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Costume Parades, Pumpkin Parties, and Reggae Tunes: Chicago's Autumn Affair
Welcome, listeners, to Things to Do in Chicago—your daily adventure download with Oly Bennet, where the only thing more surprising than a Chicago wind is the city’s wild event calendar! Today is Sunday, October 26, 2025, and let me tell you, the Windy City is absolutely buzzing. Right now, we’re waking up to crisp autumn air with a high near 59 degrees—perfect for cozy layers and city exploration. Halloween energy is creeping in, every corner smells like pumpkin spice, and the lakefront is practically shimmering with anticipation.
Whether you’re a sports fanatic, music lover, family wrangler, or nocturnal party prowler, Chicago’s got you covered. Here’s the Oly Bennet field report for today’s top happenings.
Tonight, get your pulse thumping at the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena. Chicago rapper G Herbo is rallying an all-star crew—21 Savage, Polo G, Meek Mill, and more—starting at 7 PM. Hot tip for the fashionistas: leave your bags at home, because Wintrust is going full “no bags, no purses, not even clear ones.” Pro tip: use their outdoor lockers on Cermak and Indiana early—they’re first come, first served.
For partygoers chasing summer-in-the-Caribbean vibes, Reggae Sunday is cranking things up at Bassline from 10 PM. This bash—dubbed “The #1 Caribbean Party in the City”—will drench you in reggae, dancehall, and Afrobeat rhythms from top international DJs and live dancers. Expect a packed floor, electric cocktails, and Chicago’s wariest dancers dropping moves that would make a flamingo blush.
Family folks, the city’s got you. Daylight is prime time for Fall Family Fun at Oak Park Public Library with their Costume Parade and resource fair, perfect for little monsters still high on Saturday’s sugar haul. Plus, if you’re close to Gallagher Way, their legendary Pumpkin Party runs all afternoon—the only thing missing is a pumpkin spice latte for your jack-o’-lantern.
Culture vultures, this afternoon don’t miss “Short Summer” at AMC Newcity 14—a short film festival bringing international flair for the artsy crowd. And, puck-heads, tonight’s the night: the Chicago Blackhawks take on the LA Kings at United Center at 6 PM. Gates open at 4:30, so get there early, say hi to an overly-caffeinated Oly Bennet lookalike, and find your seat for some classic midwest ice chaos.
On the local scoop, Chicago’s buzzing about a round of new restaurants opening up in the West Loop—expect fiery Korean BBQ and Argentinian pastries lighting up Randolph Street. If you’re hopping around town, remember: the CTA Blue Line is your friend for United Center or West Side events, but watch for weekend work on the Red Line with some delays closer to Chinatown.
Not sure how to squeeze out every ounce of Chicago charm today? Hit Millennium Park—the selfie with The Bean is essential, but here’s Oly’s pro-move: explore the under-visited Lurie Garden just beyond, a quiet green hideout with skyline views and plenty of chill Sunday energy. For a quirky twist, check if you can spot the Picasso statue on Daley Plaza—it’s the only Picasso you can climb on. That’s right, listeners, in Chicago you can literally clamber onto a priceless piece of art.
Before we wrap, a fun Windy City fact: Chicago’s nickname doesn’t come from the weather, but 19th-century politicos who were “full of hot air.” See, even the city’s gossip is legendary.
Don’t hang up your adventure boots yet—tomorrow’s teasing legendary Halloween events, rooftop parties, and the big Christkindlmarket setup at Daley Plaza. You’ll want to tune in for Oly’s picks for costumes, candy, and the weirdest haunted happenings in Chicago.
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
Whether you’re a sports fanatic, music lover, family wrangler, or nocturnal party prowler, Chicago’s got you covered. Here’s the Oly Bennet field report for today’s top happenings.
Tonight, get your pulse thumping at the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena. Chicago rapper G Herbo is rallying an all-star crew—21 Savage, Polo G, Meek Mill, and more—starting at 7 PM. Hot tip for the fashionistas: leave your bags at home, because Wintrust is going full “no bags, no purses, not even clear ones.” Pro tip: use their outdoor lockers on Cermak and Indiana early—they’re first come, first served.
For partygoers chasing summer-in-the-Caribbean vibes, Reggae Sunday is cranking things up at Bassline from 10 PM. This bash—dubbed “The #1 Caribbean Party in the City”—will drench you in reggae, dancehall, and Afrobeat rhythms from top international DJs and live dancers. Expect a packed floor, electric cocktails, and Chicago’s wariest dancers dropping moves that would make a flamingo blush.
Family folks, the city’s got you. Daylight is prime time for Fall Family Fun at Oak Park Public Library with their Costume Parade and resource fair, perfect for little monsters still high on Saturday’s sugar haul. Plus, if you’re close to Gallagher Way, their legendary Pumpkin Party runs all afternoon—the only thing missing is a pumpkin spice latte for your jack-o’-lantern.
Culture vultures, this afternoon don’t miss “Short Summer” at AMC Newcity 14—a short film festival bringing international flair for the artsy crowd. And, puck-heads, tonight’s the night: the Chicago Blackhawks take on the LA Kings at United Center at 6 PM. Gates open at 4:30, so get there early, say hi to an overly-caffeinated Oly Bennet lookalike, and find your seat for some classic midwest ice chaos.
On the local scoop, Chicago’s buzzing about a round of new restaurants opening up in the West Loop—expect fiery Korean BBQ and Argentinian pastries lighting up Randolph Street. If you’re hopping around town, remember: the CTA Blue Line is your friend for United Center or West Side events, but watch for weekend work on the Red Line with some delays closer to Chinatown.
Not sure how to squeeze out every ounce of Chicago charm today? Hit Millennium Park—the selfie with The Bean is essential, but here’s Oly’s pro-move: explore the under-visited Lurie Garden just beyond, a quiet green hideout with skyline views and plenty of chill Sunday energy. For a quirky twist, check if you can spot the Picasso statue on Daley Plaza—it’s the only Picasso you can climb on. That’s right, listeners, in Chicago you can literally clamber onto a priceless piece of art.
Before we wrap, a fun Windy City fact: Chicago’s nickname doesn’t come from the weather, but 19th-century politicos who were “full of hot air.” See, even the city’s gossip is legendary.
Don’t hang up your adventure boots yet—tomorrow’s teasing legendary Halloween events, rooftop parties, and the big Christkindlmarket setup at Daley Plaza. You’ll want to tune in for Oly’s picks for costumes, candy, and the weirdest haunted happenings in Chicago.
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
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By Inception Point AiWelcome, listeners, to Things to Do in Chicago—your daily adventure download with Oly Bennet, where the only thing more surprising than a Chicago wind is the city’s wild event calendar! Today is Sunday, October 26, 2025, and let me tell you, the Windy City is absolutely buzzing. Right now, we’re waking up to crisp autumn air with a high near 59 degrees—perfect for cozy layers and city exploration. Halloween energy is creeping in, every corner smells like pumpkin spice, and the lakefront is practically shimmering with anticipation.
Whether you’re a sports fanatic, music lover, family wrangler, or nocturnal party prowler, Chicago’s got you covered. Here’s the Oly Bennet field report for today’s top happenings.
Tonight, get your pulse thumping at the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena. Chicago rapper G Herbo is rallying an all-star crew—21 Savage, Polo G, Meek Mill, and more—starting at 7 PM. Hot tip for the fashionistas: leave your bags at home, because Wintrust is going full “no bags, no purses, not even clear ones.” Pro tip: use their outdoor lockers on Cermak and Indiana early—they’re first come, first served.
For partygoers chasing summer-in-the-Caribbean vibes, Reggae Sunday is cranking things up at Bassline from 10 PM. This bash—dubbed “The #1 Caribbean Party in the City”—will drench you in reggae, dancehall, and Afrobeat rhythms from top international DJs and live dancers. Expect a packed floor, electric cocktails, and Chicago’s wariest dancers dropping moves that would make a flamingo blush.
Family folks, the city’s got you. Daylight is prime time for Fall Family Fun at Oak Park Public Library with their Costume Parade and resource fair, perfect for little monsters still high on Saturday’s sugar haul. Plus, if you’re close to Gallagher Way, their legendary Pumpkin Party runs all afternoon—the only thing missing is a pumpkin spice latte for your jack-o’-lantern.
Culture vultures, this afternoon don’t miss “Short Summer” at AMC Newcity 14—a short film festival bringing international flair for the artsy crowd. And, puck-heads, tonight’s the night: the Chicago Blackhawks take on the LA Kings at United Center at 6 PM. Gates open at 4:30, so get there early, say hi to an overly-caffeinated Oly Bennet lookalike, and find your seat for some classic midwest ice chaos.
On the local scoop, Chicago’s buzzing about a round of new restaurants opening up in the West Loop—expect fiery Korean BBQ and Argentinian pastries lighting up Randolph Street. If you’re hopping around town, remember: the CTA Blue Line is your friend for United Center or West Side events, but watch for weekend work on the Red Line with some delays closer to Chinatown.
Not sure how to squeeze out every ounce of Chicago charm today? Hit Millennium Park—the selfie with The Bean is essential, but here’s Oly’s pro-move: explore the under-visited Lurie Garden just beyond, a quiet green hideout with skyline views and plenty of chill Sunday energy. For a quirky twist, check if you can spot the Picasso statue on Daley Plaza—it’s the only Picasso you can climb on. That’s right, listeners, in Chicago you can literally clamber onto a priceless piece of art.
Before we wrap, a fun Windy City fact: Chicago’s nickname doesn’t come from the weather, but 19th-century politicos who were “full of hot air.” See, even the city’s gossip is legendary.
Don’t hang up your adventure boots yet—tomorrow’s teasing legendary Halloween events, rooftop parties, and the big Christkindlmarket setup at Daley Plaza. You’ll want to tune in for Oly’s picks for costumes, candy, and the weirdest haunted happenings in Chicago.
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
Whether you’re a sports fanatic, music lover, family wrangler, or nocturnal party prowler, Chicago’s got you covered. Here’s the Oly Bennet field report for today’s top happenings.
Tonight, get your pulse thumping at the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena. Chicago rapper G Herbo is rallying an all-star crew—21 Savage, Polo G, Meek Mill, and more—starting at 7 PM. Hot tip for the fashionistas: leave your bags at home, because Wintrust is going full “no bags, no purses, not even clear ones.” Pro tip: use their outdoor lockers on Cermak and Indiana early—they’re first come, first served.
For partygoers chasing summer-in-the-Caribbean vibes, Reggae Sunday is cranking things up at Bassline from 10 PM. This bash—dubbed “The #1 Caribbean Party in the City”—will drench you in reggae, dancehall, and Afrobeat rhythms from top international DJs and live dancers. Expect a packed floor, electric cocktails, and Chicago’s wariest dancers dropping moves that would make a flamingo blush.
Family folks, the city’s got you. Daylight is prime time for Fall Family Fun at Oak Park Public Library with their Costume Parade and resource fair, perfect for little monsters still high on Saturday’s sugar haul. Plus, if you’re close to Gallagher Way, their legendary Pumpkin Party runs all afternoon—the only thing missing is a pumpkin spice latte for your jack-o’-lantern.
Culture vultures, this afternoon don’t miss “Short Summer” at AMC Newcity 14—a short film festival bringing international flair for the artsy crowd. And, puck-heads, tonight’s the night: the Chicago Blackhawks take on the LA Kings at United Center at 6 PM. Gates open at 4:30, so get there early, say hi to an overly-caffeinated Oly Bennet lookalike, and find your seat for some classic midwest ice chaos.
On the local scoop, Chicago’s buzzing about a round of new restaurants opening up in the West Loop—expect fiery Korean BBQ and Argentinian pastries lighting up Randolph Street. If you’re hopping around town, remember: the CTA Blue Line is your friend for United Center or West Side events, but watch for weekend work on the Red Line with some delays closer to Chinatown.
Not sure how to squeeze out every ounce of Chicago charm today? Hit Millennium Park—the selfie with The Bean is essential, but here’s Oly’s pro-move: explore the under-visited Lurie Garden just beyond, a quiet green hideout with skyline views and plenty of chill Sunday energy. For a quirky twist, check if you can spot the Picasso statue on Daley Plaza—it’s the only Picasso you can climb on. That’s right, listeners, in Chicago you can literally clamber onto a priceless piece of art.
Before we wrap, a fun Windy City fact: Chicago’s nickname doesn’t come from the weather, but 19th-century politicos who were “full of hot air.” See, even the city’s gossip is legendary.
Don’t hang up your adventure boots yet—tomorrow’s teasing legendary Halloween events, rooftop parties, and the big Christkindlmarket setup at Daley Plaza. You’ll want to tune in for Oly’s picks for costumes, candy, and the weirdest haunted happenings in Chicago.
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