THE BEST PLACES
FOR A SURPRISE PROPOSAL
IN CHICAGO
North Avenue Beach
Skyline View
Romantic city backdrop with the Chicago skyline reflecting on Lake Michigan. Especially stunning at sunset or just after dusk when the skyline lights up.
Milton Lee Olive Park
Less crowded than Navy Pier, but still with spectacular skyline and lake views. It’s tucked away and feels more private.
South Pond at Lincoln Park
(by Café Brauer & the Boardwalk)
Boardwalk paths with water, city reflections, and nature all around. Very photogenic, especially in fall or spring.
Adler Planetarium
Lakefront Point
One of the most classic spots for proposals in Chicago. Sweeping, unobstructed skyline views across the water — especially stunning at golden hour or twilight when the lights sparkle. Plenty of space to find a quiet corner, despite its popularity.
The Honeycomb
(People’s Gas Pavilion)
Architectural wood pavilion with nature and skyline in the background. Perfect for framing a proposal.
Alfred Caldwell Lily Pool
Peaceful, nature filled escape tucked near Lincoln Park Zoo. Lush greenery, stone paths, and water features.
Humboldt Park Boathouse
Beautiful lagoon and arched stone bridges with European charm. Lots of space to find a quiet spot.
Lurie Garden at Millennium Park
Less crowded than “The Bean” and filled with flowers, grasses, and seasonal blooms. Offers both nature and city views.
Montrose Harbor & Bird Sanctuary
Romantic walking paths, wildflowers in summer, and skyline peeking over the lake. Offers both open water and cozy, secluded corners.
