Welcome to Things to Do in Chicago! I’m your tour guide of tomfoolery, Oly Bennet—your globetrotting sportster dropping in on the Windy City for a mashup of marvels, music, and moxie. Today is Sunday, November 16, 2025, and let’s just say the city’s in full pre-Thanksgiving swing, bursting with energy as crisp as the autumn air. The weather’s toggling between “bring a jacket” brisk and “no, seriously, winter is coming,” but Chicagoans don’t slow for a little cold—they rev up!

Now, what’s shaking around town? The Chicago Artisan Market in Fulton Market is whirling open its doors at 11 am, so warm up your shopping muscles and get ready for handmade wares, gourmet treats, and crafty finds galore. It’s practically Olympic-level browsing—who needs the mall when you can strut among local legends? If you’ve ever wanted to witness the intersection of art and identity, the Magic of Light show wraps up at the Wirtz Center, shining a beacon on creative spirit with Yara Arts Group’s visually lush performance at 2 pm. Museum-level drama, but with more jazz hands. For those who need culture with a splash of mystery, try The Dinner Detective True Crime Murder Mystery Dinner Show at Courtyard by Marriott in the downtown Magnificent Mile at 6 pm. Pit your wits against some criminally good actors—don’t forget to order something suspicious from the bar.

Let’s talk tunes! Slide over to Kingston Mines around 5:30 pm for Chicago’s homegrown blues—nothing shouts “Sunday night” like stomping your feet with fellow music lovers. If your stride’s more slow-and-steady and less “lightning on the dance floor,” then get contemplative with “Street: Photographs by Ann Kogen” running all day at Norris University Center in Evanston. It’s street photography meets emotional sledgehammer; bring a friend for maximum analysis.

Parents and kids—listen up! The Chicago Kids calendar spins up workshops and outdoor fun, perfect for burning off post-brunch chocolate chip pancakes. So whether you’re wrangling little athletes or future Nobel laureates, there’s always something to ignite their city spirit.

For the night owls and insomniacs, don’t tiptoe out until you hit The Shawshank Redemption: Laugh-Along, Live! at Stars & Garters near midnight. Imagine snark meets classic cinema—yes, you can laugh where Morgan Freeman pondered hope.

Switching over to local buzz, new flights have landed at O’Hare to Punta Cana via Arajet. If you’ve got an irrepressible urge to swap lake effect snow for sand, start plotting! And bat an eye at restaurant news—Randolph Street’s Holiday Market tempts with pop-up vendors and next-level snacking, just in time for holiday prep. CTA trains are running on regular schedules; no major delays, so you can zigzag across the city with minimal grumbling and maximum sightseeing.

For must-do moments: Stroll the Riverwalk’s mosaic murals, beam at Cloud Gate (aka “The Bean”) in Millennium Park, and if you’ve never devoured a proper Italian beef, the Albert hosts Nights of Little Italy reflecting the golden age of Italian American cuisine from 5 pm. Insider tip: Locals never order deep-dish pizza with a knife and fork. Fold that cheesy wedge in half like it’s a winning lottery ticket and wear your tomato stains with pride.

Did you know Chicago invented the “street lamp timer” in the early 20th century? That’s right—before everyone’s porch got fancy, we were timing the very glow that defines the city’s nightlife.

Before you dash off, tomorrow’s calendar teases FREE tours at the Chicago Cultural Center and grooving live music coming up at Epiphany Center for the Arts. And we’re only warming up. Tune in again for the freshest scoop—from secret speakeasy bingo nights to next-level family science fairs.

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