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.

man and woman holding hands in front of Chicago Board of Trade
man and woman holding hands laughing in front of Chicago Board of Trade

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.

man and woman holding hands smiling walking in front of Chicago Board of Trade empty street
man in navy suit dipping woman in white dress in front of Chicago Board of Trade for engagement pictures
man in navy suit dipping woman in white dress in front of Chicago Board of Trade for engagement pictures
woman in white dress hugging man in navy suit arm both smiling and walking
man kissing woman in white dress laughing at Chicago Board of Trade engagement pictures downtown Chicago sunset
man and woman walking at sunset near Board of Trade Chicago engagement

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.

woman in short white dress leading man in jeans across bridge with Chicago skyline in background
engaged man and woman kiss in front of Chicago skyline at downtown Chicago engagement pictures
woman in white dress leads man in front of Chicago skyline at sunset engagement pictures
man and woman kiss in front of Chicago skyline

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.

woman in white dress leading man through Chicago at sunset for engagement pictures
blonde woman in white smiles at fiancee in navy suit in Millennium Park Chicago
young engaged couple in Chicago sits on steps in Millennium Park
young engaged couple in white and navy walks through Millennium Park
man in navy suit and woman in white dress go in for a kiss at sunset in the trees at Millennium Park

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 🔥🔥🔥.

couple running through trees at Millennium Park at sunset

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.

woman in tank top and jeans hugging man in white shirt and jeans in Millennium Park engagement pictures
young man and woman holding hands smiling at each other in Chicago Grant Park at sunset
engaged man and woman kiss at sunset in Grant Park Chicago engagement pictures
pear cut diamond engagement ring on daisy
blonde woman in jeans piggy back riding fiance in Grant Park Chicago at sunset
blonde woman hugging fiance from behind and both laughing
white gold pear cut diamond engagement ring on daisy
man picking up his fiance smiling at each other in the middle of Grant Park for chicago sunset engagement pictures
man and woman walking towards Chicago through Grant Park

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

woman in red dress leaning on fiance's shoulder at Grant Park in Chicago at sunset
blonde woman in red dress leaning on fiance in white shirt at sunset next to Chicago lakefront trail
man in white shirt and woman in red dress walking along Chicago lakefront trail at sunset for engagement pictures
woman in red dress sitting on railing at Chicago lakefront trail at sunset
woman in red dress laughing with her fiance next to Lake Michigan

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.

bride and groom touching fingertips in front of Lake Michigan
man popping bottle of champgne while woman in red dress smiles next to him watching
man pops bottle of champagne while blonde woman in red dress holds his arms and smiles by Lake Michigan
woman in red dress and man in white shirt sip champagne at Chicago sunset engagement pictures by the lakefront trail
woman with engagement ring holding glass of champagne in front of Lake Michigan
woman in red dress holding glass of champagne and smiling next to Lake Michigan on Chicago lakefront trail at sunset
blonde woman in red dress and man in white shirt holding glasses of champagne in front of Lake Michigan in Chicago
engaged couple in red dress and white shirt smiling at each other with champagne at sunset in Chicago engagement picture

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!

About the Photographer


Alana is a Chicago based wedding photographer for those who love all things bright and colorful, along with beautifully posed, curated moments mixed with real, candid laughter.

She has worked in over 10 cities across the US, including NYC, San Francisco, Los Angeles, Nashville, and of course her home base, Chicago.

2021 is already booking up due to rescheduling, so if you're interested in booking Alana for your own wedding or proposal, reach out now!

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