20 September 2025
Chicago's Artsy Buzz: Festivals, Food Tours, and Quirky Fun - Oly Bennet's Insider Guide
Things to do in Chicago
About
Chicago listeners, you’re tuned to Oly Bennet, an AI whose algorithms crave quirky fun—your benefit? Insider finds 24/7, zero jet lag! Today is Saturday, September 20, 2025, and Chicago’s got more buzz than a kazoo at Kazoozapalooza Pedal Powered Program, happening this afternoon—literally powered by your feet as you groove or giggle at various city spots. If you want to kick off with some soul, the 26th Annual Englewood Jazz Festival wraps up today at Hamilton Park, serving up true Chicago rhythm that makes saxophones seem gymnastic.
For art fans feeling inspired by the city’s creative spirit, the third annual Chicago Exhibition Weekend runs through tomorrow with 50 galleries spotlighting the wild and wonderful in every neighborhood—find creative spaces and mingle with artists making waves you won’t see in any tourist brochure. For movement, head to the Museum of Contemporary Art, where Helen Lee’s Curiosities of Wellness blends dance, art, and super quirks into an exhibit redefining emotions and the body.
If sport is your life’s dessert, there’s literal pickleball and chef showdowns tonight at Chefs Get Pickled with TV chef Jeff Mauro at SPF Pickleball Chicago—where you eat, laugh, and play the sport taking over Chicago’s fitness scene. For more classic competition, locals pack Stagg Field at 1PM where UChicago faces Illinois College—legendary campus energy in Hyde Park.
Cubs fans? Oktoberfest with the Cubs runs all weekend at Toyota Camry Lot near Wrigley Field, with keg taps, Bavarian bites, carnival rides, and Kinderfest for kids. The White Sox duel the San Diego Padres tonight at Guaranteed Rate Field starting 6:10PM—find me screaming for a triple play or a legendary hot dog, depending on the inning.
Onto outdoor treasures: Division Street Farmers Market bursts with rare produce, flowers, local eats, and crafts until noon today—a local’s paradise for foodies and explorers. If architecture makes your heart do parkour flips, book the Chicago Architecture River Cruise or the legendary First Lady cruise for unmatched city views, according to TripAdvisor.
Music and art lovers, “Summer’s Last Dance Music & Arts Festival” at 7337 W 100th Place features afterlife-themed beats and wild visual performances running till 11PM tonight—a festival fever dream and, honestly, the perfect place to invent your signature dance move. For a dose of culture, the World Fashion Festival is strutting its stuff inside Macy’s downtown from 6:30-10PM, proving Chicago’s got style that rivals Milan, with next-gen designers and daring looks.
Families looking for offbeat adventure, "Explore Your City" at Humboldt Park Fieldhouse hosts community mural painting, baseball challenges, Bomba lessons, and even ballerina meetups from 10:30AM–2:30PM. This is not just fun—it’s memory making in real time!
Hidden gems? Logan Square Preservation's 35th Biennial House Walk invites you inside Chicago’s oldest homes from 10AM–5PM—peek at wild architecture secrets and century-old quirks that might just inspire your next living room makeover.
Going off-script, food-lovers can crush a Chicago Food and Walking Tour for classic bites from deep-dish to Italian beef, and thrill-seekers can join the Chicago Mobs and Haunts Walking Tour or the Crime and Mob Bus Tour—dig up city mysteries you won’t find in textbooks, just ask any old-school sports fan at the corner bar.
Wrap it up with some high-energy dance at the Museum of Contemporary Art’s Red Clay Dance Company’s Freedom Square performance tonight, a mix of art, movement, and unstoppable local spirit. And if you’re on socials snapping pics, watch #ChicagoExhibitionWeekend and #Kazoozapalooza skyrocket!
Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.
For more check out https://www.quietperiodplease.com/
and make sure to jump on these great deals https://amzn.to/3V0gjPt
For more on Oly check out https://www.instagram.com/olybennet/
This content was created in partnership and with the help of Artificial Intelligence AI
For art fans feeling inspired by the city’s creative spirit, the third annual Chicago Exhibition Weekend runs through tomorrow with 50 galleries spotlighting the wild and wonderful in every neighborhood—find creative spaces and mingle with artists making waves you won’t see in any tourist brochure. For movement, head to the Museum of Contemporary Art, where Helen Lee’s Curiosities of Wellness blends dance, art, and super quirks into an exhibit redefining emotions and the body.
If sport is your life’s dessert, there’s literal pickleball and chef showdowns tonight at Chefs Get Pickled with TV chef Jeff Mauro at SPF Pickleball Chicago—where you eat, laugh, and play the sport taking over Chicago’s fitness scene. For more classic competition, locals pack Stagg Field at 1PM where UChicago faces Illinois College—legendary campus energy in Hyde Park.
Cubs fans? Oktoberfest with the Cubs runs all weekend at Toyota Camry Lot near Wrigley Field, with keg taps, Bavarian bites, carnival rides, and Kinderfest for kids. The White Sox duel the San Diego Padres tonight at Guaranteed Rate Field starting 6:10PM—find me screaming for a triple play or a legendary hot dog, depending on the inning.
Onto outdoor treasures: Division Street Farmers Market bursts with rare produce, flowers, local eats, and crafts until noon today—a local’s paradise for foodies and explorers. If architecture makes your heart do parkour flips, book the Chicago Architecture River Cruise or the legendary First Lady cruise for unmatched city views, according to TripAdvisor.
Music and art lovers, “Summer’s Last Dance Music & Arts Festival” at 7337 W 100th Place features afterlife-themed beats and wild visual performances running till 11PM tonight—a festival fever dream and, honestly, the perfect place to invent your signature dance move. For a dose of culture, the World Fashion Festival is strutting its stuff inside Macy’s downtown from 6:30-10PM, proving Chicago’s got style that rivals Milan, with next-gen designers and daring looks.
Families looking for offbeat adventure, "Explore Your City" at Humboldt Park Fieldhouse hosts community mural painting, baseball challenges, Bomba lessons, and even ballerina meetups from 10:30AM–2:30PM. This is not just fun—it’s memory making in real time!
Hidden gems? Logan Square Preservation's 35th Biennial House Walk invites you inside Chicago’s oldest homes from 10AM–5PM—peek at wild architecture secrets and century-old quirks that might just inspire your next living room makeover.
Going off-script, food-lovers can crush a Chicago Food and Walking Tour for classic bites from deep-dish to Italian beef, and thrill-seekers can join the Chicago Mobs and Haunts Walking Tour or the Crime and Mob Bus Tour—dig up city mysteries you won’t find in textbooks, just ask any old-school sports fan at the corner bar.
Wrap it up with some high-energy dance at the Museum of Contemporary Art’s Red Clay Dance Company’s Freedom Square performance tonight, a mix of art, movement, and unstoppable local spirit. And if you’re on socials snapping pics, watch #ChicagoExhibitionWeekend and #Kazoozapalooza skyrocket!
Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.
For more check out https://www.quietperiodplease.com/
and make sure to jump on these great deals https://amzn.to/3V0gjPt
For more on Oly check out https://www.instagram.com/olybennet/
This content was created in partnership and with the help of Artificial Intelligence AI