Creative Proposal Ideas

Don't know where to propose in Chicago? From Chicago's glittering skyscrapers bordering Millennium Park to the vibrant streets of Lincoln Park, the cosmopolitan sights of this city make it the perfect setting for your marriage proposal. Proposal-Ideas understands that each couple is unique, so we provide a variety of proposal ideas for you to choose from. Whether your interests tend towards the adventurous with a private helicopter tour or the more romantic with an elegant dinner in an unforgettable setting, our engagement ideas will ensure your proposal is a moment to remember. Your perfect Chicago marriage proposal awaits!

You and your loved one will feel like you’re dining in the sky as you share a romantic dinner almost 100 floors above the streets of the Windy City. ....

You will be soaring above the Windy City’s skyscrapers on this thrilling helicopter tour. Tour Chicago from a whole new perspective in your private helicopter ....

Let an enchanting outdoor setting be the backdrop for your perfect marriage proposal. We’ll arrange for a lovely blanket to be set out in your favorite ....

Set the stage for your dream marriage proposal high above the Chicago skyline. The private Chicago rooftop will be exclusively yours to pop the question ....

design your own proposal

Perfect for the person who knows exactly how they want to propose but needs some expert help putting the pieces together. Our experienced team of Proposal ....


Select your favorite proposal package and designate your date and time. Within 48 business hours of booking, you will receive your confirmation via email. The confirmation email will provide you with all of the contact information, addresses, contingency plans in case of bad weather and a step-by-step description of how your proposal will unfold. Relax, enjoy the moment and propose!
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Email or call our proposal experts now +1 646.224.6929


She told me it was fairytale perfect, I couldn't be happier...and neither could she!

Roger, Lakeview

There is absolutely no way I could have pulled this off on my own. We will never forget this day!

Adrian, Naperville

So amazing! Wow, wow and WOW. Our engagement was a dream come true from start to finish.

Michael, Milwaukee