Whether you love it or loathe it, planning the perfect Valentine's Day in Chicago can be a bit stressful. Between hunting down the ideal dinner venue and choosing the perfect gift, the Valentine's Day bar has been set pretty high.
Luckily, you've got the Windy City on your side. In a city like ours, there's always something fun to do. So why not skip the predictable box of chocolates and try something completely different this year? If you are looking for the absolute best unique things to do on Valentine's Day in Chicago, we have you covered.
Here are 6 unique, out-of-the-box ways to celebrate with your sweetie.
Skate on top of the world at The Peninsula Chicago’s amazing Sky Rink, a glamorous rooftop rink located four stories above the city's beautiful Magnificent Mile. Surrounded by twinkling pine trees and dramatic skyscraper views, it is easily one of the most romantic backdrops in the city. Afterwards, you can cuddle up in their heated, rustic chalet and warm up with a hot chocolate, hot apple cider, or mulled wine.
Ogle over high-horsepower engines and daydream about your next romantic road trip at the Chicago Auto Show. As the nation's largest and longest-running auto show, it takes over McCormick Place every February. Grab shotgun with your sweetie and take a spin on one of the indoor test tracks, or check out the latest concept cars. It’s a fun, high-energy date day that breaks completely away from traditional Valentine’s clichés.
Instead of just sitting at a restaurant table, create a memorable meal together by booking a couples' cooking class at The Chopping Block in Lincoln Square. Their Valentine’s weekend calendar is always packed with hands-on, festive options like Romantic Valentine's Dinners, French macaron workshops, and bubbly brunches. Best of all, their interactive events are designed to be social, educational, and incredibly delicious.
If you want a dynamic dining experience without the hassle of fighting for a single, overpriced restaurant reservation, let us play matchmaker. Booking an experience with Chicago Food & City Tours is one of the most unforgettable things to do on Valentine's Day in Chicago.
Take a walk down Randolph Street for an insider’s culinary peek on our Gateway to The West Loop Food Tour, or stroll hand-in-hand through Chicago's vibrant and culturally rich Pilsen neighborhood on our Street Foods of Pilsen food tour. You’ll enjoy enough premium food for a full dinner, paired with incredible history. You and your date will leave with full hearts, minds, and stomachs!
Nestled in the heart of River North, The Escape Game Chicago is a top-tier attraction for couples who love a good challenge. Team up with your favorite person to search for clues, crack codes, and solve a high-stakes mystery before the one-hour timer runs out. For the ultimate date day, we highly recommend booking a midday neighborhood food tour to fuel up, and hitting The Escape Game in the evening!
Travel to Italy without ever leaving the Midwest by spending a romantic afternoon at Eataly Chicago, the massive Italian mega-market and upscale culinary oasis in River North. You can share an authentic wood-fired Neapolitan pizza, shop for artisanal Italian sweets, and toast to your love with a glass of imported wine at one of their vibrant bars. It's the perfect indoor escape from the February chill.
Can't make it out on February 14th but still want to blow your sweetie away? Give them a flexible culinary adventure with our Chicago gift cards that allow them to choose the perfect date night whenever they want, whether they want to dive into The Chinatown Adventure Food Tour or try the famous flavors on our Yes, Chef! Chicago: A Bear-Inspired Food Tour.
