31 of the Best Things to Do in Chicago and the North Shore This October

While for some, leaving behind summer in Chicago is an annual grievance, for many others it means fall is here and with it all the cozy, colorful and tasty things there are to love about this time of year. As we bid farewell to the heat and welcome the briskness of autumn, read on for the best things to do in Chicago and the suburbs this month — from pumpkin and apple festivals to theater, fundraising and Halloween fun.

As you enjoy all that the city and suburbs have to offer this month, don’t forget to tag us in your posts on Instagram @betterchicago!

All Month

Howl-O-Ween Canine Cruise Series

mercury cruise dog in flower costume
Photo courtesy of Mercury Cruises

Set sail on the waters of Chicago and get into the Halloween spirit while you’re at it. At Mercury Cruise’s Howl-O-Ween Canine Cruise Series, humans and their furry friends are welcome to dress up in costume and enjoy the serenity and history of Chicago’s waterways. This cruise will be held the first three weekends of October, so grab your tickets now from Mercury Cruises.

112 E. Wacker Dr.


Frankenstein Oil Lamp Theater
Photo courtesy of Oil Lamp Theater

Just in time for the scariest month of the year, “Frankenstein” is running at the Oil Lamp Theater now through November 6. Share in the thrill of Chicagoland’s latest rendition of this tale that has captured audiences for years. Recommended for ages 11 and up, tickets and more information can be found on the Oil Lamp Theater website.

1723 Glenview Rd., Glenview

Twist Out Cancer Exhibit at WNDR Museum

In celebration of a decade of service, Twist Out Cancer will be sponsoring two organization-inspired exhibits this month and a Brushes With Cancer Art Exhibition and Celebration at WNDR Museum in Chicago in November. “The two exhibits feature the work of world-renowned artist Giorgia Lupi and her team at Pentagram Design who created ‘Brushes With Cancer,’ as well as Architect Inti Velez Botero and designer Daniel Mancini from Wanda Barcelona, who are presenting ‘Woven Wonders.’” From October 7 through November 30, audiences can share in the wonder at WNDR. Tickets and more information are available at Twist Out Cancer.

1130 W. Monroe St.

Asleep With The Fishies Overnights

Prepare to see the Shedd Aquarium like never before with their Asleep With The Fishies Overnights program — which invites families or groups with children between 5-12 to sleep over at the Shedd. The evening will include animal and science activities, animal encounters, aquatic crafts, a scavenger hunt and tons more, including exploring open exhibit spaces. The program runs Oct. 15-16, Oct. 28-29 and Nov. 18 – 19, get your tickets now from Shedd Aquarium.

1200 S. DuSable Lake Shore Drive

Chim: Between Devastation and Resurrection

At the Illinois Holocaust Museum & Education Center now through February 4, experience the powerful work from photojournalist Dawid Szymin, who published under the name David Seymour following WWII. Audiences can bear witness to over 50 photographs, each depicting the rarely captured images of life and reality during post-war reconstruction in Europe, and more. Additional resources and information can be found at IHMEC.

9603 Woods Drive, Skokie

October 1: Ravinia Brewing Highland Park Fall Fest

Beginning at the end of September, this weekend-long Fall Fest is just the activity needed to shift into the autumn season. Enjoy live music, delicious tacos, tasty drinks and even a carnival on Saturday. Dozens of local businesses will be in attendance — show some love at the top of this month and stop by! Free and family friendly, visit Highland Park Fall Fest for more information.

486 Roger Williams Ave, Highland Park

October 1: The Field Associates’ Annual Gala

EVOLVE field museum

This October, The Field Associates will host their annual fundraising gala, EVOLVE, from 8pm – midnight. The evening will include “Field Museum scientists, food from BIPOC and women-owned restaurants around Chicago, a silent auction, and many other surprises.” Funds from the gala go to support the Field’s community programs, exhibits and scientific discoveries. Register at Field Museum.

1400 S. Lake Shore Dr.

October 1-2: Lincoln Square Ravenswood Apple Fest

Picture courtesy of the Lincoln Square Ravenswood Chamber of Commerce

No truer way to mark the beginning of the fall harvest season than an entire festival devoted to apples, and all the delicious treats local vendors whip up with this year’s supply. Head over to Lincoln Square this month to help celebrate the 35th anniversary of this North Side tradition, and pick up some of the tastiest baked goods, freshest produce and neatest knick-knacks the fall has to offer. More information can be found on the Lincoln Square Ravenswood Chamber of Commerce website.

Lincoln Avenue between Lawrence and Wilson

October 1-2: Fall Lincoln Roscoe Art & Craft Fair

The folks over at the Fall Lincoln Roscoe Art & Craft Fair know how to give the people what they want, that’s why they are kicking off the month with an art-packed event. From 10:00am – 5:00pm peruse 40 different artists and makers from countless artistic mediums. The addition of live music, delicious food, kids art activities and drinks curated by Bitter Pops makes this event all the more enticing. Find more information on the fest lineup and logistics on the Fall Lincoln Roscoe Art & Craft Fair website.

Lincoln Ave., School to Roscoe

October 2: 31st Annual AIDS Run & Walk Chicago

AIDS run walk chicago

Back again this year — as it has since 2001 — the 31st Annual AIDS Run & Walk Chicago is calling anyone and everyone to participate in their mission to get moving and raise funds to help end HIV/AIDS. While online registration has closed, potential participants can still sign up on the day of the event at Soldier’s Field — and spectators are more than welcome to cheer on the pack as they navigate the streets of the city. Information on racing and registration logistics can be found on the AIDS Foundation of Chicago website.

Soldier Field, 1410 Special Olympics Drive

October 2: 7th Annual Susan Steel Memorial Fall Walk

Photos courtesy of Skin of Steel

Skin of Steel founder and melanoma warrior Susan Steel has been an inspiration to many both in and outside the world of skin cancer research. In her memory, this month Skin of Steel — which is also a winner of a MIBMG Philanthropy Award — will host its 7th Annual Susan Steel Memorial Fall Walk to raise funds for melanoma research and awareness. Not only is the walk a special space for community building but its cause is beyond worthy. And in further support of their own mission, sunscreen will be provided too. Interested parties can find more information on the Skin of Steel website.

West Fork River Trail, Glenview

October 6-7: Shop For Schools

shop for schools

In its 15th year, and for a limited time only, Shop For Schools at a participating store in Roscoe Village and they will donate 20% of your purchase to a participating school of your choosing. Get a little something for yourself and give a lot back while you’re at it! For a full lineup of businesses and schools in partnership with the program, visit the Lakeview Roscoe Village website.

October 7-9: The Great Highwood Pumpkin Fest

Photo by Joel Lerner Photography
Photo by Joel Lerner Photography

The 12th annual Great Highwood Pumpkin Fest delivers all the trademarks of the Halloween season — pumpkin carving, delicious fall treats, decorations and more. There will also be a pie-eating contest, live music, trick-or-treating, a carnival and other activities for a family-friendly weekend of fall fun. More details can be found on the Highwood community website.

Downtown Highwood

October 7-9: Sesame Street Live!

For kiddos and nostalgic adults, Sesame Street Live! is returning to Chicagoland once again for the first time since 2019. Held at the Rosemont Theater, audiences can share in the wholesome fun and electrifying music of some of television’s favorite puppets, including Elmo and The Count. Tickets are on sale now on the Sesame Street Live! website.

5400 North River Rd., Rosemont

October 8: Ghostbusters Live in Concert

Who ya gonna call? Hopefully friends or family to join in the perfect harmony of cinema and live music. Watch one of Hollywood’s most iconic films in Chicago’s famous Auditorium Theater, accompanied by a live performance of the soundtrack by the Chicago Philharmonic. Tickets to this one-of-a-kind event are available now on the Chicago Philharmonic website.

50 E. Ida B Wells St.

October 9: JCC Chicago’s Daffodil Project

To commemorate the 1.5 million children tragically murdered in the Holocaust, JCC Chicago and partners will be participating in the The Daffodil Project — which aims to plant 1.5 million daffodils, and also supports children who are currently at crisis worldwide. This “living Holocaust memorial” welcomes anyone in the Chicagoland to join them for a garden dedication and speech from survivor Gdalina (Lin) Novitsky; this location will contribute over 500 flowers to the program. This event is free but registration is required, more details can be found the Jewish United Fund website.

Bernard Weinger JCC, 300 Revere Dr., Northbrook

October 9: Downtown Evanston Fall Fest

Head over to Fountain Square in Downtown Evanston for a day of fall activities, including music, art and crafts activities, food, craft beer and cider, artist and makers market, henna designs and a whole lot more. While the complete day’s lineup is yet to be announced, attendees can trust the experience will be well worth it, as this is Downtown Evanston’s only fundraising event. Get more information on entry and donation fees at Downtown Evanston.

1601 Sherman Ave., Evanston

October 9: Chicago Marathon

Runners pass through Greektown during a past Chicago Marathon
Runners pass through Greektown during a past Chicago Marathon | Photo courtesy of Greektown Chicago

Runners of Chicago and beyond unite! The annual Bank of America Chicago Marathon is here again, meaning the city will be crawling with athletes and countless spectators ready to share in the heart-pumping excitement. For folks looking to celebrate the annual event or to honor the Greek origins of the marathon, head over to Greektown — between miles 14 and 17 — where a sign-making station, free coffee and Greek pastries, Greek music by a DJ and more is available. Make the most out of these 26.2 miles and check out the Greektown community website for more information.

October 9: Music of the Baroque: Baroque Heroes

This Music of the Baroque program centers on “Baroque Heroes,” a concept guest conductor Patrick Dupre Quigley explores in this “energetic, whimsical program.” With upcoming dates including October 9, 11 and 14, audiences can have their pick of when to attend this thought-provoking experience on the history of the genre. Details and tickets can be found on the Music of the Baroque website.

25 East Washington St.

October 12-23: Chicago International Film Festival

Returning for an outstanding 58th year, the Chicago International Film Festival is as entertaining as ever. This year, as always, the lineup includes films from around the world and from varying perspectives — all of which evokes thought and passion from both filmmakers and audiences. As is tradition with the CIFF, the screenings will take place at different venues across the city; this year from October 12-23. Curious audience members can find more information and register at Cinema/Chicago.

Various locations

October 13: Sip & Swing at Illinois Holocaust Museum & Education Center

The Illinois Holocaust Museum & Education Center is always providing Northern Illinois with important, necessary history and programs. This time around, they are bringing the fun to their mission, with a post-WWII celebration featuring era-specific music from Chicago’s Big Band Boom!, dancing and spirits provided by KOVAL distillery. Register at IHMEC.

9603 Woods Dr., Skokie

October 14: Meals on Wheels’ 2022 Celebrity Chef Ball

In commemoration of 35 years of the Chicago Meals on Wheels program, top chefs and mixologists are coming together to bring an evening of fine dining and fundraising for the Celebrity Chef Ball. This unique evening will allow guests an up-close view of their food preparation with a table-side cooking demonstration of their six-course meal. The night will also include a live auction and paddle raise. Proceeds will go toward homebound seniors and people with disabilities who struggle with food insecurity. Buy tickets at Meals on Wheels.

The Geraghty, 2520 S. Hoyne Ave.

October 15-16: Chicago Architecture Center’s 2022 Open House Chicago

Avondale Bowl | Photo by Sean Henderson
Avondale Bowl | Photo by Sean Henderson

Many of Chicago’s greatest wonders are its architectural gems. Annually, the Chicago Architecture Center holds their Open House Chicago series, which features over 150 sites across 20+ neighborhoods — and this year is no exception to the fun. While guided tours are available on October 15-16, self-guided tours are also available for the duration of 2022’s series through this month. Pictures, locations and logistics can be located on the Chicago Architecture Center website.

Various locations

October 17: Howl-O-Weenie Costume Contest

Halloween isn’t all frights and fears, it can be pretty cute too! That’s the case over at etta in River North, where this month they are hosting a Howl-O-Weenie Costume Contest for pooches and their owners. Registration for humans is $10, which ensures your four-legged friend a spot in the costume contest; a pup menu; a pup party tote-to-go; a specialty cocktail for each human; and a patio table for dinner. Register online at etta.

700 N. Clark St.

October 19: 15th Annual Beacon of Hope

Celebrating its 15th anniversary, the annual Beacon of Hope Luncheon returns this October at The University Club of Chicago. The afternoon will honor Rush Medical Center and the Doulas & Parent Educators of Project Hope “for their ongoing dedication to the Mission of MSV.” The event will also feature a discussion about Maternal & Infant Health in Communities of Color. To register or for more event specifics, visit the Beacon of Hope website.

The University Club of Chicago, 76 E. Monroe St.

October 22: Upside Down Halloween Parade

Photo courtesy of LUMA8

Calling all Halloween lovers! Come join in one of the largest public spooky events of the season with the Upside Down Halloween Parade — featuring dance performances, circus acrobats, musical groups, sports mascots and more — from 12pm – 3pm, presented by LUMA8 and the City of Chicago. Attendees are more than encouraged to dress up in costume, the event is also free and family friendly. More information about the event and upcoming parade dates can be found on the Arts in the Dark website.

Washington Park, Russell Drive

October 22: Spooky Zoo

The Lincoln Park Zoo is back at it again with holiday events, especially this October, as they invite people of all ages to join them for Spooky Zoo. The event will lead costumed participants through the zoo as they trick-or-treat from 10am – 1pm and enjoy live entertainment along the way. Looking for a family-friendly way to spend the spookiest holiday, consider checking out the LPZ website for more information.

2001 N. Clark St.

October 23: Vintage Garage

Have you been on the hunt for that new item? Or maybe just new to you? Head over to the Vintage Garage located at Highland Park’s new event space, The Lot. Shop vintage home decor, clothing, antiques, vinyls and more! Specifics can be found at Vintage Garage.

The Lot, 523 Central, Highland Park

October 24: Trick or Treat on Southport

Photo courtesy of Lakeview Roscoe Village Chamber of Commerce

While trick or treating will be taking place all across the city in the latter half of October, over in the Lakeview Roscoe Village community, they are putting their own twist on things. While decked out in costume, you and your family can enjoy trick or treating at local businesses on Southport, plus family fun activities, a pumpkin patch, craft beer and more. For the full lineup of participating businesses and event activities, visit the Lakeview Roscoe Village community website.

Up and down Southport

October 29: Book Stall: “Our World of Dumplings” with Francie Dekker

From 10am – noon, join the Book Stall in welcoming author Francie Dekker as she discusses and signs her book “Our World of Dumplings,” which focuses on the different types of dumplings across the world and how food unites us all. Get more information at the Book Stall.

811 Elm Street, Winnetka

October 29: Halloween Bar Crawl

If you’ve yet to secure plans for Halloween this year, consider the Halloween Bar Crawl through parts of Lincoln Park, Wicker Park and River North. The evening will be filled with costume contests, live music, a scavenger hunt and other spooktacular activities. The crawl takes place over six hours, giving participants plenty of time to get their ghoul on! Get specifics at the 2022 Halloween Bar Crawl webpage.

Event begins at Beaumont Bar & Grill, 2020 N. Halsted St.

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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.