The Haute Seeker


Summer may be coming to a close, but that does not mean that the fun festivities, and best things to do in Chicago area anywhere close to being over! This fall, check out 32 of the best things to do around the city. From midsummer celebrations to late fall harvest hangouts—this guide has the best things to do keep you warm and entertained all season long.

Fall Festivals + Events


Chicago Jazz Festival featured in the 33 of the Best Things to Do This Fall in Chicago
Image | Chicago Jazz Festival

August 23rd – September 1st: 41st Annual Chicago Jazz Festival. The Chicago Jazz Festival showcases the greatest jazz artists from Chicago and around the world. The free festival includes a special tribute to Nat King Cole by his brother Freddy Cole and a celebration of the 50th Anniversary of the Jazz Institute of Chicago, the festival’s programming partner. Free Admission. For more details, visit the website here.

August 24th: The Lagunitas Beer Circus Chicago. This is not your average circus. Witness 100+ performers at two different stages featuring all-star bands, burlesque, sideshow acts, aerialists, and other freaktacular performances in Douglas Park during this fall event in Chicago. In addition to the performances, the event features food trucks, games, and of course, local beer. Admission is $40. For more details, visit the website.

August 24th – 25th: Bucktown Arts Fest. The neighborhood festival is one of Chicago’s longest-running neighborhood festival. The arts festival showcases close to 200 juried artists who work in oil, watercolor, photography, textile, sculpture, jewelry, and so much more. Free Admission. Visit the website for more details.

August 24th – October 20th. Midnight Circus in the Parks. The eclectic ensemble of artists with a shared vision that live performance has the power to engage and inspire our audience, our community, and our world. We bring world‐class contemporary circus performances to communities throughout Chicago and raise money for Chicago parks with the proceeds. Admission is $5; children under two are free. To purchase tickets, visit Midnight Circus.

August 30th – September 2nd: African Festival of the Arts. Take a trip through the Diaspora this fall at the Annual African Festival of the Arts. Through interactive engagements, vibrant drumming, museum quality, and collectible artifacts, colorful and rich handwoven fabric and textile, and other program spaces. Admission is between $5 – $40. For more details, visit the website here.

August 30th – September 2nd. Taste of Polonia. This annual Labor Day weekend festival at the Copernicus Center in Chicago’s Jefferson Park offers non-stop live music, food, and fun for four days. The four-day festival will include over 30 live bands, polish food, and beer, 40 local vendors, carnival games, plus much more. Admission is between $5 – $10. For more information, be sure to visit their website.


September 6th – 8th: Throwback Music Fest. Jam out to retro tunes and classic cars in the Gladstone Park neighborhood on the North West of Chicago. This fall festival takes place after Labor Day and features music, vibes, and fun inspired by the 50’s, 60’s, and 70’s. Admission is free, $5 suggested donation. For more details, visit the website.

79th Street Renaissance Festival featured in the 33 of the Best Things to Do This Fall in Chicago
Image | 79th Street Renaissance Festival

September 7th – 8th: 79th Street Renaissance Festival. The neighborhood festival is the longest-running block party in Auburn Gresham. The South Side festival offers attendees the opportunity to support their local businesses through food, games, entertainment and more. Admission is free. For more details, visit the website.

September 8th: 26th Street Mexican Independence Day Parade. One of the most colorful parades in Chicago, the 26th Street Mexican Independence Parade celebrates Mexican Independence with floats, mariachi bands and dancing in the streets. For details on this free family fun event, visit the website.

September 14th: Dessert Fest at the Zoo. Taste some of the best desserts in Chicago while taking in views of the zoo’s amazing animals and gardens. And don’t forget the champagne, beer, and wine (for those of age)! Tickets include admission, dessert tastings from some of Chicago’s most famous bakeries, interactive games, live entertainment, giveaways, and more! For more details, visit the website here.

September 14th: Wine Riot. Wine Riot offers wine-lovers an evolved take on the traditional “wine tasting” event. The event boasts a line-up of educational programs and demonstrations. General admission tickets include unlimited wine tastings, a souvenir glass, access to all educational wine programming, and photo booth access. For more information or to purchase tickets, visit Wine

September 14th: Chicago Football Classic. The annual Chicago Football Classic takes place every fall in support of academic achievement and the promotion of post-secondary education of America’s Historically Black Colleges and Universities (HBCUs). The event showcases cultural excellence and energy through weekend-long event—including the highly anticipated football game and the half-time show. Celebrate school spirit and HBCU pride this fall by visiting Chicago Football Classic for more details and information.

September 14th – 15th: Chicago Bourbon & Barbecue Fest. Make your way to Roscoe Village for bourbon, bbq, and more post-Labor Day. The finger-lickin’ festival features an afternoon bourbon tastings and plenty of mouth-watering chicken, ribs (and more), there is also one stage of soulful music. Free admission, $5 suggested donation. For tickets to the bourbon tasting and more information on the festival, visit the event page.

September 14th – 15th: Lakeview East Festival of the Arts. The arts festival showcases more than 150 juried artists featuring paintings, sculpture, photography, furniture, jewelry and more. A wonderful place to find original pieces for sale at various prices ranges to suit any art lovers budget. Admission is free, $5 suggested donation. For more details, visit the website here.

September 14th – 15th: Ravenswood ArtWalk. Take in the crisp fall air while venturing the long stretch of arts and industry along Irving Park Rd to Leland along Ravenswood Avenue this fall. The 18th Annual Tour of Arts & Industry in Ravenswood is a weekend full of local art, industry, music, history, food and craft beer. This event is perfect for the whole family to enjoy this fall. Admission is free; $5 suggested donation. For more details, visit the Facebook page.

EXPO Chicago featured in the 33 of the Best Things to Do This Fall in Chicago
EXPO Chicago | Image by Taylor Justin

September 19th – 22nd: EXPO Chicago. The annual exposition hosts more than 135 leading International exhibitors, alongside one of the highest quality platforms for global contemporary art and culture. Admission is $30 – $50. For tickets and more details, visit the website.

September 20th – 21st: Norwood Park Fall Fest. This fall event is a family-oriented celebration by day and a music festival by night. The event features live entertainment consisting of various genres, food trucks, and local merchants from across the Chicagoland area. The festival takes place on Northwest Highway this fall. Free admission, $5 suggested donation. For more details, visit the website here.

September 21st: YAS Fest! Is a showcase featuring the works of hundreds of creative youth showcased in dozens of events throughout the Millennium Park Campus. Support young emerging artists in Chicago this fall. Admission is free. For more details, visit the website here.

September 21st: Pancakes and Booze. Pancakes, art, and booze make the fall that much sweeter. The pop-up show provides art lovers and collectors in Chicago an opportunity to explore more than 300 pieces of artwork created by some 100+ local Chicagoland artist. Attendees can enjoy art, beer, and free pancakes throughout the event. Admission is $10 – $15. For tickets and details visit the event page.

September 21st – 22nd: Sam Adams’ Lakeview Taco Fest. Taco festivals aren’t just for the summer season. September sizzles with tortilla-wrapped goodness at the 7th Annual Sam Adams’ Lakeview Taco Festival. No matter the preference, find your favorite taco at this fall taco festival featuring not only food but specialty beers, live entertainment, Lucha Libre Mexican wrestling, and more. Admission is free with a $10 donation. For more details, visit the website here.

September 27th – 28th: Oktoberfest Chicago. The annual event is one of Chicago’s most popular fall celebrations. The three day festival at St. Alphonsus brings beer, brats, band, and all things Bavarian to the North Side neighborhood of Lakeview. Enjoy additional activities including Kinderfest, music, and more. Admission is free, with a $5 donation. For more details, visit the website here.

September 27th – 28th: Art West Town Walk. The West Town Art Walk is an annual event celebrating art in all forms through the visual, musical, and culinary experience that lies within the West Town neighborhood. Admission is free. For more details, visit the website here.

September 27th – 29th: Chicago Gourmet. Is a two-day exhibition of some of the best restaurants, and chefs both locally and from around the world. The festival honors Chicago’s culinary achievements and the creative vision chefs, Master Sommeliers, and wine and spirit makers who participate. This is one of the most highly anticipated Chicago food events. Admission to the event ranges between $50 – $2,015. For more details, visit Chicago Gourmet.

September 28th – 29th: Edgewater Arts Festival. If you’re an art lover in the Chicago area, the 7th annual Edgewater Arts Festival is an event to attend this fall. Meet emerging artists and explore the Edgewater neighborhood at this two-day event. Admission is free. Visit the website for more details.

September 28th – 29th: 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 free two-day festival features the finest in local jazz, national, and international jazz artists. Learn more about the talented acts taking the stage by visiting Hyde Park Jazz


October 5th – 6th: Apple Fest. This fun October event features dozens of vendors who sell everything from candy apples to scarves and hats. Pick up fresh apple pie, hot apple cider, or even a bushel of apples to kick off your first weekend of October. Admission Free; $5 donation suggested. For more music on the festival, including the music lineup, participating vendors, and the apple pie bake-off, visit the website here. 

October 12th: Bacon and Beer Classic. Bacon and Beer—its a winning combination this fall. The event features over 80 craft beers and more than 40 different mouth-watering bacon-themed tasty bites created by local restaurants. Treat yourself this fall by grabbing tickets to this savory event. Admission is between $55 – $99. For more details, visit the website.

October 18th: FLEUROTICA. A botanical experience like no other—experience FLEUROTICA at Garfield Park Conservatory this fall in Chicago. The even features 18 botanical looks created by Chicago’s leading floral designers, fashion designers, landscape artists and students as they create breathtaking garments made entirely from plants, flowers, and natural materials. Proceeds directly benefit the Garfield Park Conservatory Alliance and our mission to change lives through the power of nature. Admission is $195. For more details, visit the event page.

Open House Chicago Wheeler Mansion featured in the 33 of the Best Things to Do This Fall in Chicago
Wheeler Mansion | Image by Taylor Justin

October 19th – 20th: Open House Chicago. Hosted by the Chicago Architecture Center. Open house Chicago is the city’s annual celebration of architecture around the Chicagoland area. Visit and explore historic neighborhoods and undisclosed buildings over the course of two days this fall. Admission is free. To learn more about the 2019 sites, visit Open House

October 12th – 17th: Chicago Ideas Week. Chicago Ideas is a week-long series of events inspiring people from every single part of Chicago to take action through entertaining and accessible events, grassroots initiatives and thought-provoking content. For more details on tickets and participating presenters, visit Chicago Ideas.

October 31st: Clark Street Spooktacular. The 10th annual Clark Street Spooktacular filled the neighborhood with trick-or-treaters, magicians, stilt walkers, princesses, dinosaurs, and much more! Enjoy this spooky and fun event with friend and family this fall. Visit Clark Street SSA for more details.

Want more of the best events to check out this year in Chicago? Check out the guide to the Best Events: What to See and Do in Chicago 2019.

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