Engagement is the most romantic event for every couple in love. Let us help you to create a very special fine jewelry that will become a family heirloom to be passed down for generations through family members holding amazing memories and a special meaning.

If you live in Chicago or you are planning a destination proposal for a Windy City trip with your special someone, it almost goes without saying that you want the location to be perfectly picturesque. read on for our suggestions for the best Chicago proposal locations. If you are wondering where to propose in Chicago, read on for our suggestions for the best Chicago proposal locations.


Originally planned to celebrate the new millennium, Millennium Park was not actually completed until 2004. Despite the citywide headache caused by its delayed completion, the finished product of 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 propose 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. TRUMP TOWER – Sixteen Restaurant

Sixteen Restaurant, located on the 16th floor of Trump Tower in downtown Chicago, is one of the most picture-perfect places for proposals in Chicago. Sixteen offers a spectacular view of Chicago’s urban landscape, making it an eye-catching and dramatic proposal location.

There is an outdoor terrace where you can eat and enjoy drinks among the Chicago skyscrapers, but during engagement season the weather probably won’t permit this option. However, there are plenty of window tables where you can enjoy gourmet food, delicious drinks, and the warmth of the restaurant before you propose. Sixteen is a classy, romantic engagement spot in Chicago.


When it comes to Chicago proposals, Shedd Aquarium is fun, interesting, and scenic. It is one of the largest indoor aquariums in the world, with over 25,000 fish and 5 million gallons of water. Because they are all indoors, the exhibits in Shedd Aquarium are visually and architecturally beautiful. From the 3,000,000-gallon Oceanarium featuring dolphins, belugas and sea lions, to the incredible recreations of the Amazon and the Caribbean, Shedd Aquarium is an excellent place to propose for animal lovers, ocean lovers, or even world travelers.

The outside of Shedd Aquarium also happens to be one of the best locations for a lakeside proposal in Chicago. Shedd Aquarium is a part of Museum Campus Chicago, which is situated right on the waterfront. If you think you’ll have trouble working up the nerve to propose to your significant other, a long visit to the Shedd Aquarium followed by a walk around the Museum Campus is an excellent, visually striking option. Ask the big question here and make sure she knows that she is the only fish in your sea!


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 propose in Chicago during engagement season: 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.


The Magnificent – or “Mag” – Mile, is adjacent to downtown Chicago and positively packed with activities and attractions. This makes it one of the most classic and well-loved places to propose in Chicago. It seems like there is an upscale restaurant, historic landmark, or luxury hotel everywhere you turn on the Mag Mile, meaning you will be spoiled for choice if you choose it as your Chicago proposal location.

During engagement season, the Mag Mile is spectacularly lit up for the holidays, giving the entire area a soft, romantic twinkle. For an even dreamier and more glamorous proposal, consider popping the question during a horse and carriage ride down this scenic street.

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 your 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.


A quiet and private option: pop the question in a sea of dusty books. Hide the ring near one of her childhood favorites, bring your own hollow book safe, or simply drop to one knee in the check-out line. Be prepared for some excited whispers of congratulations.


Downtown Chicago is filled with these lakefront open spaces. Perfect for picnicking, impromptu meet ups with friends and of course a magical moment like this lakeside proposal.Ask for her hand with the famous Chicago skyline as your backdrop. Aiming for something a little quieter? Any of the Evanston beachfronts are good candidates. Wait until dusk and you’ll get your yes to the faint glow of the city lights.


Spend some time under the stars and then take her outside for a lakeside proposal. Romance levels? Running high!


Home to the oldest music festival in the United States (the appropriately named Ravinia Festival), Ravinia Park attracts some 600,000 visitors each summer with its world-class concert series. The park was created in 1904 and over the past 100 years has hosted concerts by Louis Armstrong, Yo-Yo Ma, Ella Fitzgerald, Frank Zappa. Today, it serves as the summer home of the Chicago Symphony Orchestra. The open-air, 36-acre grounds invites concertgoers to pack a picnic and enjoy music under the stars.


The 385-acre Chicago Botanic Garden features 26 gardens spread across nine islands and surrounded by four natural habitats. This living plant museum hosts an array of permanent and seasonal gardens and exhibits. It's open to the public every day of the year. Be sure to also join the free photo tour of the garden led by a staff photographer the first Saturday of each month.


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