Hi there, fellow Chicagoans! Summer is starting to say goodbye, but that doesn’t mean that the outdoor fun has to end. September is full of unique markets, festivals, and shows – and I put together a little list to keep on hand for you. Let’s enjoy the wonderful weather and show support for events big and small this month!
Live Music and Shows
Thirsty Ears Festival | 9/7 – 9/8
Chicago’s only classical music street festival is here. Ensembles and soloists will be sharing their music with audiences along Wilson Street between Hermitage and Ravenswood, with local vendors selling goods from booths alongside trucks serving food, beer and wine.
World Music Festival | 9/20 – 9/29
Held in the city for over two decades, World Music Festival sweeps the city near the end of September, bringing over thirty artists from twenty two countries. Local venues such as Sleeping Village, Schubas, Chicago Cultural Center and even Navy Pier all host a variety of shows – highlights include the Global Peace Picnic and Ragamala (the largest all-night performance of Indian classical music in the country).
Riot Fest | 9/20 – 9/22
Rock out in Douglass Park to Fall Out Boy, Beck, Pavement, St. Vincent and more at this annual three-day rock festival. Riot Fest is one of the largest independently owned music festivals in the country. Can’t make it out to the big event? No problem – several acts will also be putting on aftershows around the city, and are posted on the festival’s website.
Chicago Live! | 9/21 – 9/24
Watch performances of all kinds take over Navy Pier across five stages for the largest free performing arts festival in the midwest! Over 110 artists and organizations are listed in the extensive lineup, headlined by Wilco frontman and Chicago native Jeff Tweedy. Listen to solo artists and orchestras, view an array of visual performance from Joffrey ballet to the Blue Man Group and even catch a few drag queens at this one-of-a-kind experience.
Hyde Park Jazz Festival | 9/28 – 9/29
Two whole days of Chicago’s best local jazz performers, in addition to renowned acts from around the country and the world? Yes, please! Witness a meshing of academic, community, and cultural groups playing their finest tunes on any of fourteen stages in Hyde Park. Over 20,000 are expected to attend (for free!!), so grab a water bottle, a blanket and your favorite picnic snack and join them for community, culture and all that jazz.
Food and Drink
Taste of Chicago | 9/6 – 9/8
For over forty years, The Taste has been bringing the flavors of the city together in one space, resulting in the largest food festival in the world. Without paying a dime for admission, attendees can not only relish in all the cuisine the city has to offer, but also participate in community dance lessons, watch – or compete in – a karaoke competition, and even catch a CeeLo Green concert!
Taste of Greektown | 9/6 – 9/8
Only a few years younger than The Taste mentioned above, Taste of Greektown strives to highlight the Greek restaurant scene. Vendors set up on Halste, lining up from Adams to Van Buren ready to share bites and beverages. Indulge in all of the Mediterranean delicacies your heart desires, from sizzling gyros to crispy sweet baklava! While you eat, make sure to take in the traditional Hellenic performances and live music to complete the experience, and rest easy knowing there are activities for the kiddos, too.
Lakeview Taco Fest | 9/7 – 9/8
Those near Lakeview must go to 3500 North Southport to experience the live music, beer pairings, and all the tacos you could ever imagine! Festival-goers can find traditional carne asada and carnitas in their tortillas or spice it up by getting goat, mushrooms, duck and so much more. Try selections from about a dozen eateries attending, and cast your vote for best taco!
Taco Fest is in one of my favorite areas of the city— the Southport Corridor!
World Dumpling Festival | 9/21
Sundays at Logan Square are normally centered around the Farmer’s Market (which is deserved – it is just as great as you’ve heard), but for nearly twelve hours on the 21st, the World Dumpling Festival is shaking things up. From 11:00a to 10:00p, those visiting the Square can sample dumplings in the style of several cultures, including Japanese, Vietnamese, Latin American, Middle Eastern, and Polish. Other highlights include interactive crafts, dance performances and live music. Funds will be given in part to the Chicago Cultural Alliance to support their work of supporting and advocating for over forty heritage centers.
Chicago Gourmet | 9/26
Hosted on the Harris Theatre Rooftop, this distinguished food festival lifts up the cuisine scene in Chicago with culinary events showing off all that the top chefs of the city have to offer, set each year to a different theme. 2024’s concept is titled “Fashion, Plated” and seeks to highlight the relationship between the worlds of culinary and couture. With this theme, Chicago Gourmet asks us to not simply to taste but rather feast our eyes on the meals created specifically for the weekend. Start with Rick Bayless’ ‘Tacos & Tequila,’ a vibrant display of specialty tequilas, mezcals, and Mexican eats accompanied by DJs and Mariachi. Or, if your tastes lean more towards American cuisine, attend the Hamburger Hop to sample a collection of burger and booze tastings served by iconic local chefs! Those experienced with both fine wine and dining will adore attending one of two Grand Cru sessions, where they can sample the best cuisine and decadent wine or cocktails from the experts themselves. And if the rooftop lineup isn’t your vibe, go on down to Late Night Gourmet and have a night of dancing, drinks and late night eatery at TAO Chicago.
Across the Arts
RNDD Fall Gallery Walk | 9/6
The River North Gallery Walk is bigger than ever this year, with Chicago’s top designers sharing their vignettes across more than twenty showrooms and galleries. Participating locations have extended business hours until 8:00 pm and entry is free for all showings, aside from the VIP kick-off and safari-themed after-party.
Printers Row Literary Festival | 9/7 – 9/8
Approaching its fortieth anniversary, the largest free outdoor literary celebration is taking over five city blocks with the tents and tables of over one hundred booksellers, broken up by stages for nearly eighty author presentations. 100,000 booklovers are expected to attend – you can join them, for no cost at all! Headlining this year’s festival is poet Tracy K Smith, author of Life on Mars: Poems and Ordinary Light: a memoir, among other titles.
Renegade Craft Fair | 9/7 – 9/8
The next iteration of this local favorite is in Wicker Park along Division, between Damen and Ashland. Peruse various works from local artists and small businesses and feel good about giving back to your community.
Lakeview East Festival of the Arts | 9/14 – 9/15
Hundreds of artists. Two stages. Local food. Family activities. Live music into the night. All at one event along Broadway, spanning from Belmont to Hawthorne! 2024 marks the nineteenth year, and the neighborhood is eager to present this year’s best original works of several mediums, specifically selected from juried artists. If you need to get away or love a natural walkthrough, the interactive garden oasis will provide the escape you need. Go anytime between 11:00 am and 7:00 pm, or swing by later on Saturday for late night drinks, dinner and dancing (or listening) to live music.
Reeling Film Festival | 9/19 – 9/29 with additional online dates and events
Immerse yourself in an international collection of filmed media made by, for, and about the LGBTQ+ community. The second-longest running film festival of its kind, Reeling will screen award-winning international films, experimental shorts, social documentaries and more both online and at in-person venues around Chicago, including The Music Box and Landmark Century Centre Cinema. The goal since 1981 has been to recognize the artistic contributions that LGBTQ+ members add to culture and to educate folks of all sorts by sensitizing them to issues within and involving the community. Descriptions of the materials being screened and more information on dates, times and locations can be found on their website!
Chicago Horror Film Festival | 9/28 – 9/30
The Logan Theatre is presenting over 200 independent horror films this year, with the theme of “Final Girl / Women in Horror”. Three screening rooms over three days, full of the coolest new spooks, haunts and slashers. Catch a scary flick of your choosing, or if you’re in the filmmaking industry, you may find yourself networking in the VIP lounge.
Seasonal
German American Oktoberfest | 9/6-9/8
This year’s festival has a new location in Lincoln Square! Don your lederhosen and join the festivities, starting with the 8:00 pm opening ceremony. A parade will take place on Saturday afternoon, and those interested can attend a German Mass before noon on Sunday. Four bands will be playing music throughout the weekend, with traditional song and dance being highlighted, and the amusement section will be full of carnival games to entertain younger attendees!
El Grito Festival | 9/14 – 9/15
For the first time in over a decade, this celebration of Mexican Independence Day is back at Grant Park with a dazzling array of activities for all. Mariachi bands and traditional ballet folclorico dancers are sure to impress, and the event will be completed with authentic cuisine, merchandising, and experiences for the whole family as provided by local organizations.
Urban Birding Festival | 9/14-15
Bird lovers unite! This first annual event is a gathering to celebrate our many various feathered friends throughout Chicagoland. Whether you’re an expert in the field or a casual enthusiast, you’re sure to enjoy the presentations, guided bird outings, workshops and other avian activities taking place around the city.
26th Street Mexican Independence Day Parade | 9/15
Pilsen’s 53rd annual parade will start at noon, marking the first day of Hispanic Heritage Month. 26th Street will be full of hundreds of thousands of people, viewers and performers alike, celebrating cultural traditions and Mexican Independence Day. It’s considered one of the largest parades in the midwest! Performances will display traditions from several regions and cultures, such as folkloric dancing and mariachi. Take in the size and color of the parade floats, representing different states of Mexico! And after the conclusion, the neighborhood invites you to explore the local shops and eateries along the corridor. The route starts at 26th and Albany, under the Little Village arch!
Jack’s Pumpkin Pop Up | 9/15-10/31
For over a month, two acres of Goose Island are transformed into an autumnal wonderland of pumpkin patches, axe throwing, carnival games and the largest cornmaze in the city. Get your fortune read, mine for gems, and grab a bite (or a drink) from the food trucks! The space is bookable for parties and group activities, and is just as fun with a plus one. All ages are welcome at the Pop Up, but there are age restrictions for axe throwing.
West Loop Bavarian Block Party | 9/20-9/21
This year, Chicago is throwing its first ever sober-friendly Oktoberfest! If you want to grab a bratwurst or listen to German folk music with plentiful NA drink options, this is where to be. There will also be activities to entertain the kids while you grab a pretzel! The event is on Randolph in West Loop.
From music to parades to holidays, Chicago always has something for everyone. I hope this guide can help you get out and try something new, or remind you about an old favorite. I know I’ll be doing a bit of both. Cheers, friends!
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