Valentine’s Day is quickly approaching, and there’s no better place to celebrate the most romantic day of the year than in Chicago. Whether you’re planning an extravagant night out, a quiet evening, or a budget-friendly outing, the Windy City offers endless possibilities for you and your special someone. From cozy dinners to memorable outings, this guide is here to help you create the perfect Valentine’s Day in Chicago.

Want to find the vibes that match your style? Download Vibemap today and never miss a vibe!

Active Date Night Ideas in Chicago

Tired of the usual dinner-and-movie routine? Switch things up this Valentine’s Day with these active activities. There's more to Chicago than walking around Navy Pier!

Ice skating at Maggie Daley or Millennium Park

Glide hand-in-hand with your partner while taking in the unbeatable views of the city skyline. The Maggie Daley Ribbon is particularly romantic as it winds through the park.

A stroll through Lincoln Park Conservatory

Escape the cold and enjoy the tropical environment of the Lincoln Park Conservatory. Take a leisurely walk under a canopy of exotic plants and fragrant flowers. It’s Instagram-worthy, perfect for that hard launch you've been waiting for.

Relax at Aire Ancient Baths

Looking for something extra indulgent? Aire Ancient Baths is your answer. Unwind together in luxurious thermal baths and enjoy couples' massages in this impressive oasis near River West.

Sunset views by Lake Michigan

Few things are as romantic as a walk along the Lake Michigan shoreline. Walk the scenic Lakefront Trail or snag a quiet bench to watch the sun dip below the horizon. Even in winter, the views are magical.

Romantic Restaurants to Celebrate Valentine's Day

A romantic dinner is at the heart of celebrating Valentine’s Day, and Chicago’s award-winning food scene delivers. Here are some of the top spots to spark romance.

Geja's Café – Fondue Lovers’ Paradise

Located in Lincoln Park, Geja’s Café is synonymous with romance. This intimate fondue restaurant offers candlelit tables and live music featuring the flamenco guitar.

Aba – Mediterranean Magic

If you’re looking for a trendy vibe, Aba in Fulton Market cooks up Mediterranean-inspired dishes in a chic, cozy atmosphere. Their rooftop patio (weather permitting) adds to the ambiance, making it the perfect way to reconnect with your honey,

Sepia – Michelin-starred Fine Dining

For couples who want to elevate their February with something exceptional, Sepia offers a Michelin-starred experience. Just a short walk from Union Station, the restaurant showcases farm-to-table ingredients and a curated wine selection.

The Most Romantic Hotels in Chicago

Planning a staycation or hosting a Valentine's getaway? Book the perfect gift for your sweetheart by staying at one of these romantic hotels:

Hotel Zachary 

Hotel Zachary is a staple in the Chicago boutique hotel scene. Just steps away from the iconic Wrigley Field, this hotel offers luxury accommodations with a touch of nostalgia. Take advantage of their Valentine's Day package, called Love, Alma, which includes specialty cocktails, chocolate-covered strawberries, and late checkout.

The Fairmont Chicago, Millennium Park

Located in the heart of downtown Chicago, The Fairmont Chicago, Millennium Park provides delightful views of Lake Michigan and Millennium Park. Their romantic package, called Fairmont Chicago’s Romance Awaits, includes a bottle of sparkling wine and a handcrafted chocolate amenity created by the hotel’s Executive Chef.

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel is a historic property that still boasts modern amenities. The Love in the Windy City package includes a glass of prosecco, a $50 daily dining credit, and late check-out from the Gwen Hotel.

Final Thoughts on Valentine's Day in Chicago

Chicago provides the perfect place to make this Valentine’s Day one to remember. Whether you’re dining at a Michelin-starred restaurant, ice skating under the city lights, or strolling hand-in-hand by Lake Michigan, the possibilities are endless.

Found this guide useful? Share it with your friends so they, too, can make the most of Valentine’s Day in Chicago.

About the Author:

Cait Kontalis

Cait is a Chicago-based Greek-American but spends most of her year floating around the globe. She holds a B.A. in Communications and a M.A. in Nonprofit Management. Her favorite destinations include visiting her homeland in Greece, the Black Hills of South Dakota, and wherever her partner is stationed abroad. Cait is also a powderhound, taking to ski slopes in the Rocky Mountains and throughout the country.