Get the latest tips & Tricks right in your inbox.

Romantic Winter Proposal in Chicago

Santa Claus, Snow Flurries, and a Gorgeous Ring, Yes this is the Perfect Setting for a Romantic Winter Proposal!

While most of us don’t dream of the day he will propose, we envision maybe the walk down the aisle as the big moment that plays in our minds from the time we are little.  For this bride, she will get both!  A winter proposal that dreams are made of and a walk down the aisle that will begin the journey of the rest of their lives together.

When Roy hired Visions Event Studio to plan his over-the-top winter proposal, we had exactly seven days from our first phone call to on bended knee.  Yes, I said SEVEN days!

After sitting down with Roy over a brainstorming session, we hit the ground running with the creative process, we planned every detail within 24 hours!  It was, I think the craziest 24 hours in Visions history.  Like all of our customized proposals, we wanted for Roy and Stacey to be interwoven into all details of this proposal.  Details that only the two of them would recognize through sharing this moment over and over again.

We don’t have a standard list of ideas, so we always start the creative process with a blank slate.  Well not exactly, we do have a cheat sheet of sorts, it’s called PINTEREST!

Upon gathering all the information from Roy, one of the key points is to stalk our bride-to-be, to gain a sense of who she is, and what her style is, so we can meet all her expectations as well.

As with all proposal planning, Roy received three unique concepts (all planned again in 24 hours) that he was able to choose from.  I believe the word he used when hearing the Winter Wonderland concept was WOW-GOOSEBUMPS!! We were so excited to move forward with implementing all the details with the florist, photographer, and videographer.

The day of the event we met with Roy to go over last-minute details and pick up the GORGEOUS engagement ring so he didn’t have to carry it through dinner.  The plan of events was carried through with no hiccups, and no fires to put out, it was perfect.

Roy and Stacey arrived at the Waldorf Astoria after having dinner, they were to go to the lounge for a few drinks for Visions to put everything in place.  We hired a Santa (Stacey loves Christmas and Santa, not sure if I mentioned that) and while they were in the lounge Santa was to be waiting for Stacey outside.

The stage was set and then it happened, Stacey ran into Santa, our Santa ahead of schedule!!

Of course, she didn’t know that this Santa was hired for her gorgeous winter proposal, and as she saw him in the lobby, she couldn’t resist asking a nearby photographer (oh just so happens this is her photographer for her proposal that she knows nothing about) to take a few couples of pictures with Santa and Roy.  After her brief encounter with Santa they go back into the lounge for drinks, this is Roy’s cue to “use the restroom”, probably the longest wait of Stacey’s life.

She begins to get suspicious when Roy doesn’t return to her in the lounge after a few minutes and begins texting and calling him trying to figure out what’s going on.  Little does she know, Roy is on his way to the Wyndham Grand hotel to get in place for the proposal.  He texts her back, “Go outside” where she is greeted by Santa.  He hands her a card from Roy, and gets in the limo that escorts her to the most amazing Chicago proposal the world has ever seen!

As she arrives, I greet her, and clearly she isn’t 100% unaware that this is a proposal, as you can read below by her Diary of the Busy Bride answers- she knew there was some sort of surprise but not a ring on her finger at the end of it.  As we opened the doors to her white hydrangea infused winter wonderland, Roy got down on one knee to profess his love for her.  It was breathtaking, talk about goosebumps!! It was so wonderful to be apart of such a special moment for the two of them.

We sat down with Stacey after the proposal to see how planning is going as well as talk details on what was going through her mind while all of this was unfolding. Check back tomorrow for the Diary of the Busy Bride from Stacey.

Waldorf Astoria Proposal

Waldorf Astoria Proposal 2
Waldorf Astoria Proposal 3
Waldorf Astoria Proposal 4
Waldorf Astoria Proposal 5a
Waldorf Astoria Proposal 5
Waldorf Astoria Proposal 6
Waldorf Astoria Proposal 7
Waldorf Astoria Proposal 8
Venues | Waldorf Astoria & Wyndham Grand Hotel- Ballroom
Visions Event Studio | Stylist & Proposal Planners
Evan Hunt Photo | Photographer
One Fine Day Productions | Videographer
Natural Beauties Floral Inc. | Florist
Windy City Limousine | Transportation

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.

Leave a Reply

Your email address will not be published. Required fields are marked *

What’s Good