While the winter months can be dreary, dark, and icy, there are some things to look forward to. Let us introduce you to a decades-old unapproved theory that someone feels true—cuffing season! Yes, it’s about to be a bleak few months, but it’s the quintessential time to grab drinks by a fireplace, dip skewers in a creamy fondue, or skate on the ribbon at Millennium Park. So, here are the best winter date ideas in Chicago.
1. Escape the city for a winter getaway
Located an hour north of Chicago at the Illinois-Wisconsin border, it awaits a landscape of rolling hills and immaculate views. This is the perfect winter getaway to explore some of the best slopes in the Midwest or the magical Winter Realm with your date. This open-air experience allows you to explore ice volcanoes, igloos, tubing activities, mesmerizing ice sculptures, ice slides, and ice thrones.
2. Go ice skating
Maggie Daley Park’s quarter-mile skating ribbon is one of Chicago’s most famous ice rinks, offering the chance to glide and glimmer a 40-foot climbing wall in the heart of Chicago.
The rink curves up and down around pine trees, with the city’s stunning skyline providing a stunning backdrop—it’s the perfect place to skate hand in hand with a date.
3. Be amazed by the Nutcracker
Dress up and take your date to the Joffrey Ballet’s critically acclaimed reimagined classic, The Nutcracker. Lead Tony Award®-winning choreographer Christopher Wheeldon returns to celebrate the magic of the holiday season—one of the most coveted Chicago Christmas shows.
4. Explore a holiday market
During winter, annual traditions like Christkindlmarkt become our shining lights in times of darkness, early nightfall, and chilly temperatures. If you’re looking for winter date ideas in Chicago to blank out the notorious winter sweeping through the city, the festive market counters it with jubilance and cheer.
5. Go on a blind-taste dinner
Calling all foodie couples! Try out Dining in the Dark, a unique blindfolded dinner experience where you can let your tastebuds go wild! Choose from meat, seafood, or vegan menus and dive into a secret 3-course feast designed to tantalize your senses. By being blindfolded, you’ll be able to take in aromas and textures like never before and take on this awesome sensual journey!
6. Snuggle on top of a winter rooftop bar
While Chicago is home to an array of astounding rooftops, few offer 360-degree views of the city. Up at The Kennedy Rooftop, however, you will have front-row seats to the Chicago skyline. With indoor and outdoor seating, a glass retractable roof, and floor-to-ceiling windows, plenty of options exist to sit and enjoy the scintillating views— it’s a stunning winter spectacle.
7. Experience the magic of a Tchaikovsky classic like never before at ‘We Call It Ballet’
‘We Call It Ballet’ puts a dazzling spin on an iconic ballet in Chicago. Dressed head-to-toe in glow-in-the-dark costumes, ballerinas twist and twirl to the sounds of Tchaikovsky’s timeless Sleeping Beauty, literally lighting up the stage as they go. The colors of their ensembles change depending on the tone of each scene and a narrator guides audiences through the famous tale of the cursed princess. It’s the ideal spectacle to warm the soul during the wintertime, and you don’t want to miss out.
8. Jam out to live music
Chicago has some of the most exquisite spaces to listen to live music on a date. Whether you’re heading to the iconic Metro for your favorite artist or the Bassment for a night of blues, a concert is one of Chicago’s essential winter date ideas.
9. Sip and Neon Brush
If you are more of an artistic couple, now you can experience a different painting workshop where classic meets fluorescent! An artist will guide you through creating your masterpiece, all while enjoying drinks available for purchase. Join the fun in a retro-futuristic ambiance with black lights and groovy tunes. And you can leave with your glowing creation to proudly display at home!
10. Warm up with a fondue dinner
As winter date ideas in Chicago, Geja’s Cafe will be a meal to remember. From dipping grapes, apples, vegetables, and assorted pieces of bread into a creamy Gruyere to cooking various types of meat, seafood, and assorted vegetables to your desire and then creating that perfect bite with one of our eight house-made sauces, to roasting marshmallows over a flamed pot of Belgium chocolate and dunking various types of fruits, pound cake, and rice Krispy treats.
11. Drinks and a comedy show
One of the more intimate Chicago comedy clubs, Zanies is a decades-old comedy club for comedians starting their careers. It’s the perfect place to take your date if you’re trying to giggle while slowly becoming inebriated with the endless flow of drinks.