Timeless Chicago Engagement Photos at the Art Institute & Around the City

Audrey and Shane's fall engagement session took us all over downtown Chicago, and these Chicago engagement photos are one of my favorite examples of what a session in this city can look like.

Audrey found me because I photographed her sister's wedding back in 2023, and she knew right away she wanted me for her own big day too. That kind of trust means everything to me, and getting to photograph her engagement session before her wedding felt like such a full circle moment. We started at the Art Institute and made our way to North Avenue Beach, chasing that perfect fall light the whole way.

Chicago engagement photos on the lakefront, with a man twirling his fiancée in a red dress in front of the skyline

Chicago Engagement Photos at the Art Institute

The Art Institute is one of my favorite spots for Chicago engagement photos, and you don't even need a permit to shoot there just a ticket to get in! We spent our time inside the galleries; we walked around and took photos with the moody gallery walls, the grand staircases, and all that incredible artwork surrounding these two!

It's such a fun location because it doesn't feel like your typical outdoor engagement session. You get to walk through room after room, and every space gives you a completely different backdrop, from classic paintings to bold architecture. If you want your Chicago engagement photos to feel a little more artistic and unique, the Art Institute is such a great spot to add to your list.

Golden Hour at North Avenue Beach & Wandering Around the city

One of my biggest tips for couples: where you shoot should decide when you shoot! We planned our second location at North Avenue Beach around sunset specifically so you can have stunning photos on the water with the sunset on the city! It also helps if your photographer knows the lighting and the spot ahead of time so you can plan the whole session around getting there at exactly the right moment.

The shift from the museum's old-world charm to the open lakefront and skyline gave us two completely different moods in one session, and that contrast is part of what makes Chicago such a fun city to shoot in. You get history and skyline in the same afternoon!

Chicago engagement photos at sunset, with a couple embracing along Lake Michigan, the skyline behind them and her in a red dress

Go Bold: Why Color Works So Well in Chicago Engagement Photos

Audrey wore two outfits for this session: a bold red dress and a softer cream sweater dress for something more neutral, and both worked so well with the museum and the city aesthetic. She even splurged on a pair of designer Louboutin shoes just for the shoot, which was such a fun addition!

And if you're worried about fitting in an outfit change like that, don't be! Audrey and Shane's session ran almost 3.5 hours between two locations, two outfits, and some Chicago traffic, and that's exactly why I don't put a time frame on engagement sessions. Most run about 45 minutes to an hour and a half, but if you need more time to change, travel, or just soak up a second location, I’m always happy to keep shooting! I'd rather you leave with photos you love than watch the clock the whole time.

Here's what Audrey had to say about working together:

"I was fortunate enough to have met Rachel because she shot my sister's wedding in 2023! She was so much fun to work with, and I could not be more impressed with how all the photos turned out. Rachel did an amazing job making our engagement shoot dreams come to life. We were able to go around to our favorite places in downtown Chicago, and she captured our love in such an amazing way! Not only did she have our previews ready for us within 3 days, but she was also so timely in delivering our full gallery as well. I could not recommend Rachel more; I tell everyone I know about our amazing experience with her."

Ending the Day With a Celebratory Drink

Once we wrapped up, Audrey and Shane treated me to a drink at Gus' Sip N Dip, one of my go-to recommendations since our original spot closed down. We sat and talked through their wedding plans, and it was such a sweet way to end the day.

One of my favorite parts about my wedding packages is that each one comes with an engagement session. I do this because I think it is super important to work together before the big day and so that you and your partner get more comfortable in front of the camera! Engagement pictures are also fun to use for Save the Dates and Invitations- you best believe I want a copy so I can proudly put it on my fridge. Engagement sessions can be during whatever season you prefer, normally last about 1-2 hours, consist of a formal & casual outfit, and can involve multiple locations!

Chicago engagement photos on the lakefront, with a woman in red wrapping her arms around her fiancé, skyline behind them

Ready to book your Chicago engagement photographer?

Chicago engagement photos like these start with a location you love and a little bit of confidence in what you wear. Give me all the details about you two, and I'll help you plan a session that feels just as good years from now as it does today!

Rachel Ruth Photography | Chicago Wedding Photographer