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Chicago's Autumn Playbook: Toys, Talents, and Trivia Delights
Welcome, listeners, to Things to Do in Chicago, coming at you from the Windy City this Sunday, November 9th, 2025! Oly Bennet here, your globe-trotting champion of quirky fun, and if you’re craving more action than a Wrigley Field extra-innings thriller, you’ve tuned in to the right spot.
Let’s set the scene: It’s a crisp, classic November day, the Lake Michigan breeze is doing its thing, autumn leaves are swirling through Millennium Park, and the city’s electric as folks pack into neighborhoods from the South Loop to Wicker Park. The holidays are peeking around the corner, and Chicago is ready to turn up the volume on Sunday Funday.
Kicking off with today’s high-energy happenings—there’s something for every flavor of fun. First up: the Chicago Toy & Game Fair is in full swing at the Donald E. Stephens Convention Center, boasting a whirlwind of interactive exhibits, yo-yo championships, live toy battles, and even mascot sightings. If you want to catch Benny the Bull in the wild or vote on the Toy of the Year, this is your wonderland. Bonus points if you challenge a stranger to Giant Jenga—Oly’s official recommendation for making instant friends, or frenemies, depending on your skills.
If culture and the arts are calling your name, Dorothy Menker Theater is serving up chills and chuckles with their final showings of The Mel Brooks Musical: Young Frankenstein. For families, Brookfield Zoo is wrapping up its Tree Trim event, inviting you to channel your inner squirrel and help decorate the zoo for the holidays. Meanwhile, poetry lovers can dive into Earth & Echo: A Black Nature Poetry Gathering at Sand Ridge Nature Center, for a blend of words and the wild.
But hold onto your socks, there’s more: Columbia College Chicago’s Terranium Exhibit, The Conundrum of Coexistence, with stunning wildlife art, is still on display and free to attend, making a perfect pit stop for curious minds. And for a twist of history, check out the Halma board game event at Chicago Public Library—did you know Halma is German, not Chinese? Minds blown, trivia points earned.
Turning to city news and buzz, Queensyard has officially opened near River North, dazzling foodies with its British-American menu and sweeping river views—a hot new brunch destination in a city already obsessed with brunch. The CTA just announced enhanced train service for the holidays, so snag those ventra cards and leave gridlock to the taxis. For those wanting the inside scoop, Chicago’s newest immersive playground, EmotionAir by the Balloon Museum, is causing a stir in West Loop. Think epic balloon sculptures, interactive installations, and more Instagrammable moments than you can shake a selfie stick at.
Oly’s must-dos for today: Grab a slice at Pequod’s, warm up with a walk on the Lakefront Trail, or skate through Maggie Daley Park—those outdoor rinks are now open, and nothing says Chicago like trying to stay upright on ice as skyscrapers gleam overhead. If you’re in the mood for mischief, spot all 16 public art cows now scattered around the Loop—a citywide scavenger hunt that’s pure bovine brilliance.
Pro tip: For the real local vibe, never call it Willis Tower. It’s Sears Tower, full stop. Bonus Chicago cred if you work “dibs” into a conversation today—locals will know exactly what you mean.
On the horizon for tomorrow, Tuesday, be sure to catch Columbia College’s Veterans’ Day Celebration and the start of the Veterans Art Exhibition. Plus, the Christkindlmarket is prepping for its grand return—get ready for mugs of hot spiced wine and the original stuffed pretzel.
Don’t miss a beat—tune in tomorrow for more wild and wonderful ways to conquer Chicago like a true fun-seeker.
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
Let’s set the scene: It’s a crisp, classic November day, the Lake Michigan breeze is doing its thing, autumn leaves are swirling through Millennium Park, and the city’s electric as folks pack into neighborhoods from the South Loop to Wicker Park. The holidays are peeking around the corner, and Chicago is ready to turn up the volume on Sunday Funday.
Kicking off with today’s high-energy happenings—there’s something for every flavor of fun. First up: the Chicago Toy & Game Fair is in full swing at the Donald E. Stephens Convention Center, boasting a whirlwind of interactive exhibits, yo-yo championships, live toy battles, and even mascot sightings. If you want to catch Benny the Bull in the wild or vote on the Toy of the Year, this is your wonderland. Bonus points if you challenge a stranger to Giant Jenga—Oly’s official recommendation for making instant friends, or frenemies, depending on your skills.
If culture and the arts are calling your name, Dorothy Menker Theater is serving up chills and chuckles with their final showings of The Mel Brooks Musical: Young Frankenstein. For families, Brookfield Zoo is wrapping up its Tree Trim event, inviting you to channel your inner squirrel and help decorate the zoo for the holidays. Meanwhile, poetry lovers can dive into Earth & Echo: A Black Nature Poetry Gathering at Sand Ridge Nature Center, for a blend of words and the wild.
But hold onto your socks, there’s more: Columbia College Chicago’s Terranium Exhibit, The Conundrum of Coexistence, with stunning wildlife art, is still on display and free to attend, making a perfect pit stop for curious minds. And for a twist of history, check out the Halma board game event at Chicago Public Library—did you know Halma is German, not Chinese? Minds blown, trivia points earned.
Turning to city news and buzz, Queensyard has officially opened near River North, dazzling foodies with its British-American menu and sweeping river views—a hot new brunch destination in a city already obsessed with brunch. The CTA just announced enhanced train service for the holidays, so snag those ventra cards and leave gridlock to the taxis. For those wanting the inside scoop, Chicago’s newest immersive playground, EmotionAir by the Balloon Museum, is causing a stir in West Loop. Think epic balloon sculptures, interactive installations, and more Instagrammable moments than you can shake a selfie stick at.
Oly’s must-dos for today: Grab a slice at Pequod’s, warm up with a walk on the Lakefront Trail, or skate through Maggie Daley Park—those outdoor rinks are now open, and nothing says Chicago like trying to stay upright on ice as skyscrapers gleam overhead. If you’re in the mood for mischief, spot all 16 public art cows now scattered around the Loop—a citywide scavenger hunt that’s pure bovine brilliance.
Pro tip: For the real local vibe, never call it Willis Tower. It’s Sears Tower, full stop. Bonus Chicago cred if you work “dibs” into a conversation today—locals will know exactly what you mean.
On the horizon for tomorrow, Tuesday, be sure to catch Columbia College’s Veterans’ Day Celebration and the start of the Veterans Art Exhibition. Plus, the Christkindlmarket is prepping for its grand return—get ready for mugs of hot spiced wine and the original stuffed pretzel.
Don’t miss a beat—tune in tomorrow for more wild and wonderful ways to conquer Chicago like a true fun-seeker.
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, coming at you from the Windy City this Sunday, November 9th, 2025! Oly Bennet here, your globe-trotting champion of quirky fun, and if you’re craving more action than a Wrigley Field extra-innings thriller, you’ve tuned in to the right spot.
Let’s set the scene: It’s a crisp, classic November day, the Lake Michigan breeze is doing its thing, autumn leaves are swirling through Millennium Park, and the city’s electric as folks pack into neighborhoods from the South Loop to Wicker Park. The holidays are peeking around the corner, and Chicago is ready to turn up the volume on Sunday Funday.
Kicking off with today’s high-energy happenings—there’s something for every flavor of fun. First up: the Chicago Toy & Game Fair is in full swing at the Donald E. Stephens Convention Center, boasting a whirlwind of interactive exhibits, yo-yo championships, live toy battles, and even mascot sightings. If you want to catch Benny the Bull in the wild or vote on the Toy of the Year, this is your wonderland. Bonus points if you challenge a stranger to Giant Jenga—Oly’s official recommendation for making instant friends, or frenemies, depending on your skills.
If culture and the arts are calling your name, Dorothy Menker Theater is serving up chills and chuckles with their final showings of The Mel Brooks Musical: Young Frankenstein. For families, Brookfield Zoo is wrapping up its Tree Trim event, inviting you to channel your inner squirrel and help decorate the zoo for the holidays. Meanwhile, poetry lovers can dive into Earth & Echo: A Black Nature Poetry Gathering at Sand Ridge Nature Center, for a blend of words and the wild.
But hold onto your socks, there’s more: Columbia College Chicago’s Terranium Exhibit, The Conundrum of Coexistence, with stunning wildlife art, is still on display and free to attend, making a perfect pit stop for curious minds. And for a twist of history, check out the Halma board game event at Chicago Public Library—did you know Halma is German, not Chinese? Minds blown, trivia points earned.
Turning to city news and buzz, Queensyard has officially opened near River North, dazzling foodies with its British-American menu and sweeping river views—a hot new brunch destination in a city already obsessed with brunch. The CTA just announced enhanced train service for the holidays, so snag those ventra cards and leave gridlock to the taxis. For those wanting the inside scoop, Chicago’s newest immersive playground, EmotionAir by the Balloon Museum, is causing a stir in West Loop. Think epic balloon sculptures, interactive installations, and more Instagrammable moments than you can shake a selfie stick at.
Oly’s must-dos for today: Grab a slice at Pequod’s, warm up with a walk on the Lakefront Trail, or skate through Maggie Daley Park—those outdoor rinks are now open, and nothing says Chicago like trying to stay upright on ice as skyscrapers gleam overhead. If you’re in the mood for mischief, spot all 16 public art cows now scattered around the Loop—a citywide scavenger hunt that’s pure bovine brilliance.
Pro tip: For the real local vibe, never call it Willis Tower. It’s Sears Tower, full stop. Bonus Chicago cred if you work “dibs” into a conversation today—locals will know exactly what you mean.
On the horizon for tomorrow, Tuesday, be sure to catch Columbia College’s Veterans’ Day Celebration and the start of the Veterans Art Exhibition. Plus, the Christkindlmarket is prepping for its grand return—get ready for mugs of hot spiced wine and the original stuffed pretzel.
Don’t miss a beat—tune in tomorrow for more wild and wonderful ways to conquer Chicago like a true fun-seeker.
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
Let’s set the scene: It’s a crisp, classic November day, the Lake Michigan breeze is doing its thing, autumn leaves are swirling through Millennium Park, and the city’s electric as folks pack into neighborhoods from the South Loop to Wicker Park. The holidays are peeking around the corner, and Chicago is ready to turn up the volume on Sunday Funday.
Kicking off with today’s high-energy happenings—there’s something for every flavor of fun. First up: the Chicago Toy & Game Fair is in full swing at the Donald E. Stephens Convention Center, boasting a whirlwind of interactive exhibits, yo-yo championships, live toy battles, and even mascot sightings. If you want to catch Benny the Bull in the wild or vote on the Toy of the Year, this is your wonderland. Bonus points if you challenge a stranger to Giant Jenga—Oly’s official recommendation for making instant friends, or frenemies, depending on your skills.
If culture and the arts are calling your name, Dorothy Menker Theater is serving up chills and chuckles with their final showings of The Mel Brooks Musical: Young Frankenstein. For families, Brookfield Zoo is wrapping up its Tree Trim event, inviting you to channel your inner squirrel and help decorate the zoo for the holidays. Meanwhile, poetry lovers can dive into Earth & Echo: A Black Nature Poetry Gathering at Sand Ridge Nature Center, for a blend of words and the wild.
But hold onto your socks, there’s more: Columbia College Chicago’s Terranium Exhibit, The Conundrum of Coexistence, with stunning wildlife art, is still on display and free to attend, making a perfect pit stop for curious minds. And for a twist of history, check out the Halma board game event at Chicago Public Library—did you know Halma is German, not Chinese? Minds blown, trivia points earned.
Turning to city news and buzz, Queensyard has officially opened near River North, dazzling foodies with its British-American menu and sweeping river views—a hot new brunch destination in a city already obsessed with brunch. The CTA just announced enhanced train service for the holidays, so snag those ventra cards and leave gridlock to the taxis. For those wanting the inside scoop, Chicago’s newest immersive playground, EmotionAir by the Balloon Museum, is causing a stir in West Loop. Think epic balloon sculptures, interactive installations, and more Instagrammable moments than you can shake a selfie stick at.
Oly’s must-dos for today: Grab a slice at Pequod’s, warm up with a walk on the Lakefront Trail, or skate through Maggie Daley Park—those outdoor rinks are now open, and nothing says Chicago like trying to stay upright on ice as skyscrapers gleam overhead. If you’re in the mood for mischief, spot all 16 public art cows now scattered around the Loop—a citywide scavenger hunt that’s pure bovine brilliance.
Pro tip: For the real local vibe, never call it Willis Tower. It’s Sears Tower, full stop. Bonus Chicago cred if you work “dibs” into a conversation today—locals will know exactly what you mean.
On the horizon for tomorrow, Tuesday, be sure to catch Columbia College’s Veterans’ Day Celebration and the start of the Veterans Art Exhibition. Plus, the Christkindlmarket is prepping for its grand return—get ready for mugs of hot spiced wine and the original stuffed pretzel.
Don’t miss a beat—tune in tomorrow for more wild and wonderful ways to conquer Chicago like a true fun-seeker.
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