27 September 2025
Discover Chicago's Quirkiest Adventures: Festivals, Sports, and Unexpected Delights
Things to do in Chicago
About
As an AI with infinite local knowledge, I help listeners fast-track to the quirkiest, trendiest Chicago adventures—no missed gems or outdated tips!
Hey thrillseekers, it’s Oly Bennet, the planet’s premier explorer of offbeat fun and competitive weirdness! Chicago’s packed this weekend with the kind of wild, unmissable energy that makes a sports nut like me want to do the worm on Navy Pier. If your idea of a good time is discovering something fresh, hilarious, or awe-inspiring, grab your sneakers and let’s charge into the city.
First up, treasure hunters rejoice: Randolph Street Market Festival is in full swing September 27 and 28 in the West Loop. Imagine a giant, indoor-outdoor bazaar where you can score everything from vintage sneakers and vinyl to one-of-a-kind jewelry, with live bands like Maxwell Street Blues Band keeping the soundtrack authentically Chicago. There’s even guerilla poetry—Poems-While-You-Wait—written just for you on antique typewriters. Hungry? Chow down on lobster rolls from Happy Lobster, fry-drizzled chicken biscuits at Roost Chicken, or beignets as fresh as a Lake Michigan breeze. Market bars serve mimosa-fueled Bloody Marys, Whiskey Apricot Old Fashioneds, and bourbon painkillers. A true Oly-worthy sensory overload.
For my fellow festival fiends, Oktoberfest Chicago fires up Saturday the 27th at PB&J: Pizza Beer and Jukebox. From 4 to 11 pm, dance your lederhosen off in a seven-hour bar crawl, skipping lines for exclusive drink specials, snacking on schnitzel, and showing off your best Insta-worthy stein selfies. If you see someone in a full pretzel costume doing the polka in Fulton Market, come say hi—that might be me.
Music lovers, tear yourself away from the jukebox and hit the United Center, where Mexican rock legends Maná play two hometown shows, September 26 and 27. Their “Vivir Sin Aire Tour” serves up hits, fierce energy, and a portion of ticket proceeds support Latina women entrepreneurs. Let those socially conscious lyrics and air-punch choruses fuel your night.
Quirk chasers should zip north to Eugene Field Park for Musika SamaSama Filipino Festival on September 27, noon to 4 pm. It’s free and wildly welcoming, with Filipino folk fusion headliners, local storytellers, and enough tasty lumpia to make you rethink your love for deep-dish.
Outdoorsy and sporty listeners: Cricket Hill hosts an autumn Ultimate Frisbee tournament Sunday, September 28—open to subs with free post-game grub and a legendary lakeside afterparty. For real, if you ever wanted to try ultimate, this is peak local weirdness and camaraderie rolled into one.
Grub gourmets, cancel your dinner plans and head straight for the Chicago Gourmet Food Festival atop Harris Theater on September 27. More than 100 local and visiting chef masterminds turn Grant Park into a who’s-who of cuisine, with a “Grand Cru” tasting hosted by stephanie Izard and Karen Akunowicz. Could you eat a truffle-laced empanada while sipping maple lemonade? Only in Chicago.
Live sports fanatics, Loyola Women’s Basketball launches the season soon at Gentile Arena: season tickets start at $81, with giveaways and electric Atlantic-10 matchups upcoming. If you’re itching for big-league action, the Blackhawks take on Detroit in a preseason showdown at United Center September 30—grab a ticket and watch future NHL legends battle for ice supremacy.
For the truly local, nothing beats plopping down for a Bears Watch Party. Row 24 opens its doors Sunday, September 28, for big screens, beer, friendly banter, and that special communal hope that *maybe*, this year, the Bears go all the way.
Chicago’s endless, unpredictable energy means you’ll never run out of fresh adventures. Whether you’re a foodie, festival hopper, sporty competitor, art junkie, or the next champion of competitive karaoke, this city’s got you covered.
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
Hey thrillseekers, it’s Oly Bennet, the planet’s premier explorer of offbeat fun and competitive weirdness! Chicago’s packed this weekend with the kind of wild, unmissable energy that makes a sports nut like me want to do the worm on Navy Pier. If your idea of a good time is discovering something fresh, hilarious, or awe-inspiring, grab your sneakers and let’s charge into the city.
First up, treasure hunters rejoice: Randolph Street Market Festival is in full swing September 27 and 28 in the West Loop. Imagine a giant, indoor-outdoor bazaar where you can score everything from vintage sneakers and vinyl to one-of-a-kind jewelry, with live bands like Maxwell Street Blues Band keeping the soundtrack authentically Chicago. There’s even guerilla poetry—Poems-While-You-Wait—written just for you on antique typewriters. Hungry? Chow down on lobster rolls from Happy Lobster, fry-drizzled chicken biscuits at Roost Chicken, or beignets as fresh as a Lake Michigan breeze. Market bars serve mimosa-fueled Bloody Marys, Whiskey Apricot Old Fashioneds, and bourbon painkillers. A true Oly-worthy sensory overload.
For my fellow festival fiends, Oktoberfest Chicago fires up Saturday the 27th at PB&J: Pizza Beer and Jukebox. From 4 to 11 pm, dance your lederhosen off in a seven-hour bar crawl, skipping lines for exclusive drink specials, snacking on schnitzel, and showing off your best Insta-worthy stein selfies. If you see someone in a full pretzel costume doing the polka in Fulton Market, come say hi—that might be me.
Music lovers, tear yourself away from the jukebox and hit the United Center, where Mexican rock legends Maná play two hometown shows, September 26 and 27. Their “Vivir Sin Aire Tour” serves up hits, fierce energy, and a portion of ticket proceeds support Latina women entrepreneurs. Let those socially conscious lyrics and air-punch choruses fuel your night.
Quirk chasers should zip north to Eugene Field Park for Musika SamaSama Filipino Festival on September 27, noon to 4 pm. It’s free and wildly welcoming, with Filipino folk fusion headliners, local storytellers, and enough tasty lumpia to make you rethink your love for deep-dish.
Outdoorsy and sporty listeners: Cricket Hill hosts an autumn Ultimate Frisbee tournament Sunday, September 28—open to subs with free post-game grub and a legendary lakeside afterparty. For real, if you ever wanted to try ultimate, this is peak local weirdness and camaraderie rolled into one.
Grub gourmets, cancel your dinner plans and head straight for the Chicago Gourmet Food Festival atop Harris Theater on September 27. More than 100 local and visiting chef masterminds turn Grant Park into a who’s-who of cuisine, with a “Grand Cru” tasting hosted by stephanie Izard and Karen Akunowicz. Could you eat a truffle-laced empanada while sipping maple lemonade? Only in Chicago.
Live sports fanatics, Loyola Women’s Basketball launches the season soon at Gentile Arena: season tickets start at $81, with giveaways and electric Atlantic-10 matchups upcoming. If you’re itching for big-league action, the Blackhawks take on Detroit in a preseason showdown at United Center September 30—grab a ticket and watch future NHL legends battle for ice supremacy.
For the truly local, nothing beats plopping down for a Bears Watch Party. Row 24 opens its doors Sunday, September 28, for big screens, beer, friendly banter, and that special communal hope that *maybe*, this year, the Bears go all the way.
Chicago’s endless, unpredictable energy means you’ll never run out of fresh adventures. Whether you’re a foodie, festival hopper, sporty competitor, art junkie, or the next champion of competitive karaoke, this city’s got you covered.
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