October is an event-filled month, with the inaugural Chicago Art Fair, which runs October 7-10 at THE MART, being one of the first. This fair features nearly fifty local, national and international galleries presenting contemporary and modern paintings, mixed media, photography and sculpture.
Congratulations to the four Chicagoans who are on TIME magazine’s inaugural The TIME100 Art 2026 list of “the most influential people shaping the future of art”: “globe-trotting curator” Naomi Beckwith; artist, professor, and civic leader Theaster Gates; painter Kerry James Marshall; and Renaissance Society director Myriam Ben Salah. The exhibition “Kerry James Marshall: The Histories” is currently on view at the Musée d’Art Moderne de Paris.
You can see the future of art at the Hyde Park Art Center’s biennial exhibition “Ground Floor,” through November 1, which features the work of twenty artists who have recently (in 2025 and 2026) graduated from one of Chicago’s five outstanding Master of Fine Arts (MFA) programs: Columbia College; Northwestern University; The School of the Art Institute of Chicago; the University of Chicago; and The University of Illinois at Chicago.
The School of the Art Institute of Chicago’s Department of Fashion Design and the Driehaus Museum present “Beauty Standards: A Salon Discussion” at the Murphy Auditorium on October 13. It’s just one of over eighty events that are part of the 3rd edition of Chicago Fashion Week®, October 8-18. All the events are open to the public, and most are free with advance registration. Another event, “A Walk Down the Fairway: Clothing Drive, Golf Outing and Fashion Show” at the South Shore Cultural Center on October 10, includes a Best Dressed Golfer Contest.
It is certainly the case that garments made of synthetics are the right fashion choice at the Bank of America Chicago Marathon® October 11. The first Chicago Marathon was September 25, 1977 and has since become one of the world’s top marathons.
The following day is Columbus Day (and October is Italian American Heritage and Culture Month). The 74th annual Columbus Day Parade kicks off at Dearborn and Wacker and continues down Dearborn to Van Buren.
That same day, October 12, a new museum, the Florence Scala Chicago Italian American Museum, is scheduled to open at 1501 Taylor Street in Chicago’s Little Italy neighborhood. Scala (1918-2007) was a lifelong resident of the neighborhood who attended programs at Jane Addams’ Hull House when she was growing up and later worked with Jane Addams to advocate for immigrants. In the early 1960s, Scala unsuccessfully fought to save her neighborhood from displacement by urban renewal and the construction of the University of Illinois at Chicago, which opened in 1965. Later in life, she was the proprietress of Florence’s restaurant. Last month a plaque honoring Scala was unveiled at her former home at 1030 Taylor Street. She was featured in “The Boss and the Bulldozer: How Richard J. Daley and Urban Renewal Reshaped Modern Chicago and Built Boundaries,” one of the 2023 episodes in the WTTW’s “Chicago Stories” series of documentaries about the people, companies, communities, and events that helped shape Chicago.
The sixth season of “Chicago Stories” opens this month with four new episodes: “World’s Fair of 1893” (October 2); “Toy Town” (October 9); “Skyscrapers” (October 16) and “Home of the Irish” (October 23).
I attended Our Lady of Mount Carmel Church and Our Lady of Mount Carmel Academy on West Belmont in the 1960s and 1970s. Our pastor from 1960-1976 was the Rev. Thomas Byrne, who always marched in the Saint Patrick’s Day parade, either next to or near Mayor Richard J. Daley (1902-1976). The connection was a mystery to me until a few years ago when I asked the mayor’s son Mayor Richard M. Daley why -- he said that his father and Father Byrne had grown up together in Bridgeport.
Another new museum in Chicago is the Muddy Waters MOJO Museum, which was the home of Chicago Blues legend Muddy Waters. The museum is one of nine recipients of the Landmarks Illinois/Driehaus Foundation Preservation award and is also one of twenty new sites that are part of the 16th annual Open House Chicago® October 17-18. The Chicago Architecture Center’s free architecture festival is your chance to explore Chicago and visit more than two-hundred sites across thirty neighborhoods. Other new sites this year include TimeLine Theatre’s new home in Uptown and the Woman’s Athletic Club of Chicago on Michigan Avenue. The Chicago Architecture Center’s grand opening ceremony of its second location, the Marquette Hub, in Holabird & Roche’s Marquette Building (1895), is October 5, World Architecture Day.
Famed architect Howard Van Doren Shaw built his summer estate Ragdale in Lake Forest in the Arts and Crafts style in 1897. The home and barn are listed on the National Register of Historic Places. In 1976, Shaw’s granddaughter Alice Judson Hayes founded the Ragdale Foundation, an artist residency program on the estate fostering musicians, visual artists, writers and choreographers. To celebrate the 50th anniversary of both the Ragdale Foundation and the Lake Forest Preservation Foundation, the organizations will host a Historic Preservation Symposium on October 16-18 at Ragdale and other locations in Lake Forest. The History Center of Lake Forest-Lake Bluff presents an exhibition “Alice’s Gift of Ragdale: 50 Years of Inspiring Creativity & Preserving History” through April 3, 2027.
About twenty minutes south of Ragdale, the Writers Theatre in Glencoe presents Marco Ramirez’ “The Royale” October 22-November 29 inspired by the story of boxer Jack Johnson (1878-1946). Johnson was the first black world heavyweight boxing champion and opened an integrated “black and tan” upscale restaurant and nightclub in Chicago in 1912. He’s buried in Graceland Cemetery. The 1967 Broadway play “The Great White Hope” and the 1970 film adaptation both starring James Earl Jones and Jane Alexander are based on Jack Johnson’s life.
It’s the first time in Chicago Shakespeare Theater’s forty-year history that they’re performing two plays in repertory: “The Winter’s Tale” (October 13-December 12) and “A Midsummer Night’s Dream” (November 11-January 3, 2027).
The League of Chicago Theatres’ 2nd annual “It’s Theatre Season” campaign, offering “buy 1, get 1 half-off” on select shows, is October 6-31.
David Byrne and Mala Gaonkar’s “Theater of the Mind” presented by the Goodman Theatre is still packing them in for an extended run at the Reid Murdoch Building. One of the Chicago Humanities Fall Festival events this month is “David Byrne on Sleeping Beauties.” The musician, writer and filmmaker discusses his new book “Sleeping Beauties” on October 15 at the Athenaeum Center.
Cartoonist Chris Ware, a special guest at the 2nd edition of the Pretty Good Fest, debuts his new book “The Acme Novelty Library #21” at the small press and comics fair which features over 120 cartoonists, book artists, small press publishers, and zine-makers on October 24 at the Chicago Athletic Association Hotel. The inaugural Chicago Rare Book Fair runs October 23-25 at the Quadrangle Club on the campus of the University of Chicago. In conjunction with the 50th anniversary of the Chicago Map Society, the Newberry Library hosts the Rare Map & Book Fair, October 30-31.
Developed in partnership with the American Library Association, the travelling exhibition “Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire” debuts in Chicago with a launch event at the Harold Washington Library Center on October 14.
Exile in Bookville presents “An Evening with Pulitzer winner Hernan Diaz” at the Studebaker Theater on October 11. Diaz talks with Greta Johnsen about his new novel “Ply” which is set in the future and deals with the place of technology in society. His Pulitzer Prize-winning novel “Trust” is being adapted into an HBO series starring Kate Winslet and directed by Todd Haynes.
The 62nd Chicago International Film Festival, billed as “North America’s longest-running competitive film festival,” is October 14-25 at various venues around the city and features the latest films from around the globe, including the world premiere of Frankie Nasso’s “Ever After” about the launch of Michelin-starred Chef Curtis Duffy’s restaurant Ever during COVID.
October ends with Halloween, and what would Halloween be without scary movies? On October 24, Aurora’s Paramount Theatre presents “Behind The Scream - A Live Conversation with David Arquette following a 30th Anniversary Screening of Scream.” Also on the 24th are (1) the Arts in the Dark Halloween Parade, the 12th annual family-friendly nighttime parade previously on State Street and now on Columbus Drive and (2) the Haunted Museum family-friendly event at the Institute for the Study of Ancient Cultures Museum at the University of Chicago. There aren’t any mummies on display, but one of the activities is a mummification demonstration!
Just in time for Halloween, Chicago Opera Theater (COT) makes its collection of pieces worn in past COT productions available for sale at its “Take Home the Drama: COT Costume Sale” at the Fine Arts Building on October 9. Proceeds from the sale benefit COT’s education program serving thirty classrooms across the Chicago area.
Dates, times, locations and availability are subject to change.
