Sunset Engagement Pictures in Downtown Chicago | Jenna + Adam

The dreamiest downtown Chicago engagement pictures there ever were...

Ya know those days where everything goes right? You wake up in a good mood, the weather is awesome, and you're getting more excited as the day goes on? That was this.

I met Jenna and Adam at the West Loop Wedding Walk back in January, and we all planned another day to meet up for some drinks to chat about all the wedding things. Fast forward a few months and we finally got to get these two's engagement pictures in despite all the curveballs thrown at everyone lately because of Covid. Jenna and I had been texting about this shoot probably every week once we started getting closer, exchanging outfit ideas and pictures, tips on how to make the most of her session (like doing your wedding hair and makeup trial the day of engagement pics!), and figuring out the exact plan for the evening. Jenna chose a couple dresses from a list I had sent over, including one from this list, and a casual outfit for their evening engagement pictures.

Afterwards, we drank what was left of the champagne on the walk back to their apartment where we hung out for a bit, watched some trash tv (the best kind, obviously), played with their dog, and I tried the Spotted Cow for the first time (!). Needless to say, I'm obsessed with these two and can't wait for their wedding next spring at the Drake Oakbrook.

I'm so thrilled with how this session turned out, and even though I'm usually more of a fan of nature in pictures, I can't get over how beautiful the city turned out in these downtown Chicago engagement pictures.

As I'm writing this, I'm having such a hard time picking which of the ~140 pictures to share because I truly love them all. These two were SO much fun, laughing all day, being goofy and sweet and open to anything I suggested.

After starting off their engagement pictures at the Board of Trade for those classic Chicago shots, we headed a few blocks east to Millennium Park to soak up more of the gorgeous Chicago skyline at sunset.

Tip for an awesome engagement session:

Choose a location where you can easily walk a few blocks to another spot for completely different scenery. We were able to fit in the Board of Trade, the Chicago Skyline from this bridge and from further south in Grant Park, and the Lakefront Trail in these Chicago sunset engagement pictures since they're all pretty close (and we had comfy shoes for the walks)! This adds so much variety and gives you way more options to choose from later.

We had the best light all evening after a day full of storms and clouds in the forecast, and this set in the trees at Millennium Park is e v e r y t h i n g. I love how the trees look more blue as they get farther away, and nothing beats that romantic golden hour light that makes you feel like you're in a movie for sunset engagement pictures in Chicago 🔥🔥🔥.

A quick outfit change and we were off again to see the skyline from another view.

This used to be my favorite part of the park to go hang out at during breaks between class in my college days (like what, a year ago? lol) and I haven't been to downtown much lately, so it was fun to go back and see everything in bloom and alive and thriving even though the city is a little more empty. Chicago has so many great green spaces around, and the mix of nature + city is my happy place.

Finally, we headed to the lakefront for some red-dress, champagne popping engagement pictures!

I love every mood that happens during a wedding day, but I am SO DANG OBSESSED with Jenna's laugh that I'm going to make it my goal to get tons of laughing pictures of her. They make me so happy!!!!!

This red dress (also in black) also popped so well with the blue of the lake and the champagne just added an extra touch.

Get Jenna's outfits here and here or look at more white dresses here for your engagement pictures, bridal shower, rehearsal dinner, microwedding, or just because!