Welcome, listeners, to Things to Do in Chicago with your globe-trotting sports nut pal, Oly Bennet! It’s Sunday, December 28, 2025, and the Windy City is in full cozy-winter-hustle mode: chilly temps, holiday lights still glowing, and just enough lakefront breeze to make you question your life choices if you forgot a scarf.

Let’s fire off today’s vibe check. Downtown, The Chicago Theatre is wrapping up its run of ’Twas the Night Before… by Cirque du Soleil, with performances this afternoon at 1 and 4 p.m., turning 175 North State into a flying-reindeer-meets-elite-acrobatics playground, according to The Chicago Theatre’s event listing. Over at Cadillac Palace, Ticketmaster shows The Phantom of the Opera hitting the stage at 1 p.m., so if you like your Sunday drama with masks, chandeliers, and big notes, that’s your matinee. Hockey fans, the United Center is your cathedral tonight: the Chicago Blackhawks face the Pittsburgh Penguins at 6 p.m., with gates opening at 4:30, per the United Center’s schedule. Navy Pier is in full festive mode too; Navy Pier’s own calendar has the Winter WonderFest Artisan Market running from noon today, packed with local makers, artists, and one-of-a-kind gifts. And for a soulful Sunday, House of Blues Chicago is hosting its World Famous Gospel Brunch today, as listed on the House of Blues Chicago shows page—live music, big flavors, and bigger vibes.

Now, a few local tidbits to keep you in the loop. The United Center notes that CTA Blue, Green, and Pink Lines all drop you within a short walk of the arena, and buses like the 20 Madison and 19 United Center Express are clutch for game nights, so this is a great evening to skip the parking hunt and ride like a local. Navy Pier highlights that its Winter WonderFest market is part of a broader push to support Chicago small businesses, giving emerging makers a platform, so your last-minute holiday-season shopping is basically civic pride with glitter.

If you’re planning your perfect Chicago Sunday, here’s Oly’s game plan. Start at Millennium Park for an icy lap around the skating ribbon at Maggie Daley Park, then wander to State Street for lunch and slide into that Cirque du Soleil matinee. After the show, jump on the Red Line to Lake or Monroe, connect over toward the West Side, and head to the United Center for Blackhawks–Penguins under the lights. Not feeling the sports chaos? Hit Navy Pier instead: stroll the Winter WonderFest Artisan Market, then warm up with a ride on the Centennial Wheel for skyline views that absolutely slap in winter air.

Local tip from your roaming sports weirdo: Chicago’s wind isn’t usually strongest by the lake—it’s the skyscraper wind tunnels downtown that’ll smack your hat into orbit. Walk a block off the big streets like Michigan or State if the gusts get wild; it’s like discovering a secret “easy mode” for the Loop.

Tomorrow, keep your ears open for more holiday-week happenings, from lingering winter markets to comedy shows and maybe a sneaky live music gem to close out the year. Tune in next time as we dive into more Chicago magic, one quirky adventure at a time.

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