Dear readers, not to alarm you, but our precious days of summertime Chicago are slyly approaching their end. When the twinge of fall air sweeps across the city, that can only mean that the roll-out of autumnal activities is soon to follow. But lovers of summer needn’t worry — as we straddle both this season and the next, our comprehensive list of things to do in the Chicagoland this September will give you the best of both!
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Chicago is a melting pot of culture from around the world, and one of the many ways it manifests itself is through art. This month, specifically, the folks at Chopin Theatre are displaying just that through the art of dance, with exhibitions that stem from Indian and West African cultures, to name a few. Come and share in the enriching experience, tickets and more information on specific productions can be found on the Fever website.
1543 W. Division St.
Making its world debut at the Chicago Shakespeare Theater this summer, “The Notebook Musical” — based on the fan-favorite book by Nicholas Sparks — is sure to entice many, whether they are romance-enthusiasts or not. The production, which runs until October, will follow the same storyline as the book and iconic 2004 movie by the same name, with the distinct difference being that this time around there will be the introduction of music by Ingrid Michaelson. For more information about the production you may visit Better’s previous coverage or the Chicago Shakespeare Theater website; tickets are on sale now.
800 E. Grand Ave.
While Shedd Aquarium’s Jazzin’ at the Shedd series may be coming to a close for the summer, their latest event where music meets aquatic life, Shedd After Hours: House Party, is around the corner. These programs, which will take place the first three Sundays of September, will be devoted to house music with a stellar lineup of DJs. Listen to great music; enjoy some food and beverages; take in the gorgeous city skyline; and spend the evening with the Shedd’s cutest residents. This event is for folks 21 and over. Find more information on the Shedd Aquarium website.
1200 S. DuSable Lake Shore Drive
One of the most iconic tales of horror and love is coming to Chicago via Wicker Park’s Chopin Theater. The production of Sweeney Todd: The Demon Barber of Fleet Street will run from early September until November but eager audiences can purchase tickets now. This blood-soaked evening may not be to everyone’s taste, but a good thrill is awaiting curious audience members. Programming specifics can be found on the Chopin Theater website.
1543 West Division St.
Before we slide into chillier weather, soak up the last drop of summer while munching away on some of the best pizza slices in town. This pizza crawl — on Sundays, 11am – 2pm — will bring you to four pie shops in the Wicker Park/Bucktown area, all of which have a different style, like classic Chicago deep dish or East Coast artisan style. However, if you’re looking for a slice in another part of town, Pizza City also offers walking tours in the West Loop and bus tours across town. Hungry participants can find more information on the Pizza City USA website.
Tour starts at 2010 N. Damen Ave.
The first three Wednesdays of this month, in thanks to Cinema/Chicago, there will be film screenings at the Chicago Cultural Center and the Chicago History Museum. The series will highlight cinema from other countries; September’s lineup includes films from Taiwan, United Kingdom and Sweden. Film junkies or audience members hoping to experience a little culture can see these films for free, but a limited number of tickets will be available — stay up to date on ticketing by checking out the Chicago International Film Festival website.
September 2 – 4: The Great American Lobster Fest
One delicious way to celebrate the official end of summer is the Midwest’s largest lobster and seafood festival: The Great American Lobster Fest. Located at beautiful Navy Pier, this Labor Day weekend enjoy live music and get your claws on endless, fresh lobster cuisine — don’t forget the beverages! Tickets are on sale now and the sooner you buy the cheaper they are, so don’t wait, head over to the Great American Lobster Fest website.
800 E. Grand Ave.
September 2 – 4: ARC Music Festival
House music was born in Chicago, so it’s no wonder the ARC Music Festival — held at Union Park and dedicated strictly to that genre — is returning for its second year just as strong as before. Dance to your heart’s content to some of your favorite local and international DJs and take in the final days of this Chicago summer. Tickets and programming information can be found on the ARC Music Festival website.
1501 W. Randolph St.
September 2 – 4: Nashwood Music Fest
At the crossroads of Highwood, Illinois and Nashville, Tennessee you’ll find a one-of-a-kind festival that’ll have you in the “honky tonk” spirit — the Nashwood Music Fest. Over Labor Day weekend, put on your cowboy boots and head to the heart of Highwood for three days of southern comfort food and free music that ranges from bluegrass to country rock. Over 100 performances at 25 venues will be the perfect backdrop to this all-out country extravaganza. All ages are welcome, admission is free but don’t forget to tip the good people who made this fest happen.
September 3 – 4: Bulls Fest 2022
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Calling all Bulls fans! Come spend the afternoon outside the United Center and watch 3v3 games with pre-registered teams; join youth basketball clinics; enjoy live music from artists like Chicago-native G Herbo; see art exhibits; munch on food; and much more. The line-up of games and activities can be located on the NBA Chicago Bulls website.
1901 W. Madison St.
September 10: Highland Park Literary Fest
Book worms ought to inch over to the Literary Fest held at Highland Park’s new event space, The Lot. From noon – 6pm, enjoy programming on two different stages, including interactive live storytelling; a Poetry Pentathlon dubbed “Olympics for Poets”; over 35 authors onsite to sign and sell their books; new and used books on sale; and a plethora of other activities! Visit the HP Literary Fest website for more information.
The Lot, 523 Central Ave., Highland Park
September 10: 22nd Annual PAWS Chicago 5K
Ready. Set. Bark! Bring your furry friend over to Montrose Harbor for the animal-friendly 22nd Annual PAWS Chicago 5k. The race is in support of making Chicago a no-kill city and helping homeless pets get a second chance. After the run, participants — both human and canine — are welcome to share in the lineup of fun for the afternoon, including: live entertainment, an interactive dog agility course, a doggy oasis with pools, PUPP-arazzi stations and a whole lot more! Specifics about the race and registration are available on the PAWS Chicago website.
Montrose Harbor, Grove 16
September 10 – 11: Printers Row Lit Fest
A long-standing end-of-summer tradition in the South Loop is the Printers Row Lit Fest, this year celebrating its 37th anniversary. Endless tents and tables of literary finds sprawl across five blocks in addition to five stages which will feature readings from authors, discussions, programming for kids and more. This family- and community-friendly series is free, and encourages people to come and go as they please. More details about the fest and its history are available in Better’s previous content; or visit the Printers Row Lit Fest.
From Dearborn St. to Ida B. Wells Dr.
September 10 – 11: Lakeview East Festival Of The Arts
All over the city there are art and music festivals, but can you ever really get enough? Head on over to the Lakeview East and check out over 125 juried artists who will be displaying world-class art in a number of mediums, like painting, sculpture, jewelry, photography and more. Additionally, there will be multiple stages with live music, a children’s play area and, of course, wine, beer and food booths. Hours vary per day and the festival asks for a $5 donation — more information can be found on the Lakeview East Festival Of The Arts website.
Along Broadway, Belmont to Hawthorne
September 11: Grandparents Day at the Book Stall
Grandparents Day can be a source of joy for many people, young and old. The Book Stall wants to celebrate that by welcoming families of all shapes and sizes to join them for a debut reading of Sarah Aronson’s new picture book, “Brand-New Bubbe.” The book follows a child as they begin to accept a new family member and learn that change can be a good thing. Additionally, author Laura Ruby will be sharing her book “Me and Ms. Too,” also about blended families. All are welcome to this event that runs 3 – 4pm. Additional information is available on the Book Stall website.
811 Elm St., Winnetka
As fall continues to draw closer, get your kids into the spooky spirit with this Book Stall workshop for kids. Recommended for ages 9 – 12, this workshop will feature author Lindsay Currie as she navigates kids through both discussions and exercises on writing spooky stories. Each participant will also receive a copy of Currie’s book “The Girl in White.” Registration prices and information can be found on the Book Stall website.
811 Elm St., Winnetka
The annual Risa K. Lambert Midwest Event, hosted by the United States Holocaust Memorial Museum, is upon us again — this year featuring Pulitzer Prize-winning historian, journalist and writer for The Atlantic, Anne Applebaum. The event, which begins at noon, puts a special emphasis on the importance of remembering and learning from the Holocaust, especially in today’s socio-political climate. To reserve a space or for more information, visit the United States Holocaust Memorial Museum website.
301 East North Water St.
September 16: Norwood Park Fall Fest
Unsure when to make that transition from summer to fall? Let the Norwood Park Fall Fest help you, with a weekend they describe as a “fall-themed haven” for delicious local food, tasty beer and beverages, live music with a range of genres, a children’s area with live entertainment and over 35 merchandise booths with local goods. Whether or not you’re ready for autumn, come share in this community fun! There is a $5 recommended donation for entry; this is a family-friendly event. More information is available on the Fall Fest site.
Northwest Highway (between Raven & Newark) and Centennial Park, Norwood
September 16 – 17: Oktoberfest at The Lot
Oktoberfest has been adopted by many and this year’s celebration in Highland Park is going all-out. The free event will feature an impressive seven-piece German band, Die Musikmeisters, who will play a variety of music from waltzes to folk — as well as a number of other German musicians throughout the weekend. And, true to tradition, sip on a cold brew from the Ravinia Brewing Company in their pop-up Beer Garden with a wide seasonal selection, not to mention the tasty food from local restaurants. Times vary per day; those looking for specifics can find them at the Highland Park website.
The Lot, 523 Central Ave., Highland Park
September 16 – 18: Riot Fest
Since 2015, Riot Fest has been rocking stages in Douglass Park with some of rock music’s grittiest, alternative, fan-loved bands. This year’s line-up boasts names like My Chemical Romance, Misfits, Nine Inch Nails and many other classics of the genre. While dedicated fans may have already nabbed their tickets, there are still daily and weekend passes available to one of Chicago’s newer, favorite concert series. Additional information and tickets can be found on the Riot Fest website.
1401 S. Sacramento Dr.
September 17: Out of the Darkness Chicagoland Walk
September is Suicide Prevention Awareness Month and organizations are showing their support through events and education. Once again, the annual Out of the Darkness Chicagoland Walk will be held at Montrose Harbor and all are encouraged to join, donate and celebrate the lives of those lost to or affected by suicide. Sponsored by The American Foundation for Suicide Prevention, the event will encourage hope and community. Register on the AFSP website where more information is also available.
September 17 – 18: Lakeview Taco Fest
Another plus to living in the Chicago area is access to delicious food festivals throughout the year. That, of course, also includes the Lakeview Taco Fest which returns for a triumphant ninth year. Fill up on tacos made authentically with beef or chorizo, or mix it up a little with goat or duck. Whatever you pick you won’t be disappointed — especially if you wash it down with a specially paired beer. While you’re at it enjoy music stages, wrestlers, activities for kids and more! Specifics can be found on the Taco Fest website.
On Southport between Addison and Roscoe
September 18: Highwood Bloody Mary Fest
Celebrate Highwood does it again this month with a deliciously fun Bloody Mary Fest. Attendees can not only sip on some of the best local bloodies, but can vote for “Best Bloody Mary” and “People’s Choice” as well. Taste test for dozens of vendors as they challenge each other for the coveted titles, and enjoy yourself along the way. Open 10am – 5pm; more information is available on the Bloody Mary Fest webpage.
111 North Ave., Highwood
September 20 – 25: Anastasia
Need your fix of arts and culture, look no further than Broadway in Chicago’s Anastasia — on run at the CIBC Theatre for one week only this month. The musical follows the well-known story of Anastasia, the missing princess of the Romanov empire, as she finds her way back home against many unusual odds. The production has a 2 hour and 25 minute run time with intermission; suited for ages 7 and up. Tickets can be purchased on the Broadway in Chicago website.
18 W. Monroe St.
September 22: NextHaus Panel: Building the Sustainable Home
Join NextHaus Alliance’s team of sustainable designers and builders for their Celebration of the Autumnal Equinox. All over the world for years and years, the Equinox has been celebrated as a time to appreciate balance, nature and our role in all of it. At this panel, learn about how the built environment plays into mankind’s ability to live in harmony with nature. Registration for the event can be found on the NextHaus Alliance website.
September 22: Jack’s Pumpkin Patch Pop-Up
For lovers of fall or those always on the hunt for the next photo-op, Jack’s Pumpkin Patch — an always-anticipated autumnal event in Chicago — is opening for another season on the 22nd. Located near Goose Island, the pop-up boasts a line-up of axe throwing; corn mazes; pumpkin patches; food trucks and a full bar; carnival games; and, incredibly, so much more. While large groups and folks over 21 are welcome, the event is open for people of all ages. Tickets can be found on the Jack’s Pop-Up website
1465 N. Elston Ave.
September 24: Chicago Country Crawl
Country music is making the rounds this month, with yet another Chicagoland country music fest. Ticket holders will receive access to the fest in Wrigleyville, a free breakfast, gift cards and much more. Giddy up and grab your ticket, they won’t be available at this price for long. Find more information on the Chicago Country Crawl website.
3506 N. Clark Street
September 24: Potter & Potter Circus Auction
Yes, you read that right! This month there will be an auction dedicated to Chicago-area circus memorabilia such as photos, costumes, relics and more. The auction is made possible by collectors John and Jan Zweifel as well as the Museum of Science and Industry — which is home to an authentic circus exhibit. While the auction only lasts one day, curious buyers can preview lots beginning September 1. More information about items for sale and auction specifics can be found on the Potter & Potter Auctions website.
5001 W. Belmont Ave.
September 24 – 25: Hyde Park Jazz Festival
Well loved by jazz heads from near and far, the 16th annual Hyde Park Jazz Festival is back for another music-packed year. With over 30 acts ready to take the stage, attendees who range from devote jazz lovers to newbies of the genre will find something to love. Find more information on the celebration of all things jazz on the festival website.
Venues across Hyde Park
September 30 – October 2: 38th Annual American Craft Exposition
This year’s event will be held at the Chicago Botanic Gardens in Glencoe. The expo is in honor of SAVE MOMS, which is a data-driven initiative at NorthShore University HealthSystem that seeks to protect maternal health. Interested attendees can find more information on ticket pricing and event programming on the American Craft Expo website.
1000 Lake Cook Rd., Glencoe
More from Better:
- New in Town: Rainbow Cone and Fabio Viviani’s Bar Siena Open in Skokie, Big Star Mariscos Showcases Seafood, Plus a New Location for Hometown Coffee & Juice
- Fiddler’s Night at the Opera: Steven Skybell on his Return to Play Teyve at the Lyric Opera
- Teachers Have Never Been More Important — Honor Your Favorites and Help Us Raise Money for Education Nonprofits
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.