Start your date off on an adorable note with puppy yoga at Puppysphere. This unique experience lets you practice your downward dog alongside frolicking puppies in a heated room. After working up an appetite, enjoy a bubbly drink or non-alcoholic alternative. It's the perfect way to bond with your date while getting your cuteness fix.

Find your tickets on Puppysphere’s website, here !

Lace up your skates and hit the ice ribbon at Maggie Daley Park . This winding skating path offers stunning skyline views as you glide hand-in-hand with your date. Warm up with hot cocoa from the on-site cafe or explore the park's other winter attractions like the 40-foot climbing wall.

Step into a traditional German holiday market in the heart of the Loop. Christkindlmarket  is a charming maze of wooden stalls selling handmade gifts, tasty treats, and spiced glühwein. Sip from a commemorative mug as you browse the festive wares and soak up the merry atmosphere with your date.

Head to Wrigleyville for the immersive Chimes light and art display at Gallagher Way. This free event features a glowing, musical LED installation that responds to touch and movement. Grab dinner at Hotel Zachary  and drinks at Mordecai  before exploring the luminous, interactive show.

For a sultry, sophisticated night out, catch a live jazz show at the historic Green Mill  in Uptown. This 1940s-era lounge hosted famous acts like Billie Holiday and Al Capone back in the day. Sip classic cocktails, admire the vintage decor, and enjoy world-class music with your date in this intimate, atmospheric club.

Spark your playful side at the wacky WNDR Museum . This immersive art space is filled with colorful, innovative installations that are perfect for quirky photo ops with your date. Highlights include the Infinity Mirror Room, a ceiling dripping with disco balls, and the infamous selfie-ready neon "Let's Get Pizza" marquee sign.

Challenge your date to friendly competition at the Chicago Athletic Association Game Room . Set on the second floor of the historic hotel, this swanky playground boasts bocce, shuffleboard, billiards, chess, and checkers tables. Order shareable snacks and clever cocktails as you play to your heart's content.

See the Lincoln Park Zoo in a dazzling new light at the annual ZooLights event . This free display illuminates the grounds with 2.5 million twinkling LED lights and dynamic light shows set to music. Sip spiced wine and nibble on snacks from the holiday market as you stroll through the luminous exhibits. For an extra special touch, reserve a spot at the exclusive Adults Night Out evenings.

Cap off your wintery weekend with a leisurely brunch at Lula Cafe  in Logan Square. This farm-to-table favorite offers a seasonal, locally-sourced menu in a charming, laid-back setting. Split savory dishes like the Yucatan Eggs and Masa Hotcakes or go sweet with Brioche French Toast. Customize your own breakfast cocktail at the Bloody Mary Bar for the perfect personalized toast to your weekend together.