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Chicago Winter Proposal Ideas

Winter Proposal Ideas
Photo by Google Images

When the weather outside is frightful, here’s how to make your winter proposal delightful!

It’s winter–the ring is burning a hole in your pocket. The holidays have passed and so has your chance for a romantic winter proposal.

We’ve got good news: Winter is the BEST season to propose! There are so many romantic winter proposal ideas to choose from. 

In fact, waiting to propose until after the holidays will help to ensure that your proposal is a total surprise! 

A holiday proposal is predictable and overdone, but that doesn’t mean a winter proposal will be too. So how can you come up with the perfect winter proposal ideas?

Find the elements that make winter so romantic and infuse them into your winter proposal. 

While the weather outside is frightful, the fire is so delightful. And yet we sing “let it snow, let it snow, let it snow”. Why? Because there is an undeniable romance that accompanies the blanket of cold that surrounds us. The falling snow, the city lit up with twinkling lights, a roaring fireplace.

Winter is a time all about taking in the magic of the season. It literally provides the perfect setting for a romantic proposal.

Don’t believe us? Do a simple Google search on “winter proposal ideas” click on images and take a look.

What is it that you see over and over again?

You see that winter makes for georgous photos! Couples embracing in the falling snow, the warm glow of candles and twinkling lights, and the cozy sweaters, hats and mittens makes for a picture-perfect backdrop.

Seems simple enough to find a beautiful spot filled with snow. Pair it with her dream ring, and voila, romantic winter proposal! You’re looking for better winter proposal ideas.

So how can we bring the romance of the picture-perfect snowy proposal inside without losing the charm? First, we have to identify what exactly makes winter the most romantic season. 

Chicago’s winters are romantic, it sets the perfect backdrop for your romantic proposal

I don’t think there is a city in all the country that glows quite like Chicago. The romantic mood that is set when winter comes to the city is a proposal planner’s dream. Let’s take a stroll through the endless possibilities of a winter proposal. 

Our first stop…let’s talk about the obvious freezing temperatures. While you might think we are crazy for even saying this just wait. Give us the opportunity to paint the picture that we see as the perfect winter proposal.

The cold weather and the falling snow add a cozy aesthetic that isn’t found any other time of year. This is what we were talking about before, you google winter proposal, what do you see?

It’s nothing but snow falling and men on their bended knee with ring in hand. Chicago is practically begging for you to propose during the coldest season.

This is the exact mood that we try to duplicate when planning summer proposals. We do it by bringing in the romantic details of dripping candle aisles and decor. But old man winter does it all for you if you choose a winter proposal.

As I said there is not another city quite like Chicago especially at night! With the twinkling lights that line the streets of downtown all season long, it’s a winter wonderland. 

All of a sudden everywhere you look, ordinary things become whimsical and charming. Like a street made for a hallmark movie. This built-in charm only comes around this time of year and adds a sense of magic to the city. 

Our second stop is another automatic romantic touch to any setting, the simplicity of a fire.  This could be an outdoor fireplace or indoor, but it’s the mood that comes with the setting.

The sound of crackling logs, the warm amber glow illuminating the room. The heat radiating throughout, it’s just another part of why winter is the absolute most romantic time to propose.

All winter long, these beautiful romantic fireplaces can be found all over the city. As proposal planners, we know just how to combine all of these elements to create the perfect winter proposal ideas. So keep reading to learn our tips and tricks!

Chicago Date Night Guide

A Picture Perfect Winter Proposal Idea Without The Chance Of Frostbite

Now that we’ve identified a few of the most romantic elements of winter, let’s take a look inside. How can we bring those elements inside for the bride-to-be that can’t stand the cold?

It’s not as hard as you may think! While the snow gives the city an added sparkle, it doesn’t have to be the central focus of your proposal to make it romantic. 

One way to keep the magic of the snow as a supporting role would be to through photos.

The number one request of all girlfriends is to have their nails done. The second request is to have the moment photographed.

We highly suggest you hire a local proposal photographer to capture the moment. This is a big moment in your life that you don’t want to leave as just memories.

When you are on your way to the proposal have your photographer get photos of you outside in the snow. As you enter the venue have the photographer snap a few photos. Not only does this help tell the story of the entire proposal from the beginning to the end, but you can still capture the winter.

From the blanket of snow, the warm coats, to the winter hats, it’s all part of the romance, without having to be outside for the entire proposal. This is the best of both worlds when planning a winter proposal.

As We Said Warmth Is A Central Theme To Romance, Set The Mood By Bringing The Twinkling Lights Inside

That’s right, Christmas lights aren’t just for the holidays.

There are so many possibilities of places to hang or wrap lights with an indoor venue to make your proposal jaw-dropping. Stringing them across the ceiling, wrapping support beams like trees outside, creating a curtain of lights for her to walk through as she enters…the possibilities are truly endless!

Bringing the lights inside not only provides the most romantic lighting, but the glow it adds to the photos is SO romantic. Just add lights and instantly you have a different setting all together!

Now, you’ve got the snowy walk-in and the beautiful twinkling lights…What would be the cherry on top of an indoor winter proposal? Getting down on one knee in front of a beautiful fireplace!

Yes, we mentioned how this simple element lends itself to romance but we are taking it to another level by getting down on one knee with the fireplace as the focal point.

What better backdrop for a stunning winter proposal than an elegant fireplace with a fire glowing warmly behind you? This also provides an opportunity to create an aisle with candles or rose petals leading up to the fireplace and adding even more soft romance.

At Visions, we even have a favorite fireplace in the Gold Coast that is absolutely perfect for a winter proposal and is the most romantic backdrop. 

Romantic winter proposal in front of fireplace at Ambassador Chicago
Photo By: Golden Hours

Still not convinced? Looking for a romantic winter proposal idea that still allows you to be outside? We’ve got a few tricks up our sleeve to help keep you stay warm if you’re committed to an outdoor proposal.

Commited to the Cold? Here’s How To Bring Warmth To Your Outdoor Winter Proposal  

For those of you that are still stuck on those google search images of the picturesque outdoor winter proposals, there are a few winter proposal ideas that will achieve your dream outdoor proposal without being too cold to speak. 

A little secret from a proposal planner , use the weather to your advantage.

Here in Chicago, the temperature from one day to the next can change drastically.

Take this week, yesterday’s high was 43 degrees, and today, it’s already down to a high of 19 degrees! Objectively, 40 degrees is not warm, but when it’s immediately following a stretch of much colder days, suddenly 40 degrees feels like spring! 

Let that work to your advantage!

Track the weather and choose a day that comparatively will feel much warmer. While it may sound counterintuitive, choosing a day with high chances of snow may actually feel warmer as well—and give you the most romantic photos. 

Working with the weather will only get you so far, and the weather in Chicago will always be somewhat unpredictable. So what other winter proposal ideas can also bring warmth to your outdoor proposal? 

My favorite tip is to set up a hot cocoa stand as part of your proposal. Not just your standard hot cocoa, but a specialty chocolatier will have delicious options to choose from, help to keep you warm, provide a sweet memory for the two of you, and will give you a great prop for taking photos afterward! Go the extra mile by getting personalized tumblers you can keep and remember your perfect proposal each time you use them in the future. 

A simple way to add a little warmth to an outdoor winter proposal is to bring a cute blanket or two that you can wrap up in together!

You may not want to do this until after the on-bended-knee moment, but having a warm blanket available after to cuddle up in will not only keep you warm but is another great way to add some charm to the photos. 

If you’re more of a practical guy, another way to stay warm would be to rent an outdoor heater or two to set up at your proposal location. Admittedly, these do have the potential to be an eyesore in your photos, so setting them up off to the side will at least allow for somewhere to warm up! 

The Most Romantic Winter Proposal Locations In Chicago 

Now that we know why winter is the most romantic season, we have several romantic winter proposal ideas for how we can make an indoor or outdoor proposal come to life in the cold. What are some of the stunning winter proposal locations in the city?

For your indoor proposal, we suggest finding hotels with a private or intimate space. These are just a few of our favorite venues we work with:

An outdoor winter proposal in Chicago could be done almost anywhere! Some of the most popular include:

These are all beautiful options and will give you the romantic backdrop easily, however, the issue you run into with these venues is that they aren’t exactly private.

If you are lucky you may have the entire space to yourself but, by hiring a proposal planner, you can ensure crowd control and not worry about a thing. 

If you know your girlfriend would prefer an intimate and private proposal, might we suggest the absolutely breathtaking views of the courtyard at the Ivy Room, complete with fully lit trees, beautiful brick architecture, and did I mention it’s completely private?! 

The list is never-ending with hidden gems in the city, but these are a few of our favorites for your winter proposal ideas. Curious about more venue options for your winter proposal?

Reach out today to learn more of our favorite proposal spots throughout the city!

Download Your Top Ten Date Nights Winter Edition Guide

Now let’s have a little sit down before we come to an end with our all-time favorite season to propose in Chicago.

Let’s talk about dating your girlfriend leading up to the proposal.

Yes, we are going to walk you through how to do this but we have also curated a list of the TOP TEN WINTER DATE NIGHTS IN CHICAGO. This guide is not just a list of your hot date spots but curated experiences thought-out the city. You do not want to skip this, it’s invaluable for all couples.

  1. If you are planning to propose any time soon, might we suggest that you continue to date your girlfriend. Take her on romantic dates! We aren’t talking about the typical dinner and drinks date night, I mean like when you first started dating how you purseued her and went out of your way to “date” her. What better way to come to your proposal than weeks of intentional romantic dates that lead up to the “on bended knee” moment. It’s often said you should never stop dating your spouse. Let’s start with the proposal!!
  2. If you don’t live in Chicago and are coming into the city for your big day I highly suggest you plan out your entire stay with some unforgettable date nights. This is will make the surprise fool proof as she will be so enthrolled in all the memories you are creating, a proposal won’t even be on her radar! Surround your proposal with a few of our curated date nights and you will be golden.
Your perfect winter proposal awaits!

At the end of the day, there is so much about the winter season that makes it the perfect time to propose, and there are so many romantic winter proposal ideas to choose from. Not only is this season filled to the brim with romance, but it also is not the most popular season for weddings, which makes finding a venue for a proposal much easier when you’re not competing with wedding bookings every weekend. 

Whether your girlfriend would prefer a romantic outdoor winter proposal complete with snow and hot cocoa, or an intimate indoor fireside proposal, there are endless possibilities to make your winter proposal romantic and unforgettable. 

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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