Winter Dates for You and Your Chicago Lover
Winter is coming—strike that. This is Chicago, winter’s already here. As we Chicagoans know, when the snow starts to fall, that means it’s time to hunker down and hibernate. This shouldn’t stop us from having a love life, though; after all, below-zero temperatures give us a nice excuse to snuggle up to our dates. We’ve found the best winter-themed dates for you to enjoy this holiday season.

Ice skating at The Rink at Wrigley.

An outdoor activity in Chicago’s harshest winter? No, we’re not crazy. If you’re looking for something romantic (and what’s more romantic than holding hands), go for a crisp, outdoor skate at The Rink at Wrigley. During the winter months, the iconic baseball diamond closes and is replaced with an outdoor skating arena. Bundle up with your date and bring some (spiked) hot chocolate to enjoy while going for a few laps.

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Hot Chocolate Segway Tours of the Second City.

winter tour
Millennium Park

Chicago natives love the city in spite of the cold, even when it dips to -15 degrees. That may sound crazy to your friends who are looking to visit you over the holidays, but you can convince them to join you for some sightseeing adventures in the cold with this hot chocolate and segway tour. Bundle up and enjoy the beauty of Chicago with your out-of-town besties while devouring Chicago’s famous hot dogs and sipping on hot chocolate.

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Dashing through the snow in a horse-drawn carriage.

This classic Christmas carol actually offers some great winter date ideas; why not cozy up with your gf/bf in a horse-drawn carriage for two? Touring the city in style under a light dusting of snow makes for the perfect romantic evening. You and your partner can snuggle up under a blanket while seeing the best parts of your favorite neighborhoods. Make it a double date and bring another couple as the carriages can hold up to four adults.

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Hit the slopes!... or the park for some cross country skiing.

winter workout
winter running

The Midwest isn’t known for its mountain ranges, but fans of outdoor snow sports know something you don’t: Illinois parks are home to some pretty stellar cross-country ski trails. Geared for newbies, this class teaches you the ins and outs of skiing on all-natural terrain in a park about an hour outside the city. Prepare for a cardio workout and a wonderful escape from city life for the day.

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Robots need love too.


Add an extra spark to your love life during this robot building BYOB date night for couples. Choosing from 12 robot starter kits, you and your partner will work to build a simple circuit while watching your favorite robot movies in the background. Get inspired by the Omnibot 2000, who will also be your waiter for the evening, bringing you food and drinks. Wrap up the night with a quick round of robot movie trivia before heading home to see if those sparks will continue to fly.

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Whiskey walks for those windy winter weekends.


Afraid of freezing in Chi-town this season? When in doubt, DRINK. And drink with like-minded fans of your favorite hard liquor. For many in the River North area, whiskey is more than a drink of choice; it’s a lifestyle. On this walking tour, you’ll soak up as much whiskey as you can while munching on cheeses, meats and breads that pair perfectly with aged rye. If nothing else, the whiskey will keep both of you warm!

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Swing your partner round and round.

swing dancing
open event
dance class
live music

Swing into a world you never even knew existed when you sign up for First Friday Swing Dancing with your partner. After an introductory lesson, you and your partner will hit the dance floor to learn moves like the Lindy Hop and the Charleston, to name a few. If by the end you’ve picked up a little Friday Night Fever, stick around afterwards for an open floor dance party until midnight.

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Seasons may change but brunch never does.


Who doesn’t love second breakfast? Learn to bring the joy of brunch into your own home when the weather looks too dire by taking this all-levels brunch class. From Bloody Mary’s and mimosas, to fried chicken and waffles to a special brunch dessert, you’ll learn all the skills necessary to have an at-home, mid-morning feast.

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The couple who naps together, stays together.


Science says that couples who sleep close together are ultimately happier. We say an afternoon nap with your SO does the trick just as well! Perfect for a post-date activity and couples with strict no-sleepover policies, forget your noisy roommate and the construction outside your house and come for a mid-day siesta at Bottom Line Yoga. Conserve warmth this winter season by sleeping close together and take time out of your day to relax and enjoy being close to your partner.

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‘Game of Thongs’ a saucy, satirical burlesque.


When you play the Game of Thrones, you win or you die. When you play the ‘Game of Thongs’ in this Game of Thrones-themed burlesque show, you’ll think you’ve died and gone to heaven. In the mythical world of ‘Breasteros’ (sorry, not sorry), you’ll follow the exploits of Ned Stark, Tyrion Lannister and Jon Snow through musical numbers, gags, jokes and more. Let your evening heat up with this racy and humorous performance that both you and your date are sure to enjoy.

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Stand up for stand up trivia.


Jeopardy fans, drinking fans, pub fans and trivia fans alike flock to the WIP Theater for stand up trivia night. In this weekly event, you and your friends form teams to compete in a comical version of a traditional pub trivia game. Get competitive, order some drinks and see if you and your guy or girl make a great team.

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Take advantage of Chicago’s museum scene

One of the perks of winter is staying inside as much as possible by a toasty fire, but you can only look at the same walls in your apartment for so long. Luckily for you and the bf/gf, you have access to all of Chicago’s top museums and galleries. Take a trip to Millennium Park and you can decide spur-of-the-moment style to go to the Field Museum, the Art Institute of Chicago, the Adler Planetarium or the Chicago Children’s Museum, to name a few.