Evan & Jordan’s Winter Holiday Surprise Proposal at Chicago’s Olive Park

Evan & Jordan had a truly unique proposal at the beginning of the winter during the holiday season when many couples are visiting downtown to holiday shop and enjoy holidays festivities. Evan knew a few important things about his partner when it came to planning a Chicago trip. He knew Jordan wanted a professional to photograph the proposal. He also knew how much Evan loved the holiday season in Chicago. Jordan has great taste as Chicago is simply magical during the holidays.

The proposal itself took place at Olive Park in the lookout ledge. When I arrived I noticed the most gorgeous pancake ice had formed on the lake and because it was close to sunset the sun was making a door of light that was shining over the lake illuminating the ice in the most uncanny cinematic scene. It’s such a rare occasion to see pancake ice. I couldn’t believe I got to capture it all for the backdrop of a Surprise Proposal. Once the proposal took place we ventured to Michigan Ave where we stopped at The Wrigley Building to capture them around the Holiday decor.

As a Chicago proposal photographer, I have the honor of documenting some of the most meaningful moments in people’s lives—and Evan & Jordan’s winter surprise proposal at Olive Park is one I won’t forget. If you’re planning a surprise proposal in Chicago and looking for an LGBTQ+ friendly photographer, their story is a perfect example of how thoughtful planning and the right location come together beautifully. As someone who proudly works with all couples, creating an inclusive and affirming experience is a core part of what I do. When you’re planning something as personal as a proposal, you deserve to feel completely comfortable being yourselves.

 

 

a landscape of the chicago skyline from Olive Park with pancake ice on the lake

Man kneels to propose by the lake with Chicago skyline behind them as partner reacts with surprise

Man places engagement ring on partner’s finger by the lake as Chicago skyline glows in the background during a surprise proposal

Close-up of one man placing an engagement ring on his partner’s finger by the lake during a Chicago surprise proposal

One man kisses his partner’s cheek by the lake with Chicago skyline behind them, celebrating their surprise proposal

 

 

Close-up of hands intertwined with engagement ring , lake water softly blurred in background after a Chicago proposal

Close-up of blurred hands intertwined with engagement ring , lake water with ice in focus in background after a Chicago proposal

Couple sitting together by the lake with Chicago skyline behind them, posing for an engagement photo

Couple sitting together by the lake at sunset with Chicago skyline behind them, posing for an engagement photo

Couple holding hands by the lake with Chicago skyline behind them, posing for an engagement photo

Couple holding hands by the lake with Chicago skyline behind them, posing for an engagement photo at Olive Park

 

 

Couple on Chicago Riverwalk posing for an engagement photo

Couple walking down Chicago Riverwalk steps with skyline behind them, posing for an engagement photo

A same sex couple holds hands and walk across michigan ave during a chicago winter

A same sex couple poses for an engagement photo at the Wrigley Building in Chicago with Christmas Decor

A same sex couple poses for an engagement photo at the Wrigley Building in Chicago with Christmas Tree

A same sex couple poses for an engagement photo at the Wrigley Building in Chicago with Lit Christmas Tree

Couple smiling on Chicago Riverwalk steps with skyline behind them, posing for an engagement photo

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