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Chicago, the Windy City, is nestled on the banks of Lake Michigan; it’s no surprise there are water views from nearly every vantage point. Chicago is a city of rich, vibrant neighborhoods, each with its own flavor and style. On the Southend of Chicago, you’ll find the international flavors of Little Italy and Chinatown, as well as the culturally diverse Hyde Park which is home to galleries, museums and venues. North Chicago is home to an eclectic mix that ranges from exotic eats and boutique shopping in Wicker Park to live jazz in Lincoln Park.

Whether you’re planning a destination proposal in the Windy City or simply seeking fresh ideas for a romantic date, it almost goes without saying that you’ll want to visit a location that’s both fun and perfectly picturesque. Read on for our 10 favorite romantic things to do in Chicago.


For a quick look at our top places for romance in Chicago, we’ve created a handy infographic:

best places to propose chicago infographic

Now, on to the details!

1. Millennium Park – Pritzker Pavilion

Pritzker Pavilion. Photo credit: Wikimedia Commons.
Pritzker Pavilion. Photo credit: Wikimedia Commons.

Originally planned to celebrate the new millennium, Millennium Park was not actually completed until 2004. Millennium Park is beloved by all who visit it: the entire park has won awards for its beautiful public art and green spaces, but Pritzker Pavilion is definitely Millennium Park’s most eye-catching feature.

Designed by famous architect Frank Gehry, Pritzker Pavilion is so stunning that it is technically classified as a work of art. If you and your partner love the arts and music, Pritzker Pavilion is one of the optimal places to visit in Chicago. Pop the question at one of the pavilion’s many concerts and performances, or during an intimate picnic on the pavilion’s lush green lawn.


2. Sixteen Restaurant

Chicago's most romantic locations - Sixteen Restaurant
Sixteen Restaurant. Photo credit: Sixteen Chicago

Sixteen Restaurant, located in downtown Chicago, is one of the most picture-perfect places in Chicago. Sixteen offers a spectacular view of the city’s urban landscape, making it an eye-catching and dramatic proposal location. Sixteen has been awarded two Michelin stars and promises an unforgettable dining experience.

Enjoy dining among the Chicago skyscrapers on the outdoor terrace or sit by one of the 30-foot floor-to-ceiling windows, where you can enjoy gourmet food and high-end cocktails. Sixteen is a classy, romantic engagement spot in Chicago.


3. Shedd Aquarium

The most romantic places in Chicago's Shedd Aquarium
Shedd Aquarium. Photo credit: Chicago Architecture.

Looking for the perfect place to make a splash during your time in Chicago? The Shedd Aquarium is one of Chicago’s finest date destinations. As one of the largest indoor aquariums in the world, it houses over 32,000 fish! On top of that, the exhibits in Shedd Aquarium are visually and architecturally beautiful. They range from the 3-million-gallon Oceanarium, featuring dolphins, belugas and sea lions, to the incredible smaller exhibits featuring a wide array of species from the Amazon and the Caribbean. The Shedd Aquarium is the perfect place to spend a romantic afternoon hand-in-hand, exploring the beauty of an aquarium with your beloved.

Shedd Aquarium is a part of the Museum Campus Chicago, which is situated along the waterfront. This makes the outside of Shedd Aquarium one of the best locations for a lakeside proposal in Chicago. If you think you’ll need extra time to work up the nerve to propose to your significant other, a long visit to the Shedd Aquarium followed by a walk through the Museum Campus is a soothing, visually striking option.


4. Grant Park – Buckingham Fountain

Chicago's most romantic locations: Grant Park – Buckingham Fountain
Buckingham Fountain in Chicago. Photo credit: Layover Guide.

Everyone loves a water feature! Inspired by the Palace of Versailles, Buckingham Fountain is one of the largest fountains in the world, and one of Chicago’s most popular tourist attractions. Buckingham Fountain is situated in the middle of Grant Park, a 319-acre greenspace known as “Chicago’s front yard.” In fact, the fountain has been nicknamed Chicago’s “front door” for its central location within the park.

A caveat if you’re considering Buckingham Fountain as a place to visit: the fountain does not run from mid-October through March. You can still visit the fountain, and it will be decorated with glamorous holiday lights, but the water will not be running.


5. The Magnificent Mile

Chicago's Most Romantic Places, the Magnificent Mile
The Magnificent Mile – Michigan Ave Tulips in Chicago. Photo credit: Imgur User ChicagoPhotoSho

The Magnificent – or “Mag” – Mile is adjacent to downtown Chicago and positively packed with activities and attractions. The section of Michigan Avenue that runs between the Chicago River and Oak Street is known as the Magnificent Mile. Everywhere you turn on the Mag, there is an upscale restaurant, historic landmark or luxury hotel. If you want to splurge, high-end Oak Street is your destination. The Magnificent Mile is lined with upscale boutiques and department stores like Cartier, Chanel, Gucci, Harry Winston, Louis Vuitton, Neiman Marcus, Saks Fifth Avenue, Nordstrom, and Barneys New York. This makes it one of the most classic and well-loved places to visit in Chicago. If you’re looking for an unexpected proposal location, this might just be it. Take your bride-to-be out for a day of shopping, then surprise her with a proposal along the riverwalk with a Flytographer proposal photographer waiting in the crowd to capture the moment.


6. See a show

Chicago Theater Art by Brian Gaynor
The Chicago Theater. Photo Credit: Brian Gaynor Photography

Go see a show at one of the many theaters Chicago has to offer: The PrivateBank Theatre, The Paramount, The Chicago Theater, or The Chicago Shakespeare Theater. Many Broadway shows make their way to Chicago theaters soon after appearing in New York. Be sure to book your tickets in advance for more popular shows like Hamilton.


7. Take me out to the ball game!

The Cubs win the World Series!
Chicago Cubs win the 2016 World Series! Photo Credit: Time

Chicago is a big baseball city, with two Major League Baseball Teams, the Cubs and the White Sox. If you’re visiting Chicago April through September, go to a Cubs game at the historic Wrigley Field, which has been hosting ball games since 1914, or a White Sox game on the other side of town at Guaranteed Rate Field. The Cubs just won their first World Series since 1908, so it’s prime time to see the team play in real life! Might as well try one of those world famous Chicago Dogs while you’re there too…


8. Laugh it up at an improv show

Chicago Improv date
Improv at Second City, Chicago. Photo Credit: Arts Partnership

There’s no shortage of comedic talent in the Windy City: about half of the current SNL cast got their start in Chicago’s improv scene. They say laughter is the best medicine — so why not spend an evening laughing at Second City, iO or The Annoyance? Notable alumni of Second City include: Bill Murray, Tina Fey, Amy Poehler, Steve Carell and Stephen Colbert.


9. Foodie central

Chicago date ideas - Alinea
Dark Chocolate Dessert at Alinea. Photo Credit: Travel and Leisure

While Chicago cuisine is best known for handheld delicacies of the hot dog and deep-dish pizza variety, there is also an established foodie scene, including many restaurants that have earned Michelin Star honors. If you love fine dining, make a reservation at Alinea, an avant-garde “modernist dinner theater” renowned for its art-inspired New American tasting menu. For a more casual meal, try Girl and The Goat, a farm-to-table eatery by celebrity chef Stephanie Izard. Former President Barack Obama’s favorite in Chicago? Spiaggia, where the Obamas celebrated his bid to become the 44th President of the United States.


10. A day at the museum

Chicago date ideas - Chicago Museum on Contemporary Art
Chicago Museum of Contemporary Art. Photo Credit: Time Out

If you and your partner are lovers of the arts, be sure to check out the Art Institute of Chicago, which highlights works by the Impressionists (it has an entire room dedicated to Monet). The Museum of Contemporary Art and the Field Museum (home to the largest Tyrannosaurus rex fossil ever found) are also both worth spending an afternoon in.

Proposing in Chicago?

Are you looking for an engagement ring for your Chicago proposal? Here’s a tip: the engagement rings Chicago residents most admire tend to be halo styles, beloved for their vintage charm. If you’re shopping for engagement rings in Chicago, you can have a Ritani ring shipped to one of our local Chicago jewelers to preview it in person, obligation-free. Before you do so, make sure you know your partner’s ring size. We offer a handy and free ring sizing tool so you can choose the perfect fit.