You’ve found “the one.” You’ve bought the ring. Now all you have to do is plan the perfect spot to ask that once-in-a-lifetime question. In Chicago, you’ve got plenty of options when it comes to romantic backdrops. Here are just a few of our very favorites, featuring waterfront views, hidden gardens, and intimate lookouts that offer a picture-perfect proposal location.
Alfred Caldwell Lily Pool
Escape to a beautiful hidden garden in the heart of Chicago’s Lincoln Park neighborhood. Meander the stone walk encircling the Alfred Caldwell Lily Pool, a tranquil oasis featuring native plants, blooming water lilies, and a gentle waterfall. The historic gardens are especially scenic in spring and fall, when the surrounding plantlife brims with color. It’s an ideal location for a quiet proposal, especially if you’re looking for stunning photos.
Promontory Point
You can’t go wrong with a proposal along Chicago’s stunning lakefront, but Promontory Point is a particularly perfect spot. Located within Burnham Park, this small peninsula offers less crowds and truly jaw-dropping views of Lake Michigan and the downtown skyline. Plan a waterfront picnic or a romantic stroll to surprise your sweetheart.
Explore more: Plan a romantic couples trip to Chicago.
Osaka Garden
Also in the Hyde Park area, Jackson Park offers a multitude of secluded spots to pop the question. The ornate Japanese gardens are an especially romantic option, filled with picture-perfect bridges and lagoons. The historic gardens were created for the Japanese pavilion during the 1893 World’s Columbian Exposition.
Navy Pier’s Centennial Wheel
An iconic part of Chicago history, the Centennial Wheel at Navy Pier makes for an epic proposal location. The wheel soars to heights of nearly 200 feet, offering breathtaking 360-degree views of the surrounding lakefront and cityscape. Book the VIP gondola for an extra-special experience, with plush seating and a glass bottom for even better views.
Garfield Park Conservatory
The historic Garfield Park Conservatory is one of the largest botanical conservatories in the country. Brimming with thousands of plant species from around the world, the Conservatory offers a variety of proposal spots. Get on one knee in their lush outdoor gardens or step inside the glass greenhouses to discover lush tropical flowers and calm pools. Plus, they also rent their space for weddings.
Chicago helicopter tours
Looking to splurge for the big day? Vertiport Chicago offers a romantic proposal experience that lets you pop the question in a truly unforgettable way. Their luxury helicopter tours provide one-of-a-kind views of the skyline, lake, and iconic monuments and landmarks — creating a moment that you and your partner will never forget.
