Personal

Travel

Tips

Podcast

Environmental

Portraits

Couples

Elopements

Browse by Category

A collection of stories. We are all about photography for those who are crazy in love and education for photographers who love capturing the madly in love.

The Journal

Proposals

A Surprise Proposal with the Chicago Skyline: Lincoln Park Boardwalk Edition

There’s something undeniably romantic about a skyline view at golden hour—and when it’s paired with a heartfelt proposal, it becomes pure magic. Will and Addison’s Lincoln Park Boardwalk Surprise Proposal was just that.

Engagement Photos in front of the People's Gas Pavilion in Lincoln Park

Nestled between the serene South Pond and the iconic Chicago skyline, the Lincoln Park Boardwalk has become one of my favorite spots for proposals. Its undeniable, the way the light dances across the water, the soft rustle of the trees, and the peaceful hum of the city in the distance—it all adds up to an atmosphere that’s effortlessly romantic and intimate.


For Will, this location is the perfect scenic backdrop. He reached out to me with a clear vision: a low-key, genuine proposal moment with Addison, followed by some candid portraits that would capture the joy and emotion of the day. No elaborate staging—just real emotion and a timeless city view.

Surprise Proposal moment on the Lincoln Park South Pond Bridge.

As they walked up the path, the moment felt suspended in time. Her reaction was filled with surprise, laughter, and emotion—the kind of authentic response I always hope to witness behind the lens. The skyline stood tall behind them, grounding this milestone in the city they love.

After she said yes, we wandered the boardwalk for a short portrait session. The simplicity of their outfits paired perfectly with the urban-meets-natural vibe of the location. Every glance between them was filled with warmth, love, and the unmistakable excitement of what’s to come.


Proposing at the Lincoln Park Boardwalk: What to Know

If you’re considering a proposal at the Lincoln Park Boardwalk, here are a few tips to make the most of the moment:

  • Timing is everything: Sunset offers the most flattering light and paints the skyline in a soft, golden hue. Early mornings are also quiet and beautifully serene.
  • Know the layout: The boardwalk loops around the South Pond and offers several picture-perfect angles. I can help you scout the ideal spot based on light and crowd levels.
  • Keep it simple: This location doesn’t need a lot of extras. Its natural beauty, skyline views, and calming water create a romantic atmosphere all on their own.
  • Hire a photographer in advance: Capturing the reaction—the joy, the surprise, the emotion—is something you’ll never regret. I’ll be there early, blend in discreetly, and help guide the post-proposal portraits so you can just soak in the moment.

Thinking of popping the question?
Let’s create something unforgettable—I’ll be there to document every laugh, every tear, and every yes.

📍 Explore more surprise proposal photography at Lincoln Park Boardwalk and beyond at Ashlee Cole Photography.

Read & Leave a Comment 

Share Post

Leave a Reply

Your email address will not be published. Required fields are marked *

You might like these latest posts:

Let's make waves

Meet me in the City or at theLake