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10 Best Places to Propose in Chicago

So, you’ve decided it’s time to pop the question, and now it’s you need to figure out when and where you might get down on one knee and ask, “Will you marry me?”

Don’t worry if you’re not sure where to go. Chicago is a huge city, and I’ve compiled my top 10 best places to propose in Chicago to help you plan the perfect proposal.

London House Cupola

By far, the London House Cupola is at the top of my list of best places to propose in Chicago, and for good reason, too. You can’t beat the grandeur of this spot, situated at the top of one of Chicago’s most luxurious hotels. With 360-degree views of the city, you’ll feel like you’re on top of the world. And better yet, the London House offers a private proposal package with a rose petal walkway, champagne, and more, so can have the cupola all to yourselves when it comes time to ask that oh-so-important question.

Ping Tom Memorial Park

Located a little bit off the beaten path in Chicago’s Chinatown neighborhood, Ping Tom Memorial Park is the perfect spot for a sunset marriage proposal. This 17-acre park has plenty of room for the two of you to take in the twinkling city lights and the Chicago river, lit up pink and gold by the setting sun.

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North Avenue Beach

North Avenue Beach is one of Chicago’s largest public lakefront spaces, so you’ll have plenty of space to call your own. Beautiful at both sunrise and sunset, North Avenue Beach is the perfect spot for a romantic summer proposal.

best places to propose in chicago

Navy Pier

While Navy Pier is a popular tourist destination, it’s still one of the best places to propose in Chicago because of all it has to offer. With commanding views of Lake Michigan and the city, you’ll be sure to find the perfect viewpoint. And if you want to take the romance up a notch (or two or three!) consider booking a ride on Navy Pier’s Centennial Wheel, and pop the question as you look down on the city in perfect seclusion.

Buckingham Fountain

Located in Chicago’s Grant Park, Buckingham Fountain is another favorite on my list of best places to propose in Chicago because it’s incredibly romantic at twilight. From May through October, the park lights the fountain with a simultaneous music and water show each dusk. You have options to time your proposal — the light and water show plays every hour on the hour, ending at about 10:30 pm.

Alfred Caldwell Lily Pool

If secluded, fairytale beauty is for you and your partner, look no further than the Alfred Caldwell Lily Pool. The stone path circling the pool is filled with secluded and romantic spots, perfect for your Chicago proposal. A few of my favorites are the prairie-style pavilion, the waterfall, and the charming bridge.

Lincoln Park Conservatory

The Lincoln Park Conservatory is a lush, majestic indoor garden, perfect if you want to incorporate the beauty of the natural world into your proposal, no matter the time of year. You’ll feel like you’re alone in a tropical oasis if you visit the conservatory right after opening in the morning, or about an hour before closing at night.

best places to propose in chicago

Chicago Botanic Garden

It doesn’t get better than this. The Chicago Botanic Garden is the ultimate urban oasis, and its place on this list of best places to propose in Chicago is well-deserved. Filled with beautifully-tended gardens in a variety of styles and themes, there’s almost limitless possiblities for how and where you could propose here, but if you want my two cents, do it in the English rose garden — I think it’s the most romantic spot there!

The Skydeck at Willis Tower

If heights and grand gestures are your thing, then consider the Skydeck at Willis Tower. You’ll have an unapparelled view of the city (especially romantic with the city lights at night!) and the team at Willis Tower often accommodates special requests to help make your proposal personal and memorable.

City Winery Chicago

If you and your special someone love good dining and live theatre, a proposal at City Winery Chicago would be the perfect end to an amazing date night! City Winery has three distinctive dinner options: the main dining room, the wine garden patio, and a concert dining set up, so you can enjoy a romantic dinner, surrounded by the music and artists you love.

Best Places to Propose in Chicago — What’s next?

Now that you’re all set with ideas for where to propose to your forever person, what’s next in the proposal plan?

A proposal is a beautifully intimate and emotional experience, and a hidden photographer can help you capture every special moment of your proposal. If you’d like me to help you make your proposal even more memorable with some candid photographs and a brief “just engaged” photo session afterward, I’d love to connect!