30 of the Best Things in Chicago and the Suburbs This September

This September, enjoy the last bit of summer Chicago has to offer with events like Printers Row Lit Fest, North Shore Art League’s Art in the Village, Highwood’s Bloody Mary Fest and more. Here are 30 of the best activities September has to offer.

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All Month

Chicago Gourmet

September is a food lover’s dream, with Chicago Gourmet kicking off a month-long schedule of special events, including the citywide Hamburger Hop, Chef Rick Bayless’ Tacos & Tequila, and Go Gourmet.

Sleepy Hollow: An Immersive Cocktail Experience

170 W Washington St.

Can’t wait to dive into the Halloween season? Grab your tickets for the Sleepy Hollow experience, where you will be invited into the universe of Sleepy Hollow during a 90-minute experience in a haunting tavern, full of spirits, woodland cocktails, interactive experiences, and more.

Art of Banksy

360 N State St.

Courtesy of The Art of Banksy

Chicago is now home to the world’s largest Banksy exhibit, displaying over 80 original works from the most talked-about artist in modern history.

Shedd Aquarium Free Days

The Shedd’s Great Lakes Exhibit. Courtesy of Shedd Aquarium.


Illinois residents can enjoy the Shedd for free on Mondays, Tuesdays and Wednesdays, starting Sept. 7 through Sept. 29 from 9 a.m. to 7 p.m. On Sept. 28, hours are 9 a.m. to 5 p.m. Residents must present a valid ID. Reserve your tickets on Shedd’s website.

Concerts at the United Center

West Madison Street

Renowned artists will be making their way back to Chicago this fall. Highlights include Tame Impala on Sept. 7, Harry Styles Sept. 24-25 and more. Most concerts are requiring proof of vaccination or a negative Covid-19 test.

Human + Nature at Morton Arboretum

4100 IL-53, Lisle

Human+Nature at The Morton Arboretum
Human+Nature at The Morton Arboretum

Morton Arboretum’s Human+Nature (pronounced Human Nature) outdoor art exhibition includes five sculptures by internationally renowned artist Daniel Popper. Intended to connect people with trees, Popper’s 15- to 26-foot-tall sculptures are exclusively for the Arboretum, and are spread out in various locations across its 1,700 acres, leading guests to areas they may not have explored before. Admission to the exhibit is included with your timed-entry ticket.

Helmut Jahn: Life + Architecture

111 E. Wacker Dr.

A new exhibit honoring the late Chicago architect and style icon — Jahn was known for as a powerhouse architect who designed the James R. Thompson Center, Michigan City Public Library, and more. The exhibit is free with general admission to the Chicago Architecture Center.

Apple Picking at Apple Holler

500 S. Sylvania Ave, Sturtevant, WI

Apple Holler has become the Chicagoland destination for all things apple: pie, caramel-covered, wine, apparel, and top-notch Apple Cider Donuts, plus acres of pick-your-own orchards.

Van Gogh for All

333 N. Michigan Ave.

van gogh for all

Designed by Highland Park’s Dolores Kohl Education Foundation, the “Van Gogh for All” exhibit is an interactive experience that allows you to literally step into Vincent Van Gogh’s art. Now at a new location on the Mag Mile at the corner of Michigan and Wacker, the exhibit will be open to the public seven days a week through September 26. Tickets are $20 for adults and $10 for children ages 12 and under. Grab your tickets at Van Gogh for All.

Cristina Mittermeier and Paul Nicklen “Origins” Exhibition

Hilton | Asmus Contemporary, 3622 S. Morgan St. Chicago

World-renowned National Geographic wildlife photographers and conservationists Cristina Mittermeier and Paul Nicklenmake their Chicago debut with an exhibition at Hilton | Asmus Contemporary’s new second gallery location at the Morgan Arts Complex in Bridgeport. “Origins” opens on Aug. 27 and will showcase a curated collection of Mittermeier and Nicklen’s stunning photography which continues to spark impassioned conversation and inspire action to help save our oceans and planet.

Sept. 3-5: Roscoe Village Burger Fest

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The best burgers in Roscoe Village will be put to the test in this annual competition and street festival. Local vendors will be selling delicious burgers, and more fare, and there will be plenty of music to keep you moving.

Sept. 2-4: Out of Space – Concert Series at Temperance

On Thursday, Sept. 2 Big Boi with Twista will take the stage, and on Friday Sept. 3 Drive-By Truckers and JD McPherson will perform.

Sept. 5: Fifth Third Bike the Drive

Bike along a car-free Lake Shore drive in a fundraiser for the Active Transportation Alliance, which improves conditions for walking, biking and public transit throughout Chicagoland.

Sept. 10: JourneyCare: Allstars of Project Runway

JourneyCare serves as the largest provider of supportive, palliative and hospice care in Illinois. They provide quality care for nearly 3,000 adult and pediatric patients and their families each day. This September, you can support their organization by attending — in person or virtually — their Allstars of Project Runway event. The afternoon will feature a celebrity fashion show by stars from TV’s ‘Project Runway,’ a silent auction, and more. Tickets for both the in-person and virtual options can be purchased on their website.

Sept. 10-12: 100th Anniversary of the German-American Day Festival

Celebrate German-American heritage and Oktoberfest in Lincoln Square with a parade, great food and beer, and plenty of German music to dance to all weekend long.

Sept. 11-12: Printers Row Lit Fest

The midwest’s largest free outdoor literary showcase return to Printers Row with their beloved book market and free programming. Headliners this year include award-winning journalist, former Chicago Tribune columnist and novelist Dawn Turner, and two-time Pulitzer Prize winner and National Book Award winner Colson Whitehead.

Sept. 11-12: North Shore Art League’s Art in the Village

Hubbard Woods Park, Winnetka

Art in the Village, sponsored by the North Shore Art League, will take place at Hubbard Woods Park in Winnetka on Sept. 11 and 12 from 10 am – 5 pm. The event will feature 45 artists from across the country showcasing their work, including oil paintings, mixed media, photography, sculpture and more.

Sept. 11-12: Ravenswood ArtWalk

Berteau & Ravenswood, Chicago

The 19th Annual Ravenswood ArtWalk takes place on Saturday, Sept. 11  and Sunday, Sept. 12, showcasing the bustling hub of artisans, musicians, manufacturers, and brewers in the Ravenswood Corridor. The event also includes access to historical buildings along Ravenswood, with exclusive looks at makers, glass workers, museum archives and more.

Sept. 18: Hawthorn 2.0 Fall Kickoff

122 Hawthorn Center, Vernon Hills

Join in on the festivities celebrating Hawthorn Mall’s redevelopment. Located outside in the outer AMC lot, guests will find live music, food trucks, a kid-zone, and more.

Sept. 18: PAWS Chicago Annual 5K Run/Walk

400 W Montrose Harbor Dr.

PAWS Chicago (Pets Are Worth Saving) is committed to ending the killing of homeless cats and dogs. They find homes for 5,000 dogs and cats annually through their adoption centers and operate one of the largest high-volume free and low-cost spay/neuter clinics in the country. You join PAWS in their mission to build a No Kill city at their annual 5K Run/Walk Sept. 18.

Sept. 18: Craft Brews at Lincoln Park Zoo

Beginning at 5pm, guests can enter the Zoo and enjoy souvenir tastings from local breweries until 10 p.m. Tickets range from $55-65.

Sept. 18: Adler Planetarium Celestial Ball

This September, the Adler Planetarium Celestial Ball will be held as a “virtual experience under the stars.” The annual Celestial Ball, hosted by the Adler Planetarium’s Woman’s Board, is the Planetarium’s biggest fundraising event of the year. Attendees are able to join one another from the comfort of their own living room for a celebration of “community, connection, and the universe that unites us.”  

Sept. 18: Western Springs Tower Trot

Run for a good cause during the Western Springs Tower Trot. This year they are partnering with the Healing Hearts for Ashley Foundation, in memory of Ashley Jurjovec, a former Western Springs middle school teacher who passed away suddenly from a genetic heart condition called Arrhythmogenic Right Ventricular Cardiomyopathy (ARVC) in 2016.

Sept. 19: Highwood Bloody Mary Fest

17 Highwood Ave., Highwood

Amateurs and experts prepare elaborate Bloody Mary recipes judged by a panel of local celebrities. The daylong festival features food, music and children’s activities.

Sept. 20-26: NorthShore University HealthSystem: American Craft Exposition

From September 20-26, art admirers can tune into the American Craft Exposition’s virtual show week — presented by The Auxiliary of NorthShore University HealthSystem. The craft show incorporates over 100 artisans exhibiting their one-of-a-kind pieces, including jewelry, ceramics, furniture, and basketry. Proceeds from the event go towards research initiatives at NorthShore University HealthSystem.

Sept. 22: Designs 4 Dignity: Spirit of Design

This fundraiser promises to be a night filled with raffle prizes, craft cocktails, entertainment, and more. Proceeds will help Designs 4 Dignity “continue its commitment to empower lives through design.”

Sept. 23: Children’s Service Board of Ann & Robert H. Lurie Children’s Hospital of Chicago: 65th Annual Gold Coast Fashion Show

For over half a century, the Children’s Service Board has served as one of the most successful philanthropic affiliated organizations of Ann & Robert H. Lurie Children’s Hospital of Chicago. The Board is comprised of a group of women who supporting the programs at Ann & Robert H. Lurie Children’s Hospital through “service opportunities, collaborative energy and purpose-driven fundraising.” Their annual Gold Coast Fashion Show is their signature fundraising event, and raised over $1 million in 2019 for the Department of Family Services at Lurie Children’s. The event itself includes a fashion show from their exclusive retail sponsor, Neiman Marcus, food catered from Chicago’s top restaurants, dancing, and more.

Sept. 25: ​​Lyric Opera of Chicago’s Lyric Under the Stars

20 N Upper Wacker Dr

We are lucky to have one of the leading opera houses in the US so close to home. Lyric is hosting an al fresco season opening gala on Saturday, Sept. 25 titled “Lyric Under the Stars,” held at a plaza just across the river from the opera house.

Sept. 25: Lincoln Park Zoo Breakfast with the Animals

2001 N Clark St

Learn all about Jamaican iguanas and Hoffman’s two-toed sloths from Curator Dan Boehm while enjoying fresh fruit and pastries sponsored by Nutella.

Sept. 25-26: Hyde Park Jazz Festival

1130 Midway Plaisance

A celebration of the arts, the Hyde Park Jazz Festival is a collaborative platform dedicated to supporting the presentation and ongoing development of jazz, particularly on the South Side of Chicago. The event is free with a $5 suggested donation.

Sept. 28: After School Matters’ 30th Anniversary Gala

66 East Randolph St

After School Matters is a nonprofit organization that provides after-school and summer programming to almost 19,000 Chicago public high school students each year. They aim to provide these students with new opportunities, so that they can see their potential and develop their talents going into the future. Proceeds from their upcoming 30th Annual Gala will go toward supporting various After School Matters programming.

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Macaire Douglas

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.

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