A Summer Chicago Engagement Session with Beers, Fries, and a Lake Jump

There’s something so fun about a Chicago engagement session that feels like date night, and that’s exactly what Carley and Zak created! Their session was the perfect mix of casual, playful, and romantic. We started at Hopleaf, their go-to Andersonville bar for beers and fries, and ended the night at Montrose Beach, where they spend their summer evenings playing volleyball and swimming in Lake Michigan. From cozy barstools to splashing in the lake, every part of this shoot felt like a celebration of their love and their city!

Drinks and Fries at Hopleaf For Their Chicago Engagement Session

Carley and Zak wanted their engagement session to feel like them, so of course, we had to start at their favorite spot. Hopleaf has been the backdrop for countless date nights and dinners together, making it the perfect choice to set the scene. Between sipping on pints, sharing “the best fries in the city,” and sneaking kisses at the bar, they looked so comfortable and happy. The warm, lively environment of Hopleaf paired perfectly with their playful energy, and I loved how the photos captured that balance of fun and romance. Choosing a meaningful spot like this makes the images feel so much more personal and timeless.

Summer Nights at Montrose Beach

After drinks, we headed to Montrose Beach to soak up the summer vibes and the beautiful evening light. This spot holds so many memories for them, playing volleyball, swimming, and enjoying long Chicago summer nights. We started with sweet, candid moments walking along the sand and laughing together, then let the session unfold naturally as they splashed in the water. By the end, they were both in the lake, fully dressed and totally carefree, sharing kisses and laughter as the skyline lit up behind them. It was such a perfect way to capture their adventurous side and the joy they bring out in each other!

Ready for Your Chicago Engagement Session? Let’s Chat!

Sarah Kellie | St. Louis Engagement Photographer

Carley and Zak’s session is proof that the best engagement photos happen when you pick locations that mean something to you! Whether it’s your favorite bar, the beach you love, or a hidden Chicago spot you can’t get enough of, I’d love to capture your story in a way that feels real and personal. If you’re planning your own Chicago engagement session and want it to be as fun and authentic as this one, let’s make it happen together! Head to my contact page so we can chat about all the amazing ideas you have! If you want to learn more about me and what I do, click here. Can’t wait to hear from you!