Robert + Ellen

The Gwen | Jinsei Motto

How to Plan a Private Proposal at The Gwen Hotel in Chicago

Why is The Gwen Hotel a great choice for a private proposal?

When Robert reached out to me about proposing to Ellen, he had a clear vision: an intimate, romantic moment with a breathtaking view of Chicago, followed by a surprise celebration with family and friends. After considering a few options, we landed on The Gwen Hotel—a luxury spot known for its elegant suites and stunning terrace views. The Gwen stood out because of its unique blend of privacy and sophistication, making it the perfect setting for a surprise proposal. To make the moment extra special, Robert arranged for their proposal to take place in one of The Gwen’s luxury suites, with the terrace overlooking the city as the backdrop.

How do you create a romantic proposal setup at The Gwen?

To set the scene, The Gwen team worked their magic. Rose petals lined the path from the suite’s entrance, leading straight to the terrace where Robert planned to propose. The ambiance was perfect—candles flickered softly, and a tower of macarons and sweets added a touch of indulgence. Ellen’s face lit up as she took in the beautiful setting, adding to the magic of the moment. The setup created a romantic and intimate atmosphere for the big moment.

What are some creative ways to surprise your partner during a proposal?

Robert had a clever plan to keep the proposal a total surprise. Ellen thought she was attending a work event at The Gwen with a friend, and they were heading to a colleague’s hotel room before the event began. But when they knocked on the door, it was Robert who answered. Ellen was completely caught off guard!

Without giving too much away, Robert led her along the rose petal path toward the terrace. The view of the city, combined with the cozy candlelight and thoughtful setup, made the moment unforgettable. As they stepped onto the terrace, Robert got down on one knee and proposed. The moment was private, heartfelt, and filled with so much emotion.

How can you plan a surprise celebration after the proposal?

After capturing a few portraits around the suite and terrace, I let them think my time with them was over—but I had one more surprise in store that they never saw coming. While Robert and Ellen soaked in the excitement of their proposal, I  made my way over to Jinsei Moto, where an even bigger surprise was waiting.

Where can you celebrate your engagement after a proposal at The Gwen?

Robert had arranged for Ellen’s closest family and friends to fly in from across the country to celebrate this incredible moment. Everyone gathered in a private room at Jinsei Moto. Friends and family eagerly waited for the newly engaged couple to arrive. When Robert and Ellen walked in, Ellen’s reaction was pure joy and shock. Seeing her friends and family there to celebrate made the day even more special.

Why is capturing the proposal and celebration important?

I captured Ellen’s emotional reaction as she realized how much love and effort had gone into planning this surprise. After some group photos with their friends and family, the couple spent the rest of the evening celebrating with dinner, drinks, and lots of laughter. The energy in the room was contagious, and it was clear that this was a moment they would never forget.

What makes a private proposal with a surprise celebration unforgettable?

What made Robert and Ellen’s proposal so unique was how perfectly it blended intimate, private moments with a lively celebration. The quiet romance of the proposal at The Gwen was followed by an outpouring of love and support from family and friends at Jinsei Moto. It was the best of both worlds—thoughtfully planned and flawlessly executed.

Ready to plan your private proposal at The Gwen Hotel?

If you're considering The Gwen Hotel for your proposal, it’s hard to beat the elegance, privacy, and stunning views it offers. Whether you want a cozy moment with just the two of you or a surprise celebration with loved ones after, The Gwen provides the perfect setting. And if you’re looking for someone to help capture it all, I’d love to brainstorm ideas and make your vision come to life.

Ready to start planning a proposal that feels like you? With years of experience capturing surprise proposals, I’m here to help bring your vision to life. Let’s make it happen!

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