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Downtown Chicago Engagement Photos | Rose + Connor

Having your engagement photos done in downtown Chicago is a magical experience for any couple! The city’s diverse landscapes offer a unique blend of urban charm and natural beauty. It’s an ideal backdrop for documenting love stories! From the towering skyscrapers and historic landmarks to the serene lakeside and vibrant street life, every corner of Chicago provides a picturesque setting for memorable engagement photos.

About Rose + Connor and Their Session

Capturing the love story of Rose and Connor was truly memorable. Our engagement session began at the exact street corner where Connor proposed to Rose, a spot filled with sentimental value and the start of their beautiful journey together. As we visited each location, the city’s vibrant energy and picturesque backdrops provided the perfect setting for their engagement photos throughout Chicago!

Next, we went to their favorite hotdog joint, Byron’s Hot Dogs, a cherished spot where many of their meals together took place. The bustling atmosphere and delicious food added a personal touch to their session! Our next stop was Union Station, where the grandeur of the architecture offered a timeless elegance to their portraits. Walking along the Riverwalk, we captured candid moments of joy against the serene waters and urban landscape. Finally, we ended our day at North Avenue Beach, walking along the Chicago skyline and chasing the birds on the beach. This engagement session beautifully encapsulated the essence of their love in the city they adore!

Next up, Rose and Connor will tie the knot in October of 2025 at Sarabande, a modern and private venue in downtown Chicago. To say we are HYYYYYYPE is an understatement!

Need Your Own Engagement Photos in Downtown Chicago?

We’re excited to show you all the hidden gems Chicago has to offer! And of course the iconic locations, too – if that’s your thing. We really love crafting an engagement session that feels authentic to each and every couple. We take the time to get to know you and your boo before your session so we can help you choose the perfect locations to document your love story. If you’re ready to get in touch, fill out our contact form here, and we’ll get back to you ASAP! Can’t wait to chat and stroll around the city with you! <3

“I really have no words to describe how amazing these are! You captured so many amazing moments and we are so grateful!”

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