Romantic Winter Date Ideas in Chicago: Our Top 5 Picks

By Kiersten Weed

Photo Credit: @waywelling on Instagram

Activities to Battle the Chicago Winter Blues

We know that the winter months can be tough - freezing temperatures, dark at 4:30pm, and little to no desire to go outside. However, with the right motivation and ideas, winter can be a lot of fun! The snow and twinkle lights provide a cozy ambiance for the perfect date night. 

Below, we’ve compiled some of our favorite date ideas around the windy city.

Sunset Walk at North Avenue Beach

*Cue Snow On the Beach by Taylor Swift*

What’s more romantic than a dreamy snowy landscape, warm mittens, and strolling the beach with your special someone? Take advantage of the off-season and visit North Avenue Beach for a scenic spot with minimal crowds. Make it extra special and time your walk around sunset. Finish the evening with dinner at 3 Arts Club Cafe at RH Chicago. With an extensive wine collection and gorgeous decor, it has the marks for a memorable experience.


Photo Credit: Brian Cassella - Chicago Tribune

Ice Skating at McCormick Tribune Ice Rink

This one is for our sporty couples - nothing screams winter more than ice skating. Located in Millennium Park, you can reserve a time slot for you and your partner to skate for 90 minutes. They have free sessions if you bring your own skates, or rentals for as low as $17 depending on the time of your visit.

Don’t know how to skate? They also have free ice skating lessons you can take! Pair the date with a warm hot chocolate from Ghirardelli and you have the recipe for a perfect day.

Photo Credit: Choose Chicago

Try on Wedding Bands or Engagement Rings at Hitched

Looking to get engaged or are in your bridal era? Schedule your wedding band or engagement ring consultation at Hitched in Bucktown to try on our large variety of styles. Our showroom is bistro-esque, with complimentary prosecco, and our appointments include 1:1 dedicated time with one of our Sales Associates. Celebrate the milestone purchase with drinks at Truce, or dinner at Antico to round off the night!

Spend the Evening at Emporium Arcade Bar

Who doesn’t love an arcade? With three different Emporium Chicago locations in Fulton Market, Logan Square, and Wicker Park, it makes finding a location close to you easy. They have a variety of vintage arcade games, along with live music several times a month. You can also bring your own food, so we recommend grabbing takeout nearby and settling in for a competitive game night you’ll remember.

Photo Credit: Emporium Arcade Bar

Attend a Chicago Blackhawks Hockey Game

Even if you aren’t the biggest sport fanatic, in person hockey games are fast-paced, high impact, and highly entertaining. They make a great choice for date night - you get to bundle up, eat your favorite snacks, and celebrate for your home team. Pro-tip: tickets during week nights tend to be cheaper, so it’s a great option for getting out during the work week.

Date Nights in Chicago

Whether you want to stay inside or get outdoors, there are a variety of different activities to keep you busy during the cold months in the city. Get creative and make the most of the chilly season!

Looking to get engaged? Learn more about Hitched engagement rings on our custom engagement ring page.