Fall is quickly approaching, and 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!

🧡Attend Open House Chicago

If you haven’t done Open House Chicago with the Chicago Architecture Center, you’re truly missing out! It’s happening October 19-20 this year. This is your chance to explore buildings and parts of the city normally closed to the public and learn its history. It’s FREE and a cool way to explore the city. Many sites will indicate if they are family-friendly, accessible, etc. This is awesome for tourists and residents to explore the city! Tickets are required to reserve your spot because some locations fill up quickly.

🧡Go Pumpkin and/or 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. Buy tickets ahead of time and go early, especially on the weekends. You can see our list of other apple and pumpkin orchards here.

🧡Fall Fest at Lincoln Park Zoo

This free to enter festival is fun for the kiddos! There are rides, games, and other fall decor throughout the zoo. The attractions are ticketed but entrance is always free. It does get crowded, so I recommend going early or early Friday morning.

🧡See a Halloween Movie Outdoors

There are quite a few places to watch a movie outdoors this fall! The Rooftop Cinema Club hasn’t released their fall schedule yet but last year their last showings on Halloween sold out quickly, 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 a screening of Twilight in September, and the Chicago Park District is offering outdoor movies through September 13.

🧡Browse an independent bookstore

There’s nothing cozier than browsing a bookshop and then finding a coffee shop nearby to read! Check out our huge list of independent bookstores here and I heard there is a new wine + bookshop opening in West Town soon!

🧡Experience Live Theater

Broadway in Chicago is bringing Harry Potter and the Cursed Child to the stage beginning Sep 10, 2024. Other than that, here are my top five picks:

• Natasha, Pierre & the Great Comet of 1812 by Writer’s Theatre, Sep 5 – Oct 27, 2024
• Noises Off at Steppenwolf Theatre, Sep 12 – Oct 27, 2024
• Ironbound at Raven Theatre, Sep 26 – Oct 27, 2024
• Coronation by Refracted Theatre Company at The Den Theatre, Oct 11 – Nov 16, 2024
• Little Shop of Horrors by Music Theater Works Oct 24 – Nov 17, 2024

🧡Marvel at the Gethsemane Fall Decorations

Gethsemane Garden Center is an amazing local garden center in Andersonville, Chicago. They go all out for Halloween! You have to see it

🧡Enjoy a Coffee Flight at October Cafe

October Cafe in Norwood Park is the cutest fall-themed coffee shop. Check it out here!

🧡Register for a Walking tour

Whether it’s architectural or foodie themed, get out there and learn something! There’s a ton to choose from. The Chicago Architecture Center is usually my go-to, but the Backstage Tours of the Auditorium Theatre, Inside Chicago Walking Tours, and Chicago Food Tours are all highly recommended. Wrigley Field offers tours through September 29, too!

🧡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?

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.

🧡Hear Live Music

The Hyde Park Jazz Festival is September 28-29 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!

The Salt Shed has turned into one of my favorite venues. PJ Harvey, Sturgill Simpson, and Lupe Fiasco are just a few of the performers in their fall lineup!

🧡Have a drink for Oktoberfest

• Oktoberfest Chicago at St. Alphonsus, Sep 27-29, 2024.
• West Loop Bavarian Block Party, Sep 20-21
• Oktoberfest at Lincoln Park Zoo, Sep 21

🧡Enjoy a Fall Festival

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

• Taste of Chicago – Sep 6-8
• Printers Row Lit Fest – Sep 7-8
• Andersonville Arts Weekend – Oct 4-7

🧡Take the kids Trick or Treating

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. Details aren’t out yet so check out their website for more info.

🧡Savor the sun on a patio or rooftop

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?

🧡Start your holiday shopping

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:

• Pixie & The Boy and The Sunday Standard in Logan Square
• Tribeca, Smitten, Unwaste Shop, and The Fig Tree in the West Loop
• Kido Chicago and Chicago French Press in the South Loop
• Foursided, Alice + Wonder, and Love, Charlie in Lakeview
• Midwest Nice, ENJOY, an Urban General Store, and The Eco Flamingo in Lincoln Square

🧡Explore a neighborhood

Chicago has 77 neighborhoods! How many have you been to? I recently explored Chinatown (watch here!) and had such a great time! We have a few guides for you here!

• Andersonville
• Lincoln Square
• Pilsen
• West Loop

🧡Volunteer

• Share Our Spare provides families with resources to make sure every Chicago area child has a healthy, safe start. Volunteers can help sort donations, make clothing kits, or pack diaper orders.
• Bernie’s Book Bank distributes books for Chicago area children annually from birth through sixth grade. Volunteers can help sort books, sticker covers, or other activities!
• Paws Chicago is an animal shelter always looking for volunteers to cuddle, socialize, and help with other operational support!

🧡Go on a leaf-peeping walk with a friend

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).

🧡Take a Road Trip

Check out our favorite fall midwest road trips here!

🧡Support a Farmer’s Market

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

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!

Christine