Venues & Hotels

Best Places to Propose In Chicago – According to Locals

So you’re planning to get down on one knee and pop the all-important question. I bet you can’t wait to ask the love of your life to marry you. And there’s no better place to do so than Chicago — the city of low-key awesomeness, fine dining, and romance.

A marriage proposal is one of the biggest moments in your life, and it deserves an unforgettable place to honor this special occasion. That’s why we’ve put together the best places to propose in Chicago. These romantic places we’ve picked aren’t your run-of-the-mill clichés but are anniversary-worthy spots where you can create a lasting memory.

What makes a proposal special?

A proposal is one of the most important things in your life that you have to plan and execute to perfection. It marks a new chapter in your life as a couple, so you need to go the extra mile to ensure it’s a truly special moment worth remembering forever. But what really makes a proposal special?

It’s all about being specific and personal. Asking your sweetie for their hand in marriage may be a timeless tradition, but you need to personalize the whole thing to make it extra special. You should pour your heart and soul into the planning to make it specific to your loved one’s taste, style, and personality.

There’s of course no wrong way to propose — you can pop the question via Zoom, spell it out on beach sand, or plant the ring in her favorite dessert. But appealing to your sweetie’s personality and taste in a great way ensures the proposal goes off without any fuss. Their personality should shine through in every element of your proposal.

A romantic setting is everything. The location can make or break your proposal, which is why most people love to propose on Valentine’s Day. To create a meaningful and unforgettable memory, pick one of the best places to propose in Chicago. Ideally, the place and atmosphere should be private, romantic, and sincere.

This is where your better half’s personality and taste in places should also shine through. If they love sunsets, consider a rooftop proposal with Chicago’s skyline providing the perfect backdrop.

Let the ring steal the spotlight. The perfect ring can turn any place into a memorable proposal spot. Make sure the ring is just the right size, ensuring that it resonates well with your partner’s lifestyle, preference, and personality.

Surprise, surprise, surprise. Part of the charm that makes a marriage proposal so special is the surprise, especially when you open the precious box with the ring. And, well, nearly everyone loves a good surprise. If your bride-to-be is a shy, reserved, or private individual, perhaps you should stick to a more intimate setting where you can set up the perfect surprise without making them nervous.

If your to-be is an outgoing person who loves all the attention, you should think of a way of incorporating your family, friends, or coworkers. Perhaps a flash mob can do the trick. No matter the case, see to it that you hide the ring.

Make sure she’s looking her best. If you’re proposing to a lady, it’s wise that you time the proposal to when she’s dazzling and Instagram-ready. The day before the big day, you could treat her to a pedicure and manicure spree.

It must be memorable. Think about it — the proposal is one key moment that’ll be retold and remembered for decades to come. So, it’s crucial to go above and beyond to make the event unforgettable.

A proposal is memorable when it’s done in a place that’s special to your bride-to-be. It can be their favorite restaurant, country, city, beach, you name it.

If you’re an outdoorsy couple, you can go down on your knee and propose on a camping or hiking trip. For a nature lover, you could take your partner to a place with amazing natural sights and scenic beauty. They will make for an awe-inspiring proposal background.

Make it meaningful. If there was ever a perfect occasion to get all sentimental, this is one of them. Take note of the important moments you’ve had in your relationship. Take your partner where you first kissed, said you loved them, or met. Do you share a passion for a particular book, movie, song, view, or restaurant? Draw on these noteworthy moments to make the proposal even more special.

Regardless of which route you take, always plan your proposal with all your heart and soul. Be specific to what appeals most to your partner, and your love will certainly shine through and make the proposal extra special. Keep details in mind, choose the right date, and hire a photographer to snap every precious moment.

What makes Chicago such a great city to propose in?

What’s not to love about Chicago? It’s a city of romance and love. The Windy City has charmingly lush neighborhoods where you’ll fall in love with each other all over again. It has breathtaking skylines, stunning skyscrapers, and a gorgeous lakefront with picture-perfect vistas.

Plenty of proposal-worthy spots – While planning a killer proposal might seem daunting, the perfect setting can surely go a long way toward making it beautiful. Lucky for you, there’s a huge variety of the best places to propose in Chicago. The Second City is soaring with romantic spots that include lush parks, swoon-worthy restaurants, vintage and contemporary museums, stunning beaches, and lakefront gardens, just to name a few picturesque places to pop the question.

Whether you’re a shy couple looking for an off-the-beaten-track experience, foodies interested in the culinary scene, or outgoing people who want the ultimate nightlife, Chicago is the place to be. The city has charming and walkable neighborhoods that make for romantic hand-in-hand walks.

The food scene is to die for – There’s no shortage of romantic restaurants spread throughout Chicago, from Central Loop to South Shore and Rogers Park. If you’re itching for an intimate restaurant setting to propose, you’re in for a special treat. They range from scrummy rooftop lounges to lakefront garden restaurants with scenic views.

Chicago is a melting pot of cuisines, offering classics like deep-dish pizza, fine dining, and the world’s best eats, from garlicky enchiladas to Polish pierogi and much more. Just loosen your belt as there’s a lot for you, your partner, and other invitees to your event.

Chicago’s art scene is as romantic as it comes – The Windy City plays host to some of America’s highly-regarded museums, festivals, art galleries, and more. If you’re planning to propose to someone with a passion for all things cutting-edge and avant-garde, there are several modern and contemporary museums and art galleries to propose in.

Music and food festivals are a big part of the awesome Chicago culture. The city sure knows how to rock a festival, with more than 180 festivals held in Millennium Park.

Impressive architecture – If your spouse-to-be has an eye for architecture, you will be spoiled for the choice of the best places to propose in Chicago. Wow-inspiring architecture is ubiquitous, from Frank Lloyd Wright’s Robie House to the gothic architecture of the University of Chicago to the sky-high glass-floored Willis Tower.

You’re probably familiar with the Picasso statue, but Chicago streets are also studded with quirky public art and installations that will make your proposal truly special. For something especially whimsical yet romantic, you won’t go wrong with the majestic Ferris wheel at Navy Pier.

What do Chicago locals look for in a place to propose?

Once you have decided how you want to propose, the next sensible step is to choose where it will take place. While it’s true that there are some of the best places to propose in Chicago, you’ll want to find a spot where the proposal will go off without any hitch.

Here are top things Chicago locals look for in a place to pop the question:

– They consider the privacy of the place

If your sweetie is a private and shy person, they most definitely don’t want to be in the spotlight. Some people of course dream of sharing their big proposal with the world. If you’re unsure what your partner would prefer, it’s best to choose a quiet, romantic setting away from the hustle and bustle of the city.

– They consider costs

You’ve probably spent a small fortune on the rock, and she’ll obviously adore it. If you’ve got a big budget, you can go all-in – after all, this is something that you get to do once in your lifetime. Plan an elaborate shindig with a flash mob.

However, if you’re on a lean budget, it makes sense to pick a place that’s wallet-friendly yet romantic. Proposals can be as costly as people want to make them—ring, dinner, limo–but you don’t have to splurge if you can’t afford it. If you put all of your heart into it, the passion in your actions will certainly show.

– Sentimental aspect of the place

Chicago locals love a place that’s special, scenic, or has some sentimental value for their partner. For instance, some locals may choose to propose in a place they first kissed their bride-to-be rather than a high-end restaurant.

– They think about the weather

Chicago has one of the harshest winter seasons in the US, so proposing outdoors may not go so well in January and February. That’s why most locals have to mind the weather before choosing the perfect spot for proposing.

The weather is pleasant outside in May and September, which makes for a great beach, nature, or waterfront proposal. Besides, you’ll want to check that there’ll be no heavy rainfall, snow, or storm during your proposal.

All things considered, choosing the perfect spot to ask your partner for a hand in marriage will depend on the person. And locals have plenty of the best places to propose in Chicago to choose from.

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