09 January 2026
Chicago in Winter: Ice Skating, Music Fests, and Staying Warm Like a Local Champ
Chicago News and Information
About
Welcome, listeners, to Things to Do in Chicago for Friday, January 9, 2026. I’m your globe-trotting sports nut Oly Bennet, and today the Windy City feels like a chilly-but-game-day-ready locker room: cold temps, crisp air off the lake, and just enough winter sunshine to make you say, “Yeah, I can totally handle this… if there’s hot chocolate involved.”
Let’s kick off with today’s vibe. Indoor culture and outdoor ice are tag-teaming the city. Third Coast Review notes that ice skating at Millennium Park and Maggie Daley Park is running through the season, so expect bundled-up crowds carving wobbly figure eights while the skyline does its best stadium-light impression. Over at Gallagher Way, Winterland is rolling with public skating and themed nights all month, turning Wrigleyville into a full-on winter playground.
Now, today’s standout events. At the Ruth Page Center for the Arts, the morning started with Floor Balance with Paula Sousa, a dance-focused movement class that keeps the arts scene buzzing right in the Gold Coast, according to See Chicago Dance. Chicago Theater’s concert listings highlight shows across the city tonight, from rock to tribute bands, so if you’re craving live music, there’s almost certainly a stage with your name on it. Third Coast Review also spotlights Tomorrow Never Knows Festival kicking off this weekend across venues like Lincoln Hall, Schubas, Metro, and more—perfect if you want to brag later that you saw the next big band in a cozy room. And if you’re in a family mood, Garfield Park Conservatory is gearing up for its Winter Wonderland series this month, with bonfires, s’mores, and outdoor play sessions, as listed on the conservatory’s event calendar.
Sliding into local news and city buzz: Newcity reports that the Chicago Architecture Biennial has extended its exhibition at 840 North Michigan Avenue, so culture fans can still wander through “SHIFT: Architecture in Times of Radical Change” and warm up mentally while their toes thaw. On the food front, Crain’s Chicago Business, via Newcity, reports that 174 North Michigan near Millennium Park is being revived with at least three new restaurants, including Velvet Taco and a new Japanese spot called Genki—great news if you like your art and your tacos within walking distance of each other. And over on the cultural honors scoreboard, the City of Chicago has named Alexandra Del Valle the new Chicago Poet Laureate, as covered by Newcity, adding some serious spoken-word swagger to the local arts scene.
If you’re planning your perfect Chicago day, here are some must-do plays. Hit Millennium Park or Maggie Daley for ice skating, then stroll to the Loop for a warming food stop—soon you’ll even have those new Michigan Avenue restaurants to add to your rotation. Duck into the Chicago Architecture Biennial space on North Michigan for an inspiring, low-cost cultural break. For families, keep Garfield Park Conservatory on your radar this month for Winter Wonderland afternoons that combine nature, play, and necessary s’mores. And if nightlife calls, chase down a Tomorrow Never Knows show at Lincoln Hall or Schubas and let your ears do the sightseeing.
Local tip from your pal Oly: Chicago winter looks brutal, but locals dominate it by thinking in “indoor pit stops.” Plan your route like a relay—train or bus to an attraction, warm up in a coffee shop, sprint to the next spot. Also, on the CTA, if a train door looks packed, check the next car; often it’s way emptier, and you’ll look like a seasoned pro.
Before we wrap, a quick tease for tomorrow: Winterland at Gallagher Way will keep cranking out skating and festivities, Bill Murray & his Blood Brothers are set to hit Thalia Hall this weekend according to Third Coast Review, and more Tomorrow Never Knows sets will keep Chicago’s January music energy high. Tune in tomorrow for fresh picks, new openings, and more ways to conquer the city like a local MVP.
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 kick off with today’s vibe. Indoor culture and outdoor ice are tag-teaming the city. Third Coast Review notes that ice skating at Millennium Park and Maggie Daley Park is running through the season, so expect bundled-up crowds carving wobbly figure eights while the skyline does its best stadium-light impression. Over at Gallagher Way, Winterland is rolling with public skating and themed nights all month, turning Wrigleyville into a full-on winter playground.
Now, today’s standout events. At the Ruth Page Center for the Arts, the morning started with Floor Balance with Paula Sousa, a dance-focused movement class that keeps the arts scene buzzing right in the Gold Coast, according to See Chicago Dance. Chicago Theater’s concert listings highlight shows across the city tonight, from rock to tribute bands, so if you’re craving live music, there’s almost certainly a stage with your name on it. Third Coast Review also spotlights Tomorrow Never Knows Festival kicking off this weekend across venues like Lincoln Hall, Schubas, Metro, and more—perfect if you want to brag later that you saw the next big band in a cozy room. And if you’re in a family mood, Garfield Park Conservatory is gearing up for its Winter Wonderland series this month, with bonfires, s’mores, and outdoor play sessions, as listed on the conservatory’s event calendar.
Sliding into local news and city buzz: Newcity reports that the Chicago Architecture Biennial has extended its exhibition at 840 North Michigan Avenue, so culture fans can still wander through “SHIFT: Architecture in Times of Radical Change” and warm up mentally while their toes thaw. On the food front, Crain’s Chicago Business, via Newcity, reports that 174 North Michigan near Millennium Park is being revived with at least three new restaurants, including Velvet Taco and a new Japanese spot called Genki—great news if you like your art and your tacos within walking distance of each other. And over on the cultural honors scoreboard, the City of Chicago has named Alexandra Del Valle the new Chicago Poet Laureate, as covered by Newcity, adding some serious spoken-word swagger to the local arts scene.
If you’re planning your perfect Chicago day, here are some must-do plays. Hit Millennium Park or Maggie Daley for ice skating, then stroll to the Loop for a warming food stop—soon you’ll even have those new Michigan Avenue restaurants to add to your rotation. Duck into the Chicago Architecture Biennial space on North Michigan for an inspiring, low-cost cultural break. For families, keep Garfield Park Conservatory on your radar this month for Winter Wonderland afternoons that combine nature, play, and necessary s’mores. And if nightlife calls, chase down a Tomorrow Never Knows show at Lincoln Hall or Schubas and let your ears do the sightseeing.
Local tip from your pal Oly: Chicago winter looks brutal, but locals dominate it by thinking in “indoor pit stops.” Plan your route like a relay—train or bus to an attraction, warm up in a coffee shop, sprint to the next spot. Also, on the CTA, if a train door looks packed, check the next car; often it’s way emptier, and you’ll look like a seasoned pro.
Before we wrap, a quick tease for tomorrow: Winterland at Gallagher Way will keep cranking out skating and festivities, Bill Murray & his Blood Brothers are set to hit Thalia Hall this weekend according to Third Coast Review, and more Tomorrow Never Knows sets will keep Chicago’s January music energy high. Tune in tomorrow for fresh picks, new openings, and more ways to conquer the city like a local MVP.
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