Winter Lights & Date Night Ideas In Downtown Chicago (2025)

Winter Lights & Date Night Ideas in Downtown Chicago (2025)

Table of Contents

1. A Quarter-Mile of Ice Skating: The Ice Ribbon

The Maggie Daley Park Ice Ribbon has been compared to a Mario Kart track or a lazy river at a tropical resort, however, this quarter-mile-long, 20-foot-wide ribbon is purely for ice skating against the gorgeous backdrop of Chicago’s skyline. The sloped loop, located in the heart of downtown Chicago, is unlike any other rink in the city. Complementing the ribbon are places to enjoy a cup of hot chocolate, rent skates, and scale the climbing wall. The only downside? It can hold up to 700 skaters at any given time, meaning the lines can be painfully long. However, a $40 Fast Pass allows you to skip the skate rental line and includes skates and locker for one person.
Where: Maggie Daley Park, 337 E. Randolph St, Chicago, IL 60601
Season: Open now until January 12, 2025 10am-10pm
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The Maggie Daley Park Ice Ribbon Chicago

2. Christkindlmarket In The Daley Plaza

The Daley Plaza, located in the Chicago Loop, is home to Christkindlmarket. Stroll down the sidewalk of this German-themed market and you will find yourself in a fairytale. The market is dotted with vendors and their red and white striped awnings draped with displays of Christmas lights. Visit the Bavarian Pewter and find speciality holiday ornaments from Munich, Germany. Then head over and try the original Sternthaler Glühwein from Nuremberg, Germany (hot spiced wine) and a savory strudel.
Where: Daley Plaza, 50 W Washington Street, Chicago, IL 60602
Season: Open now until December 24, 2025
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Christkindlmarket In The Daley Plaza Chicago

3. Lincoln Park Zoo Lights

ZooLights at Lincoln Park Zoo has been Chicago’s holiday tradition for 24 years. This one-of-a-kind experience offers holiday celebrations that feature luminous displays and incredible seasonal activities…all under the glow of 2.5 million lights!
Where: Lincoln Park Zoo, 2001 N Clark St, Chicago, IL 60614
Season: Open now until January 5, 2025 4:30pm-9pm
Free admission – no ticket necessary!
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Lincoln Park Zoo Lights Chicago

4. Ice Skating in Millennium Park

Maybe it’s just us, but we think ice skating is damn romantic (we blame John Cusack in Serendipity). And in particular, ice skating in the McCormick Tribune Ice Rink in Millennium Park is damn romantic. You have views of the Chicago skyline and the Chicago Christmas Tree. Admission is free and you can rent skates for $13-$15. Similar to the Ice Ribbon, lines can get painfully long, so show up early.
Where: 201 E Randolph St, Chicago, IL 60602
Season: Open now until March 8, 2025
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5. Make Mulled Wine or Hot Toddies

Feel like avoiding the crowds and staying inside the comfort of your home? We have something for that too. There’s nothing better than a warm cup of mulled wine or a hot toddy when cool weather hits. This is a great second (or third or fourth!) date option when you want to get to know your date better. Trying a new recipe with your date is a great way to learn a skill together which enriches your bond and gives you lots to talk about. Check out Jamie Oliver’s famous mulled wine recipe, or this delicious Hot Toddy recipe from Epicurious.