Chicago surprise proposal Posts
Summer Alfred Caldwell Lily Pool Proposal – Tristan & Jess
This summer was indeed a whirlwind, but one of my favorite moments to capture was Tristan’s Alfred Caldwell Lily Pool proposal! With Chicago weather on our side, an unsuspecting fiancée-to-be, and one of the most romantic proposal locations in the city, I knew it was going to be the best day. I am always so thrilled and honored to be part of these moments. This was no exception!
I arrived at the Lily Pool before Tristan and Jess to guard our chosen spot, which happened to be popular on a Saturday! Luckily, by the time they took a stroll around the pond it was clear… just like we’d planned it! He asked, she said yes – and you know the rest! I was lucky enough to take these two around the park for some engagement photos before they headed to their next destination. The Lincoln Park Conservatory gardens were in full bloom, and a gorgeous backdrop for these two! Smiles like this make me so grateful to do what I do 🙂
CONGRATULATIONS, Jess and Tristan!! I absolutely loved being part of your engagement and wish you nothing but happiness in your future. Thank you again for having me this summer!
Looking for more Alfred Caldwell Lily Pool proposal inspiration? Check out the post below!

Chicago Boat Proposal with Double Surprise – Haley & Taylor
At the end of June, I was lucky enough to capture Taylor and Haley’s Chicago boat proposal on Lake Michigan. This was one of the most unique surprise proposals I’ve ever been asked to document, and it ended in a way I never expected! Taylor asked me to capture the moment she asked Haley to marry her, but what neither of us knew is that Haley was prepared with a ring for Taylor, too!
That morning I met Haley and Taylor’s families at Monroe Harbor, who had just arrived in town for the occasion. We boarded the Guppy together and enjoyed the morning sunshine with Captain Charles of Sailing Chi! Once we received word that Taylor and Haley were on their way, family assumed their hiding positions below deck. We arrived at a picturesque spot on the water, and the next thing we knew these two were ENGAGED 🙂
Shortly after they said YES, family revealed themselves with hugs and congratulations. We spent the rest of the morning celebrating on the boat with champagne, music, and good times! Haley and Taylor were all smiles, and we even got to have a mini photoshoot before getting back to the harbor. This was my first ever Chicago boat proposal, but I don’t think it gets any better than this!
Taylor and Haley: Thank you again for having me capture these moments for you! I had a blast on your engagement day and wish you nothing but the best. CONGRATULATIONS to you both!!

Surprise Chicago Ice Skating Proposal – Amy & Rob
It’s Valentine’s Day Weekend… which means that Engagement Season is coming to an end! And by “Engagement Season,” I mean the period between Thanksgiving and Valentine’s Day when nearly 40% of couples get engaged. This is a time when wedding vendors tend to stay busy during the “offseason” – and photographers get to tag along for the surprise proposals!!
Proposals are my absolute FAVORITE thing to photograph… and I was so excited to hear from Rob! When he told me about Amy (a fellow Green Bay Packers fan) and his plan to surprise her in January, I knew it was going to be awesome. Although I’d be in quarantine on their engagement date, we were lucky to have associate Laëtitia capture the moment!
A fellow ice-skating enthusiast, I just loved Rob’s idea of a downtown Chicago ice skating proposal. After a few laps around the rink at Maggie Daley Skating Ribbon, he got down on one knee and asked Amy to marry him! The look on her face was priceless!! In case you couldn’t tell… she said YES 🙂
Amy and Rob: Thank you again for having us capture these moments for you! CONGRATULATIONS to you both!!!
Love the idea of a Chicago ice skating proposal? Looking for more inspiration?! Check out these favorites on the Blog!
Amit & Maya’s Lincoln Park Proposal
Gabriel & Sueyi’s Millennium Park Proposal
Alex & John’s Harold Washington Library Proposal
Erik & Claire’s Chicago Lakefront Proposal
