Arts & Entertainment
10+ Can’t-Miss Things To Do In IL This October
Your complete guide to October fun in Illinois from Patch.
October typically hits a weather sweet spot — not too hot and not too cold — making it the perfect time to squeeze in some can’t-miss events in Illinois.;
October is known for Halloween, but it’s also a great time for harvest festivals, public awareness walks, Oktoberfest celebrations, and cultural traditions.
Before you know it, the winter holidays will overtake your calendar. Be sure to schedule date night, family day or even “you” time before October slips away.
Find out what's happening in Chicagofor free with the latest updates from Patch.
To help you fill out your calendar, we’ve rounded up 13 can’t-miss events from around the Chicagoland
Oktoberfest on Division Street Festival: Prost in the Gold Coast
Dust off your lederhosen and celebrate Oktoberfest as Division Street transforms into a lively Bavarian block party for Prost in the Gold Coast, Chicago’s premier Oktoberfest street festival on Friday, October 3 from 3pm to 10pm and Saturday, October 4 from 12pm to 10pm. Located between State Street and Dearborn Street, Oktoberfest on Division Street will feature live band entertainment, games and contests, authentic Oktoberfest beer selections, food offerings, and more.
Find out what's happening in Chicagofor free with the latest updates from Patch.
Raise the Barn! Fall Fest
Join us for Raise the Barn on October 4th from 4-8 pm, a special fall fest that supports urban agriculture while celebrating the harvest season in a fun, festive fall atmosphere. This year, we are partnering with Third Coast Soif to make this an Off Soif event featuring earth-friendly natural wines and ciders, chef collaborations, live music, fire pits, and s’mores — all set on our idyllic 2.5-acre urban farm in Skokie (2 blocks west of Kedzie). This event features wine/cider/beer and chef collaborations with All Together Now!, Tripping Billy, Virtue Cider, middle brow, Chef Tom Carlin’s Burl in Evanston, and many, many more! Think of our fest as a post-game, pre-game, or a destination for the night!
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17th annual Oktoberfest at The Renaissance Room
Join us for our third fundraiser event to support individuals with intellectual disabilities. Doors open at 5 p.m. on Oct. 4 and will feature great music, dancing, and great food direct from Milwaukee.
Making Strides Against Breast Cancer of South Suburban
The Making Strides Against Breast Cancer of South Suburban is an inspirational, non-competitive 2.2-mile walk that unites us in the fight to end breast cancer. The focus is to raise awareness and funds to support the American Cancer Society to save more lives from breast cancer. We want to celebrate and provide hope to those who have been touched by breast cancer.
Native American Harvest Pow Wow
Save the Dates! Don't miss Midwest SOARRING Foundation's spectacular 29th anniversary Native American Harvest Pow Wow on Oct. 11 and 12. A weekend of celebration, tradition, excitement, learning, shopping and fun for the entire family in a comfortable indoor venue.
Chainsaw Manor
Chainsaw Manor is back, bigger and scarier than ever! Brave the fog, flickering lights, and sinister shadows while facing our newest terror: Arachnophobia’s Lair. With all-new animatronics, chilling props, and monstrous surprises, every scream helps support the NICU at Lurie Children’s Hospital.
Farnsworth Fall Festival
Join us for a day of family fun, local food, and creative exploration! Enjoy the colorful autumn setting with art activities, artisan vendors, seasonal treats, and more. Paint, sketch, stroll the trails, or simply relax and take in the stunning view of the House.
Witches Night Out
Grab your broomsticks and gather your coven—Witches Night Out returns to downtown Libertyville on Friday, October 17 for a night of shopping, sipping, and spooky-good fun! Participating businesses will keep their doors open late, offering magical deals, discounts, and specialty drinks from 4-8 p.m. Shoppers are also encouraged to dress in their witchiest attire and enjoy the spirited atmosphere as they stroll through town.
Lincoln Square Greektober Fest
Feeling a little chilly now that Autum is here? Missing the summer sun? Come and grab some of the warmth of Greece at the Lincoln Square Greektoberfest the weekend of October 18 and October 19, hosted by St. Demetrios Greek Orthodox Church of Chicago, located at 2727 W Winona in Lincoln Square.
Hops & Haunts
On Oct. 24, enjoy local craft beer under the stars as our storytellers share eerie legends, unsettling true tales and spine-tingling folklore by the flicker of the campfire. It’s a casual evening of haunted history and nature’s mysteries, perfect for those who like their brews with a side of boo.
Candlelight: A Haunted Evening of Halloween Classics
Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Chicago. Get your tickets now to discover the best Halloween-inspired music on Oct. 24 at Stan Mansion under the gentle glow of candlelight.
Halloween Candy Stroll: Ravinia District of Highland Park
Join the Ravinia District of Highland Park for its annual Halloween Candy Stroll on Friday, October 24, from 3:30 to 5 PM! Trick-or-treaters can collect candy from participating businesses while strolling the streets and enjoying the festive fall décor throughout the District.
Haunted Halloween Ball 2025
Experience a night of thrills with party-goers at Chicago’s biggest Halloween costume party, Haunted Halloween Ball, on Friday, October 31, 2025 at the Congress Plaza Hotel, classified as one of the most haunted hotels in the world by USA Today! Located on Michigan Avenue by Millennium and Grant Park, the Congress Plaza Hotel will be the backdrop for Chicago’s best Halloween party, the Haunted Halloween Ball.
Are you planning an event this fall? Feature it, so nearby readers see it all across Patch — including in roundups like this!
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