Montrose Harbor Engagement Session – Sydney & Dylan

On one of the last seasonably winter days in Chicago, I met Sydney, Dylan, and canine Conan at their home in Lakeview. The four of us went for a chilly afternoon stroll around the neighborhood, stopping by the historic Music Box Theatre for a few portraits. Conan was such a trooper! We were able to squeeze in some family photos (and puppy kisses) before heading back to their living room to warm up a bit. I think Conan liked that part the best 🙂

After some couch time, we said goodbye to Conan and headed to Montrose Harbor. I learned that Sydney and Dylan met while living in Kansas in a theatrical performance of A Streetcar Named Desire. Sydney even showed me a photo of them on stage together! What an awesome piece of history to hold on to. We talked about their upcoming wedding in Lake Tahoe, which will be a low-key affair in a park that shares Dylan’s last name. With my personal love for both intimate wedding ceremonies and travel out west… let’s just say, we had plenty to talk about.

Sydney and Dylan: thank you for braving the end of winter with me! We made some incredible images together, and I truly enjoyed meeting you both (Conan too!). I hope your wedding this summer turns out to be everything you dream it will be.

black and white Chicago engagement photo
lifestyle engagement session walking dog in Lakeview
couple crossing the street with dog
lifestyle engagement session in Chicago crossing street
lifestyle engagement documentary photography
Music Box Theatre sign in Lakeview
Music Box Theatre lifestyle engagement photo with dog
candid moment of couple with dog at Music Box Theatre
Chicago lifestyle engagement session at Music Box Theatre in winter
candid moment of couple giggling with dog outside of Music Box Theatre
Chicago lifestyle engagement session family photo at Music Box Theatre
couple with dog at home engagement session
black and white engagement ring closeup
Chicago lifestyle home engagement session with dog
dog looking at owners at home engagement session
lifestyle home engagement photo with dog
lifestyle engagement session with couple at Montrose Harbor
engagement ring closeup at Montrose Harbor
lifestyle engagement couple giggling together at Montrose Harbor
winter engagement session at Montrose Harbor
bird sanctuary at Montrose Harbor lifestyle engagement session
Chicago lifestyle engagement session at Montrose Harbor bird sanctuary
spooky black and white lifestyle engagement photo
lifestyle engagement session couple looking at each other
couple walking through bird sanctuary at Montrose Harbor
lifestyle engagement session at Montrose Harbor
documentary lifestyle engagement photo at Montrose Harbor
Chicago lifestyle engagement session couple walking by the lake
windy lifestyle engagement session in Chicago
artistic engagement photography
couple embrace with Chicago skyline at Montrose Harbor
winter engagement portrait at Montrose Harbor
closeup of engagement ring at Montrose Harbor
black and white artistic lifestyle engagement photo
winter lifestyle engagement session at Montrose Harbor
black and white engagement photo at Montrose Harbor

7 Replies to “Montrose Harbor Engagement Session – Sydney & Dylan”

  1. Megan Saul says:

    This is a gorgeous session!

    1. Emma says:

      Thanks Megan!! One of my favorites to date.

  2. Adam Hart says:

    Great photos of the couple in a variety of settings. Loved the pictures with their ‘furry’ family member, Conan.

  3. I love lifestyle engagement sessions, but even more when they include pets! The photos between the big trees, as well as the ones by the water are my favourite <3

  4. Emma says:

    Thanks everyone! Lifestyle is definitely the direction my work is taking me, I really enjoy at-home sessions too.

  5. Hanna says:

    What gorgeous couple! I love how you capture them exploring the city!

  6. Audrey says:

    That first photo is EVERYTHING!! Love the dog family 🙂

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