With the weekends affording many of us time to take a break from our work lives, we must fill them with memories. Whether exploring the parks, spending valuable time with friends and family, or enjoying an event somewhere in Chicago, weekends are designed to be enjoyed!
Luckily, in a city as sensational as Chicago, options are abundant. To help you make the most of your weekend, we’ve rounded up the best things to do in Chicago from January 9th to January 10th.
Visit The Forbidden Forest Experience
If you’re hoping a little enchantment will come your way this winter, it’s closer than you think. A shadowy trail, a hint of wonder, and somewhere deep in the woods, you may run into a glowing stag. Warm up with Butterbeer or hot cocoa under twinkling lights as you explore the magical forest.
Indoor Farmers Market at Water Tower Place
The indoor farmers market at Water Tower Place is back! It will open on Sunday, January 11, and run weekly through March 29. The market will be held from noon to 4 p.m. Admission is free, and the market features over 75 vendors, live entertainment, and family-friendly activities.
Visit the Largest Design Event in North America
You have only one month left to explore the future of architecture at the 10th annual Chicago Architecture Biennial, the largest architecture and design exhibition in North America.
This year’s theme is “Shift: Architecture in Times of Radical Change.” It features projects from architects, artists, and designers from 30 countries, all addressing the question: How does architecture impact our world, and how can it inspire us to imagine new possibilities?
Head to the Bears Playoff Watch Party
Recess is throwing a Bears playoff watch party, and trust us, it’s better than paying for those playoff ticket prices. The watch party will feature drink specials, including an 88 oz beer tower, shot skis, Bears jello shots, a Malort cocktail, delicious tailgate bites, and a variety of life-sized games!
Decompress at a Winter Wellness event
Kick off 2026 at Timeout Chicago with a series of wellness events designed to help you decompress and find mindful movement.
11 AM | Pilates Sculpt with Laken Browning ($55): Finish the morning strong with a live DJ Pilates Sculpt class with Lane Browning. The class includes a small gift and $15 Time Out Market gift card to enjoy after class.
9 AM | Yoga & Sound Bath with The Space Between ($55): Kick off the morning with a transformative live DJ Yoga + Sound Bath experience led by The Space Between. The class includes a Palo Santo gift and a $15 Time Out Market gift card to enjoy after class.
10 AM | Pilates Fusion with Jordan Hana ($55): Get your blood pumping with an intentional live DJ Pilates Fusion class led by Jordan Hana. The class includes a pair of Pilates Socks from Pilates University and a $15 Time Out Market gift card to enjoy after class.
Bears–themed pregame celebration at the Brookfield Zoo Chicago
The playoffs are here, and Brookfield Zoo in Chicago is ready for kickoff! This Saturday, January 10, guests are invited to a free Chicago Bears-themed pregame celebration ahead of the Wild Card showdown, from 10 a.m. to 2 p.m.
Free admission day: Guests are encouraged to wear their favorite fan gear and explore the zoo.
Free stickers will be given to the first 1,000 guests through the gates.
Enjoy game-day decor and a soundtrack featuring “Super Bowl Shuffle,” “Bear Down,” and other football-inspired hype songs throughout the park.
“Grill Out” specials at Wild Burger—come hungry and enjoy delicious food from 11 a.m. to 2 p.m.
Animal adoptions for brown bears Tim and Jess are available for $18 in honor of quarterback Caleb Williams.