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Chicago's Haunted Happenings: Pumpkins, Parades, and Playboi Carti
Welcome, wild wanderers and curious competitors, to Things to Do in Chicago with your globetrotting, game-obsessed guide, Oly Bennet! It’s Thursday, October 30th, 2025, and Chicago is absolutely buzzing — think deep-dish oven heat with a side of electric excitement as Halloween creeps ever closer. The weather’s got us in classic fall mode: jackets at the ready, scarves out in force, pumpkin spice in the air, and probably a toddler in a dinosaur costume waving at a Dalmatian-dressed dachshund somewhere on Michigan Avenue.
Chicago’s current vibe is a glorious mashup of haunted hilarity and serious style. According to Mommy Poppins, trick-or-treating is officially on today, and the whole city is candy-fueled and sugar-hyped. Not to be outdone, Dia de Los Muertos festivities are lighting up neighborhoods like Wrigleyville and Marquette Park with vibrant altars and dance performances—colorful skulls and even livelier spirits.
Let me hit you with today’s top events, guaranteed to fit every interest from headbanging to hand-holding:
Playboi Carti’s Antagonist Tour explodes into the United Center tonight at 7 pm, with Ken Carson, Destroy Lonely, and Homixide Gang joining the chaos. If your ideal cardio is pogoing in a sea of hypebeasts, this show is your jam.
Culture seekers, the Chicago Writers' Bloc Fall Festival lands at City Lit Theater, starring a fresh crop of new plays and musicals by local masterminds—expect drama, laughs, and maybe a flying pie or two just for that classic twist, as reported by Travel and Tour World.
Art lovers, feast your eyes at the Norris University Center, where “Street: Photographs by Ann Kogen” offers a black-and-white time machine into the city’s most candid moments. From Chicago sidewalks to Cairo’s chaos, Ann Kogen’s snaps capture humanity’s quirks in all their glory.
For the family crew, the big Halloween parade on Halsted Street is your costume contest, creative chaos, and candy extravaganza all rolled into one. Word is, even pets in tutus are highly encouraged—no judgment, just cheers.
Night owls, the House of Blues has you covered with live blues and the Chicago Comedy Club tonight. Drop by for toe-tapping tunes and, who knows, an impromptu dance-off as the music seeps into your soul.
How about what’s new off the field? A few fresh tidbits got locals talking: The Chicago Architecture Biennial is dazzling with massive art installations tucked between beloved skyscrapers — the perfect reason for a spontaneous selfie marathon. Meanwhile, Green City Market is still serving up fresh local bites, so come hungry and leave with arms full of apples, pumpkins, and the best damn donuts this side of Lake Michigan.
Heads up on city logistics: With all the action downtown and Halloween crowds, public transit is your friend. The CTA’s ramping up service, especially along the Red and Blue lines, so ditch the car and ride the rails like a true Chicagoan.
Top must-do activities: Snap an iconic selfie at “The Bean” before the crowds descend, then skip the usual river cruise for a stroll through Jack’s Pumpkin Pop-Up—it’s a pumpkin patch, corn maze, and full-throttle autumn fairground smack in Goose Island. Or duck beneath the ghostly glow of ghost tours winding through River North’s hidden speakeasy bars. Feeling extra? Hunt for quirky murals in Pilsen—your Instagram will thank you.
Local tip for maximum cred: If someone invites you for an Italian beef, say yes, then order it “dipped”—because the sandwich is supposed to soak up so much juicy gravy you need two hands and a whole stack of napkins. Trust Oly: get messy and earn your Chicago stripes.
Coming up tomorrow, get ready for CreepAid 25 at the Copernicus Center and the city's spookiest dance parties lighting up the night. Spoiler: costumes are strongly encouraged, and glitter is practically mandatory.
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
Chicago’s current vibe is a glorious mashup of haunted hilarity and serious style. According to Mommy Poppins, trick-or-treating is officially on today, and the whole city is candy-fueled and sugar-hyped. Not to be outdone, Dia de Los Muertos festivities are lighting up neighborhoods like Wrigleyville and Marquette Park with vibrant altars and dance performances—colorful skulls and even livelier spirits.
Let me hit you with today’s top events, guaranteed to fit every interest from headbanging to hand-holding:
Playboi Carti’s Antagonist Tour explodes into the United Center tonight at 7 pm, with Ken Carson, Destroy Lonely, and Homixide Gang joining the chaos. If your ideal cardio is pogoing in a sea of hypebeasts, this show is your jam.
Culture seekers, the Chicago Writers' Bloc Fall Festival lands at City Lit Theater, starring a fresh crop of new plays and musicals by local masterminds—expect drama, laughs, and maybe a flying pie or two just for that classic twist, as reported by Travel and Tour World.
Art lovers, feast your eyes at the Norris University Center, where “Street: Photographs by Ann Kogen” offers a black-and-white time machine into the city’s most candid moments. From Chicago sidewalks to Cairo’s chaos, Ann Kogen’s snaps capture humanity’s quirks in all their glory.
For the family crew, the big Halloween parade on Halsted Street is your costume contest, creative chaos, and candy extravaganza all rolled into one. Word is, even pets in tutus are highly encouraged—no judgment, just cheers.
Night owls, the House of Blues has you covered with live blues and the Chicago Comedy Club tonight. Drop by for toe-tapping tunes and, who knows, an impromptu dance-off as the music seeps into your soul.
How about what’s new off the field? A few fresh tidbits got locals talking: The Chicago Architecture Biennial is dazzling with massive art installations tucked between beloved skyscrapers — the perfect reason for a spontaneous selfie marathon. Meanwhile, Green City Market is still serving up fresh local bites, so come hungry and leave with arms full of apples, pumpkins, and the best damn donuts this side of Lake Michigan.
Heads up on city logistics: With all the action downtown and Halloween crowds, public transit is your friend. The CTA’s ramping up service, especially along the Red and Blue lines, so ditch the car and ride the rails like a true Chicagoan.
Top must-do activities: Snap an iconic selfie at “The Bean” before the crowds descend, then skip the usual river cruise for a stroll through Jack’s Pumpkin Pop-Up—it’s a pumpkin patch, corn maze, and full-throttle autumn fairground smack in Goose Island. Or duck beneath the ghostly glow of ghost tours winding through River North’s hidden speakeasy bars. Feeling extra? Hunt for quirky murals in Pilsen—your Instagram will thank you.
Local tip for maximum cred: If someone invites you for an Italian beef, say yes, then order it “dipped”—because the sandwich is supposed to soak up so much juicy gravy you need two hands and a whole stack of napkins. Trust Oly: get messy and earn your Chicago stripes.
Coming up tomorrow, get ready for CreepAid 25 at the Copernicus Center and the city's spookiest dance parties lighting up the night. Spoiler: costumes are strongly encouraged, and glitter is practically mandatory.
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, wild wanderers and curious competitors, to Things to Do in Chicago with your globetrotting, game-obsessed guide, Oly Bennet! It’s Thursday, October 30th, 2025, and Chicago is absolutely buzzing — think deep-dish oven heat with a side of electric excitement as Halloween creeps ever closer. The weather’s got us in classic fall mode: jackets at the ready, scarves out in force, pumpkin spice in the air, and probably a toddler in a dinosaur costume waving at a Dalmatian-dressed dachshund somewhere on Michigan Avenue.
Chicago’s current vibe is a glorious mashup of haunted hilarity and serious style. According to Mommy Poppins, trick-or-treating is officially on today, and the whole city is candy-fueled and sugar-hyped. Not to be outdone, Dia de Los Muertos festivities are lighting up neighborhoods like Wrigleyville and Marquette Park with vibrant altars and dance performances—colorful skulls and even livelier spirits.
Let me hit you with today’s top events, guaranteed to fit every interest from headbanging to hand-holding:
Playboi Carti’s Antagonist Tour explodes into the United Center tonight at 7 pm, with Ken Carson, Destroy Lonely, and Homixide Gang joining the chaos. If your ideal cardio is pogoing in a sea of hypebeasts, this show is your jam.
Culture seekers, the Chicago Writers' Bloc Fall Festival lands at City Lit Theater, starring a fresh crop of new plays and musicals by local masterminds—expect drama, laughs, and maybe a flying pie or two just for that classic twist, as reported by Travel and Tour World.
Art lovers, feast your eyes at the Norris University Center, where “Street: Photographs by Ann Kogen” offers a black-and-white time machine into the city’s most candid moments. From Chicago sidewalks to Cairo’s chaos, Ann Kogen’s snaps capture humanity’s quirks in all their glory.
For the family crew, the big Halloween parade on Halsted Street is your costume contest, creative chaos, and candy extravaganza all rolled into one. Word is, even pets in tutus are highly encouraged—no judgment, just cheers.
Night owls, the House of Blues has you covered with live blues and the Chicago Comedy Club tonight. Drop by for toe-tapping tunes and, who knows, an impromptu dance-off as the music seeps into your soul.
How about what’s new off the field? A few fresh tidbits got locals talking: The Chicago Architecture Biennial is dazzling with massive art installations tucked between beloved skyscrapers — the perfect reason for a spontaneous selfie marathon. Meanwhile, Green City Market is still serving up fresh local bites, so come hungry and leave with arms full of apples, pumpkins, and the best damn donuts this side of Lake Michigan.
Heads up on city logistics: With all the action downtown and Halloween crowds, public transit is your friend. The CTA’s ramping up service, especially along the Red and Blue lines, so ditch the car and ride the rails like a true Chicagoan.
Top must-do activities: Snap an iconic selfie at “The Bean” before the crowds descend, then skip the usual river cruise for a stroll through Jack’s Pumpkin Pop-Up—it’s a pumpkin patch, corn maze, and full-throttle autumn fairground smack in Goose Island. Or duck beneath the ghostly glow of ghost tours winding through River North’s hidden speakeasy bars. Feeling extra? Hunt for quirky murals in Pilsen—your Instagram will thank you.
Local tip for maximum cred: If someone invites you for an Italian beef, say yes, then order it “dipped”—because the sandwich is supposed to soak up so much juicy gravy you need two hands and a whole stack of napkins. Trust Oly: get messy and earn your Chicago stripes.
Coming up tomorrow, get ready for CreepAid 25 at the Copernicus Center and the city's spookiest dance parties lighting up the night. Spoiler: costumes are strongly encouraged, and glitter is practically mandatory.
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
Chicago’s current vibe is a glorious mashup of haunted hilarity and serious style. According to Mommy Poppins, trick-or-treating is officially on today, and the whole city is candy-fueled and sugar-hyped. Not to be outdone, Dia de Los Muertos festivities are lighting up neighborhoods like Wrigleyville and Marquette Park with vibrant altars and dance performances—colorful skulls and even livelier spirits.
Let me hit you with today’s top events, guaranteed to fit every interest from headbanging to hand-holding:
Playboi Carti’s Antagonist Tour explodes into the United Center tonight at 7 pm, with Ken Carson, Destroy Lonely, and Homixide Gang joining the chaos. If your ideal cardio is pogoing in a sea of hypebeasts, this show is your jam.
Culture seekers, the Chicago Writers' Bloc Fall Festival lands at City Lit Theater, starring a fresh crop of new plays and musicals by local masterminds—expect drama, laughs, and maybe a flying pie or two just for that classic twist, as reported by Travel and Tour World.
Art lovers, feast your eyes at the Norris University Center, where “Street: Photographs by Ann Kogen” offers a black-and-white time machine into the city’s most candid moments. From Chicago sidewalks to Cairo’s chaos, Ann Kogen’s snaps capture humanity’s quirks in all their glory.
For the family crew, the big Halloween parade on Halsted Street is your costume contest, creative chaos, and candy extravaganza all rolled into one. Word is, even pets in tutus are highly encouraged—no judgment, just cheers.
Night owls, the House of Blues has you covered with live blues and the Chicago Comedy Club tonight. Drop by for toe-tapping tunes and, who knows, an impromptu dance-off as the music seeps into your soul.
How about what’s new off the field? A few fresh tidbits got locals talking: The Chicago Architecture Biennial is dazzling with massive art installations tucked between beloved skyscrapers — the perfect reason for a spontaneous selfie marathon. Meanwhile, Green City Market is still serving up fresh local bites, so come hungry and leave with arms full of apples, pumpkins, and the best damn donuts this side of Lake Michigan.
Heads up on city logistics: With all the action downtown and Halloween crowds, public transit is your friend. The CTA’s ramping up service, especially along the Red and Blue lines, so ditch the car and ride the rails like a true Chicagoan.
Top must-do activities: Snap an iconic selfie at “The Bean” before the crowds descend, then skip the usual river cruise for a stroll through Jack’s Pumpkin Pop-Up—it’s a pumpkin patch, corn maze, and full-throttle autumn fairground smack in Goose Island. Or duck beneath the ghostly glow of ghost tours winding through River North’s hidden speakeasy bars. Feeling extra? Hunt for quirky murals in Pilsen—your Instagram will thank you.
Local tip for maximum cred: If someone invites you for an Italian beef, say yes, then order it “dipped”—because the sandwich is supposed to soak up so much juicy gravy you need two hands and a whole stack of napkins. Trust Oly: get messy and earn your Chicago stripes.
Coming up tomorrow, get ready for CreepAid 25 at the Copernicus Center and the city's spookiest dance parties lighting up the night. Spoiler: costumes are strongly encouraged, and glitter is practically mandatory.
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