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Things To Do in Chicago in October (2021)

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Chicago in October October is a wonderful time to enjoy Chicago. With the peek tourist season having past with the summer months, you can enjoy the beautiful fall streets with the locals. 

Top Things to Do in Chicago in October

October provides cooler weather, 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. 



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

Music lovers will have plenty to do in October, as there are going to be a lot of famous musicians performing in and around Chicago this month.



Here are a few of the best shows scheduled for October 2021:

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

The Windy City tends to attract a lot of famous comedians, so it shouldn't come as a surprise that there will be a lot of great stand-up to enjoy in Chicago this month.



Here are some of the best shows taking place in October:

If you're looking for even more opportunities to enjoy a good laugh, check this list of comedy performances in Chicago for even more shows happening this month.

4. Attend a Sporting Event

There will be a lot of great games to see in Chicago this month.

The Chicago White Sox will be finishing off the regular season in town with one final series against the Detroit Tigers.

There's also a chance that either the Sox or the Chicago Cubs could make it into the postseason, which would mean even more October baseball in the Windy City!



The NBA season should also be starting this month, which means there will probably be several opportunities to see a Chicago Bulls game.

Alternatively, you might also want to see a Chicago Blackhawks game, as the NHL season should also be starting on time this year.

Last but not least, the NFL season will be in full swing, and there are 3 Chicago Bears games scheduled to take place at Soldier Field this October.

5. The Bank of America Chicago Marathon and Fitness Expo

October 10th, 2021

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

Prior to Race Day, you will find the Fitness Expo, which hosts over 200 exhibits with Bank of America Chicago Marathon Merchandise, as well as the best in running apparel, footwear, and nutrition.



The Expo is hosted in McCormick Place on Friday and Saturday, and is free to the public.

The Marathon itself is Sunday, and brings thousands of runners and spectators into the streets of Chicago, and across many of the dynamic neighborhoods.

6. Chicago International Film Festival

October 13th-24th

For more than half a century, this 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.

7. Open House Chicago

October 16th - 17th

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

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



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

8. Attend an R&B Music Festival

In addition to all the great concerts happening this month, there will also be a pretty notable music festival taking place later in October.



The R&B Spring Fest is scheduled to take place on October 30th, and several popular R&B musicians will be on hand to perform, including the following artists:

  • Brian McKnight
  • Tevin Campbell
  • El DeBarge
  • And more!

Fans of the genre won't want to miss out on this special opportunity to see some of the greatest R&B performers live on stage.

Purchase tickets or learn more.

9. Wizard World Comic-con

The Wizard World Comic convention will be making its way to Chicago on October 15th - 17th in 2021.



This is a great opportunity for fans of comic books, movies, television shows, and anything geeky to meet up and celebrate their favorite things.

In addition to the celebration of nerd culture, several celebrities will also be on hand to talk with fans and sign autographs.

Purchase tickets or learn more.

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.

RESCHEDULED: St. Alphonsus OktoberfestChicago in October

Admission: $5 before 5pm, $10 after 5pm. (Free admission on Sunday)

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 as the festival season and month of September draws to a close.

Chicago in OctoberUNDETERMINED: Lincoln Park Zoo: Adults Night Out

Tickets: $15 ($12 for Lincoln Park Zoo members) /$20 at the door if tickets remain

Enjoy this night out, away from the kids, as you can visit the animals after hours! Explore the zoo with animal chats, live entertainment, and cash bars scattered throughout. Must be 18+ to attend.

NOTE: Although they have not yet announced 2021 dates for this event, the zoo will be open and you can save money on tickets using a Chicago tourist pass!


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Things to Do at Night in October

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, the R&B Music Festival and more.

Northalsted Halloween Parade
October 31st, 7:30pm
On Halsted Street from Belmont to Addison

Register to suit up in your costume or enjoy the spectacle from the sidelines for this Chicago tradition. Known across the country for the creativity of this event, this is a parade you won’t want to miss.


Haunted Halloween Ball
October 30th, 8pm - 2am
Grand Ballroom at Navy Pier

Unlike some other costume parties you might have attended, this event brings in 3,000 ghostly guests to enjoy the panoramic views of the lake and skyline, cash bars, and multiple DJs who will keep the party going all night long.

Arts in the Dark
October 30th, 6-8pm
On Columbus Dr. moving North from Balbo to Monroe St. 

This festive parade showcases Chicago's diverse creative community through a nighttime parade. Featuring unique floats, giant puppets, live music, this proves to be a great experience for the whole family.


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Things To Do with Kids

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 Wizard World Comic-Con, the Columbus Day Parade, 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 obviously 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.

UNDETERMINED: Spooky Zoo Spectacular

For the past 30 years, the zoo has provided kids with a fun, safe, and festive way to celebrate Halloween!

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

NOTE: Although this event has yet to be confirmed, the zoo will be open and you can use a Chicago tourist pass to save money on tickets!

RESCHEDULED: St. Alphonsus OktoberfestChicago in October

Admission: $5 before 5pm, $10 after 5pm. (Free admission on Sunday)

This German tradition is a family-friendly event you can enjoy in the Windy City.

Grab some cold beer, bratwurst, and pretzels as you enjoy the authentic German bands and culture as the festival season and month of September draws to a close.


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Free October Events

This section will cover some additional free 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 Arts in the Dark parade, the Northalsted Halloween Parade, the Bank of America Chicago Marathon and more.

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.

RESCHEDULED: Andersonville Arts Weekend

This Arts Weekend kicks off for the 15th year with the tradition of the Night of 100 pARTies! -- as there are receptions and parties lining Clark Street.

Throughout the weekend, enjoy the work by local artists and designers displayed throughout the neighborhood, accompanied by live entertainment.

UNDETERMINED: Columbus Day Parade

For almost 50 years, Chicago has been enjoying this parade that has been sponsored by the Joint Civic Committee of Italian Americans.



The parade is preceded by mass at the Shrine of Our Lady of Pompeii and a wreath laying ceremony at the Columbus Statue located in Arrigo Park.

Then over 150 floats and bands march down State Street.


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Chicago Weather in October

October weather brings fall into full swing, as the temperatures begin to drop. This month has the first frost, and in some years, even provides the first snowfall.

Chicago in OctoberChicago quickly cools during this month, and by the end of October, the temperature has often dropped 12 °F (7 °C) from where it started.

The temperatures reach between 59 °F and 65 °F (15-19 °C), with an average high of 62 °F (17 °C).

On the other end, the temperature this month can cool down to 40 °F and 46 °F (4-8 °C) with an average low of 43 °F (6°C). An average of 18 days will reach above 60 °F (16 °C), and a few days will even peak above 70 °F (21 °C).

The pleasant fall weather this month has little rainfall, with 3.2 inches (80 mm) of rain over the course of about 10 days. Very rarely will this precipitation fall as snow.

This month sees a decline in thunderstorms from the previous months, with about two days of thunderstorms, and the average wind speed is 10.0 mph (16.1 kph) 

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What to wear/pack for Chicago in October

With cooler fall weather this month, you will want to pack appropriately. That means layers!

As with many other months in this great city, the weather can be pretty unpredictable.

While overall October tends to be a pleasant month, you will want to be prepared to layer up with light jackets, sweaters, and hoodies to get you through the cooler hours and days.

No winter clothing will be necessary this month (hopefully!).

You might even want to throw in a Halloween costume, as there are many Halloween traditions throughout the month.

Comfortable walking shoes are also essential for your stay in Chicago. Be sure to throw in an umbrella, just in case.


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About The Author

Canden Arciniega

Canden is a historian and tour guide in Washington DC with 4 published books about the city. She has written for HuffPost Travel and has been featured in the Washington Post, WTOP, and numerous other DC papers. She's also been interviewed by the BBC, NPR, Travel Channel and Discovery Family Channel. Canden is the producer of our podcast, Tour Guide Tell All With a M.A. in History from University College London and a B.A. in History from Elon University, she is an authority on D.C. history, and has led tours in the city for over 10 years. She currently resides in DC, but has also lived in London and South Korea, and has travelled to 28 countries. Her two children (both under the age of 4) have their passports and own frequent flier accounts.
Updated: September 26th, 2021
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