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Things To Do in Chicago in October

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October is a wonderful time to enjoy Chicago, and in this post, we list some of the top things to do in 2022.

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


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. 

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

Music lovers will have plenty to do in October, as there are going to be some well known musicians performing in this month.

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.

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

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

4. Attend a Sporting Event

There will be a lot of sporting events 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 Minnesota Twins.

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 is at least one Chicago Bears game scheduled to take place at Soldier Field inOctober.

5. Get Your Fitness On

The annual Bank of America Chicago Marathon and Fitness Expo takes place October 6th through 9th, 2022.

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, and is free to the public.

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

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 at Cinema Chicago, October 12th-23rd, 2022.

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 visites are October 15th-16th, 2022.

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

8. Listen to R&B

In addition to all the great concerts happening this month, a notable music festival is taking place in October.

The Chicago R&B Music Experience is scheduled to take place on October 8th, 2002, at Wintrust Arena.

Several popular R&B musicians will be on hand to perform, including the following artists:

  • Brian McKnight
  • Tevin Campbell
  • Monica
  • 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.

Click here to purchase tickets or learn more.

9. Attend a Chicken Wing Block Party

If you are looking for the best smelling festival in Chicago, the Wing Out Festival is for you!

Over 20 flavors of wings will be on offer from dozens of Chicago's restaurants, in addition to other entrees and options. The best wings will be judged and awarded, by both an expert and by people's choice.

There will also be music and adult beverages (so attendance is age 21+)

The festival takes place in Old Town at St. Michael Church parking lot.

  • Saturday, October 1st - Noon to 2pm (For VIP), 2pm to 8pm (for GA and walk-ups)
  • Sunday, October 2nd - Noon to 2pm (For VIP), 2pm to 8pm (for GA and walk-ups) 

Click here for more information and to purchase tickets.

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.

Chicago Beer Festival

Over 65 breweries will present their seasonal beers on October 8th, 2022, at the Field Museum.

General admission tickets are $50 and give you access from 8:00 PM to 11:00 PM, plus access to samples from all vendors.

Early admission tickets are $65 and give you an additional hour for sample, 7:00 PM to 11:00 PM, plus access to specialty beers.

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.

Lincoln Park Zoo: Adults Night Out Howl-o-ween

Enjoy this night out, away from the kids, and visit the animals after hours!

The Lincoln Park Zoo presents Adults Night out, Howl-o-ween on September 27, 2022 from 6:30 PM - 10:00 PM.

Activities and offerings include:

  • Cornhole
  • Foosball
  • Giant Jenga
  • Giant Connect Four
  • Carosel rides
  • Animal chats
  • Cash bars and food (for purchase)

Tickets cost: $15 Super Early Bird /$25 Early Bird / $50.00 Late Registration + fees.

Explore the zoo and enjoy the live entertainment! Must be 18+ to attend.



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.

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 the creativity of this event, 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 31st, 2022 from 9:00 PM to 3:00 AM.

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 bellman.

Tickets cost: $20 General Admission / $750 & $1,000 VIP.

Visit the Upside Down Parade

On October 22nd, 2022, on Russel Drive (between Moran Drive and E. Best Drive) the UPSIDE DOWN Halloween Parade takes place.

This festive parade showcases Chicago's diverse creative community, as well as artists from some of the most respected institutions in the world.

The parade will inlcude floats, puppets, music, acrobats, mascots, dance performances and more.

This free event takes place between 12 PM to 3 PM and has proven to be a great experience for the whole family!



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.

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 years event takes place on October 22, with trick-or-treating starting at 10:00 AM.

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



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 UPSIDE DOWN 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.

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.)

Andersonville Arts Weekend

The Andersonville Arts Weekend takes place September 30th - October 2nd, 2022.

Throughout the weekend, the work of over 100 local artists and designers is displayed throughout the neighborhood.

There are art activities for children, live music, and loads of options for shopping and food.

And of course, admission is free!

2022 Information is coming soon.

Columbus Day Parade

For now 70 years, Chicago has been enjoying this parade that has been sponsored by the Joint Civic Committee of Italian Americans.

Over 1250 floats head down State Street (from Wacker Drive to Van Buren Street) on October 10, 2022, starting at 12:30 PM.

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.

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: October 9th, 2022
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