Amol + Anna | The Robey Chicago | The Up Room
Private Rooftop Proposal at The Robey Hotel in Chicago | The UP Room
Why The Robey Hotel | The Up Room makes for a great proposal location.
When it comes to proposing in Chicago with rooftop vibes and skyline views The Robey Hotel in Wicker Park really checks all the boxes. The hotel’s Up Room rooftop lounge sits on the 13th floor and offers amazing views of the Chicago skyline and neighborhoods including downtown, Wicker Park, and Bucktown. It’s the perfect mix of cozy and elevated, especially for couples who want something private but still city‑centered.
The Robey offers a blend of historic architecture and modern luxury, making it a great indoor proposal option all year round. Whether you’re planning a winter engagement or a sunset summer proposal, this space provides a comfortable and romantic backdrop with a big touch of class.
How To Plan A Proposal At The Robey, The Up Room?
Amol and Anna are both locals to Chicago. They moved into Wicker Park just over a year ago and The Robey had always been on their date night list since it was a place they’d talked about but hadn’t yet visited. Amol decided it would be the perfect location for their proposal and visit together!
He told Anna they were going to brunch at Café Robey, located right inside the hotel. After brunch, the plan was simple. They would take the elevator up to The Up Room rooftop for a quick drink and view. Anna had no idea what was really waiting for her there.
How to Book The Up Room for a Private Rooftop Proposal at The Robey Hotel
If you’re planning your own proposal at The Robey, you’ll be happy to know that the hotel offers private reservations for The Up Room and other event spaces. You can contact their event or guest relations team directly through the Robey’s official website or by calling the hotel. I can also always help with putting you in contact too. Packages often include private seating, custom floral setups, champagne toasts, and access to both indoor lounges and the outdoor terrace, But I would always check with them to see what they are currently offering.
Tips for booking The Robey for a proposal:
Book early – weekends and golden hour times fill up fast.
Ask for semi‑private or private access to ensure your proposal feels intimate.
Coordinate with staff for timing, logistics, or decor setup.
Pair your proposal with brunch or dinner at Café Robey for a complete experience.
Hire a local photographer familiar with The Robey, The Up Room. me :).
What Was the Proposal Moment Like at the Up Room?
After finishing brunch, Amol and Anna took the elevator to the rooftop lounge. The Up Room’s warm indoor space and city views created the perfect setting. As they stepped onto the rooftop, surrounded by the Chicago skyline, Amol took Anna’s hands and proposed. I was hidden near the bar, camera ready, capturing every second through the doorway. Anna’s smile said it all — pure joy and surprise.
Once she said yes, I came out to congratulate them and start their portrait session.
How to Add Family or Friends to Your Proposal Moment
But Amol’s plan didn’t stop there. He had arranged a surprise for Anna! Both of their families were waiting downstairs, ready to join in the celebration. After a few portraits, I positioned Amol and Anna so their backs faced the room doors while they admired the view. Their family members quietly walked out and on my cue the couple turned around completely shocked!
It was such a sweet moment, full of laughter and happy tears. We wrapped up the session with family photos, toasting champagne, and a few more romantic rooftop portraits of the newly engaged couple.
Why The Robey Hotel is Perfect for Rooftop Engagement Photos in Chicago
What makes The Robey’s rooftop ideal for photos?
Iconic views of Chicago’s skyline and neighborhood architecture
Elegant mix of indoor comfort and outdoor beauty
Stylish modern‑vintage decor that looks timeless in photos
Natural light and skyline glow during sunset
A private setting for a proposal
Indoor location for winter proposals or rainy days.
congrats again!
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