When it comes to unforgettable marriage proposals, few settings rival the elegance of a private yacht gliding through downtown Chicago at sunset.
Yesterday evening, the Windy City played host to one of its most romantic moments as Connor proposed to Claire aboard a luxurious 38-foot Sea Ray Sundancer.
Originally, Connor had envisioned a picture-perfect proposal on Lake Michigan with Buckingham Fountain shimmering in the background. But true to Chicago’s nature, high winds and rolling waves had other plans. Ever the romantic and quick thinker, Connor embraced the moment and pivoted. With the sun beginning to dip behind the skyline, the yacht’s captain charted a new course, steering through the calmer waters of the Chicago River.
As the Sea Ray Sundancer cruised past iconic Chicago architecture — from the Wrigley Building, part Marina Towers and toward City Winery — the golden hour cast a breathtaking glow over the city. With the wind in their hair and the soft hum of the water beneath them, Connor dropped to one knee beneath the illuminated cityscape and asked Claire to be his forever.
Clarire was again surprised when she realized Connor had arranged for family and friend to join them on the Chicago Riverwalk at City Winery to host an initiate afterparty following their proposal.
Thinking of Proposing in Chicago?
At Jason Kaczorowski Photography, we’re honored to be trusted with capturing luxury proposals like Connor and Claire’s. Whether it’s a surprise engagement at the Field Museum, a romantic engagement at the Alder Planetarium, or a private proposal aboard a luxury yacht sailing along the Chicago River, we specialize in photographing the kind of moments that feel straight out of a dream and delivering images that preserve those memories forever.
Connect with us today to begin planning your Chicago proposal. We would be honored to help orchestrate and photograph your proposal in Chicago!
Chicago Proposal Photographer, Luxury Proposal in Chicago, Yacht Engagement Photography, Sunset Proposal on Chicago River, Best Places to Propose in Chicago, Private Yacht Proposal, Chicago Engagement Photography, Romantic Chicago River Proposal, Chicago Skyline Proposal, Surprise Enga 
