Eric+ Ariana

The Rookery

How to plan a Proposal at The Rookery Building in Chicago: Q&A with a Chicago Proposal Photographer

The Rookery Building is one of Chicago’s most iconic and historically significant buildings, making it a stunning location for a proposal. Eric recently planned an unforgettable surprise proposal for his girlfriend, Ariana, by using the building’s architectural history as part of the plan. Here’s how I helped him pull off this memorable moment and some tips for planning your own proposal at The Rookery.

Is The Rookery Building a great place for a proposal?

If you’re looking for a private proposal location with an Iconic Chicago skyscraper then The Rookery is the spot. The Rookery Building, located in the heart of Chicago's financial district, is a National Historic Landmark and one of the most beautiful examples of architecture in the city. Originally completed in 1888, the building was later redesigned by Frank Lloyd Wright, adding even more historical significance. The Rookery's Grand Staircase and iconic Oriel staircase provide a romantic, elegant setting for proposals, making it a perfect spot for proposals, engagements, and wedding photos for those who appreciate architecture and Chicago’s history.

How did Eric plan his proposal at The Rookery?

Eric's proposal was both creative and personal. He’s studying to be an architect, so he used that as the perfect cover story, telling Ariana they were attending an architectural expo at The Rookery. When they arrived, I greeted them at the door, playing along by asking if they were there for the event. As they entered the building, I directed them to wait by the Grand Staircase, saying their guide would meet them shortly. Once they reached the center of the staircase, Eric surprised Ariana by getting down on one knee and popping the question! She was completely caught off guard, thinking they were at the expo, and was thrilled to find out it was her proposal instead!

Can you rent out The Rookery for a private proposal?

Yes! You can obtain a permit to rent out The Rookery for a private proposal. This allows you to have exclusive access to the building, ensuring a more intimate experience without the hustle and bustle of the city. We can pop the question in front of the Grand Staircase and wrap up the session with photos in the famous Oriel staircase! Renting The Rookery ensures you’ll have a stunning and private proposal.

Where do you like to take pictures at the Rookery?

After the proposal, we took advantage of The Rookery’s gorgeous architecture for a photoshoot. We explored different parts of the building, including the Oriel staircase, which is a standout feature of the space. The session wrapped up with some nighttime shots outside the Chicago Board of Trade, just steps away from The Rookery.

What are some tips for planning a proposal at The Rookery?

• Create a believable cover story: Eric’s story of attending an architectural expo was perfect because it aligned with his studies and gave a great reason for them to be dressed up. You could also plan a "fake office party" or an architecture tour as a cover.

• Rent the space: If you want a private, uninterrupted proposal, consider renting The Rookery. This will give you exclusive access to the space, allowing you to take your time and enjoy the moment.

• Dress up and celebrate after: The Rookery is close to many of Chicago’s top restaurants, so planning dinner after the proposal is a great way to continue the celebration. Plus, dressing up for the occasion makes for stunning photos!

Ready to plan your proposal at The Rookery?

If you’re thinking about proposing at The Rookery or another unique location in Chicago, I’d love to help you capture every moment. With its historic charm and stunning architecture, The Rookery offers a truly unforgettable setting for one of the biggest moments in your life!