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.
1. ROMANTIC COUPLE: SNUGGLE UP IN A HORSE DRAWN CARRIAGE
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.
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.
2. SPORTY COUPLE: SKATE at MILLENNIUM PARK, HAND HOLDING REQUIRED
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.
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!
3. FOODIE COUPLE: A TOUR FOR LOVERS WHO ARE CHOCOLATE LOVERS
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.
4. ARTSY COUPLE: GET NAUGHTY AT the ART INSTITUTE of CHICAGO
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.”
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:
- Chicago Attractions With a View – Seeing the City from Up High
- See all of our Hilton hotels in Chicago
Hilton Mom Voyage writers receive free night certificates to use at Hilton Hotels & Resorts worldwide. To learn more, visit our About Us page.
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.