Seventy-four degrees and sunshine in Chicago at the end of October?! What a night for Kaylee and Jonathan’s engagement session! With fall color around Lincoln Park’s Honeycomb and the skyline at North Avenue Beach, we had such a beautiful mix of nature and city. I LOVE this session, and I’m so excited to share a few favorites!


I first met these two this past summer at Meghan and Matt’s wedding at Cog Hill, where I was second shooting with Rachael Watson. Kaylee is Meghan’s sister, so getting to see them both again and celebrate their engagement was extra sweet!


Their story began in 2016, when a school exchange program brought Jonathan from Barcelona to Chicago. He and Kaylee first met at the Art Institute, and that introduction turned into years of friendship, hours-long Skype calls, and eventually love. Even through college and three years without an in-person visit during Covid, they kept showing up for each other.


When Jonathan was ready to propose, he secretly flew to Chicago for just 48 hours to ask for Kaylee’s parents’ blessing! He later proposed in a rose garden in Madrid, choosing a spot facing west toward Chicago. Such a thoughtful way to include the two countries that have been part of their story from the beginning!


That made photographing their engagement in Chicago even more meaningful. We got to celebrate where it all started while they look forward to their June wedding in Barcelona! They’ll gather with both of their families for Mass at the Marist school there, bringing their story full circle. After so many years of flights and goodbyes, there is so much to celebrate!


Kaylee and Jonathan, I loved spending this evening with you! Thank you for trusting me to capture such an exciting season. I’m so happy for you both! Now grab a blanket and snuggle up, your sneak peek is LIVE!!

Couple embracing beneath the stone arch of a historic monument topped with an equestrian statue, framed by autumn trees at sunset.
Solitaire diamond engagement ring with a six-prong setting resting on a red autumn leaf with a softly blurred background.
Smiling couple embracing in a stone tunnel with warm golden light glowing behind them during an engagement photo session.
Smiling woman with long blonde hair in a navy sweater laughs as her partner embraces her, his wristwatch and her ring visible.
Smiling couple holding hands while walking up weathered stone steps surrounded by large stone walls and green trees.
Couple in neutral outfits dancing hand in hand beneath a historic stone arcade with rounded arches and greenery in the background.
Couple embracing on a paved park path surrounded by trees and golden grass in soft morning light during an outdoor engagement photo session.
Smiling couple embracing outdoors in a golden grassy field with soft autumn light, the woman in a navy top and the man in a beige sweater.
Couple holding hands and walking along a sunlit dirt path surrounded by tall golden grasses and trees during an outdoor engagement photo ses
Couple embracing in a romantic dip beneath a curved orange wooden arch pavilion with greenery and a city skyline in the background.
Smiling couple embracing outdoors as a man in a tan quarter-zip leans in to kiss a woman in a navy sweater on a sunny wooden boardwalk.
Couple embracing and about to kiss beneath a curved orange wooden lattice archway on a sunny day, outdoors.
Couple holding hands and walking inside a modern wooden lattice pavilion with sunlit curved arches and a scenic hillside view.
Black and white photo of a smiling couple embracing closely, the woman's hand resting on the man's chest, in an engagement-style portrait.
Smiling couple embracing inside a modern wooden pavilion with curved lattice arches during a sunlit engagement photo session.
Smiling couple in casual sweaters embracing on a sunny wooden boardwalk beneath a curved orange wooden pavilion with a city skyline behind.
Smiling couple walking arm in arm across a sunlit wooden pavilion with curved slats and green trees in the background.
Couple embracing and about to kiss beneath a curved wooden lattice pavilion with a lush green park and city skyline in the background.
Couple walking arm in arm along a curved wooden boardwalk beside tall grasses and trees with a hazy city skyline in the background.
Smiling couple holding hands and walking through a golden autumn field, he in a cream sweater and she in a navy cardigan and white jeans.
Couple embracing on a wooden pier over a calm pond, with autumn trees and a hazy city skyline rising in the background.
Gold solitaire diamond engagement ring resting on colorful red, orange and yellow autumn leaves against a soft teal background.
Couple holding hands and walking along a lakefront path at sunrise with a hazy city skyline across the water in the background.
Couple embracing and smiling along a lakefront at sunset with a hazy city skyline and calm blue water in the background.
Couple dancing along a lakefront promenade with a hazy city skyline across the water, the woman in a light blue dress twirling at sunrise.
Black and white engagement photo of a smiling couple embracing near a lakefront with a blurred skyscraper skyline in the background.
Smiling couple embraces as he lifts her by the lakefront, with a hazy city skyline rising across the calm water behind them.
Smiling couple holding American and Spanish flags by a lakeside with a hazy city skyline behind them.
Black and white double exposure of a couple touching foreheads in an embrace, blended with a city skyline.
A couple holds hands while walking along a lakefront path with a hazy city skyline across the water at sunrise.
A man and woman cover their eyes with a Spanish flag and an American flag in front of a lakeside city skyline.
Couple holding hands and walking along a waterfront promenade with a hazy city skyline behind them, the woman in a light blue dress.
Couple holding hands on a beach, she in a blue striped dress with a ring, he in a white shirt and khaki pants wearing a bracelet.
Couple holding hands and walking along a sandy beach at sunset with calm water and a pier in the background.
Couple holding hands and dancing on a sandy beach at sunset, the woman in a blue dress and the man in a white shirt and khakis.
Couple kissing on a beach at dusk while the woman extends her hand to show off a sparkling engagement ring in the foreground.
Couple holding hands and walking along a wide sandy beach at sunset, woman in a blue dress and man in a white shirt, with a soft pastel sky.
Couple holding hands walking on a sandy beach at sunset, the woman in a blue dress and the man in a white shirt and khaki pants.
Smiling couple embracing and touching foreheads on a sandy beach at sunset, with calm water and a pier in the background.

Thank you again, Kaylee and Jonathan for having me! I had the hardest time narrowing down these favorites, and I cannot wait for you to see your full gallery soon!!

Thanks for reading,

Handwritten script signature reading xo xo, Cassie in soft taupe cursive lettering on a white background.