Sanjit & Shivani’s Pendry Chicago Rooftop Winter Surprise Proposal
On this winter day, snow gently blanketed the city, transforming the rooftop into a quiet, magical escape above the bustling streets below. Sanjit led Shivani to the rooftop under the guise of a casual outing, where the skyline framed the moment perfectly.
As the snow fell around them, he got down on one knee—and Shivani said yes.
A snowy proposal in Chicago adds a level of romance that’s hard to replicate. The soft snowfall naturally diffuses light, creating a dreamy atmosphere that photographers love. Rooftop venues like Pendry’s Château Carbide provide both indoor and outdoor spaces, allowing couples to stay warm while still enjoying breathtaking city views. The rooftop decor was a cozy holiday scene with fire heaters, cozy booths and Christmas greenery covered in snow.
After the proposal, Sanjit & Shivani continued their session at Milton Lee Olive Park—one of the most iconic skyline photo locations in Chicago.
With Lake Michigan in the foreground and the city rising behind them, Olive Park offers a clean, unobstructed view of downtown Chicago. Even in winter, it remains a favorite for engagement sessions thanks to its peaceful atmosphere and stunning perspective.
Their portraits here felt completely different from the rooftop—open, expansive, and filled with that unmistakable Chicago skyline energy.
Sanjit & Shivani came all the way from Texas to get engaged and to later share a celebration with local family. It was a subzero day and they were such good sports, even bringing a change of shoes to be able to scale the icy platform at Olive Park. There is no such thing a proposal season, couple are choosing Chicago all year round to be the place for their Surprise Proposals.
For tips on planning a surprise proposal in Chicago, check out my blog on How to Plan a proposal here. For help finding the perfect location for your surprise proposal, check out my blog on popular Chicago locations here. For specifically skyline locations , Click here to see a list of skyline locations.
When you are ready to book please reach out to me so we can get your desired date locked in! Contact Me Here!
Check out my Instagram ( Click Here ) for frequent photo updates