4 Great Ways to Celebrate Valentine’s Day in Chicago

I love Chicago, but truth be told, our city can get a bit dreary in February when the glamour of the holidays and the anticipation of the new year are long over. And though spring offers many exciting things to do when warmer and sunnier weather arrives, it is still far from reality. Luckily, to help brighten things up until then, there is Valentine’s Day in February.

Whether you are a romantic, sporty, foodie or an artsy couple, here are a few simple, but fun suggestions on how to spend Valentine’s Day in Chicago, in case you are still looking for ideas. Feel free to mix and match.

The romantic in me often falls for the classics. A cozy ride under a blanket through Chicago’s Gold Coast or some other customized route definitely counts as one. And while I’m normally ready for spring by mid-February, this is one occasion when snowflakes make things even better.

There are a number of different companies to choose from. Carriage Booking, for example, will pick you up at your hotel with not only a horse and a beautiful carriage, but also flowers and chocolate covered strawberries waiting.

Valentines Day Chicago - Carriage ride
Looking for a classic romantic option? A horse drawn carriage ride definitely qualifies! (Photo courtesy of Carriage Booking)

Kick it up a notch: After your ride, head over to the John Hancock building and take the elevator to the 96th floor Signature Lounge. Have a cocktail or a glass of champagne at one of the highest bars in the world and one of the city’s most unique venues while you watch the sun set over Chicago.

Are the two of you both active types? Because it’s still cold this time of year, ice-skating at Millennium Park can be a perfect choice. Glide smoothly holding hands or compete in who can skate the fastest lap, it’s totally up to you. Just don’t forget to take a Valentine’s Day selfie at the famous Bean sculpture that’s close by.

Valentines Day Chicago - Ice skating Millennium Park
Skating at the McCormick Tribune Ice Rink in Chicago is a perfect Valentine’s Day activity for a couple who likes to move.

Kick it up a notch: To double the action, get an Uber and head over to Duet Dance Studio in Wicker Park. Attend their Valentine’s Day Dirty Dance Party, a beginner salsa class where you will also learn a simplified “Dirty Dancing routine,” followed by open dancing, hors d’eouvres and BYOB. Sign up soon, it’s filling up fast!

You simply can’t celebrate Valentine’s Day without chocolate! A Chocolate Tour of Chicago will have you trying some of the city’s best desserts with several different tasting stops. Enjoy chocolate infused samples such as donuts, cupcakes, chocolate drinks and, of course, truffles.

Kick it up a notch: Head south on Michigan Avenue to Cindy’s Rooftop, one of the hottest newcomers to the Chicago dining scene. Besides the food, described as “classic comfort combined with culinary invention,” this restaurant’s main allure is the open-air terrace with fantastic views overlooking Millennium Park. This time of year, the romantic fire pits are where you will want to hang out with that special someone, either before or after your dinner.

Here is a fresh and slightly naughty idea for enjoying the Art Institute of Chicago: view its most famous nudes and learn about art history along the way by signing up for the Naked at the Art Museum scavenger hunt offered by Watson Adventures. The company promises “no previous experience with art or nudity is required.”

Chicago Valentines Day - Art Institute of Chicago
Imagine you’re strolling down the streets of Paris with your sweetie and take in other romantic pieces at the Art Institute of Chicago this Valentine’s Day.

Kick it up a notch: Looking for more artsy options? You’re in luck! Chicago Theater Week, a celebration of Chicago’s world class theater scene, now in its 4th year, runs from February 11 through 21, offering more than 100 productions at special discounted prices. Go for one of the classic venues such as the Lyric Opera, Steppenwolf or the Goodman Theater or try something different like an improvised parody of The Bachelor at the Under the Gun Theater.

You may also enjoy:

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Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.

Ice skating at Millennium Park photo by Hourann Bosci / CC BY-SA 2.0

Art Institute of Chicago photo by Phil Roeder / CC BY 2.0

This post was written by Hilton Suggests Team Member, Vera H. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

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