This October, enjoy the beautiful fall season with events like Lincoln Square’s Apple Fest, cheering on runners at the Chicago Marathon, Highwood’s Great Pumpkin Festival and more. Here are 31 of the best activities October has to offer.
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All Month
Trick or Treating for UNICEF
Starting Oct. 1, teachers and parents are encouraged to register children and create profiles online where they will receive a Virtual Collection Box and customized QR code. Children can earn trick-or-treat coins that add up to real-life earnings. As they collect the coins, they will be able to choose where they want them to go — giving them the power to impact other children around the world.
Open House Chicago
A popular highlight of the season, Open House Chicago is a celebration of architecturally, culturally, and historically significant sites across Chicago’s many neighborhoods. This fall, the festival will feature its new and improved Open House Chicago App, the return of in-person site visits from Oct. 16-17, and a series of virtual programs.
Jack’s Pumpkin Pop-Up
1465 N Elston Ave., Chicago
Jack’s Pumpkin Pop-Up is taking over 2 acres of Goose Island this month. The multi-sensory adventure will include Chicago’s largest corn maze, carnival games, axe throwing, a full service bar and food and drink.
Halloween at Museum of Illusions Chicago
25 E Washington St, Chicago
The Museum of Illusions Chicago is decked out with spooky and freaky décor, making their well-known Head on a Platter, Vortex Tunnel, Infinity and Anti-Gravity Room exhibits that more shocking.
Pumpkin Picking
It’s finally time, and we have your list of the best pumpkin patches around. Check it out, plus where to apple pick and more fall fun.
Shedd Aquarium Animal Encounters Return
1200 S Lake Shore Dr, Chicago
Shedd Aquarium is returning some of its onsite Extraordinary Experiences this month, to continue to connect guests with the aquatic animal world. You can come face-to-face with penguins, sharks or beluga whales, and ask experts questions. Book your experience, that includes museum admission, on Shedd’s website.
Thru Oct 23: DJ Khaled’s BLESSWELL™ x Groomed Pop Up
122 W Monroe St, Chicago
Visit the Kimpton Gray Hotel to experience DJ Khaled’s CBD-infused skincare, GROOMED x BLESSWELL, this month. The ultra-luxe self care experience provides complimentary grooming services using the premium skin and face products of the BLESSWELL collection. To make it a even more memorable experience, book The Gray and BLESSWELL “ROOM + GROOM” Package that includes a hotel stay, a complimentary BLESSWELL gift set and a VIP salon grooming experience.
Thru Oct. 24: Marvel: Universe of Super Heroes Exhibit at the Museum of Science and Industry
700 S Lake Shore Drive, Chicago
It’s the final call to explore Marvel history at the Museum of Science and Industry! The special exhibit includes artifacts, original comic book pages, costumes and props from the movies and more. An additional ticket must be purchased to experience this exhibit. Tickets cost $18 for adults and $14 for children ages 3-11.
Oct. 2: AIDS Run & Walk Chicago
Soldier Field, 1410 Museum Campus Dr., Chicago
Presented by AIDS Foundation Chicago, the 30th annual AIDS Run & Walk Chicago raises funds for individuals living with and vulnerable to HIV/AIDs and other chronic illnesses. Over 1,700 advocates and supporters will join in for this great cause.
Oct. 2: Ravinia Brewing Company Presents 2nd Annual Infusion Fest
Highland Park
Ravinia Brewing is holding its second annual Infusion Fest Oct. 2 in Highland Park. The family-friendly event will have live music, an axe throwing truck, henna art, readings from Psychic Viv and a variety of other activities for all ages. There will also be delicious food and beverage offerings from local and regional vendors.
Oct. 2-3: Apple Fest
Lincoln Avenue between Lawrence and Wilson
Lincoln Square’s Apple Fest is back for its 34th season! The festivities take place Oct. 2-3, from 9 a.m. – 6 p.m. Local farmers will bring in fresh apples, apple cider, apple cider donuts, and more treats. There will also be music, shopping and more.
Oct. 2-3: Halloween Canine Cruise
112 E Wacker Dr, Chicago
Head out on the water with your furry best friend for a ride with Mercury, Chicago’s Skyline Cruiseline. Pooches and their people are invited to come dressed in festive costumes, and there will be pumpkin dog treats and prizes for the best doggie costumes.
Ends Oct. 3: The Other Art Fair
Revel Fulton Market, 1215 W Fulton Market, Chicago
Chicago’s favorite independent art showcase takes place Sept. 30 – Oct. 3 in the West Loop. Presented by Saatchi Art, The Other Art Fair gives guests the opportunity to meet a curated selection of over 110 independent artists and browse thousands of pieces to suit every budget under one roof. With prices starting from as little as $100, this is an art fair for everyone.
Oct. 3: Bucktown 5K
1621 West Wabansia (Wabansia & Marshfield), Chicago
Run for a good cause during Bucktown’s 5K; proceeds go to MY BLOCK MY HOOD MY CITY, helping fund their mission to empower and inspire Chicago youth so they can take positive action with confidence, creating a new world of possibilities for themselves and their families.
Oct. 7: Copa Carnivale
702 West Fulton Market Street, Chicago
Head to Carivale for “Copa,” an all-new, cabaret style dining experience with limited performances in the restaurant’s iconic dining room. The 90-minute extravaganza will transport guests into the magic of the legendary Copacabana nightclub with colorful twists, delighting with world-class talent including Brazilian dancers, feathered showgirls, live music from an Afro-Brazilian band, acrobatic aerialists and more.
Oct. 8-9: Lincoln Park Wine Fest
Jonquil Park, 1001 W. Wrightwood Ave., Chicago
Lincoln Park will host its annual Wine Fest, featuring tastings of wines from all around the world, live music, a variety of food and craft vendors, and more. Festivities will take place in Chicago’s Jonquil Park, and VIP tickets are $65, with General Admission at $40.
Oct. 8-10: The Great Highwood Pumpkin Festival & Skeleton Invasion
17 Highwood Ave., Highwood
Pumpkins and skeletons will descent upon Highwood for a spooky family-friendly weekend! With multiple photo opportunities, including a great pumpkin wall and themed skeletons, Highwood is the place to be Oct. 8-10. There is no entry fee, and attendees are encouraged to “BYOP” (place their own personal pumpkins) on walls if they wish, or they can carve one at the festival. Proceeds from the festival will benefit Highland Park High School Charity Drive.
Oct. 9-10: Kohl Children’s Museum Fall Family Festival
2100 Patriot Blvd, Glenview
Grab your tickets in advance for Kohl Children’s Museum Fall Family Festival, Oct. 9-10. Tickets are $25 a person, and only $15 for members. Tickets include a kiddie train ride along a not-so-scary haunted ghost hunt path, a farm animal petting zoo, and an old fashioned cider press, where kids can make their own cider.
Oct. 10: Greektown Chicago’s Special Cheer for the 2021 Chicago Marathon
Gladys and Halsted Street
A Sunday spent cheering on marathon runners is a day well spent. Head to Greektown from 8 a.m. – 2 p.m. to support runners at miles 14 and 17. There will be a sign making station, a DJ playing Greek and American music, and complimentary coffee and Greek pastries. Stay after to enjoy some traditional food, including Flaming Saganaki.
Opens Oct. 13: 57th Annual Chicago International Film Festival
212 W Van Buren St, Chicago
North America’s longest-running competitive film festival, the Chicago International Film Festival, is back for its 57th event. Running Oct. 13-24, the festival offers moviegoers the ultimate Chicago film experience, including premiere screenings in theaters and online, post-screening artist discussions, and tributes to legendary filmmakers. Check out our guide to the 2021 Festival.
Opens Oct. 13: Botanic Garden’s Night of 1,000 Jack-o’-Lanterns
1000 Lake Cook Road, Glencoe
Experience the Garden in its colorful fall setting as over 1,000 LED-lit jack-o’-lanterns light up the night. The jack-o’-lanterns will line a festive pathway, where seasonal drinks and snacks will be provided along the way. Reservations required, available Oct 13-17 and Oct. 20-24.
Opens Oct. 15: The Office Experience
The Office comes to the Mag Mile this month, allowing fans to experience Schrute Farms, walk through the Dunder Mifflin set, and relive Jim and Pam’s iconic romance. There will be original set recreations, show costumes and props, and opportunities for fans to engage with the show in new ways between 17 rooms. Tickets are required.
Oct. 15-31: Boo Fest at the Museum of Science and Industry
700 S Lake Shore Drive, Chicago
Celebrate Halloween at the Museum of Science and Industry this month with science-themed activities, including an eyeball dissection, spooky experiments and more. Admission is included in museum entry.
Oct. 16: Charlie Berens at the North Shore Center for The Performing Arts
9501 Skokie Blvd., Skokie
Oh don’t cha know, Charlie Berens, from The Manitowoc Minute and social fame, is coming to Skokie! Berens Midwest-focused sketch comedy videos have garnered hundreds of millions of views, and he is bringing his Midwest Survival Guide Tour on the road.
Oct. 16: Field Museum 2021 Gala
1400 S Lake Shore Dr., Chicago
Support the Field Museum and their mission during a beautiful night out at their Annual Gala on Oct. 16. The Women’s Board and Board of Trustees will commemorate the Field’s Building Centennial, and 100 years in their lakefront home. The in-person event will feature cocktails, dinner, and exclusive experiences with up-close views of the Field’s hidden wonders. Tickets are required.
Oct. 16: Chicago Children’s Choir Annual Red Jacket Optional Livestream Concert
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An inspiring event will be livestreamed for free on Oct. 16 for all to enjoy. Tune in to see the Chicago Children’s Choir perform alongside a slate of high-profile artists including two-time Grammy Award-winner Kurt Elling, Chicago native singer-songwriter Natalie Bergman, Eurovision’s Vasil Garvanliev, and acclaimed opera singer Jonathan Green.
Oct. 17: Rise Up Exhibit Opening at the Illinois Holocaust Museum and Education Center
9603 Woods Dr., Skokie
The Illinois Holocaust Museum’s newest exhibit, Rise Up: Stonewall and the LGBTQ Rights Movement, examines the 1969 Stonewall Inn raid and its role in the gay rights movement.
Oct. 22: Undernights: Dinosaurs at the Field Museum
1400 S Lake Shore Dr., Chicago
The Field Museum will come to life after hours, where children and adults can safely enjoy after-hours access to permanent exhibitions and the special exhibit, The Machine Inside: Biomechanics. Tickets are $45 per person for members and $50 for non-members.
Oct. 23: Virtual James W. Foley Freedom Run
The James W. Foley Foundation’s 7th annual Freedom Run is back virtually — so anyone, anywhere can participate. It is a day to remember Jim, who was killed while reporting abroad, and to support the foundation’s mission to advocate for the freedom of Americans held hostage abroad and to promote the safety of journalists worldwide.
Oct. 23: Susan G. Komen Race for the Cure
One of the biggest annual events for breast cancer survivors and supporters, the Komen Chicago Race for the Cure, will be held virtually. Race or walk from wherever you are!
Oct. 23: Cider and Ale Festival at The Morton Arboretum
4100 Illinois Rte. 53, Lisle
Sample hard cider and seasonal beers from over 30 local breweries at The Morton Arboretum. Tasting booths will be spread out along walking paths, and your Beer Tasting ticket includes admission for the day so you can explore the grounds.
Oct. 29: Prisoner Wine Dinner
5200 Pearl St, Rosemont
Thorn Restaurant & Lounge, located in the The Rose Hotel Chicago O’Hare, will partner with The Prisoner Wine Company for an exclusive Prisoner Wine Dinner on Oct. 29 at 7 p.m.. The two-hour evening will be hosted by John Samaritano, a WSET III certified sommelier, and will feature a custom four-course menu perfectly crafted and complemented by Thorn’s Executive Chef Nicholas Malloy. Tickets are $110 per person.
Oct. 29-31: Halloweek at HideSeek
1620 N Wells St., Chicago
Jump into a world of childlike wonder at HideSeek, which is comprised of 15 multi-dimensional self-guided rooms, with excitement around every corner. From October 29-31, HideSeek invites guests of all ages to trick-or-treat through each HideSeek room and collect nostalgic candy. Guests are encouraged to come in costume, and prizes will be given to the best costumes of the night. General admission tickets are $35.00 plus taxes and fees; children’s tickets (ages 4-12) are $27.00 plus taxes and fees. Free admission to children under the age of 3. HideSeek also is offering a family pack bundle, in which two adult and two children’s tickets are priced at $110.
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Macaire Douglas lives in the Chicago suburbs with her husband and two sons. She proudly supports Save Abandoned Babies Foundation, a Chicago-based nonprofit organization that works tirelessly to prevent the illegal abandonment of newborns nationwide. Since its inception in 2000, more than 3,600 newborns have been safely surrendered and adopted into loving homes.
