Wicker Park Chicago Engagement Session

I love Colette and Gentry! They’re just one of those couples that you love talking to and are easy to get along and flow with. We had the best time during their Wicker Park Chicago engagement session. The couple wanted their session to be in their neighborhood where they live and love and show off their favorite parts of the Wicker Park area. They also wanted their images to show them in their natural and relaxed state, enjoying the city while walking together hand in hand.

Downtown Chicago from rooftop of Robey Hotel

Wicker Park Chicago Engagement Session

As we explored the nearby streets of Wicker Park, their adorable puppy, Lottie, joined us. This sweet pup is named after the bar where they had their first date. After hanging with Lottie, we went to the Robey Hotel Rooftop for drinks. It was the perfect spot with an intimate interior and amazing views of the city from the rooftop. This place was a fun and special spot to capture their engagement portraits too because you could see Colette and Gentry’s place from the rooftop, as well as the park where they got engaged. The hotel is also where Gentry’s parents stay when they are in town.

Their Story

Colette and Gentry met right after Gentry moved to Chicago from DC. The couple met at Gilt Bar in Chicago for their first date. When they arrived, it was packed and they couldn’t get a table. Instead, they stood off to the side and talked. However, fate stepped in as Colette ran into someone she knew who was leaving and offered her their seats. They stayed for another round and have continued talking and sharing cocktails together ever since.

Gentry’s proposal was incredibly thoughtful and sweet. Colette loves all the thought and detail Gentry put into it. The day started with Colette planning to go Christmas shopping. Gentry suggested they might go to the Walnut Room for lunch. However, it was all a ruse. He took her to their neighborhood park and had a friend there to document the special moment. After he popped the question and she said “YES!”, they headed to what Colette thought was a drink with her brother, but it turned out to be a huge surprise party with all their loved ones!

I could have talked to these two all day! We had such a wonderful time together and I loved learning about their love story, witnessing their chemistry, and capturing their timeless engagement portraits in the Wicker Park area they love. I am beyond excited for their upcoming March wedding!


View more resources, timeless wedding day moments, and romantic engagements on the blog: 

Classic Sunset Ridge Wedding

12 Best Chicago Engagement Session Locations

Chic Chicago Wedding Celebration at City Hall Chicago Events

Capturing Your Wedding Day: 6 Things I Won’t Do as Your Wedding Photographer 

Candid Chicago Engagement Session at Local Brewery and North Ave Beach

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