Chicago in October: Things to Do

Updated November 23, 2018

This post contains links to products from one or more of our advertisers. We may receive compensation when you click on links to those products without additional cost to you.

October in Chicago is a great time to visit. The weather is cooperative most days, the Bears have started playing, and it’s time to visit farms for popular activities like apple picking and pumpkin patch activities.

Celebrate the Arts

The West Town Art Walk features art galleries, food and drink in a fun art crawl format. Each October, the Ear Taxi Music Festival and Rocktober Beerfest in the West Loop are chances to listen to live music.

Put your wrists up for this exciting competition - The Chicago League of Lady Arm Wrestlers (CLLAW) brings a level of performance and intensity Sylvester Stallone dreams of - yes, it's over the top. Second to Nun (pictured above in a face-off vs. Lumberjack Jill) and several other contenders will strong-arm their way to the top, hoping to take down reigning champion Macho Ma'am Candy Savage.

What better way to welcome autumn than with seasonal brews at the Chicago Botanic Garden? Sample beers from craft brewers including Begyle Brewing, Temperance Brewery, Smylie Brothers, Flossmoor Station, Dark Horse Brewing, Hailstorm Brewing, Lagunitas, Peckish Pig Brewing Company, Rogue Brewery, Revolution Brewing, 3 Floyds Brewing and more at this annual event. 

You might start craving soup and comfort foods like this delicious bowl of ramen from Ramen San, which you can order on  Caviar

You might start craving soup and comfort foods like this delicious bowl of ramen from Ramen San, which you can order on Caviar

Stay Active

DMK 'Sorta Marathon'

In the words of Ditka, “You're never a loser until you quit trying.” Participants race from Da Start to Da Finish, where they enjoy live music at the Miller Lite Mustache Bash. Whether you choose to quench your thirst with water or Miller Lite, expect to see lots of 'staches, Ditka-themed attire, and smiles in support of the Chicago Special Olympics.

Chicago Marathon

Thousands of runners race to support charities such as American Cancer SocietyGirls on the Run, or Chicago Area Runners Association (CARA). See the charity program page to learn about causes and organizations supported--you can also volunteer at the race to support participants! Enjoy a 312 Urban Wheat or another libation at the 27th Mile Post-Race Party located in Grant Park’s Butler Field. 

Support a Cause

October is Breast Cancer Awareness Month, and the Susan G. Komen Foundation has a nice tool to find a local event near you. If you can't make it to an event, the National Breast Cancer Foundation also has a variety of ways to get involved. Any time is a great time to support a cause you are passionate about, and doing so while enjoying your favorite drink is icing on the cake. Here are some local events to be responsible while having a good drink in October. The Breast Health Happy Hour at City Winery is one example of drinking for a cause this October.

826 Chi inspires students ages 6 to 18 to explore creative writing and fine tune their writing skills. This culinary-filled event features top Chicago chefs and mixologists: Danny Shapiro of Scofflaw,  Dustin Drankiewicz of Punch House, and Charlie Schott of Parson's to name a few, in addition to local liquid treats from Two Brothers CoffeeRevolution Brewery and Seasons Soda. To top off an elite lineup of food and drink, Dave Eggers will accompany student and professional authors, with a musical performance by Jeff Tweedy.

Green Tie Ball supporting Chicago Gateway Green

Get your groove on at this VIP event supporting your local environment. A heavily attended fundraiser by politicians and passionate environmentalists alike, the Chicago Gateway Green Green Tie Ball is packed with premium entertainment, food and drinks. This annual fundraiser supports the Expressway Partnership Program, which not only beautifies Chicago’s expressways, but also promotes sustainable techniques to reduce air and noise pollution.

On behalf of the Les Turner ALS Foundation, the annual Holla for ALS fundraiser educates the Chicagoland community about the Amyotrophic Lateral Sclerosis (ALS) disease. It’s dealer’s choice at this Casino Night-themed event - Try your hand at a variety of table games including Roulette, Craps, Texas Hold 'Em Poker and Blackjack. Drinks, dancing, and entertainment ensue. Sponsors include Rhine Hall DistilleryJoe's Wine CellarLagunitas Brewing Company.

Play Games

Headquarters Beercade has hosted a costume party in years past, stay tuned for when to dress up and play some arcade games…or just show up in costume any time!