Chicago proposals are so freaking magical with the city in the background, lights glowing, and the crystal blue lake showing off for us.


When Etrit reached out about proposing in Chicago, we had less than 24 hours to change the plan, come up with a new one, and come up with an idea for him to tell Kristina what they were doing, all in order to make sure this proposal was a surprise! And it worked.


He originally had another photographer booked, but stopped hearing from them suddenly. With only a day before the planned Chicago proposal, which was originally going to be in Miami, Etrit told me about his plan to propose at the Trump Tower around 10 or 11pm since that was all they had available. We figured that it might be better to do it earlier, at a park or something, so naturally I suggested North Avenue Beach, one of my favorite locations in Chicago to propose or do engagement pictures. North Avenue Beach is the perfect place to propose in Chicago; it has the lake, the city skyline, sand, the pier, and clear blue skies (most days, that is). Plus, you can change up your view and lighting depending just on if you go at sunrise or sunset, or somewhere in between.


He told Kristina that they were going on a sunset boat ride and being picked up at North Ave. Beach after dinner, so while she was looking out for a boat, I was hiding behind my camera in the crowd, waiting for Etrit to get down on one knee. There were lots of Chicago proposal photographers there that evening (yay for so much love happening right now!), so luckily he stopped right in front of me, giving me the perfect angle to photograph their Chicago proposal.

man smiling at his girlfriend before North Avenue Beach Proposal
man in gray suit down on one knee for North Avenue Beach Chicago proposal
man in gray suit down on one knee for North Avenue Beach Chicago proposal
man in gray suit down on one knee for North Avenue Beach Chicago proposal
man in gray suit putting engagement ring on fiance in red leather dress after proposing at North Avenue Beach

Some proposals are loud and "are you serious?!" and some are quiet, I'm-speechless proposals. They're all so freaking fun to witness and be a part of.


Proposals go quick, and lots of time both people, but especially the one being proposed to, don't even remember all the details even 10 minutes after because they're so in shock! And I love it! That's why hiring a proposal photographer in Chicago is such a good idea. You can relive it, remember those things, see all those facial expressions, hugs and kisses, and happy tears again and again.

young woman smiling at fiance in front of Chicago skyline after North Avenue Beach proposal
young woman smiling at fiance in front of Chicago skyline after North Avenue Beach proposal
man going to hug woman after he proposed at North Avenue Beach pier
man and woman hugging after Chicago proposal at North Avenue Beach pier
man and woman kissing after Chicago proposal at North Avenue Beach pier
man and woman hugging after Chicago proposal at North Avenue Beach pier
man and woman hugging after Chicago proposal at North Avenue Beach pier
man and woman hugging after Chicago proposal at North Avenue Beach pier overlooking Lake Michigan
man and woman hugging after Chicago proposal at North Avenue Beach pier
man and woman hugging after Chicago proposal at North Avenue Beach pier
man and woman hugging after Chicago proposal at North Avenue Beach pier

After lots of hugging and crying and processing what the heck just happened, Kristina dried her happy tears and showed off her ring in front of the beautiful Chicago skyline.

woman in maroon leather dress holding up her hand showing she is engaged in front of Chicago skyline at North Ave Beach
man and woman holding hands looking at camera in front of Chicago skyline + Lake Michigan after North Ave Beach proposal
man and woman in formalwear holding hands laughing in front of Chicago skyline after man proposed at North Ave Beach
woman hugging new fiance showing off her ring and peeking over his shoulder
man and woman holding hands walking along pier at North Avenue Beach Chicago
rectangle cut diamond engagement ring on white ring box after Chicago proposal
woman hugging new fiance showing off her ring and peeking over his shoulder

Hiring a Chicago proposal photographer is way better than iPhone. Promise.


Why is hiring a Chicago proposal photographer better than just having a friend take some pictures, or taking pictures after the fact? Well, for started, phone cameras are great, but they don't have the zoom capabilities that a professional camera does. A proposal photographer can stay far away, both great for giving you some privacy, and not spoiling the surprise!


Second, hiring a proposal photographer means you get professional editing to color correct, take distractions out of the photos (which is especially a plus when you live in Chicago, a busy, crowded city), and help you plan exactly how to propose if you're not sure. We get it--you're nervous AF and probably haven't done this before--we can help.

man and woman holding hands walking along pier at North Avenue Beach Chicago
man and woman holding hands walking along pier at North Avenue Beach Chicago
man and woman holding hands walking along pier at North Avenue Beach Chicago

Hiring a Chicago proposal photographer also means you get advice on locations, time of day, and even idea on how to make it super surprising, romantic, and extra special.


I mean, it goes for any city, but a local Chicago proposal photographer will know the best spots to propose in Chicago, whether you want a landmark, a private area in public, a private restaurant, or want someone to bring you champagne and flowers to give your new fiancé after he/she says yes. Lots of people like to propose by landmarks or locations that are significant to them.

mand and woman's fingertips touching in front of Lake Michigan after Chicago proposal
man and woman kissing and woman holding up hand in front of skyline after Chicago Proposal

I was so obsessed with Kristina's dress, and of course she looks absolutely glowing after saying yes to one of the best questions to get asked. She had no idea it was coming, and Etrit kept telling her they couldn't get engaged right now...not yet...it's not the right time...so she was so excited and shocked to find out he was planning on it all along.


I'm so happy I got to be part of this beautiful sunset Chicago proposal, and give these two photos to remember this epic day.

man and woman kissing and woman holding up hand in front of skyline after Chicago Proposal
man and woman smiling holding hands in front of Chicago skyline after Chicago proposal
man and woman smiling and woman holding up hand in front of skyline after Chicago Proposal
woman hugging new fiance showing off her ring and peeking over his shoulder
man and woman smiling together and woman holding up hand in front of skyline after Chicago Proposal
rectangle diamond and white gold engagement ring on top of white ring box by Chicago proposal photographer
man and woman kissing and woman holding up hand in front of skyline after Chicago Proposal

Looking to hire a Chicago proposal photographer for your own proposal?


Contact me here or email me directly at hello@alanalindenfeld.com.