I've made this post not as Chicago-centric as usual because I think that for engagement photos it's worth it to drive the extra mile out of the city to places like Indiana and the north suburbs to get the location that suits your style as a couple more. If you're like me and my couples, having the typical skyline shot of downtown Chicago isn't really what you're going for - and trust me I recognize the irony of that, being a Chicago photographer and all. This list is made up of some of my favorite engagement photo places both in and near Chicago, unabashedly emphasizing the less stereotypical cityscapes. :)
Close to Home
Pretty much anywhere along the lakefront is beautiful, but far up on the north side is adorable Loyola Beach. It's full of sprawling gorgeous grassy areas, a long pier that leads out to a lighthouse (yes, a lighthouse!), and a nature preserve that reflects the history of Illinois. There's always people having cookouts, kids playing in Lake Michigan, and plenty of gorgeous backdrops for you and your lovey.
West Ridge Nature Preserve
I've been to this location multiple times now, and still haven't explored the whole space. There's romantic bridges, a hill with a gray stone outlook above the entire preserve, a large pond, weeping willows, and apparently a desert area that I haven't even found yet. This is truly one of the gorgeous hidden gems of the city, it makes you feel like a princess just to walk around in it, and definitely one of my best recommendations for my couples.
A Little Further Out
Indiana Dunes State Park
This one isn't exactly in Chicago, but since Indiana isn't all that far away (and believe it or not Indiana does have some pretty sights to offer), I've added it to the list! The Dunes have expansive hills of sand with trees that line the tops of them, long grass to walk through, and they also have a clay pit that could be fun to play in. :) There's also a forest area that is amazing to explore because it has great views along the entire shoreline.
County Line Orchard
County Line Orchard is this sweet little place in Indiana, the farthest place from Chicago on this list. But it's worth it! The place is gorgeous - massive apple trees, lined up as far and high as the eye can see, with a long wooden fence containing them. It smelled like spring even though it was late in the summer, and it definitely created an experience being there, away from the city and completely engulfed in nature. I could have spent hours wandering around here on my own!