used to be a cemetery, and it’s often thought to be haunted today!

Lincoln Square Apple Fest

The Lincoln Square Apple Fest is returning on October 1st and 2nd! This fest is one of my favorites and definitely should be on your Fall Bucket List! It’s very family-friendly. If you haven’t explored Lincoln Square lately, check out my guide and reel here!

Gallagher Way

Gallagher Way in Wrigleyville is having its annual free pumpkin party this year, but the date is still TBD. It’s so much fun for families! They also have other Halloween-themed movies playing throughout the fall!

Southport Trick or Treat

We love the Southport Trick or Treat event! All of Southport Avenue from Irving Park to the Southport Brown Line stop shuts down so the kiddos can trick or treat, adults can grab food from the food truck or vendors, and it’s so much fun! Many of the businesses will have special discounts and pass out candy. It will happen on Monday, October 30th. Check out their website for more info.

Pumpkin and Apple Picking

Goebbert’s Pumpkin Patch is always on our Fall Bucket List each year! It’s our favorite place to go pumpkin picking. Goebbert’s is outside the city by roughly 45 minutes, but once you are there, it’s an all-day event! There is so much to do for the kids, like a petting zoo, pony rides, games, food, and more. Definitely buy tickets ahead of time & go early, especially on the weekends. You can see a list of other apple and pumpkin orchards here.

Rent a Boat

Rent a Chicago Electric Boat on the Chicago River! It is NOT TOO LATE! It’s actually the best time to get out on the river. We actually now have done this for four years and love it! We just rented the Donut boat as a family and had the best time.

We like it because you can bring your own food and drinks and drive the boat yourself! The river tends to be less crowded, more boats are available, and they often have more deals on rentals! It’s great for a group outing, like a girl’s day out or a couples get-together. It’s roughly $200 an hour for eight people, so splitting the total with friends makes it so reasonable!

It's not too late to rent a boat this fall!

Rooftops and Patios

It’s also not too late to hit up some patios and rooftops. The weather is usually so good until mid-October, so why not have some drinks outside while we still can?

There is still time to try a new patio or rooftop this fall! Add it to your fall bucketlist!
Two years ago, The Dawson had their huge patio all decked out with fall decor and pumpkins! They might do it again this year, check their IG!

See Live Theatre

Theater is really coming back this fall. The season opens with the smash hit Hamilton, returning to Broadway in Chicago beginning Sep 13, 2023. Other than that, here are my top five picks:

Get into Nature

Check out some of the changing leaves at Jackson Park, Lincoln Park, Chicago Botanic Garden, and more! You can see a full list of other nature spots to see leaves around the city and beyond on reels here (there are three parts).

Depaul’s Campus in Lincoln Park is so pretty!

Visit a Museum

When was the last time you went to one of the big Chicago museums, like the Field or Adler Planetarium? Or one of the smaller but just as awesome museums like the Chicago History Museum or the American Writers Museum? Our favorite is the National Museum of Mexican Art in Pilsen. We like to visit the free museum as a family and then explore the neighborhood!

Outdoor Movies

There are quite a few places to watch a movie outdoors this fall! The Rooftop Cinema Club in the West Loop starts its fall season off with The Addams Family and Hocus Pocus and continues through October 31. Their last showings on Halloween are already sold out, though, so get your tickets early!

If you’re looking for a drive-in experience, head to Chitown Movies in Pilsen. Gallagher Way in Wrigleyville has two screenings in September, and the Chicago Park District is offering outdoor movies through September 9.

Fall Festivals

There are SO many festivals this fall! I can’t even keep track of them all! Here are some standouts:

Farmer’s Markets

Farmer’s Markets don’t stop after summer! Most go at least through the end of September, and some are open all the way into November. Check out my huge round-up here!

Shop Local

I know we don’t want to talk about it, but I’m starting to think about holiday gifts already! I’m excited to explore a neighborhood and find something unique and local to give to someone special. Here are some of my favorite Chicago boutiques:

OK, Chicago, that was an EPIC list! There is SO much happening this fall, so hopefully this gives you some ideas to add to your own Fall Bucket List!

I can’t wait to see what’s on your bucket list this fall!


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