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A Complete Guide to Chicago in the Fall

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Chicago is a wonderful city to visit in the fall. There are many seasonal activities at this time of year, not to mention the great things to do all year round.

This guide highlights some of the many great things to do in Chicago in the fall. 

What to do in Chicago in Fall


This is a Top 10 list of things to do in Chicago this Fall. For more ideas on popular things to do in Chicago, check out our posts on bus tours and walking tours of the city.

Some of the items listed in this post are included for free with the purchase of a tourist discount pass


1.  Take a Tour!

The best way to get out and enjoy the cool breeze in Chicago this fall is to take a tour. Free Tours by Foot offers walking tours of Chicago of various neighborhoods, including the Loop, the Riverwalk, and specialty tours like an evening Ghost Tour to learn about Chicago's Haunting History.

One of our most popular autumn tours is our Lincoln Park Gangster & Blues tour - fun history but some beautiful leaf peeping in the park as we walk along.



Explore Chicago by Boat, Bus, Segway, and Bike

If you’re not up for walking, there are many ways to explore the city.

2. Autumn Activities

Nothing says fall quite like pumpkin patches, corn mazes, and apple picking. Check out some local-ish farms for hayrides for the kids and apple cider for the adults.

For more fun things to do with kids, check out the Kids section below.

3. Oktoberfest

This German tradition continues for another year in the Windy City. Grab some cold beer, bratwurst, and pretzels as you enjoy the authentic German bands and culture.



We have a guide to drinking in Chicago - featuring best rooftop bars, historic bars, speakeasies and more, but for a true Oktoberfest experience, go to the German-American Oktoberfest in September.

4. Catch a Concert

There are plenty of great shows going down in Chicago this fall. Going to a concert is a great way to cap off an evening after spending the day touring Chicago. Some big names coming to Chicago this fall:




For a list of more things to do at night in Chicago this Fall, check out our Things to Do at Night post.

Chicago also has some free and family-friendly concerts and festivals, which you can check out in the Festival section below.

5. Attend the Theater

Chicago has an incredible Theater District, which you can not only visit to see a show but also take a tour!

To explore the history of the area on one of our pay-what-you-like tours, click to view our calendar here



There are a number of incredible performances hosted in Chicago this fall, from the very famous Hamilton musical to incredible stand-up comedians like Demetri Martin and Jerry Seinfeld.

We encourage you to browse the performances coming to Chicago here to find a performance to see that's perfect for you!

6. Sports

Chicago boasts a number of great professional sports teams. Depending on what time of year you're visiting, there's bound to be a great game going on. Fall means football and you can watch "Daaa Bears" at Soldier Field this fall!

Football  (August through December)


Ice Hockey (October through April)


  • WWE (Nov. 22-25)

For more ideas on family-friendly things to do in Chicago, check out the section below.  

7. Halloween

Time to get spooky for Halloween! If you're too old to go trick-or-treating, you can still get dressed up in your favorite costume and come out for a ghost walking tour. Explore the haunted parts of the city on the day the ghouls and ghosts are out. Click here to reserve your spot!

You can also wander down to the Navy Pier for a Haunted Halloween Ball for the big kid in you. For more things to do in Chicago on Halloween, click here

You can also celebrate Halloween in the parks! From Halloween parties to haunted houses and the annual Pumpkins 5K Run & Kids Spooky Sprint, there's something for everyone at these free events. 

For more kid-friendly Halloween activities, check out our kids' section below. 

 8. Thanksgiving

Whether or not you have family here for Thanksgiving, Chicago will make you feel at home during the holidays. With lots of things to do solo or with loved ones, you'll feel thankful for being here in the Windy City. 

The Magnificent Mile Light Festival is an annual event with beautiful lights and a series of family-friendly events for everyone to enjoy.

For a full schedule, click here to plan your visit. 



Chicago's Christkindlmarket has been around since 1996 and opens from mid-November and features Germany goodies, such as spiced wine, German beers, desserts, sausages, and potato pancakes. 

There are also vendors selling festive goods like ornaments, nutcrackers, and toys. 

For more things to do for Thanksgiving in Chicago, click here

9.  Open House Chicago

October 19-20, 2019

Ever walked around Chicago wishing you could just walk into and see the insides of its incredible buildings? Well, you can!
Once a year the city opens up to the public to explore the incredible architecture of the city not just from the outside but inside as well.
You'll be able to go behind-the-scenes to more than 250 buildings in Chicago during this free public festival, from skyscrapers to private residences.



Don't want to do it alone? Join us for a pay-what-you-like architecture tour of Chicago to learn about the cityscape. These tours include:

In addition to our walking tours, there are other walking tour companies that offer excellent architecture tours. Another popular option is to take an architectural boat cruise. There are even architectural tours by bus as well as Segway.

10. Look into a Tourist Discount Pass

Visitors who are working with a budget should think about getting a Chicago tourist pass. These services provide heavy discounts at some of the most popular attractions in the city.

Here are a few of the sites you can visit with various discount passes, which include some great fall activites such as:

These are just a few of the activities you can enjoy. If you plan to visit even a few of these attractions, you could easily end up saving a lot of money over general admission prices.

Tourist Passes Reviewed

For more details, make sure to read our full post covering Chicago tourist passes.

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Many of our Top Ten are great activities for children, like going to Navy Pier, but check out our post about Family Friendly Activities in Chicago for a more complete guide.  Below you will find a couple of other options to keep your children entertained this season!


Trick-or-treating with kids on Halloween is a must! Try a different neighborhood this year, as some communities have a whole host of activities for kids:

Trick-or-treating not your thing? Go to the zoo! On October 26, Lincoln Park Zoo host it's very popular annual Spooky Zoo, an event that hosts a number of free activities for kids of all ages. 

Do your kids walk on four legs? Don't miss the Spooky Pooch Parade hosted by the Chicago Botanical Garden. Dress your pup up and come out to this free event!

Thanksgiving Parade 

The annual Thanksgiving Day Parade can't be missed! Come out to State Street to see Santa Claus and Ronald McDonald in the lineup while tapping your feet to the tunes of marching bands. 



The parade begins at 8am and runs until 11am. Come out early to grab a good spot!

For more ideas of things to do in Chicago for Thanksgiving, check out this link

Fall Fest 

The Lincoln Park Zoo is hosting Fall Fest, a celebration of fall running from Sept.27-October 27, Friday-Sundays. The event is free and guests can enjoy viewing the animals, taking their picture with a giant pumpkin, and delicious snacks.

While a lot of activities are free, there are ticketed events as well, like a corn maze, inflatable obstacle course, and more!

For more fall festivals to enjoy with the whole family, check out our festival section below. 


Museums are a great way to spend time inside on a chilly day! Chicago has a number of great museums, many of which are free. Some paid museums have free days, such as the Chicago Children's Museum. T

his museum is free on the first Sunday of every month, from 10am – 5pm. To learn more about this great museum geared towards kids, click here

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Packing to go to a city you've never been to can feel daunting- how much is too much? There's also the fear of meeting unexpected weather and not having packed something essential.
Below are some FAQ about packing we want to answer for you:
  • Does it rain a lot in the fall? September and October have the lowest number of rainy days in the year, so while you should bring rain gear in case the forecast calls for it, you shouldn't have to worry about lots of dreary, rainy days on your visit to Chicago in the fall.  
  • What to pack: Temperatures in Chicago begin to dip in the fall, and can get a bit chilly. Pack light jackets and sweaters and comfortable, warm shoes like boots. 
  • Be sure to bring water with you. A lot of the public parks have removed water fountains due to health concerns, so bringing water along prevents you from having to buy expensive water in shops and keeps you hydrated.
  • Going out for a drink or nice restaurant in the evening? If you've been walking around outside all day it might be best to pack along a nice change of clothes. Most places in Chicago are pretty casual in dressing, but if you're going out at night to somewhere ritzy like a speakeasy, dressing up a bit is best.

We have a monthly post section below if you want to read up more on the specifics of the weather to better decide what clothes to bring on your Fall trip to Chicago.

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Most Chicago festivals are free to attend and we have LOTS of them throughout the year. There are food festivals, beer festivals, tequila festivals, music festivals, and art festivals. There is a fest for every type of visitor.  Below is a list of our most popular fall festivals:

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To learn more about what do to in specific months here in Chicago, click the links below:

About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: October 12th, 2021
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