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Things To Do in Chicago in October

Updated: December 22, 2023
 By Mel

October is a wonderful time to enjoy Chicago, and in this post, we list some of the top things to do in 2023.

With the peak tourist season having passed with the summer months, you can enjoy the beautiful fall streets with the locals. 

As local tour guides, we compiled this list based on our own experiences, but also answering your questions.

We lead thousands of people each month through the streets of Chicago and on every tour you ask us about things to do in the city.

We also grabbed ideas from the roughly 20k members of our popular Chicago Travel Tips Facebook group.

The group consists of locals, like our tour guides, veteran travelers, as well as newbies to Berlin.

You don't need to join in order to read the posts, comments, and recommendations.

Check out the group once you are finished reading this post.


October provides cooler weather, and fewer crowds, but maintains a fun calendar of events!

Before you check out our list of fun things to do this month, consider some of the following activities you can enjoy throughout the year:

Below you will discover a guide to some of the best October traditions.  Find a complete calendar for October in Chicago here.

1. Take a Ghost Tour

There are a lot of different ghost tours you can take in Chicago, including at least one pay-what-you-want walking tour which covers a lot of creepy history in the Windy City.

In addition to this option, you can also take a ghost bus tour which will take you around the city with ease. 

Chicago Ghost Tours

If you're over the age of 21, you can also go on a ghost pub tour and learn about some of the haunted history tied to Chicago's pubs and bars.

For even more creepy tours to take, check our post covering Chicago ghost tours.

2. Go to a Concert

If you are a music lover or a fan, be sure to check out a concert while in Chicago. 

There are many venues from giant spaces to intimate bars.  


These are just the most notable bands and performers on schedule, but there are many others coming to Chicago this month.

Check this list of Chicago concerts in October for even more shows to attend.

3. See Some Stand-Up Comedy

There are still plenty of great comedians planning performances in the area this October.

Each of these performances is scheduled to take place either in Chicago or within 30 minutes of the downtown area.

Comedy Shows

Comedy Clubs


If you're looking for even more laughs in Chicago, check this list of comedy performances planned for October.

4. Attend a Sporting Event

October is filled with several options if you are a sports lover.

Seeing a big game is a great way to spend an evening. For more things to do at night, check the section on nighttime activities below.




For other games, check out the full list of sports taking place in September in Chicago.

5. Get Your Fitness On

The annual Bank of America Chicago Marathon and Fitness Expo takes place on October 8th.

It is one of the six World Marathon Majors, bringing in runners from all 50 states and over 100 countries!

It also brings thousands of runners and spectators into the streets of Chicago.

Prior to Race Day, you will find the Health Fitness Expo, which hosts over 200 exhibits, as well as the best in running apparel, footwear, and nutrition.

The Expo is hosted in McCormick Place and is free to the public.

6. Attend a Film Festival

For just shy of 60 years, the Chicago International Film Festival has showcased short and full-length films from 50 different countries, while also focusing on films made by Illinois locals.

This festival has uncovered new talent and provided Chicago with a wide variety of films, accompanied by panel discussions.

This year the festival takes place October 11th-22nd.

7. See Chicago Through New Eyes

Have you ever wondered what really lies within the walls of some of Chicago’s most famous and finest buildings?

The free Open House Chicago is your chance to discover some of Chicago’s architectural treasures.

Open House Chicago lasts all month long, and in-person site visits are on October 14th & 15th.

During the course of that weekend, you will have the opportunity to explore 200 of Chicago's most exciting and mysterious buildings, ones that are normally off-limits to the public.

8. Chicago Beer Festival

Chicago is a city recognized for its vibrant craft beer scene.

At the Chicago Beer Festival over 65 breweries will present their seasonal beers on October 7th at the Field Museum.

Tickets need to be purchased ahead of time, and access is limited to those 21+.

For more information, and to purchase tickets, visit the festival's website.

9. Attend AppleFest

If you are looking for a family-friendly event, you're sure to find it at the Lincoln Square Ravenswood Apple Fest.

For almost 40 years the festival has been celebrating the start of autumn.

There will be apple-inspired dishes and ciders, various farms and vendors selling their fall wares, live music, family activities, and more.

Events take place on September 30th and October 1st.

Visit the Apple Fest website for more information.

10. Consider Getting a Tourist Pass

There are a few different tourist discount passes in Chicago which allow you to save money on a variety of popular attractions.

If you're planning to visit some of the most notable sites in the city or take a tour, we recommend looking into a tourist pass to cut your costs by as much as 50%.

Here are a few activities and locations you can visit using one of these services:

For more information about how to use them, please read our post covering Chicago tourist passes.


This section will cover some additional free activities you can enjoy in Chicago during the month of October. 

Take a Free Walking Tour

We offer many pay-what-you-wish walking tours in Chicago which allow you to learn about the city from a local without having to spend a lot of money.

We also provide GPS-Led Audio Tours for those who want to avoid large crowds of tourists to prevent the spread of Covid-19.

In addition to the ghost tours we covered in our Top 10 section, these tours are also available:

For even more options, please read our post covering free walking tours in Chicago.

Discounts for Chicago Museums & Attractions

October will also have some free days for anyone who wants to visit various museums.

Check here for the master list of museums and free admission dates.

Also, check for free or reduced admission for students, senior citizens, and members of the military and their families at any time of the year.

Many museums offer discounts or free admission to Illinois teachers and some discounts are offered to Wisconsin, Indiana, and Michigan teachers (with proper I.D.)

Columbus Day Parade

The 71st Columbus Day Parade returns to celebrate the Italian American Community.

The parade takes place on State Street and runs between Wacker Drive and Van Buren Street.

There will be a mass and wreath-laying ceremony as well.

Events take place on October 9th.

Visit the Columbus Day Parade website for more information.


This section will cover some additional nighttime activities you can enjoy in Chicago during the month of October. 

Don't forget to check our other sections for additional ideas such as concerts, sporting events, stand-up comedy, and more.

Lincoln Park Wine Festival

This festival returns to Jonquil Park for its 7th year.

Sommeliers and brand ambassadors guide you through tasting sessions. Tickets come with 12 tastings and stemmed commemorative wine glasses

The festival runs into the night hours of October 6th-8th.

For tickets and information visit the Lincoln Park Wine Festival website.

Arts in the Dark

This annual Halloween celebration is one of a kind.

There's a parade with unique floats, creative dance performances, and amazing giant puppets.

The Art Institute of Chicago is involved as are other world-renounced institutions.

The popular event draws 50,000 people to State Street.

Events take place on October 21st from 6:00-8:00 pm and more information can be found here.

Attend one of the Best Halloween Parades in the Country

The Northalsted Halloween Parade takes place on N. Halsted Street (from Belmont to Addison, 3300-3700) on October 31st each year.

Register to suit up in your costume or enjoy the spectacle from the sidelines for this Chicago tradition.

Known across the country for its creativity, this is a parade you won’t want to miss!

Attend Chicago's Largest Halloween Costume Party

The Haunted Halloween Ball takes place on October 29th.

The location, the Congress Plaza Hotel, is perfect because it's considered one of the most haunted hotels in the world!

This event brings in around 3,000 costumed guests, all of whom will have to find a way to get along with zombie cocktail servers and vampire bellmen.

For tickets, visit the Haunted Halloween Ball website.


This section will cover some additional family-friendly activities you can enjoy in Chicago during the month of October. 

Don't forget to check our other sections for additional ideas such as the Haunted Halloween Ball, sporting events, and more.

Go to a Pumpkin Patch

If you're looking for a fun family activity, consider taking the kids to a pumpkin patch near Chicago.

There aren't any farms in the city center, but you can find a lot of great places to visit within a 30-60 minute drive of the Windy City.

Here are a few pumpkin patches you might want to consider visiting this October:

For even more options, check this list of pumpkin patches near Chicago.

Visit Some Vampires

Teens might enjoy a visit to the Vampire Diaries Official Convention. It takes place October 13th-15th at the Westin Hotel in Rosemont.

Ian Somerhalder, Paul Wesley, and others are attending.

For tickets, visit the website.

Trick or Treat At the Zoo

For the past 30 years, the zoo has provided kids with a fun, safe, and festive way to celebrate Halloween with Lincoln Park's Spooky Zoo!

Kids dress up in costumes and explore the zoo with their trick-or-treat bags. There are craft stations, live music, and a haunted house.

This year's event date hasn't been announced at the time of this post, so keep checking the website for updates.

NOTE: You can use a Chicago tourist pass to save money on tickets!

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: December 22nd, 2023
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