The Most Romantic Places to Propose in Chicago

There may be affiliate links in this post, which means we may get a small commission. It's at no extra cost to you and helps keep TLT free. Everybody wins!

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 creative places to propose in Chicago.

Most Romantic Places to Propose in Chicago

Chicago Helicopter Experience

Your heart is soaring with love! For a proposal that goes "above" and beyond, take a helicopter tour. Chicago Helicopter Experience is offering a special romance package. A private tour for two is $456, and for an additional $50 your romantic evening will include a framed picture, a rose, two champagne flutes to keep, and two complimentary glasses of champagne. CHE is conveniently located in Bridgeport at 2420 S Halsted, right on the river and a block from an orange line stop.

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.

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. 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.

Photo credit: McCormick Tribune

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. 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 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 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, and during the summer months the city will celebrate with you with a rousing display of fireworks on Wednesdays and Saturdays. 

Featured photo courtesy Skydeck Chicago

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
Theresa Goodrich's picture
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

Add new comment