Are you looking for the most unique and romantic places in Chicago to propose to the love of your life? Then you've come to the right place! Chicago offers lots of beautiful sites to surprise that special someone with a breathtaking diamond ring. Here are some of our favorite Windy City romantic backdrops for the perfect proposal:

  1. Lincoln Park Conservatory - This is one of the most beautiful and serene settings for a wedding proposal in Chicago. The Lincoln Park Conservatory Show House changes its appearance with the seasons and is overflowing with flowers year-round. We recommend you plan your proposal during the closing time of the Show House to escape the crowd.

  2. Navy Pier's Centennial Wheel - Overlooking Lake Michigan, the Centennial Wheel offers an incredible view from at least 200 feet up in the air. It also provides complete privacy so you can propose in public without onlookers getting involved in your intimate moment.

  3. Alfred Caldwell Pool - Secluded and straight out of a fairytale, the Alfred Caldwell Lily Pool is one of Chicago's prime proposal spots. Its rustic stone path around a massive pool provides numerous little nooks that are ideal for popping the question. We recommend some primo spots like the charming bridge, the prairie-style pavilion and the waterfall.

  4. London House Cupola - The grandeur and 360-degree wide view of Chicago make this location one of the best places to take a knee. The majesty of the London House Cupola is unbeatable, and the hotel offers private packages to couples, including unique petal walkways, champagne, and a series of other glamorous perks to make the moment that much more special.

  5. North Avenue Beach – Simply put: nothing beats the skyline view from North Avenue Beach. It is Chicago's most extensive public lakefront, full of romantic spaces to pop the question. We recommend coordinating with sunrise or sunset for a truly picturesque backdrop to your proposal.

  6. City Winery Chicago - If you and your partner are into fine dining, then the City Winery in Chicago might be the perfect place for your proposal. With a live theater, great food, and exquisite wines, this venue is the perfect data night to satisfy all of your senses. We recommend you start with some live music in the concert room before popping the question in the wine garden.

While these are the perfect places in Chicago to propose, you'll still need the perfect ring to do it with. That's where we come in. Contact us today to let our team of diamond experts help you craft the engagement ring of your dreams so all aspects of your proposal can shine as bright as the setting.