The Most Romantic Places to Propose in Chicago

Ready to pop the question? These are some of the most romantic places to propose in Chicago
Sunday, November 5, 2017 - 9:45am

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You've met The One. You're head over heels in love with someone you cherish, respect, and honor. 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 and best places to propose in Chicago.

Most Romantic Places to Propose in Chicago

Chicago Helicopter Experience

Chicago Helicopter Tour

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

Skydeck Chicago Wedding

Photo credit: Skydeck Chicago

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

Geja's Cafe Dining Room

Photo credit Geja's Cafe

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. If you don't know where to propose in Chicago, you can't go wrong with this intimate lighting, live flamenco, and classical guitarists. Geja's Cafe is located at 340 W Armitage. Dress up some for this restaurant - it's fairly fancy.

Make reservations

McCormick Tribune Ice Rink

Photo credit: McCormick Tribune

McCormick Tribune Ice Rink

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. It's 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

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

Chicago Odyssey Dinner Cruise

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

Navy Pier Centennial Wheel

Photo credit: Navy Pier
Centennial Wheel at Navy Pier

For a ride to remember, check out the Centennial Ferris Wheel at Navy Pier. 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


Champagne and chocolate covered strawberries at Intercontinental 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

Doubletree by Hilton Magnificent Mile - get a warm cookie at check-in!

Hyatt Regency Chicago - one of Chicago's largest hotels

Intercontinental Hotel Chicago - an historic hotel on the Magnificent Mile

Loews Chicago Hotel - closest hotel to Navy Pier

Radisson Blu Aqua Hotel - located in one of the most distinctive buildings in Chicago

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Theresa Carter - The Local Tourist Founder and Publisher, a.k.a. the boss
About Theresa

Hello Fellow Traveler! I'm the Emmy-winning founder and publisher of The Local Tourist. I've got insatiable curiosity, wanderlust, and an incurable need to use my words. In fact, I

2420 S Halsted, Chicago, IL 60608
340 W Armitage, Chicago, IL 60614
The nation's most romantic restaurant. Join us for fine wines, fondue dining & live guitar.
Geja's Cafe
201 E Randolph St, Chicago, IL
How much: Skating is free and skate rental is $12.
More than 100,000 people visit this ice skating rink each year.
McCormick Tribune Ice Skating Rink
233 S Wacker Dr, Chicago, IL 60606
Located on the 103rd floor of Willis Tower, formerly Sears Tower, the Skydeck offers spectacular sweeping views and is full of interactive exhibits.
Skydeck Chicago

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