There’s something truly magical about a summer engagement session in downtown Chicago—especially at Milton Lee Olive Park during sunset. Nestled right along the lakefront, this hidden gem offers breathtaking skyline views, peaceful pathways, and the perfect golden-hour glow.


When Hannah and Dan chose this location for their engagement photos, I knew we were in for something special. The combination of stunning city views, lush greenery, and a peaceful waterfront vibe made for the dreamiest backdrop.


Why Milton Lee Olive Park is the Perfect Summer Engagement Spot

  1. Unmatched Skyline Views – The Chicago skyline feels like it’s straight out of a postcard, adding an iconic city-chic feel to every shot.
  2. Golden Hour Glow – As the sun sets over the lake, the light becomes soft and golden, making everything look warm and romantic.
  3. A Mix of City and Nature – You get the best of both worlds: the serene lakeshore and greenery, plus that bold, urban backdrop.
  4. Less Crowded Than Other Spots – While Navy Pier and North Avenue Beach are packed in the summer, Olive Park offers a quieter, more intimate setting.


A Dreamy Sunset Session

Hannah and Dan showed up in the perfect summer outfits—light, airy fabrics that complemented the golden hues of sunset. We strolled along the tree-lined paths, capturing natural, joy-filled moments, then made our way toward the water just as the sky turned shades of pink and orange.


Some of my favorite shots? The sweet, in-between moments—like Dan stealing a kiss on Hannah’s forehead or the two of them laughing as the city lights started to twinkle behind them. It was the perfect mix of romance, fun, and timeless Chicago charm.


Planning Your Own Chicago Engagement Session?


If you’re dreaming of a downtown engagement session with stunning city views, Milton Lee Olive Park is one of the best spots—especially in the summer! Whether you want chic and sophisticated or playful and romantic, I’d love to help bring your vision to life.


Let’s make some magic happen! Contact me to book your engagement session.

A couple embraces during sunset on a beach with the Chicago skyline featuring the John Hancock tower in the background.
A couple embraces along the Chicago Riverwalk with the iconic downtown skyline of high-rise buildings in the background.
A romantic embrace on North Avenue Beach in Chicago with the iconic John Hancock building and skyline at sunset.
A couple walks along the Chicago River shoreline at sunset with the iconic downtown skyline in the background.
A couple showing off an engagement ring on the beach at sunset with Chicago's skyline in the background.
A romantic couple embraces on a waterfront overlook with the Chicago skyline and Lake Michigan in the background.