Sunrise engagement pictures in Chicago are soooo dreamy, and the Chicago Riverwalk was the perfect, empty place for some early-morning romance.


Kari and Brad were the winning couple from the Chicago engagement session giveaway with The Flower Girl Company and Giselle Dozier Artistry, and we finally got some nice, cool weather for their Chicago engagement pictures! When I asked Kari and Brad where they wanted their pictures, she mentioned the Chicago Riverwalk, which seemed like the perfect place to get that classic Chicago look: some water, a few trees, and lots of beautiful architecture. There's a reason this is such a popular engagement location in Chicago :)


We met up just after sunrise at the Wrigley Building on Michigan Avenue, one of a few iconic locations in Chicago for engagement and wedding pictures. One of the perks of sunrise sessions, though they're early as heck, is that the streets are mostly empty. Yay for not having to photoshop 20 different people out of your Chicago engagement pictures!


These two stepped out of their car looking absolutely stunning (thaaaaanks, Giselle for making her look even more bomb than she already does!) and we jumped right in!

oval diamond engagement ring in a yellow ranunculus flower
woman with brown hair in a light blue dress holding hands with fiance in front of the wrigley building in chicago
woman with brown hair in a light blue dress holding hands with fiance in front of the wrigley building in chicago
woman with brown hair in a light blue dress holding hands with fiance in front of the wrigley building in chicago
colorful purple pink yellow engagement session bouquet for chicago engagement pictures

I couldn't get enough shots of this gorgeous bouquet from The Flower Girl Company, and I only took about...I don't know...15 pictures of Kari's giant engagement ring in the flowers 😂

woman with brown hair in a light blue dress holding hands with fiance in front of the wrigley building in chicago

The Wrigley Building is a fan favorite in Chicago.


It's beautiful from every angle, and I love the feeling of being in an area right off of the super busy streets. I figured this was the perfect place to take that one shot that is always overlooked, the looking-at-the-camera picture. Although I'm a sucker for candid photos, it's always nice to have one just smiling, especially when you're all dressed up, which doesn't happen too often during a pandemic lol.

woman with brown hair in a light blue dress holding hands with fiance in front of the wrigley building in chicago
woman with brown hair in blue dress sitting near chicago riverwalk and wrigley building with fiance at sunrise
young engaged man and woman looking at each other in front of Chicago River near the Wrigley building at sunrise
oval engagement ring in colorful bouquet of yellow, pink, and purple flowers for chicago engagement pictures
young engaged man and woman looking at each other in front of Chicago River near the Wrigley building at sunrise
woman with brown hair in blue dress sitting near chicago riverwalk and wrigley building with fiance at sunrise

If you want sweeping views of Chicago as the backdrop to your engagement pictures, the Riverwalk is the perfect location!


With a city like this and so many well-known buildings right on the Chicago River, I had to get alllll the angles, wide shots, and close ups with the background overflowing with the city-scape. There's something so romantic about waking up with the city and overlooking the water as the sun starts to come up and the city lights start to turn off. Kari + Brad made this spot live up to its full potential, without a doubt.


After a few more shots overlooking the river, we headed down the steps and actually walked the Riverwalk.

young engaged man and woman laughing with each other in front of Chicago River near the Wrigley building at sunrise
woman in blue dress twirling around with her fiance in white shirt for sunrise chicago engagement pictures
oval engagement ring in peach rose
young engaged man and woman looking at each other in front of Chicago River near the Wrigley building at sunrise
woman in blue dress twirling around with her fiance in white shirt for sunrise chicago engagement pictures
woman in blue dress twirling around with her fiance in white shirt for sunrise chicago engagement pictures
oval engagement ring sitting on dark purple anemone flower

A quick outfit change, and we were off the more of the Riverwalk before it got crowded. As much as I love dressier outfits for engagement pictures, casual outfits are always a great way to be able to do some more "fun" poses, like piggyback rides, anything with lots of movement or running, or just goofing off. I always recommend one casual and one nicer outfit for engagement pictures--if you need ideas, check out this blog post on what to wear for engagement pictures!

man in short sleeves shirt hugging fiance from behind at the Chicago Riverwalk
man in short sleeves shirt hugging fiance from behind at the Chicago Riverwalk steps
man in short sleeves shirt hugging fiance from behind at the Chicago Riverwalk
man in short sleeves shirt hugging fiance from behind at the Chicago Riverwalk
woman leading man up the steps at Chicago Riverwalk for engagement pictures in front of LaSalle Street Bridge

Showing off the whole cityscape is fun, but zoning in on the couple is a MUST. When Kari mentioned wanting some pictures of them two on the steps with nothing else in the background, I knewwwww she was my girl 🙌🏼 Poses on steps are a great way to add some height variation (whether that means evening it out or making there more of a gap), and a great place to sit down for a bit of a rest + snuggle. I love how clean these pictures are with nothing else but these two as the focus point 😍


You can always go somewhere epic and wear an incredible outfit, but a lot of times. favorite photos are the real-life ones where you're just having a good time with your partner, hanging out. It's a lot like real life...dressing up and partying is fun, but who doesn't love a good lazy-Sunday-in-your-sweatpants day with your almost-wife or husband? (Not that these two look anything close to that in these pictures).

woman with brown hair looking at fiance and smiling on steps at Chicago Riverwalk engagement pictures
man and woman's hands wrapped together with oval engagement ring
woman leading man up the steps at Chicago Riverwalk for engagement pictures in front of LaSalle Street Bridge
woman with brown hair laughing with fiance at Chicago Riverwalk sunrise engagement pictures
woman with brown hair laughing with fiance at Chicago Riverwalk sunrise engagement pictures
woman with brown hair laughing with fiance at Chicago Riverwalk sunrise engagement pictures
woman in gray sweater and white shorts hugging fiance's arm and walking across LaSalle Street Bridge
woman in gray sweater and white shorts hugging fiance's arm and walking across LaSalle Street Bridge
man picking up woman and kissing her on LaSalle Street Bridge for Chicago engagement pictures at sunrise

To bring the engagement session full circle, we headed back up the steps off the Riverwalk and finished up with some more pictures on the bridge. This one right here? One of my favorites from all morning!!! Brad looks like a GQ model, Kari looks like she belongs on the cover of Vogue, and together they look like a powerhouse of an Instagram couple (but probably with better personalities). Soft smiles and sunrises for dayyyyyssssssssss.

man with brown hair hugging fiance from behind, looking at the Chicago River for sunrise engagement pictures in Chicago
man with brown hair hugging fiance from behind, looking at the Chicago River for sunrise engagement pictures in Chicago
man with brown hair hugging fiance from behind kissing her by Chicago River for sunrise engagement pictures in Chicago

If you're looking for your own Chicago engagement pictures or even ready to start chatting about your Chicago wedding photographer, send me an email at hello@alanalindenfeld.com or use the contact page! Let's get this party started and soak up all the perfect, hazy fall light coming our way next month!