September signals the end of summer in Chicago, and while it breaks our hearts to bid farewell to beach days and music festivals, September truly is the city’s most pleasant month. Jacket weather means no more temptation to stay cooped up inside with the A/C—instead, soak up the fabulous weather and take advantage of the city’s autumnal buzz. With theater season back in full swing, Oktoberfest parties popping up and tons of fantastic bands performing this month, we can’t wait for September.
RECOMMENDED: Our complete September events calendar
THINGS TO DO
Sept 1–4: Celebrate Chicago’s robust Polish heritage at the Copernicus Center’s Taste of Polonia.
Sept 8, 9: The Windy City Wine Festival offers samplings of over 300 pours of wine, all around Buckingham Fountain.
Sept 8–10: Lincoln Square kicks off Oktoberfest season with the German-American Fest.
Sept 8–10: Consume beer and sausage while listening to live music at the inaugural Würst Music and Beer Fest.
Sept 10: Dozens of booksellers and community organizations gather at Nichols Park for the annual Children's Book Fair.
Sept 16–Jan 7: The Chicago Architecture Biennial returns with a series of talks, tours, exhibitions and events featuring top architects and designers.
Sept 16: Craft beer lovers flock to Old Irving Park for the Independence Park Beer Fest, with dozens of beers for sampling.
Sept 16, 17: The city’s best taco vendors converge at Southport Corridor for the annual Sam Adams Taco Fest.
Sept 16, 17: More than 150 artists from all over the country sell their art at West Loop Art Fest.
Sept 16, 17: Stroll down Ravenswood Avenue to take in local art, music and theater at Ravenswood ArtWalk.
Setp 17: Drink Atom Smasher and listen to oompah music at the Two Brothers Roundhouse at the brewery’s annual Oktoberfest celebration.
Sept 21: The 35th edition of Reeling Film Festival, Chicago's LGBTQ film fest, will include 30 feature films and 10 shorts programs with titles from 22 countries.
Sept 22–24: Three-day high end food festival Chicago Gourmet returns for a weekend of tastings, demos and talks with chefs.
Sept 28: Spend one more time hanging out in a Chicago alley as ACTIVATE ends its season of parties with another outdoor bash.
Sept 29, 30: At this year’s Revolution Oktoberfest, the local beer purveyor takes their annual fest out of their brewery and into the streets of Logan Square.
Sept 30: Celebrate Oktoberfest with the whole family at St. Alphonsus Oktoberfest in West Lakeview.
Sept 30: Satisfy all your salty breakfast meat cravings and then some at the Bacon and Beer Classic in Daley Plaza.
Sept 30: Ring in autumn with bites from West Loop’s beloved restaurateurs at the Fulton Market Harvest Fest.
MUSIC
Aug 31–Sept 3: At this year's Chicago Jazz Festival, modern artists pay tribute to legends like Dizzy Gillespie and Ella Fitzgerald with four days of concerts.
Sept 1–3: EDM, hip-hop and jam bands rule Labor Day weekend at North Coast Music Festival, where Deadmau5, Ween and Gucci Mane will headline the three-day fest.
Sept 7: Ms. Lauryn Hill and Nas, two of the biggest hip-hop and R&B stars of the ‘90s, join forces for a co-headlining concert at Northerly Island.
Sept 8–24: Bands from all around the globe come to World Music Festival, which hosts free concerts at venues throughout the city.
Sept 9: Heavy metal warriors Mastodon play an intimate benefit gig at Metro, in support of suicide prevention nonprofit Hope for the Day.
Sept 9, 10: Fleetwood Mac singer-songwriter Stevie Nicks goes solo for a pair of performances at Ravinia.
Sept 15: The Riviera hosts the hereditary harmonies and ‘80s-influenced soft rock of LA trio Haim.
Sept 15–17: Punk rock carnivals don't get any more exciting than Riot Fest, which brings Queens of the Stone Age, Nine Inch Nails and the reunited Jawbreaker to Douglas Park.
Sept 15, 16: If you're still in love with the shape of Ed Sheeran, you can catch the British pop star at a pair of Allstate Arena shows.
Sept 16: Macklemore & Ryan Lewis headline the first Get In It MusicFest, which takes place at Guaranteed Rate Field.
Sept 20: Sarcastic crooner Father John Misty serenades the Auditorium Theatre with his latest, most cynical ballads.
Sept 22, 23: Prepare for two days of great beer, accompanied by sets from Animal Collective and the Record Company at the annual 312 Urban Block Party.
Sept 23, 24: Returning after a three-year hiatus, the Hideout Block Party celebrates the anniversaries of Soviet satellite Sputnik and local studio Electrical Audio with outdoor music.
Sept 23, 24: Local players such as Makaya McCraven, Jamie Branch and Nick Mazzarella fill out the lineup at the annual Hyde Park Jazz Festival.
Sept 24: Animal Collective return to the Empty Bottle for an intimate show in celebration of the venue's 25th anniversary.
Sept 28: Expect woozy beats fit for a hip-hop backing track at electronic producer Nosaj Thing's Bottom Lounge set.
Sept 29: Canadian indie rock supergroup Broken Social Scene brings its cathartic choruses to the Aragon.
ART
Sept 7–Dec 10: The DePaul Art Museum hosts the stretched nylon sculptures of Senga Nengudi in its new exhibition, "Improvisational Gestures.”
Sept 9–Nov 5: Artist Jennifer Packer displays abstract portraits and paintings of funerary bouquets in "Tenderheaded” at the Renaissance Society.
Sept 13–17: More than 100 contemporary art galleries show off everything from towering sculptures to experimental photography during the annual EXPO Chicago at Navy Pier.
Sept 16–Mar 4: Michael Rakowitz's "Backstroke of the West” gets conceptual, with pieces like a food truck serving Iraqi dishes and a gigantic recreation of the Ishtar Gate made with cardboard packaging and newspaper.
Sept 23–Mar 11: The Block Museum celebrates the lasting influence of poet and painter William Blake, displaying ‘60s art inspired by his work in "Age of Aquarius.”
THEATER & DANCE
Sept 1: The House Theatre of Chicago’s documentary play, United Flight 232, draws on interviews and news reports about a 1989 airliner crash in Sioux City, Iowa.
Sept 7: A museum guard gives in to the urge to touch a famous painting, setting off an eons-spanning lesson in art appreciation in The Rembrandt at Steppenwolf.
Sept 8: Contemporary dance troupes and independent choreographers from Chicago and around the nation gather to celebrate the 8th annual Harvest Chicago Contemporary Dance Festival, performing a different program each weekend.
Sep 9: Belgian director Ivo van Hove brings his Tony-winning production of Arthur Miller’s 1955 A View from the Bridge to the Goodman.
Sept 14: In Matthew Lopez’s playful comedy, The Legend of Georgia McBride, a straight Elvis impersonator who turns to drag to make ends meet.
Sept 19: Chicago Shakespeare Theatre debuts its new space, the Yard, with French surrealist piece The Toad Knew.
Sept 19: Victory Gardens opens the fall season with the 2015 Tony-winning musical Fun Home.
Sept 29: A new Chicago International Latino Theater Festival features visiting companies from Cuba, Mexico, Puerto Rico and Colombia alongside productions from Chicago-based Latinx troupes.
COMEDY
Sept 14–16: Laugh at sketch comedy inspired by everything from Harry Potter to Star Trek at the Chicago Nerd Comedy Festival.
Sept 15–17: Former SNL player Jay Pharoah shows off his stand-up skills at Zanies Rosemont for three nights.
Sept 17–20: Stand-up superstar Chris Rock brings his first tour in nearly a decade to the Chicago Theatre for four nights.
Sept 23: Unapologetically feminist comic Margaret Cho performs her new special, Fresh Off The Bloat, at the Chicago Theatre,
Sept 30: A new all-woman sketch show, She The People: Girlfriends’ Guide to Sisters Doing It For Themselves opens at UP Comedy Club.
RESTAURANTS AND BARS
Early Sept: The latest from Boka Restaurant Group and chef Lee Wolen, Somerset in the Viceroy Chicago Hotel will offer American fare to Gold Coast revelers later this month.
Late Sept: Jason Hammel (Lula Cafe) brings his cheffy chops to the Museum of Contemporary Art with Marisol, an intersection between food, art and design.
Sept 25: Heisler Hospitality—the folks behind Sportsman's Club, Bad Hunter, Estereo and more—are back at it with two new projects. Regards to Edith is a culinary ode to the history of Maxwell Street, while Prairie School is a bar inspired by Frank Lloyd Wright's work.
Note: Restaurant and bar openings are subject to change and can be delayed; call ahead before setting out.
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