Propose in Chicago: 17 Romantic Chicago Proposal Ideas


If you’re planning to pop the question whilst exploring America, a couple of places immediately spring to mind: New York, LA and Vegas, perhaps. But one that we think should definitely be included on your list is Chicago, Illinois. It’s called the Heart of America for a reason (and sure, that reason was geographic and logistical originally, but now: it’s a firmly romantic moniker!) As an incredible city with a vibrant culture and inimitable energy, planning to propose in Chicago is an excellent choice. 

But how do you do it? Here’s some of the best Chicago proposal ideas.

Not Just Any Park Proposal

Chicago is home to a number of beautiful parks and open spaces, which would make an ideal Chicago proposal spot. For example, you could visit Jackson Park on the South Side of the city. This park features the beautiful Osaka Garden (celebrating Chicago’s twinned city) and a sculpture by none other than Yoko Ono (Sky Landing). Plus, if you’re planning to propose in Chicago in spring, you will catch the 160 cherry blossom trees in full, fluffy bloom. Imagine just how beautiful that backdrop would be…

If the sculpture was more your bag, you could visit the Millennium Park in downtown Chicago, which you’ll probably recognise as the location of Cloud Gate, the giant bean-shaped metallic structure that provides a perfect picture (and proposal) opportunity.

Or, alternatively, you could venture north to Lincoln Park, a picturesque, tranquil park that nevertheless has loads going on (including botanical gardens and a zoo.) However, we’d recommend the Alfred Caldwell Lily Pool for a quiet moment just the two of you.

Propose in Chicago with the best views

Like any modern city, The Windy City’s skyline is a must see. And where better to see it than from above?

One place to do this is 360Chicago, an observation deck situated on the 94th floor. As well as the 360 degree views of the city, there’s an elegant bar serving local favourites. Or, if you crave adventure, why not try Tilt – one of the world’s highest thrill rides, where you can see the stunning views beneath you.

Another place to do this is the Skydeck. The Skydeck’s Ledge glass boxes extend 4 feet from the building, so you can see the city some 1,300 feet beneath your feet. 

Or maybe you’d prefer to see the skyline somewhere a little more dynamic – why not hire a helicopter to take you around the city? (Check out our guide to helicopter proposals here.)

Whatever you choose, asking the question in the air will take your plan to propose in Chicago to the next level.

Chicago proposals for art-lovers

Chicago’s beauty isn’t just limited to its skyline; one of the world’s most renowned art museums can also be found there. Among Degas, Monet, Van Gogh, the famous American Gothic and more, The Art Institute of Chicago is a jaw dropping setting in which to propose in Chicago.

Adventurous ways to propose in Chicago

If you both love to fill your days with action and activity, there’s no reason why the day you get engaged has to be any different. Luckily, Chicago has loads of unique activities that set the perfect scene for popping the question.

There’s loads of beautiful trails you can enjoy in Chicago, such as the North Branch Trail and the Illinois Prairie Path Trail (Illinois isn’t a mountainous state, so you won’t face too much elevation on your trek. For a slightly lower-key trek, you could amble arm-in-arm down the Lakefront trail, where laidback romance is the name of the game. Or, if you love to be by the water, you could set sail across Lake Michigan, and propose whilst on the boat.

Though Chicago is beautiful in spring and summer (see above for Jackson Park), it also offers so much for winter engagements. For quintessential American romance, why not go skating at Maggie Daley Park (just watch out for other skaters if you’re down on one knee on the ice!)? Or, you can rent skis and snowshoes from the Morton Arboretum January to March, and pop the question in the middle of your exciting expedition. A snowy Chicago proposal is the ultimate in unique, romantic, adventurous engagement stories.

Luxurious Chicago proposal spots

On the flipside, Chicago is also home to many luxurious, elegant, indulgent spots, which would make equally brilliant engagement stories. So, if you and your partner prefer to relax and unwind in style when you’re away, we’d recommend the AIRE Ancient baths. These Ancient Thermal baths take inspiration from the historic Roman, Greek and Ottoman bathing traditions, where they were centres of health, wellbeing, and guilt-free relaxation. Housed in a stunning building with the original brickwork, you’ll feel like you’ve been transported to a different world.

You can book in the AIRE Ancient Baths to experience a hot bath, an ice bath and cold plunges, a warm bath, a salt bath, and a jet bath as well as steam rooms with aromatherapy, but if you want to go even fancier, you could book a pampering experience for two. This includes a massage, and even a wine bath, maximising the antioxidant properties of delicious red wine – it doesn’t get more romantic than that! (Just remember to ensure the case for the ring is waterproof, so you don’t ruin it before you ask!)

Or, perhaps you want to save the proposal for when there’s just the two of you, back in your hotel room. For this, we would recommend booking in at The Langham. The Langham is a slice of paradise in downtown Chicago: stunning architecture, world-class service and award-winning food make for a truly five-star experience. For the ultimate luxurious Chicago proposal, book one of the rooms with a granite bathtub overlooking the city skyline. It’s an experience not to be missed, that’s for sure.

Whatever you call it: The Windy City, The Second City, The Heart Of America, Chi-town or more, a Chicago proposal is a thoughtful, unique way to pop the question to your loved one.

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