Chicago family friendly Travel & City Adventures

Things on my Chicago Fall Bucket List this year

Fall is quickly approaching and the weather is perfect in Chicago! It’s that 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.

So I put a list together of things to do this fall around the Chicagoland area for everyone! 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!

Things on my Chicago Fall Bucket List:

Visit the National Mexican Art Museum

I would definitely recommend visiting the beautiful altar for Dia de los Muertos exhibit. The museum is free and we love going as a family! The museum will set up an altar inside starting September 23rd. Check their website for more details!

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!

Southport Trick or Treat

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 24th. Check out their website for more info.

Hyde Park Jazz Festival

Happening September 24th and 25th, it’s in it’s 16th year, free (suggested donation) and it’s so much fun! Grab blankets, chairs, food and it’s such a relaxing night listening to live jazz!

Open House Chicago

If you have never done Open House Chicago with the Chicago Architecture Center, I highly recommend! It’s happening October 15th-16th this year. This is your chance to check out buildings and parts of the city that are normally closed to the public and learn its history, etc. It’s FREE & 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! Like the park used to be a cemetery and it’s often thought to be haunted today!

Pier Pumpkin Nights

Starting October 1st, Navy Pier gets decked out in 1,000 carved pumpkins all over the pier. The kids love it and it’s best to go at night because they light up! It’s free, so you can just walk around the pier. Maybe catch a fall sunset from the pier and then check out the pumpkins. Also, you can grab a drink on the pier and walk around with it!

Goebbert’s Pumpkin Patch

One of our favorite pumpkin patches is Goebbert’s Pumpkin Patch and it’s always on our Fall Bucket List each year! 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.

Jack’s Pumpkin Popup

Although this has been happening for a few years now, it’s fun for the kids! This is probably one of my favorite popups they put on and kids under 4 are free! Noah loves it & he’s a great age for it! Parents can grab some drinks and let the kids enjoy! Games, go-karts, photo opportunities, ax throwing, etc. Some things are for older kids, but it’s still fun for the little ones. Starting date September 22nd.

Lincoln Square Apple Fest

The Lincoln Square Apple fest is returning October 1st and 2nd! This fest is one of my favorites and definitely should be on your Fall Bucket List! Very family friendly.

Lincoln Park Wine Fest

Drink some wine at the Lincoln Park Wine fest October 7th-9th at Jonquil Park in Lincoln Park. Not family friendly, but great for a day out with friends on a nice fall day!

Visit some Nature Spots

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 behind on reels here (there are three parts).

Depaul’s Campus in Lincoln Park is so pretty!

Visit An Apple Orchards

Visiting an apple orchard is a must for your Fall Bucket List! We have so many within 1-3 hours of Chicago. You can see all of them linked 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 4 years and love it! We just rented the Donut boat as a family and had the best time.

Donut Boat from Electronic Boat Company

We like it because you can bring your own food, 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! Great to all split the cost, roughly $200 an hour for 8 people.

Free Gallagher Way Pumpkin Party

Gallagher Way is having their annual free pumpkin party on October 22nd. It’s so much fun for families! They also have other Halloween themed movies they play throughout the fall!

Pumpkin Party at Gallagher Way this fall!
Live music, Halloween themed movie and more!

It’s really 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 can! Because we know what’s coming soon (sigh 🫤).

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!

If you’d like to participate in the Chicago Fall Bucket List BINGO, here’s the image for you to download!

There is so much happening this fall and hopefully this gives you some ideas to add to your own Fall Bucket List!

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


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