You’ve found “the one.” You’ve bought the ring. Now all you have to do is plan the perfect spot to ask that million-dollar question. In Chicago, you’ve…

He proposed on a Chicago rooftop with the Chicago skyline in the back! Read more on How They Asked! #howtheyasked #chicago #chicagoskyline #chicagoproposal #engagement #engaged #engagementideas #cityengagement #howtopropose #weddinginspo #proposalinspo #dreamproposal #summer

Planning to propose in Chicago? Discover the perfect spot to pop the question with our guide to the best proposal locations in the city. From romantic vistas to unique settings, we help you find a place that's both special and meaningful. Learn how to choose a venue with sentimental value, consider important factors like privacy and lighting, and prepare for any weather. Make your proposal unforgettable with our top Chicago proposal ideas, ensuring a magical moment filled with joy and love.

Families, engagements, couples, senior photos and more. I want to capture your story.

Chicago proposals are so sweet, especially around the holidays! Xhoi found me on Instagram and reached out for a surprise proposal at a rooftop bar. He planned out every detail! It was so lovely meeting these two and documenting their love for each other, and the city.

Will's proposal to Taylor happened on the bow of a boat floating just off of the shores of Chicago one evening in late August.

Chicago Rooftop Proposal Flowers and Candles

Chicago Proposal Engagement Photographer. Photography by Lauryn.

Thinking of proposing in the Windy City? Here's our list of the best places to pop the question in Chicago, with perfect settings for every type of person.

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