Love it or loathe it, one thing’s for sure — Valentine’s Day can be a bit stressful. Between picking the ideal dinner venue to choosing the perfect gift, the Valentine’s Day bar has been set pretty high.

Luckily, you’ve got Chicago on your side. In a city like ours, there’s always something fun to do — why not try something different this year? Here are a few options of unique things to do in Chicago this Valentine’s Day.

(Flowers and chocolates are optional.)


Be smooth at the Peninsula Sky Rink

Skate on top of the world at the Peninsula hotel’s amazing Sky Rink — a rooftop rink located four stories above Chicago’s beautiful Magnificent Mile. Afterwards, cuddle up in one of the heated lounge areas and enjoy a hot chocolate, apple cider or mulled wine from The Chalet. Rink is open daily to visitors of the Peninsula hotel, restaurant or spa. Donation suggested. Click here for hours and information.


Rev your engines at the Chicago Auto Show

Ogle over engines and daydream about your next road trip at the Chicago Auto Show — the nation’s largest and longest-running (108 years!) auto show. Grab shotgun with your sweetie and take a test drive on one of three indoor tracks, or really hit the road with the six available outdoor test drives. Tickets range from $6 – $12 and can be purchased in advance. Click here for hours and information.


Mix things up at The Chopping Block

Create a memorable meal with your Valentine at The Chopping Block. Partners classes run all weekend long and include festive options like Romantic Valentine’s Dinner, Hands-On Valentine’s Day Feast, Breakfast in Bed and more. Plus, all classes are BYOB – you can Eat, Drink and Be Merry. Prices and class times vary — see class calendar for more information.


Enjoy a Unique Date at The World’s Fare

Relax as you travel across 4 countries tasting food and drink at 4 unique highly-rated restaurants. We take care of the reservations you enjoy an out of the box experience with your valentine. You’ll experience first hand the world-wide variety of foods present in Chicago’s culinary scene. Enough food for dinner and drinks to match, you and your date will leave with full hearts, minds and stomachs! Only $65 per person — see calendar for more information.


Work Together to Escape at The Escape Game

Nestled in the heart of River North, The Escape Game Chicago has received a warm welcome from neighbors and patrons alike. Can you believe it’s already Chicago’s #1 “Fun and Games” attraction on TripAdvisor? For a fun date day, we recommend going on a Chicago Food Planet Winter Delights tour in the afternoon and visit The Escape Game in the evening!

To book a game, visit or call (312) 453-7753. To book Winter Delights go to


Reenact Lady and the Tramp at Eataly

Travel to Italy without leaving Chicago by taking a day trip to Eataly — the Italian mega-market and upscale food court in River North. Dine at one (or more) of the seventeen restaurants and cafes, shop the market, and toast to a romantic day with a glass of imported wine or beer. Click here for hours and information.


Learn something new with Dabble

From salsa dancing and massage classes to design your own bucketfeet shoes and duo trapeze class, Dabble offers a variety of fun and engaging classes in Chicago to ensure that there’s always something for everyone. So grab your sweetie, pick a class, and have fun learning something new together. Click here for full class calendar and pricing.


Have another unique way to celebrate Valentine’s Day? Let us know in the comment section below, or send us a Tweet at @ChiFoodPlanet.




Chicago Food Planet offers a variety of awesome walking food tours in Chicago

Discover why Pilsen was named one of the “12 Coolest Neighborhoods Around the World” by Forbes on our Street Foods of Pilsen Food Tour.  

Tour Length3 hours
Cost$85 Adult With Alcohol | $50 Adolescent | Free Child (6 & Under)
Tour Distance1.4 miles

Devour all five of the iconic “Chicago-style” dishes from the eateries that perfected them on our most popular downtown tour.

Tour Length3 Hours
Cost$75 Adult | $50 Adolescent | Free Child (6 & Under)
Tour Distance1.4 Miles
NeighborhoodsRiver North & Streeterville
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