Chicago Engagement Photos at Milton Lee Olive Park & the Riverwalk

These Chicago engagement photos were taken at Milton Lee Olive Park and the riverwalk downtown!

Matt & Jess found me through Stephen Hamilton, a world renown (literally) food photographer who works with the likes of McDonald’s, Arby’s, and everyone else! He owns Room 1520 in West Town and I’m lucky enough to be on his short list of preferred wedding photographers!


Our engagement session was scheduled for November and unfortunately all the leaves had fallen, so all Chicago’s parks look sad and dead. When there’s no greenery around, I always suggest skyline, city-oriented, or lakefront views to keep the photos looking nice!

Location #1: Milton Lee Olive Park

We started at Milton Lee Olive Park with the insta-famous MrKevindoodle — thinking of bringing your dog to your engagement session? Read my top 4 tips here! — Matt & Jess have been taking pictures of him since he was little so he’s a gem to work with!

Location #2: The Chicago Riverwalk

After we said bye to Kevin (always bring a handler who can watch your dog during the engagement session) we started walking downtown. We stopped by Foxtrot for a quick americano and change of clothes. With a new outfit and warmed hands, we were off again.

I love engagement sessions because they give us a chance to just chat and get to know one another. This goes a long way to helping you feel comfortable in front of the camera.

We started at The Wrigley Building in the courtyard. At this time of year there were lots of shoppers and the giant Christmas tree.

From there we just walked west along the river and stopped for photos when one of us saw something we really liked. With numerous bridges to choose from and some rad architecture along the riverwalk, it’s easy to find a ton of cool backdrops.

Enjoy these November engagement photos at Milton Lee Olive Park and the Riverwalk in downtown Chicago with the dog!!

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