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Wintry Wonders in the Windy City - Family Fun, Big Shows, and Authentic Eats
Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned city explorer, buzzing with energy on this crisp winter Saturday, December 27, 2025. Chicago's vibe is pure post-holiday magic—think chilly winds whipping off Lake Michigan around 30 degrees Fahrenheit, snow-dusted streets glowing with leftover lights, and that electric hum of folks shaking off Christmas into New Year's prep.
Kick off your day with family fun at Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall. Glide on the ice rink, conquer the Cliffhanger ride, bounce on slides, and snag a Centennial Ferris Wheel spin with epic skyline views—perfect for kids under 46 inches limited to 10 rides. Catch the acrobatic wonder of 'Twas the Night Before by Cirque du Soleil at The Chicago Theatre, with shows at 1 PM, 4 PM, and 7 PM; it's an 80-minute father-daughter holiday adventure come alive with reindeer and snowstorms. Sports fans, rev up for AEW Worlds End wrestling extravaganza at 6 PM CT in Hoffman Estates' NOW Arena—pay-per-view body slams and KultureCity sensory support included. Music lovers, sway to Candlelight: Tribute to Taylor Swift at 8:45 PM in the intimate Stan Mansion, candles flickering through Swiftie hits. Cap the night with live blues at House of Blues starting at 5 PM in the Restaurant and Bar.
Local buzz: Christkindlmarket's winding down with free holiday tunes if you're near Daley Plaza, and Navy Pier's gearing up for massive New Year's Eve fireworks and parties—book parking early via SpotHero. CTA's hinting at free late-night rides soon for revelers.
Must-dos today: Bundle up for WonderFest thrills, then hidden gem-hop to the free 360 CHICAGO Observation Deck for panoramic chills. Local tip: Chicagoans swear by Giordano's deep-dish after dark—order "stuffed" style and split it, true Windy City style, since one slice packs a pizza punch.
Tomorrow, Sunday shows of Cirque du Soleil wrap the run—don't miss! Tune in for more epic discoveries.
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
Kick off your day with family fun at Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall. Glide on the ice rink, conquer the Cliffhanger ride, bounce on slides, and snag a Centennial Ferris Wheel spin with epic skyline views—perfect for kids under 46 inches limited to 10 rides. Catch the acrobatic wonder of 'Twas the Night Before by Cirque du Soleil at The Chicago Theatre, with shows at 1 PM, 4 PM, and 7 PM; it's an 80-minute father-daughter holiday adventure come alive with reindeer and snowstorms. Sports fans, rev up for AEW Worlds End wrestling extravaganza at 6 PM CT in Hoffman Estates' NOW Arena—pay-per-view body slams and KultureCity sensory support included. Music lovers, sway to Candlelight: Tribute to Taylor Swift at 8:45 PM in the intimate Stan Mansion, candles flickering through Swiftie hits. Cap the night with live blues at House of Blues starting at 5 PM in the Restaurant and Bar.
Local buzz: Christkindlmarket's winding down with free holiday tunes if you're near Daley Plaza, and Navy Pier's gearing up for massive New Year's Eve fireworks and parties—book parking early via SpotHero. CTA's hinting at free late-night rides soon for revelers.
Must-dos today: Bundle up for WonderFest thrills, then hidden gem-hop to the free 360 CHICAGO Observation Deck for panoramic chills. Local tip: Chicagoans swear by Giordano's deep-dish after dark—order "stuffed" style and split it, true Windy City style, since one slice packs a pizza punch.
Tomorrow, Sunday shows of Cirque du Soleil wrap the run—don't miss! Tune in for more epic discoveries.
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 to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned city explorer, buzzing with energy on this crisp winter Saturday, December 27, 2025. Chicago's vibe is pure post-holiday magic—think chilly winds whipping off Lake Michigan around 30 degrees Fahrenheit, snow-dusted streets glowing with leftover lights, and that electric hum of folks shaking off Christmas into New Year's prep.
Kick off your day with family fun at Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall. Glide on the ice rink, conquer the Cliffhanger ride, bounce on slides, and snag a Centennial Ferris Wheel spin with epic skyline views—perfect for kids under 46 inches limited to 10 rides. Catch the acrobatic wonder of 'Twas the Night Before by Cirque du Soleil at The Chicago Theatre, with shows at 1 PM, 4 PM, and 7 PM; it's an 80-minute father-daughter holiday adventure come alive with reindeer and snowstorms. Sports fans, rev up for AEW Worlds End wrestling extravaganza at 6 PM CT in Hoffman Estates' NOW Arena—pay-per-view body slams and KultureCity sensory support included. Music lovers, sway to Candlelight: Tribute to Taylor Swift at 8:45 PM in the intimate Stan Mansion, candles flickering through Swiftie hits. Cap the night with live blues at House of Blues starting at 5 PM in the Restaurant and Bar.
Local buzz: Christkindlmarket's winding down with free holiday tunes if you're near Daley Plaza, and Navy Pier's gearing up for massive New Year's Eve fireworks and parties—book parking early via SpotHero. CTA's hinting at free late-night rides soon for revelers.
Must-dos today: Bundle up for WonderFest thrills, then hidden gem-hop to the free 360 CHICAGO Observation Deck for panoramic chills. Local tip: Chicagoans swear by Giordano's deep-dish after dark—order "stuffed" style and split it, true Windy City style, since one slice packs a pizza punch.
Tomorrow, Sunday shows of Cirque du Soleil wrap the run—don't miss! Tune in for more epic discoveries.
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
Kick off your day with family fun at Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall. Glide on the ice rink, conquer the Cliffhanger ride, bounce on slides, and snag a Centennial Ferris Wheel spin with epic skyline views—perfect for kids under 46 inches limited to 10 rides. Catch the acrobatic wonder of 'Twas the Night Before by Cirque du Soleil at The Chicago Theatre, with shows at 1 PM, 4 PM, and 7 PM; it's an 80-minute father-daughter holiday adventure come alive with reindeer and snowstorms. Sports fans, rev up for AEW Worlds End wrestling extravaganza at 6 PM CT in Hoffman Estates' NOW Arena—pay-per-view body slams and KultureCity sensory support included. Music lovers, sway to Candlelight: Tribute to Taylor Swift at 8:45 PM in the intimate Stan Mansion, candles flickering through Swiftie hits. Cap the night with live blues at House of Blues starting at 5 PM in the Restaurant and Bar.
Local buzz: Christkindlmarket's winding down with free holiday tunes if you're near Daley Plaza, and Navy Pier's gearing up for massive New Year's Eve fireworks and parties—book parking early via SpotHero. CTA's hinting at free late-night rides soon for revelers.
Must-dos today: Bundle up for WonderFest thrills, then hidden gem-hop to the free 360 CHICAGO Observation Deck for panoramic chills. Local tip: Chicagoans swear by Giordano's deep-dish after dark—order "stuffed" style and split it, true Windy City style, since one slice packs a pizza punch.
Tomorrow, Sunday shows of Cirque du Soleil wrap the run—don't miss! Tune in for more epic discoveries.
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