Valentine’s day is fast approaching, and though Chicago is known as the Windy City, it can be very romantic if you know where to look. That’s what we’re here for! Whether you are looking for romantic dining or fun couple activities, check out our list for an inside scoop on the romantic destinations the City that Works has to offer this winter.

Riverwalk Dining

The iconic Chicago riverwalk is a great place to start the evening. Take a romantic stroll and enjoy the winter view of the city and river. Luxurious dinner cruises on the river are also offered in the warmer months for a stunning and romantic evening out on the water. Along the way, you’ll also find many restaurant options to help you cozy up and escape the cold. 

For exquisite Italian cuisine, check out Gibson’s Italia. With a 5-Star menu and excellent view of the Riverwalk, this is a romantic escape that satisfies. Smith & Wollensky, a hip steakhouse, is another top-tier riverside option for your Chicago getaway. If you’re looking for a global menu and gorgeous view, the Kitchen American Bistro is the place for you. Regardless of the dining experience you choose, a shared meal on the Riverwalk is an unforgettable Chicago outing.

Art Institute of Chicago

A winter visit to Chicago’s largest art museum feels intimate. With fewer crowds and a quieter pace, you can take your time wandering through the galleries, pausing to admire each piece and share your thoughts along the way. Consider taking a guided or self-guided tour to experience all this beautiful institution has to offer.

Exploring art side by side encourages conversation and connection. Discover a new favorite artist together, or revisit a classic. It’s a simple yet meaningful way to spend a winter afternoon, blending culture, creativity, and quiet moments that make a romantic Chicago escape feel truly special.

‍Broadway Shows

Chicago is home to more than 250 theatres, and five Tony Award-winning theatre companies. Take advantage of this remarkable theater scene and catch a Broadway show with your partner. There is something classic, romantic, and warm about entering a historic theater like the Cadillac Palace. Settling into plush seats, and watching the curtain rise together creates a shared sense of anticipation that instantly brings you closer together. It’s the perfect way to escape the cold while being swept up in a story.

No matter the genre, live theater offers a memorable night out filled with emotion, laughter, and conversation long after the final bow. Sharing that experience makes a Broadway show an ideal highlight of a romantic winter getaway in the city.

360 CHICAGO

The Hancock tower poses a fun, breathtaking date idea with its 360° observation deck experience. From high above Michigan Avenue, the skyline feels especially magical as the lights glow against the cold winter sky. Wrapped up warm and standing side by side, it’s a moment that feels both exciting and intimate.

The observation deck offers a peaceful escape from the bustle below, giving you time to slow down and appreciate the city from a new perspective. Whether you visit during the day or as the sun sets, sharing Chicago’s sweeping views makes for a memorable and romantic stop on a winter escape.

Shedd Aquarium

Chicago’s biggest aquarium is the perfect location for an escape to the world under the sea. As you move through the exhibits together, the calm glow of the tanks and the gentle movement of marine life create a peaceful, almost dreamy atmosphere. It’s a warm retreat that invites you to slow down and enjoy the moment.

Sharing quiet conversations while watching sea creatures drift by makes the experience feel personal and memorable. Admiring vibrant fish or pausing at a panoramic view of Lake Michigan make the Shedd Aquarium a romantic way to spend a winter afternoon immersed in wonder.

Hotel EMC2

After a day spent exploring Chicago’s most charming winter experiences, coming back to a space that feels warm, comfortable, and effortless is essential. A romantic getaway is made even better by thoughtful details such as plush bedding, inviting interiors, and a quiet atmosphere that encourages you to unwind and reconnect.

At Hotel EMC2, beautifully designed accommodations, sweeping city views, and elevated amenities create the perfect setting for a cozy winter escape. From relaxing in your room to enjoying the hotel’s artful surroundings, every element is designed to make your stay feel special, intimate, and truly unforgettable.