Best Places to Propose in Chicago

Perfect places when you've found "the one" and want to make it official.

You’ve met The One. You’re head over heels in love with someone you cherish, respect, and honor.

You know you want to spend the rest of your lives together. You’ve already got the important stuff down pat – now comes the hard part: the proposal!

You want it to be perfect, but where oh where do you pop the question? Here are a few “lovely” ideas for the most romantic, best places to propose in Chicago.

Best Places to Propose in Chicago

1. Chicago Helicopter Tour

Chicago Helicopter Experience tour of downtown Chicago at night, with beautiful views of the skyline. This one of the most perfect places to propose in Chicago.

Your heart is soaring with love! For a Chicago proposal that goes “above” and beyond, take a helicopter tour around downtown Chicago with a special romance package. A private tour for two is $599 and includes champagne and chocolates. 

Book your private helicopter tour

2. Skydeck Chicago

You'll go out on a ledge for each other, so of course Skydeck is one of the best places to propose in Chicago!
Photo credit: Skydeck Chicago

You’d step out on a ledge for your loved one. Prove it 103 stories above Chicago streets with a proposal on the Ledge!

This glass-encased balcony will give you and your betrothed a view for miles – once you’re done gazing into each other’s eyes, that is. You can even get married there. Skydeck is located in the Willis Tower at 233 S Wacker Dr.

Get tickets to Skydeck Chicago

3. Geja’s Cafe

Geja's Cafe Dining Room
Photo credit: Geja’s Cafe

There’s a reason Geja’s has been named the most romantic restaurant in the country. For over fifty years they’ve celebrated fondue and created fond memories.

You can’t go wrong with intimate lighting, live flamenco, and classical guitarists. It’s truly one of the best restaurants to propose in Chicago. Geja’s Cafe is located at 340 W Armitage. Dress up some for this restaurant – it’s fairly fancy.

Make reservations

4. McCormick Tribune Ice Rink

McCormick Tribune Ice Rink
Photo credit: Millennium Park

Circling this downtown Chicago rink hand in hand is the stuff of which greeting cards are made. You’ll glide into her (or his) heart with the greatest of ease with a Chicago proposal in this romantic location.

Millennium Park‘s McCormick Tribune Ice Rink is one of best places to propose in Chicago in winter. 

If you’re a little wobbly on the ice, get to the rink an hour before it opens on Fridays, Saturdays, and Sundays for a free lesson. After you’re officially engaged you can celebrate at Park Grill with some vanilla bean cheesecake and a nice bottle of Veuve.

The ice skating rink is open from mid-November through mid-March every year, weather permitting. McCormick Tribune Ice Rink, 11 N Michigan Ave

5. Chicago Odyssey Dinner Cruise

Chicago Odyssey, a luxury yacht that offers cruises with multi-course meals, departing from its dock at Navy Pier
Photo credit: Entertainment Cruises

One of the best places to get engaged in Chicago is aboard a luxury yacht. Take a sunset cruise with Odyssey Chicago and pop the question with the skyline as your backdrop. You and your love will be treated to a gourmet three-course dinner.

During the summer months the city will celebrate with you with a rousing display of fireworks on Wednesdays and Saturdays. During the winter, you can take a Chicago River cruise

Get tickets to Odyssey Chicago

6. Navy Pier Centennial Wheel

The climate controlled cars on the Centennial Wheel make cozy places to propose in Chicago.

For a ride to remember, check out the Centennial Ferris Wheel at Navy Pier. The cars are climate controlled, so you can propose any time of year.

For the ultimate proposal, upgrade your ticket to the VIP Gondola with plush seating, glass bottom, and champagne. Your love is sure to say yes! 

Check out our guide to Navy Pier

7. LondonHouse Cupola

Romantic marriage proposal in the LondonHouse Cupola in downtown Chicago

If your love is sky-high and puts a song in your heart, then a romantic proposal in the LondonHouse Cupola will be the perfect way to pop the question.

Not only can you pop the question in the gorgeous Cupola, your love can be serenaded with a custom love song created just for you.

The historic hotel has partnered with local bespoke songwriters “With This Song” to create an unforgettable setting. Contact [email protected] for details and availability.

Check rates at LondonHouse | Book your post-proposal room

8. 360 Chicago

View of Chicago and Lake Michigan from 360 Chicago
Photo credit Janelle Rominski

Your love is your sun and stars. Well, what better place to prose than 360 Chicago, where you can see both?

360 Chicago’s Sun and Stars package lets you skip the ticket line twice to enjoy the best panoramic views or a spectacular sunset over Chicago.

Pop the question at sunset, stay next door at the lovely Ritz-Carlton, then return the next morning to toast your new lives together.

9. Shedd Aquarium

Caribbean Reef at Shedd Aquarium, photo courtesy Choose Chicago
Photo courtesy Choose Chicago

Your love will survive anything – even shark-infested waters. Prove you’re willing to navigate the depths of your commitment with a proposal at the Shedd Aquarium.

Related: check out our guide to the Shedd Aquarium, including free admission days

Where to Stay after you’ve proposed in Chicago

Champagne and chocolate covered strawberries at Intercontinental Chicago are a romantic way to celebrate after finding the perfect place to propose in Chicago.

Looking for a place to stay after you’ve popped the question? Check out one of these delightful downtown Chicago hotels:

ACME Hotel Company – fun and affordable boutique hotel | Read reviews | Book now

Doubletree by Hilton Magnificent Mile – get a warm cookie at check-in! | Read reviews | Book now

Hyatt Regency Chicago – one of Chicago’s largest hotels and located right on Wacker | Read reviews | Book now

Intercontinental Hotel Chicago – an historic and romantic Chicago hotel on the Magnificent Mile | Read reviews | Book now

Loews Chicago Hotel – a luxurious hotel with great restaurants and spa | Read reviews | Book now

Radisson Blu Aqua Hotel – located in one of the most distinctive buildings in Chicago | Read reviews | Book now

Still thinking about the best places to propose in Chicago? Save this for later! (But you might want to save it on a secret board.)

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