Surprise Rooftop Proposal at The Robey Chicago – Isaac & Amy

Isaac first contacted me about a month ago, knowing a few things for certain: he was going to ask Amy to marry him, he wanted his surprise proposal documented, and she couldn’t suspect it no matter what! He decided that The Robey Chicago was the perfect spot – with their incredible rooftop view of the skyline, what could be better? They’d have brunch at Café Robey downstairs and then make their way to the Up & Up for what Amy would think is a champagne tasting, and he’d pop the question while they were outside enjoying the view.

Well, friends – that’s exactly what happened. I posed as a bartender until they were outside, and… well, I’ll let the photos tell the rest. It was such an awesome moment – proposals are one of my absolute favorite things to photograph! As promised, there was no shortage of champagne (Dom Pérignon, anyone?). Spoiler alert: she said YES 🙂

CONGRATULATIONS, Amy and Isaac!!

Shout out to Hannah and Anna at The Robey for helping make this happen!

The Robey Chicago surprise proposal
North Avenue view of The Robey Chicago building in Wicker Park
The Robey Chicago building in Wicker Park
The Robey Chicago building at six corners in Wicker Park
The Robey Chicago entrance in Wicker Park
Cafe Robey at The Robey Chicago
The Robey Chicago address
The Robey Chicago revolving door in Wicker Park
revolving door entrance to The Robey Chicago in Wicker Park
entrance to The Robey Chicago in Wicker Park
Wicker Park Bucktown sidewalk square in front of The Robey Chicago
The Robey Chicago brunch menu
couple eating brunch at The Robey Chicago before surprise proposal
couple eating brunch at The Robey Chicago
moments before surprise proposal at The Robey Chicago rooftop
artistic photo of couple about to be engaged at The Robey Chicago rooftop
surprise proposal at The Robey Chicago rooftop
she said yes to proposal at The Robey Chicago rooftop
she said yes to The Robey Chicago rooftop proposal
she said yes to proposal on the rooftop of The Robey Chicago
she said yes to proposal on the rooftop of The Robey Chicago
surprise proposal on the rooftop of The Robey Chicago hotel in Wicker Park
surprise proposal on the rooftop of The Robey Chicago hotel in Wicker Park
surprise proposal on the rooftop of The Robey Chicago hotel in Wicker Park
she said yes to his surprise proposal at The Robey Chicago
she said yes to his surprise proposal at The Robey Chicago rooftop
happy woman after surprise proposal at The Robey Chicago rooftop
happy woman just engaged on the rooftop of The Robey Chicago
happy couple just engaged on the rooftop of The Robey Chicago
newly engaged couple on the rooftop of The Robey Chicago
newly engaged couple pops champagne on the rooftop of The Robey Chicago
newly engaged couple laughing on the rooftop of The Robey Chicago
newly engaged couple pops champagne on the rooftop of The Robey Chicago
just engaged couple pops champagne on the rooftop of The Robey Chicago
happy engaged couple pops champagne on the rooftop of The Robey Chicago
newly engaged couple pours champagne on the rooftop of The Robey Chicago
couple kissing after surprise proposal at The Robey Chicago rooftop
just engaged couple at The Robey Chicago rooftop after surprise proposal
engaged couple on rooftop of The Robey Chicago
just engaged couple outside on the rooftop of The Robey Chicago after surprise proposal
happy couple wiping tears after surprise proposal at The Robey Chicago
woman looks at her new engagement ring on rooftop of The Robey Chicago
happy engaged couple on rooftop of The Robey Chicago
newly engaged couple on rooftop after surprise proposal at The Robey Chicago
newly engaged couple enjoying city view at The Robey Chicago rooftop
couple pours champagne after surprise proposal at The Robey Chicago rooftop
couple drinks champagne after surprise proposal at The Robey Chicago rooftop
surprise proposal champagne toast and engagement ring at The Robey Chicago rooftop
surprise proposal champagne toast at The Robey Chicago rooftop
happy couple just engaged on roof of The Robey Chicago
engagement ring and Dom Pérignon champagne bottle at The Robey Chicago
diamond engagement ring and Dom Pérignon cork at The Robey Chicago
couple looks at engagement ring at Up & Up bar in The Robey Chicago
just engaged couple at Up & Up bar in The Robey Chicago
city view from Up & Up bar at The Robey Chicago rooftop

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