As a Chicago proposal photographer, I see a lot of happy couples shed a lot of happy tears.


This was no exception. Rob found me through a mutual friend in Cincinnati, where I'm from originally and where he + Costina were visiting from, and together we planned the perfect Chicago winter proposal at Millennium Park. The Millennium Park Christmas Tree is celebrated every year with a tree lighting ceremony, which didn't get to happen in 2020 thanks to COVID, but the empty park devoid of ice skating made the moment that much more private and special for Rob and Costina.


The cold, gloomy, rainy weather didn't make anyone's ideal day when it comes to exploring Chicago, but these two wanted to get the most out of their time here, which was the perfect excuse to come to Millennium Park. I posed as a photographer just "waiting on some other clients" and offered to take a few pictures of these two so they could remember their time here. Costina kept asking me if I was sure I had the time, and that they weren't taking me away from my other clients, when in fact, they were exactly the people I was waiting for :)


I took a few photos right where they were, then took them up to this iconic part of Millennium Park before the proposal. I did one of my favorite prompts for proposals, and asked them to face away from each other, then on the count of 3 turn around and go for a big bear hug. (I did this with Koray and Josephine too!) Of course, Costina turned around to her boyfriend on one knee with a ring as bright as the tree, asking for her to marry him. Pretty sure she was in shock for the rest of the time I saw them ;)

couple standing in front of Christmas Tree at Millennium Park
Man in gray coat kneeling down in front of Christmas Tree at Millennium Park in Chicago about to propose
Man in gray coat kneeling down in front of Christmas Tree at Millennium Park in Chicago about to propose
Man in gray coat kneeling down in front of Christmas Tree at Millennium Park in Chicago about to propose
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree

There was absolutely no one else around for this Millennium Park Proposal, which made the moment that much more special.

man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
man in grey coat kneeling proposing to woman in black coat and clear umbrella in front of Millennium Park Christmas Tree
couple kissing under clear umbrella at Millennium Park Christmas Tree

There are so many great spots to propose in Chicago, and this was surprisingly one I haven't had the chance to photograph before! I love photographing Chicago proposals because not only are the reactions amazing, but the locations are so iconic and add so much to the feeling of the day. If you're looking for Chicago spots to propose, you can check out these Millennium Park engagement photos, or look at other posts on my blog for Chicago proposal ideas!

young couple hugging in front of Millennium Park Christmas Tree after Chicago Proposal
young couple hugging in front of Millennium Park Christmas Tree after Chicago Proposal
man putting engagement ring on fiance in front of Millennium Park Christmas Tree
couple hugging under clear umbrella in front of Millennium Park Christmas Tree
couple hugging under clear umbrella in front of Millennium Park Christmas Tree
holding hand up with engagement ring in front of Millennium Park Christmas Tree
couple hugging under clear umbrella in front of Millennium Park Christmas Tree
young couple smiling under clear umbrella on rainy day in Chicago after Millennium Park proposal
couple kissing in rain after Chicago Proposal
couple hugging under umbrella on rainy day in Chicago Millennium Park

Christmastime in Chicago looked different this year.


With no Christkindlmarket, no in-person tree lighting ceremony, and an overall feeling of all the 2020 gloominess, it wasn't everyone's most exciting year. But Rob and Costina got the perfect proposal in a huge city they had all to themselves for the afternoon, where they got to continue exploring what Chicago has to offer.


After Costina had a minute to take in what just happened, we took a few more proposal photos in Chicago, then I headed out to let these two Facetime anyone they wanted, tell everyone the good news, and hopefully warm up somewhere away from the rain and cold weather.

couple hugging under umbrella on rainy day in Chicago Millennium Park
couple hugging under umbrella on rainy day in Chicago Millennium Park
couple hugging under umbrella on rainy day in Chicago Millennium Park

Looking to book your own Chicago proposal photographer?


Reach out to me here or over on Instagram. I'll help you plan the perfect location, time of day, and make sure this surprise stays a surprise.


Or, check out more proposals below!