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7 Romantic Things To Do in Chicago

December 20, 2022 By CityPASS

If you’re looking for a romantic getaway, look no further than the Windy City. The bright lights, beautiful skyline, and limitless things to do make this destination a no-brainer when you're looking for a weekend away. To discover the allure for yourself, here are some of the most romantic things to do in Chicago no matter the season.

Why Chicago Is One of the Most Romantic Cities in America

There are dozens of romantic places in Chicago to check out regardless of your interests. This city has a little bit of everything: fine dining, intriguing museums, and architecture that will take your breath away. With plenty of beaches along Lake Michigan and green parks sprinkled throughout the city to stroll, there are plenty of things to do if you’re looking for a fresh idea for date night.

What Are the Most Romantic Experiences for Couples in Chicago?

The most romantic date ideas in Chicago are waiting for you, no matter what kind of couple you are. Hardcore foodies? Pick a restaurant from the long list of local favorites, or try something elevated and sophisticated. Looking to tap into your cultural side? There are enough sights to see and museums to visit that you’ll have a hard time picking just one.

But of course, some of the most romantic things to do in Chicago are the simplest. Walking the city streets or exploring the charm of each of its neighborhoods, hand-in-hand, is about as romantic as it gets.

View Twinkling Stars and the Beautiful Night Sky at Adler Planetarium

You can have a romantic date under the stars no matter the weather or time of day at Chicago’s Adler Planetarium. Here, you’ll have the opportunity to explore the wonders of the cosmos as you sit back and snuggle in close.

The Adler Planetarium has a number of award-winning shows that give you an incredible look at what lies beyond our planet. You can also check out a number of exciting exhibitions or a relaxing lunch at the Cosmic Café with incredible views of the city skyline.

Check Out Amazing Views of the City Skyline

Seeing Chicago from above on the 94th floor of the John Hancock Building is something you’ll never forget. The 360 CHICAGO Observation Deck is a romantic place to watch the sunset over Lake Michigan, framed by impressive buildings.

Another fantastic vantage point is Skydeck Chicago, located in the famous Willis Tower. Even higher up on the 103rd floor, you’ll be able to get a bird’s eye view of the glittering city below.

If you’re not a fan of heights, taking a Shoreline Sightseeing Architecture River Tour might be more your speed. There’s nothing more romantic than a cruise through the city with the skyline as your backdrop.

Enjoy a Fancy Dinner at Any of Chicago's Award-Winning Restaurants

Dinner at a romantic restaurant is a date night plan that never fails. Head to the city’s Lincoln Park neighborhood and you’ll find some of the best and most romantic restaurants in Chicago. One great option is Mon Ami Gabi, a classic French bistro that has top-notch food and drinks in a cozy, romantic setting.

If you’re in the mood for pizza, Chicago Pizza and Oven Grinder Co. is one restaurant you won’t want to miss. Just a stone’s throw away from Mon Ami Gabi, this cash-only eatery is snug and intimate and will make you feel like you've taken a step back in time.

If you’re in the Loop, try The Berghoff. For more than 120 years, this legendary eatery has featured both a bar and a restaurant that offers homemade German dishes. If you don’t have a specific spot in mind, the Wicker Park neighborhood is packed with restaurants and bars to suit all tastes.

Get Up Close and Personal To Unique Marine Life at Shedd Aquarium

The Shedd Aquarium is a favorite among both locals and visitors — it gives you the opportunity to get an up-close look at a plethora of sea creatures. A walk through the Shedd can be both romantic and exciting as you and your sweetheart explore the wonders of the deep together, coming face-to-face with creatures like fish, sharks, belugas, and more.

Cozy Up During a Ride on the Centennial Wheel at Navy Pier

Imagine snuggling up next to your loved one 200 feet up in the air, looking down at the city of Chicago below. The Centennial Wheel at Navy Pier is an iconic piece of the city’s history that still delights both kids and adults alike. If you only have time for one activity at Navy Pier, this is it. Centennial Wheel offers stunning 360-degree views of the city and Lake Michigan that you can’t get anywhere else.

Spend Time Admiring Iconic Artwork at the Art Institute of Chicago

Art lovers will find hours of entertainment at the Art Institute of Chicago, located next to Grant Park. Home to many iconic pieces, a long stroll through this art museum is one of the most romantic things to do in Chicago in the winter or on a rainy day.

If you and your partner like arts and culture, you’ll love roaming the galleries and soaking in pieces by some of the world’s most famous artists, including Vincent van Gogh, Georges Seurat, Diego Rivera, and many more.

Take a Romantic Stroll Through Millennium Park or Grant Park

While Chicago is a concrete jungle, it has plenty of green spaces to explore. First up, take a stroll through Millennium Park to see the iconic Cloud Gate, known affectionately as the Bean. This futuristic sculpture is the perfect spot to huddle in close for a selfie.

Next, continue to Maggie Daley Park, a favorite for families in Chicago. This is a great location for one of the most romantic things to do in Chicago in winter. During the snowy season, you can lace up your skates and take a spin around the ice with your date while getting into the holiday spirit.

Another important green lung in Chicago is Grant Park, which is often a hot spot for concerts, festivals, or other celebrations. To end a romantic day in Chicago, stop at Buckingham Fountain. In the warmer months, you can catch a light show synchronized with music every night at dusk.

Save on Your Romantic Trip to Chicago

Start planning your romantic getaway and purchase your combined ticket to see the city’s best sights. Use Chicago C3® tickets and choose any three attractions, or check out the classic Chicago CityPASS® tickets and get entrance to five attractions. Both options let you see the best of the city while saving a little bit of money so you can splurge on even more romantic activities in the Windy City.

Chicago Lodging

To get the most out of your romantic stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you:

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