It’s that time of year in Chicago when the sidewalks are lined with crunchy leaves and a crisp breeze signals the arrival of fall events we look forward to all year. From haunting thrills just in time for Halloween to cozy afternoon outings, we’ve rounded up the best things to do in Chicago and the suburbs this October.
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All Month
Elizabeth Catlett: “A Black Revolutionary Artist and All That It Implies”
Bringing together over 100 works from across Catlett’s awe-inspiring career, this long-overdue retrospective showcases the significant role this revolutionary artist played in her time and the influence she still has today. Her powerful work continues to speak directly to all those united in the fight against poverty, racism, and imperialism. See this work in person before January 4, 2026.
Community Cinema: Free Screenings
The Chicago International Film Festival is excited to announce our 2025 Community Cinema series, bringing free film screenings to South and West side neighborhoods in Chicago. Screenings will be held at Kennedy-King College Theater (Englewood) and the National Museum of Mexican Art (Pilsen).
Revolution(s)
Revolution(s) follows Hampton Weems, a young soldier and aspiring musician who returns from Afghanistan to the South Side of Chicago and is drawn into a resistance movement. Written by Chicago playwright Zayd Ayers Dohrn and directed by Steve H. Broadnax III, with music and lyrics by Libertyville native Tom Morello (Rage Against the Machine, Audioslave and The Nightwatchman), Revolution(s) charts a multigenerational struggle for justice in all-new radical musical event to a soundtrack of punk, hip-hop and metal. The show runs from Oct. 4-Nov. 9 at the Goodman Theatre.
Jack’s Pumpkin Patch Pop-Up
For many Chicagoans, fall means sweet treats and autumn-colored photo-ops. And luckily for us, Jack’s Pumpkin Patch Pop-Up is the annual opportunity to do all of that and more. On Goose Island, the seasonal festivities go from now until early November. Here, Jack’s opens its doors to millennials looking for fun, parents seeking a family night out and anyone else who loves this season. Whether you plan on winding through the corn maze, having an inspired cocktail or just enjoying the fall air, you’ll want to head over to Jack’s Pumpkin Patch Pop-Up to grab your tickets first.
Raqib Shaw: Paradise Lost
Epic and intricate, monumental and meticulous—the paintings of Kashmir-raised, London-based artist Raqib Shaw offer fantastical meditations on identity, transformation, and the redemptive power of
beauty. Witness this masterpiece now through January 19, 2026.
Paranormal Activity
James and Lou move from Chicago to London to escape the past… but they soon discover places aren’t haunted, people are. An original story set in the world of the Paranormal Activity films, this terrifying new play from celebrated Chicago playwright Levi Holloway will haunt you long after you get home. Catch this show at Chicago Shakespeare Theater October 8-November 2.
Chicago Humanities Festival Fall 2025
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Through a stellar lineup of artists, creatives, innovators and more, the Chicago Humanities Fall Festival “connects people to the ideas that shape and define us.” By bringing in a lineup of speakers who are “leading figures from across disciplines and professions” the fest takes audiences beyond the surface level. The festival runs throughout October, which means all month long you can enjoy the curated acts they have in store. Tickets and details are available online at the Chicago Humanities Fall Festival.
Ashland Avenue at Goodman Theatre
Goodman Theatre opens its Centennial Season with the world premiere of Ashland Avenue, a heartfelt and funny new play by Lee Kirk. Pete’s TV and Video, once a thriving Chicago electronics chain, is down to its final store. Pete (Francis Guinan), a local legend thanks to his commercials, believes the business can be revived, while his daughter Sam (Emmy nominee Jenna Fischer, The Office) dreams of a different path. Directed by Artistic Director Susan V. Booth, the production also stars Will Allan, Cordelia Dewdney, and Chiké Johnson. Just extended for a second time, the play now runs through Oct. 19, 2025 in Goodman’s Albert Theatre.
Misery
Romance novelist Paul Sheldon is rescued by obsessed fan Annie Wilkes, who traps him after he kills off her favorite character. Forced to rewrite his novel under her watch, Paul is caught in a tense, life-or-death struggle for survival. Misery will run until October 12.
DESTINOS: 8th Chicago International Latino Theater Festival
8th Chicago International Latino Theater Festival returns to Chicago again this year as the citywide festival showcasing local, national and international Latino theater artists and companies. The fest has an impressive run from October 1 until November 2, so you’ve got plenty of time to join in the celebration this month. The festival lineup includes various productions that are new to the city and remains a “cultural high point of Chicago’s Latino Heritage Month.” Find more details on the Chicago International Latino Theater Festival site.
Tiffany Lamps: Beyond the Shade: Driehaus Museum
Driehaus Museum’s Tiffany Lamps: Beyond the Shade—open until March 15, 2026—casts a new light on one of the Gilded Age’s most recognizable names. The show moves past the familiar glow of Tiffany’s stained-glass shades to reveal the full scope of the studio’s work between the 1890s and 1920s — from bronze boxes and pottery vases to a monumental chandelier rarely seen by the public. With pieces drawn from both the Driehaus collection and the Richard H. Driehaus Art Exhibition Lending Foundation, guest curator Alexandra M. Ruggiero frames the story around the artistry, materials, and influential designers that helped make Tiffany a household name.
Gustave Caillebotte: Painting His World
Impressionist artist Gustave Caillebotte (1848–1894) — known and beloved by many Art Institute visitors for his monumental painting Paris Street; Rainy Day — takes center stage in this major exhibition exploring the very personal interests and relationships that shaped his world. Catch it through October 5, details at the Art Institute online.
Movies at the Parks
The beautiful Chicago Parks system is in full use this summer and fall with a number of outdoor events all over the city. But none bring in a more steady crowd than the Movies in the Parks series, a part of the city’s larger Night Out in the Parks initiative. Enjoy family-friendly movies that range from newer releases to kid favorites, all while reclining on the lawn of your local park — now through October 25. Head over to the Chicago Park District online for dates, locations and movie lineups.
October 3-5: The Great Highwood Pumpkin Festival
The 15th annual Great Highwood Pumpkin Fest delivers all the trademarks of the Halloween season — pumpkin carving, delicious fall treats, decorations, costume contests 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.
October 3-5: Lincoln Square Ravenswood Apple Fest
Returning for a delicious 38th year, the Lincoln Square Ravenswood Apple Fest always marks the beginning of the fall harvest season. Where else can you find a festival devoted to apples, and all the delicious treats local vendors whip up with this year’s supply? More information can be found on the Lincoln Square Ravenswood Chamber of Commerce website.
October 3-5: Lincoln Park Wine Festival
Sip, sip, hooray! The Lincoln Park Wine Fest returns for another year in Jonquil Park, ready to greet all wine lovers, both new and returning. This year’s fest features an open air market in the park, perfect for locals to wind through as they sample from wine and food vendors. The biggest draw of all to the fest, of course, being the ticketed wine tastings attendees can enjoy. Make your reservation now on the Lincoln Park Wine Fest website.
October 4: 2025 Walk to End Alzheimer’s
This annual tradition is not only responsible for significant fund raising and national outreach, but it serves as a community for those affected by Alzheimer’s. In September 2025, Make It Better Foundation generously offered to match every gift up to a total of $15,000 raised by participants in our Chicago, Lake County, and North Shore Walk To End Alzheimer’s. Join this powerful wave by visiting Walk to End Alzheimer’s online.
October 5: Chicago Beer Fest
A cold beer is nice, but what might make it even better is having that beer in the middle of one of Chicago’s favorite museums. This month, head over to the Field Museum where they are hosting the Chicago Beer Festival — a sampling event with tons of breweries who have brought out their best fall seasonal brews. While there, guests will have access to select exhibits and the opportunity to purchase food. If that sounds like a good time, you better head over to the Chicago Beer Festival for tickets and details.
October 8-10: Shop for Schools 2025
In its 18th year, and for a limited time only, Shop For Schools at a participating store in Lakeview Roscoe Village and they will donate 15% 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! And to top it off, the LRV Chamber of Commerce will donate $6,000 to schools as well. For a full lineup of businesses and schools in partnership with the program, visit the Lakeview Roscoe Village website.
October 8-26: Night of 1,000 Jack-o’-Lanterns
From frightening to friendly to down right fascinating, the Night of 1,000 Jack-o’-Lanterns returns to the Chicago Botanic Garden this fall to enthrall guests who weave through the outdoor exhibit. As you make your way through the grounds, take in the endless rows of artistically carved pumpkins, all while costumed entertainers walk among the grounds and a live pumpkin carving takes place. Guests come from near and far each year to take in the splendor, and you can be one of them by checking out tickets on the Chicago Botanic Garden site.
October 11: Stews and Brews
Stews & Brews returns to Downtown Highland Park for a 4th year at Port Clinton Square. Cool weather means hearty comfort foods and hot beverages; Stews & Brews is the perfect event to warm your body and soul. This is not your ordinary chili cook-off or craft beer fest. This free, all-ages event offers attendees an array of cold weather comfort foods as well as dozens of unique brews. More information can be found on the Highland Park website.
October 12: Bank of America Chicago Marathon
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. If you aren’t up for the 26.2 miles but are looking for free entertainment, head down to the Loop to join in the fun anyway. Who said spectators can’t have just as much fun? However, officials recommend taking the CTA in order to limit car traffic downtown. Visit the Bank of America Chicago Marathon website for details.
October 12: Music of the Baroque: Bach’s Brandenburg Concertos
Revel in the vibrant energy and dazzling virtuosity of Johann Sebastian Bach’s Brandenburg Concertos. The Music of the Baroque Orchestra’s talent is on full display throughout, from the swaggering hunting horns of Brandenburg Concerto No. 1 to the dark-hued Sixth Concerto. Principal Guest Conductor Nicholas Kraemer directs.
October 15-26: 61st Chicago International Film Festival
Join us this October for the 61st edition of North America’s longest-running competitive film festival. This year’s Fest will feature 100+ films from 50+ countries, bringing together filmmakers and film lovers from around the world for 12 days of screenings, conversations, panels, and special events.
October 16-18: Coco in Concert Live to Film
Join Lyric Opera of Chicago to enjoy the beloved Disney/Pixar film Coco as the score is played live. This Oscar-winning film and rare experience is not to be missed. Visit the Lyric online for tickets and more information.
October 17-18: Cornelia Arts Building October Open Studios
Mingle with artists and art enthusiasts at one of the largest artist studio building on Chicago’s North side. Shop two floors of dozens of artist studios in this 39 year old former ice-house. Free, family friendly.
October 18: Spooky Zoo
As is tradition in October, The Lincoln Park Zoo invites people of all ages to join them for Spooky Zoo. The event will lead costumed participants through the zoo grounds 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.
October 18: Arts in the Dark
Welcome to the 11th Annual Arts in the Dark Halloween Parade—held from 6-8pm on State Street in the Loop. The beauty and grandeur of this parade is brought to attendees in thanks to artists and participants who “bring performance and creativity to the streets.” Thousands of visitors “will be dazzled by music, dance, spectacle puppets, creative floats and more!” This free, family-friendly parade is open to all who want to share in the wonder of a Halloween-inspired parade that has been dubbed, the “artist’s holiday.” More details at Arts in the Dark.
October 18: Rosehill Cemetery “Crypt” 5K Run/Walk
Head up north to Rosehill Cemetery where you’re in for a ghoulishly-fun time at their annual “Crypt” 5K Run/Walk. All glow stick-covered athletes will make their way through the candle lit course in order to reach the finish line, once there, you’ll be treated to an after party with some complimentary drinks. A devilishly good time awaits you — sign up on the Rosehill Cemetery “Crypt” 5K Run/Walk website, and find more information there, too.
October 18-19: Open House Chicago
Many of Chicago’s greatest wonders are its architectural gems. Annually, the Chicago Architecture Center holds their Open House Chicago series, which features well over 100 sites across 22 neighborhoods — and this year is no exception to the fun. While in-person tours are available, there are other opportunities for behind-the-scenes info and virtual programming through their app. Pictures, locations, logistics and more can be located on the Chicago Architecture Center website.
October 24: Damon Locks’s Black Monument Ensemble
Originally conceived as a medium for Damon Locks’s sample-based sound collage work, Black Monument Ensemble (BME) has evolved into a vibrant collective of artists. Galvanized by Locks’s conceptualizing, poeticizing, and guiding vision, the contributors come from all facets of the diverse wellspring of Black artistic excellence in Chicago. See them live at the Harris Theater for Music and Dance this month.
October 25: Costumes & a Cause: Chicago’s Biggest Halloween Party Supports Medical Research
Illumination Chicago returns Oct. 25 at Moonlight Studios with glowing art, DJs, dancing, and immersive Halloween fun— all for a cause. Founded by Shawn Clark, CEO of CRG, the event has raised nearly $12M for rare disease research. This year’s goal: another $1M. Costumes highly encouraged for maximum spooky flair.
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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.
