Chicago October 2024

Chicago October 2024 Events

Chicago October 2024 Events

Get in the Spooky Spirit and Check Out Halloween-Themed Events in Chicago

Average temperature low and high: 50°- 62°
From Nightmare on Chicago Street, to the Haunted Halloween Ball, Chicago has lots of cool events in celebration of Halloween time to check out. There are also cool culinary events throughout the month to help you explore this food focused-city; check out the Cantigny Food Truck Festival or the Chicago's Taste of a Nation event. Whatever you decide, the October calendar if filled with fun options.

October Event Calendar

Dave Chappelle

Ever since breaking out on Comedy Central with his own hit sketch series, Dave Chappelle has become one of the most in-demand, arena-level comedians in the United States. The same thought-provoking humor that drew millions to "Chappelle Show" has only grown more provocative in Netflix specials like "Sticks & Stones" and "The Closer." The comic isn't afraid to take on identity politics, cancel culture and other hot button issues, putting a sly and thoughtful spin on current events with a point-of-view that's undeniable his own. See him in person for a complete experience while laughing along with thousands of other fans. Buy tickets

Drunk Shakespeare

The stage is set in the secret speakeasy behind the world-famous Chicago Theater. Five classically trained actors unite as “The Drunk Shakespeare Society”. One actor takes at least 5 shots of whiskey before playing a principal role in a Shakespearean play. Hilarity ensues as the sober actors try to keep the drunkness in check. Every show is different depending on who's drinking what. Don't miss the classical lunacy at The Lion Theatre – 182 N Wabash Ave Near E Lake St in Chicago. Book your experience now! 

1776 - The Musical

It's 1776 and the nation is on the verge of declaring independence, if only the Founding Fathers can stop arguing long enough to do it! Celebrate our nation's independence from tyranny in the classic, Tony Award-winning musical through October 13th at the Marriot Theatre at Ten Marriott Drive in Lincolnshire. Do the patriotic thing and reserve your seats now

Blue Man Group

The legendary Blue Man Group brings their unique blend of music, comedy, and wonder live to the Windy City. The Blue Man Group is a vibrant collision of music and art, mixed in a blender filled with whimsy. Words can't do the Blue Man Group justice. Experience the magic yourself when The Blue Man Group lands at the Briar Street Theatre at 3133 N Halsted in Chicago, October 3 - November 30, 2024. Get your tickets now

Lincoln Park Wine Fest

Lincoln Park Wine Fest

Spend three days sipping from a choice of more than 150 wines in the heart of Chicago's historic Lincoln Park neighborhood. It's a tranquil setting, taking places in the fresh autumn air at Jonquil Park, less than two miles from Lake Michigan. Wineries from around the world, including more than 50 countries, will be represented. Shop among food vendors and find the perfect bite to pair with your wine. The event is 5-10 p.m. Friday (October 4), 11 a.m. to 10 p.m. Saturday (October 5) and 11 a.m. to 7 p.m. Sunday (October 6).

Learn more.

Chicago Beer Festival

Chicago Beer Festival

The Chicago Beer Festival is coming back to The Field Museum this October. The festival will feature 65+ breweries showing off their best fall beers. Some of this year’s breweries include Young Blood Beer Co., Penrose, Two Brothers Brewing Co., Old Irving Brewing Co., and lots more. General admission & early admission tickets are available. General admission costs $55, while early admission is $70 and comes with additional perks such as an extra hour before the event begins and access to limited-release beers. Tickets can only be bought online, they will not be sold at the door. The Chicago Beer Festival is a 21+ event.

Pink Talking Fish - a tribute to Pink Floyd, The Talking Heads and Phish

Experience the ultimate tribute fusion with Pink Talking Fish, a one-of-a-kind live performance that combines the music of Pink Floyd, Talking Heads, and Phish into an unforgettable show. This powerhouse group blends Pink Floyd, the Talking Heads, and Phish to create a dynamic concert. Featuring musicians Eric Gould, Richard James, Zack Burwick, and Cal Kehoe, Pink Talking Fish celebrates the artistry of these legendary acts. Tickets for their Chicago show at Park West are on sale now.

Chicago Marathon

Chicago Marathon

The Chicago Marathon is one of the most celebrated races in the United States. Revel in the challenge of athletics and the thrill of exploring a great American city from a unique vantage point. The Chicago Marathon is known for a flat course that encourages high speeds among participants. Don't be surprised to see a few records broken. It's a highly competitive affair and geared toward experienced runners, although anyone is welcome to take part. Just remember to register early and be ready for the weather. The Chicago Marathon takes place rain or shine, passing through 29 historic neighborhoods.

Chicago International Film Festival

Chicago International Film Festival

Experience the 60th Chicago International Film Festival this October. Taking place over 12 days, this event combines culture, art, and education through filmmaking. Attendees will have the opportunity to pick from the screening of 80+ films and 60+ short films at local drive-ins and theaters. In-person tickets, passes, and bundles will be for sale for members and non-members. In-person tickets & passes range from $15 to $400. Be sure to check back for the latest information on passes, films, and venues.

Whiskey and Barrel Nite

Whiskey and Barrel Nite

A fun evening with unlimited tastings awaits you at Chicago's Morgan MFG. Sample with your souvenir glass from 180+ scotches, bourbons and whiskies from around the world, and enjoy a whisky-infused dinner buffet with cocktails and music. General Admission passes are $119, and entry opens at 6:30 p.m. Get early entry and access to the special experience area with a $179 VIP pass, which also includes a special VIP tasting list.

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Open House Chicago

Open House Chicago

Every year when October comes around, the Chicago Architecture Center hosts a free 2-day festival open to the public. Open House Chicago focuses on highlighting and exploring over 160 of Chicago's most significant places with behind-the-scenes access. Attendees will get to see historic mansions, private clubs, sacred spaces, hotels, offices, theaters, and more. There will also be other virtual events throughout the month.

Rosehill Cemetery ‘Crypt’ 5K Run/Walk

Rosehill Cemetery ‘Crypt’ 5K Run/Walk

Run? Walk? The choice is yours. A Halloween season favorite returns to the Windy City as the Rosehill Cemetery Crypt 5K takes hold at Rosehill Cemetery. It's a rare moment to test your athletic powers in a 5K run after dark with a course illuminated by candlelight. The atmosphere may give you shivers, but it's all in good fun at Chicago's largest and most historic cemetery. The run is 9 p.m. and the walkers start 15 minutes later. A costume contest offers prizes for the most creative outfits.

Arts in the Dark

Arts in the Dark

Arts in the Dark is an enchantingly spooky parade celebrating Halloween as the “artist’s holiday”. Artists from all over Chicago bring creativity, performance, and art to the street honoring the Windy City's rich artistic tradition. The magic happens on Saturday, October 19, 2024, from 6:00 - 8:00 pm in the heart of the Chicago Loop on State Street.

Learn more.

Halloween Bar Crawl

Halloween Bar Crawl

Crawl with Us presents Halloween Bar Crawl - where 1,000+ bar crawlers are expected to dress in their creepiest best for the chance to win a $1,000 costume contest. Set your own pace and "make your own adventure crawl," where you will have access to 2-3 drinks or shots included with a ticket as well as exclusive food & drink pricing and waived cover at all participating venues. Some of this year's venues include Bar Moxy, Fado Irish Pub, Mother Hubbard's Sports Pub and several others. If you dare…make your way to the after-party starting at 10:00 pm.

Haunted Halloween Ball

Haunted Halloween Ball

Dress to scare at the 2024 Chicago Haunted Halloween Ball Party. This year, Haunted Halloween Ball & Surreal Nightlife are joining forces to bring a spooky spectacular night at the infamous Congress Plaza Hotel. Ghosts, witches, & goblins alike will enjoy an evening of dancing, world-renowned DJs, recording artists, zombie cocktail servers dressed as French maids and other theatrical performances. Tickets, VIP tables, and group discounts are available now…but not for long. This is a frightening 21+ event. Proper ID is required - names will be checked at the door.

River North Halloween Day Crawl

River North Halloween Day Crawl

No need to wait until dark to celebrate Halloween - Start the festivities early at the River North ​​Halloween Day Crawl. All bars are within crawling distance, so there is no need to worry about finding an Uber. Ticket holders get admission, free gift cards, breakfast buffets, drink specials, costume contests, giveaways & lots more.

Haunted Halsted Halloween Parade

Haunted Halsted Halloween Parade

Celebrate Halloween at the spooktacular Haunted Halsted Halloween Parade. For 27 years, this ghostly parade draws in intricate costumes and scary fun for adults and children alike. Spectator and costume contest participation is free for all age levels. Be sure to check back for more information on performances and award show location. 

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Chicago Events in October

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Things to do in Chicago

Things to Do in Chicago in October

Try a Chicago Italian Beef Sandwich

Try a Chicago Italian Beef Sandwich
Slices of roasted sirloin cooked in a seasoned broth and stuffed inside an Italian-style roll, the Italian beef sandwich is a Chicago staple that's a must-try when in town. There's no debate about who has the best one, make sure you stop by Al’s Italian Beef’s for this mouth-watering sandwich. You won't regret it.

Visit Old Fashioned Candies

Visit Old Fashioned Candies
Get your sweet fix at this nostalgic candy store that has been open since 1969. This family-run business hooks locals and visitors with their handmade chocolates and penny candies. They even sell supply kits to take with you to make your own candy at home.