Romantic Dates » Chicago, IL

Romantic Dates in Chicago, IL

Thanks to the thriving social scene, Chicago is home to countless date options. The only limit? Your imagination.
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When the temperature is in the teens, and I'm in the mood for a romantic meal, I head to Hearty Restaurant. This cosy Boys' Town restaurant is run by local food celebrities Dan and Steve, former actors turned caterers and chefs.

The Hearty Boys have reinvented comfort food, crafting familiar dishes like tuna casserole and macaroni and cheese with luxury ingredients like Ahi Tuna and lobster. For dessert, you'll love their sophisticated takes on retro-favorites like Ginger-Snap S'mores and Baked Alaska with an orange blossom base.

What could be more romantic than  luxury comfort food for Valentine's Day? Be sure to book well in advance for the special night as the restaurant's few tables fill up fast.

Hollywood Palms

Dinner and a movie is the classic date night destination, but sometimes scheduling can be inconvenient. And during the bitter cold Chicago winters, the weather is sometimes a deterrant to walking to a nearby restaurant after a movie.

To keep things simple and fun, Hollywood Palms Cinemas are a chain of movie theaters that combine the dinner and a movie experience in one place. You will be able to order a full dinner to eat while you watch the latest blockbuster, with milkshakes and hot fudge sundaes for dessert. The theater also has a liquor license, giving you the freedom to enjoy a nice glass of red wine or a pitcher of ice cold beer to relax you even more as you watch a romantic comedy.

The menu features fun movie themed appetizers such as Godfather's Sicilian bread, Lord of the Onion Rings and Catherine Zeta Bruschetta, as well as pizza and other main courses.

More Cupcakes

When only the darkest, moistest, most decadent chocolate cupcakes will do, Chicagoans head to More Cupcakes. On Valentine's Day, these tiny little cakes are the perfect surface to make big statements of love.

You can head to the More Cupcakes storefront for a fun Valentines' day dessert treat, or simply bring an assorted box of these home for a wonderful surprise. And if chocolate is not your thing, there are other fun flavors to choose from like red velvet and butternut browned butter.

On Mondays, More Cupcakes is only open for pick-ups. All other days, the store is open til 8PM.


If you want to really impress your partner this Valentine's Day, or have a spectacular night with a girlfriend to forget that you're both single, head to Moto in the West Loop. Chef Cantu is often eclipsed by Alinea's Grant Achatz as the authority on molecular gastronomy in Chicago, but that doesn't make dining at Moto any less mind-blowing.

Indulge in the 20-course menu for a four-hour experience that will redefine your expectations of food forever. From when the waiter hands you the hot from the oven edible to menu to when he lights the fuse of your smore's bomb for dessert, every dish will shock, delight, and amaze you. Nothing is at it seems at Moto, but everything, from the risotto sushi to the Cuban Cigar made of pulled pork, is delicious and fun. In the sleek and elegant decor, you'll feel as though you're sharing a once in a lifetime experience worth every penny.

Spa Space

Come February, the winter weight has made many people feel flabby and unhealthy. Instead of splurging on an expensive meal for Valentine's Day, head to the spa instead to pamper your body.

The Spa Space in the West Loop has been voted Chicago's #1 day spa and is a great destination for a special day whether you're sharing the experience with a partner or a group of friends. The decor is designed to make you feel relaxed, indulged and at peace.

Spa Space offers every type of treatment you could possibly want from massages to microderm abrasion. They have rooms to accomodate groups and offer romantic experiences like the Art of Touch where both a masseuse and your partner massage you and side by side massages or dual pedicures.

The experience staff at the Spa Space clearly knows both massage and romance.