Welcome, listeners, to Things to Do in Chicago! It’s Friday, November 21, 2025, and the city is buzzing louder than the vendors at Wrigley selling hot dogs. Oly Bennet here, your globe-trotting, sports-loving, quirky-comp-meter is dialed to max curiosity, ready for today’s Chicago adventure. Whether you’ve already braved the early chill or you’re just shaking off your morning hibernation, the city is a dazzling mash-up of holiday cheer and big-league energy.
Today, Chicago’s got that crispy, late fall edge—think brisk wind, steamy coffee, and the distant sound of skates gliding across Millennium Park. According to local news, the high’s sitting around the low 40s, so toss on a scarf and get your best “I’m-cool-but-still-cozy” outfit together. The holiday season kicks off tonight with the 112th Annual Christmas Tree Lighting Ceremony at Millennium Park at 6 PM. It’s one of Chicago’s heartwarming traditions, with families, friends, and overseas tourists gathering for a brilliant display of lights and communal merriment. The park’s also launching its free ice skating rink today. Just remember—reservations are required, and the only thing smoother than the ice might be your best skating fall, so lace up and join lessons sponsored by the McDonald’s Active Lifestyles Endowment. If you’re more into cozy crafts than chilly spins, the Millennium Park Holiday Market pops open today through December 23, featuring local artists selling everything from pottery to hand-drawn wonders, making it a must for gift-hunters and art-lovers alike.
Never fear, night owls and scene-stealers, the city’s got you covered. Sports fanatics, get hyped: The Chicago Bulls take on the Miami Heat at the United Center at 7 PM tonight. Expect slam dunks, buzzer beaters, and—if Chicago luck holds—an epic win to kick off your weekend.
For the creative, Bridgeport Art Center throws its “Faceted Fiber” exhibition opening tonight at 7 PM, while art spaces citywide host gallery crawls as part of the Third Friday Open Studios tradition. There’s live music and Golden Hour drink specials at Epiphany Center for the Arts, where downtown vibes meet free entertainment, local DJs, and half-priced wine. If you need another dose of spectacle, the House of Blues has concerts to satisfy every genre—check their calendar and claim your spot.
Family crews and festive spirits won’t want to skip Macy’s Holiday Celebration on State Street. According to Chicago on the Cheap, it’s a wonderland of window displays and holiday performances running through December 24, perfect for memory-making without freezing your toes off.
In the world of food, word on the street is that Humboldt Park’s boathouse café—courtesy of North Pond’s all-star crew—is scheduled for a revamp next year, and new menus are popping up across town. Transit-wise, updates are rolling out for parks on the South Side, and downtown construction means that some public transit routes might face minor reroutes. Savvy locals recommend keeping an eye on the CTA tracker and bundling up a little extra for those wait times.
Local tip—if you want to sound like a real Chicagoan, when someone asks if you want a hot dog, never, ever put ketchup on it. Mustard, relish, onions, tomatoes, maybe a pickle, but ketchup is the sporting equivalent of getting a yellow card at Soldier Field.
If you’re itching for tomorrow’s plans, keep your mittens ready: The Magnificent Mile Lights Festival is coming up Saturday, with parades and mile-long illumination turning downtown into a twinkling dream. Plus, hidden gems like neighborhood archery ranges and improv pop-ups promise more adventure, so be sure to tune in for tomorrow’s scoop.
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