Jeremy asked Maddie to Marry Him in Chicago’s Grant Park Garden

It was a steamy afternoon in June and Jeremy had a very organized and carefully planned afternoon to propose to his girlfriend Maddie.  Jeremy wanted to propose to Maddie in The Grant Park South Garden but we learned that it was closed off due to the prep for the upcoming Chicago Nascar race the following weekend. Jeremy went to walk the spot to familiarize himself so he would know exactly where I suggested he get down on one knee. The Garden space was gated off but he searched for security personnel that was fencing the area off and he persuaded them to open the gates when he returned later to propose. I crossed my fingers and hoped that the security gaurd would pull through otherwise we would need to act fast and coordinate plan B without Maddie realizing what we were up to. Thankfully it all worked out and not only did the gaurd pull through but she took video of the proposal on her phone as well! Maddie’s response to Jeremy down on one knee was one of the most fun I’ve ever witnessed! She fell to her knees and they shared a kiss on the ground together. After they came back down to earth we walked around Grant Park getting photos around Buckingham Fountain and Michigan Avenue. Jeremy had also planned a second surprise and had their families flown in to surprise them when they returned to their hotel room. Maddie was definitely surprised and I was lucky to be able to capture their joy when they waited for the moment to celebrate.

Advice from a Pro: Jeremy took my advice and physically checked out the spot he planned to propose to familiarize himself upon my recommendation ( due to the event ). This made it possible to avoid a stressful situation if we had arrived to find desired spot closed off. If possible always check a space out especially if you have never been there and don’t know how to get there. If you can’t physically do that, I always offer an “Add On” site visit to prep the partner who is going to propose!

Location Features: I love this location for proposals because not only is it more private than most of the popular spots in Chicago but you get skyline, fountain and beautiful garden atmosphere all in one shot.

A couple stops to take a photos in front of the chicago buckingham fountain on a summer day

a man is down on one knee proposing to his girlfriend in front of the chicago skyline on a summer day

a man is down on one knee proposing to his girlfriend in front of the chicago skyline on a summer day

a man is down on one knee proposing to his girlfriend in front of the chicago skyline on a summer day

a man is down on one knee proposing to his girlfriend and sharing a kiss in front of the chicago skyline on a summer day

a couple embraces after getting engaged

a man takes a cell phone photo of his girlfriend who is showing off her knew engagement ring

a man is dipping his girlfriend fora kiss while posing for a photo in front of the chicago skyline

a man and women walk hand in hand in front of the chicago skyline

a man and women both in sunglasses stop for a kiss in front of the chicago buckingham fountain

a man and woman pose for a photo by spinning in front of chicago's buckingham fountain

a well dressed couple crosses the street while holding hands on michigan avenue in chicago

 a couple shares a kiss

a man and womens arms embrace showing off her new engagement ring

a man wraps his arms around his girlfriend in an embrace

a man kisses his girlfriend on the forehead while holding her hand

a man and his girlfriend embrace as she laughs with her hands around his head

a well dressed couple stands in a garden on michigan ave in chicago posing for a photo with sunglasses on

a well dress couple enters a hotel room with surprised looks on their faces

a group of 8 people stand in a hotel room yelling surprise at a couple entering the room

a family embraces in celebration

two men share a hug

For tips on planning a surprise proposal in Chicago, check out my blog on How to Plan a proposal here. For help finding the perfect location for your surprise proposal, check out my blog on popular Chicago locations here. For specifically skyline locations , Click here to see a list of skyline locations.

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