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Chicago: The Ultimate Proposal Destination

Why Chicago is the number one spot for your wedding proposal. 

Chicago rooftop proposal with evening Chicago skyline
Photo by Golden Hours

Some might not think of Chicago as a destination spot, especially for their romantic proposal. Don’t just take our word for it- see for yourself. Chicago truly is the ultimate proposal destination in the U.S. 

Not to our surprise, Chicago was just voted the 2nd most beautiful city in the world. The city was only beat by Prague, which makes it the most beautiful city in North America according to TimeOut.  

You heard me right. That means we beat Paris for the most beautiful city in the world. Paris might’ve been your first guess, considering it’s known as the city of love.

We have planned countless proposals across Chicago, and this beautiful city is the true city of love. Well, at least in our eyes. Considering we plan proposals around Chicago every single day… What else do you expect?

Not only is Chicago known for its beauty, but it’s also known for being the Best Big City overall. The prestigious recognition comes from Condé Nast Traveler’s Readers’ Choice Awards 2021.

“This year, more than 800,000 readers from all around the country voted for their favorite destinations and awarded Chicago the title of Best Big City again — making us the only city to ever win this accolade five years in a row.” – Choose Chicago 

So you have the general population of the United States telling you that Chicago is the most beautiful, best big city. You also have Chicago’s Proposal Planner™ telling you that it’s the best city to propose in. 

Clients come to us from across the globe to plan their proposals in the “Windy City”.

For the past 12 years, Chicago has been the home base for Visions Event Studio, and we’ve truly become locals.

The location you choose sets the tone for the entire proposal.

Here’s the thing- I would warn you that I may have some bias towards Chicago being the ultimate proposal destination, but we have the facts to back up that statement. Chicago is the best city, period.

Chicago Proposal Destination
Photo By: Golden Hours

Why is Chicago the best city to propose in, you may ask?

I could write pages and pages about the ins and outs of the city, but it really boils down to the beauty and diversity. I’m not just talking about the people; Chicago has everything you need, all in one spot. 

From the beautiful Lake Michigan to the jaw-dropping skyline, there are endless opportunities to create her dream proposal here.

Walking down the Mag Mile, you can find high-end fashion stops, dainty cafes, and even little secret gardens to share an intimate moment with your lover. Even more, Chicago is home to some of the world’s most famous museums and buildings, many of which prove to be beautiful spots for her dream proposal. 

The key to choosing the perfect location for your proposal is to make sure it reflects the two of you and your relationship.

While this might sound surprising coming from me, the location does not have to reflect the biggest, brightest moments of your relationship.

Yes, there absolutely needs to be reasoning behind why you chose that spot. It can be something as simple as “I chose a location with a rooftop view because one of our favorite things to do together is watching the sunset”. See? Meaningful, sentimental, and a moment she won’t forget. 

With the variety of views, seasons, and events, there truly is no better place to pop the question than Chicago.

No matter the time of year, I guarantee the perfect spot for you to propose is here. We just need to find it!

Chicago has everything for everyone: Find a neighborhood that reflects you.

For someone who is not local to Chicago, let me warn you. There are an overwhelming amount of neighborhoods you could pick to propose in. 77, to be exact.

If you’ve ever been fortunate enough to travel around town, you can see how diverse and unique each neighborhood is, and that is something Chicagoans take great pride in. 

From River North, Old Town, and Gold Coast in the heart of Chicago to Chinatown, Wrigleyville, Uptown, Lakeview, and Wicker Park, the options are truly endless.

While you may think closer to downtown means constant hustle and bustle, you’d be surprised at the amount of secret, intimate spots you can find. 

With such diversity, range of culture, and scenery, each neighborhood offers something valuable to the city, just as they can for your Chicago proposal. Whether you want it indoors or outdoors, private or public, daytime or nighttime, I promise that you can find exactly what you’re looking for in one of these 77 communities. 

Post-proposal food cravings? Dive into Chicago’s acclaimed dining scene.

Listen now and listen closely. A restaurant is meant to CELEBRATE your proposal, not where you pop the question (unless you want to be basic).

Proposal Destination Chicago in the us
Photo By: Golden Hours

Restaurants line every street, from comfort food to Michelin star meals. We all know Chicago is known for its deep-dish pizza. While I can agree it’s rather delicious, I’d recommend something else for the celebratory meal.

From Italian to seafood, Chicago has it all. Because Chicago is so people-diverse, it’s also incredibly flavor-diverse, which means there is something for everyone.

Chicago is home to 24 Michelin-star restaurants. While we don’t suggest proposing in a restaurant, all the emotions are going to make you both hungry.

What better way to celebrate your ultimate Chicago destination proposal than treating yourselves to a meal made by world-renowned chefs? 

If you’re looking to stop for food before the proposal, there are plenty of options, both sit down and to-go, that will more than satisfy your stomach.

Drinks? We’ve also got that covered. With the never-ending list of 5-star bars and rooftop lounges, your tastebuds will cry tears of joy. After all, Chicago is known for its brewing scene as well as its food scene, so it really is a must-do. 

If one of you (or both!) has a sweet tooth, you’re in luck. From ice cream to pastries, Chicago truly has it all. 

Finding a truly delicious meal can be hard in such a large city.

Lucky for you, we’ve curated a list of the most luxurious spots you can find. This isn’t just any list though- being locals, we really do know the best of the best. A few we would recommend:

No matter where you’re coming from or what food you like, Chicago is the perfect place to plan your proposal.

Chicago's number one proposal destination
Photo By: Golden Hours

Let the locals show you the best spots to celebrate the rich architecture and incredible views.

Perhaps the most obvious, yet most notable feature of Chicago is the stunning architecture and design of the city.

Home of the world’s first skyscrapers, the views are truly magnificent. Whether you’re walking around the streets downtown, or eating a meal on the rooftop, you will find yourself starstruck.

Not only are the skyscrapers impressive, but the architecture along the river is filled with rich history and jaw-dropping buildings.

If you get a chance to go on an architecture tour down the Chicago river, you absolutely must take that opportunity. Even those who grew up surrounded by these impressive works of art still find new beauty every day.

Of course, there are a variety of incredible 5-star hotels whose views will blow you away. From those right on the river to hotels along Michigan Ave, you truly cannot go wrong. Add in the world-renowned museums, and you’ve got endless options.

Now, you may be thinking, “These buildings are incredible but how does that help my proposal?”. The answer? PHOTOS! 

Chicago presents the perfect backdrop no matter where you are in the city.

One of the most important people that helps you with your proposal will be your photographer, and I can promise they will capture the entire moment perfectly.

You will be able to look back at your proposal photos and see the stunning city of Chicago reflected throughout, whether it’s the skyline, the river, or really anywhere you choose to get down on one knee.


Think about it. Would you bring your Audi R8 or Mercedes to the most generic dealership, or would you rather bring it to someone who truly knows your car and will treat it right? Exactly. 

So, why would you go to Google or Craigslist to find someone to help plan one of the most important days of your life, when you could be guided through the entire process by someone who lives, breathes, and sleeps Chicago wedding proposals? 

It just makes sense. As females, we know what your girlfriend wants. 

During our brainstorming session, we want to get to know all about her, her style, her favorites, and her expectations for her dream proposal. With that, we design a custom proposal and help you the entire process, from the first inquiry to the celebrations after you pop the question. Not only are we local, but we are truly the only proposal planners that dig into this process to create a custom experience for you both. There’s truly no one better to help plan your ultimate destination proposal in Chicago. 

It’s time to pop the question- come to Chicago, the ultimate proposal destination.

Chicago is the best city for proposals in the United States, according to We already knew that, but hopefully, you now know that too. No matter what spot you pick to propose in Chicago, it will be a magical moment for you and your now-fiancé. 

Looking for some guidance? Hire us to plan your Chicago proposal today. Book a call to start planning your dream proposal here

About Jenée Strickland

Visions Event Studio specializes in luxury events, including proposals and couture weddings. Jenée Strickland, owner, and lead visionnaire, has been an integral part of hundreds of weddings and proposals. Her job is a privilege; her work is a passion.

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