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Chicago Proposal Ideas

Calling all Chicago natives! This board is for you! Ever wondered where the hottest locations to pop the big question are in the Windy City? Look no further! From rooftops to historical downtown, to the best locations for all-season proposals...you'll find ideas and inspiration galore in this board.
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Visions Event Studio | Chicago's Proposal + Wedding Planners
This may surprise you but it's actually not that easy to ask “Will You Marry Me��”. With emotions running high and nerves shot you will enter what we call the "proposal fog" where you get lost in the midst and your mind goes completely blank. Don't worry, this is totally normal almost everyone experiences it. We will guide you through the fog so you don't get stuck in your head. Read down below to find out how to avoid proposal fog and what else to say during your special speech.
When you get down on bended knee there are certain things you want to say, we understand how hard it is to get the important stuff out while not getting tongue-tied. When you propose, it's important to keep it short and sweet, but still sentimental and meaningful. So, how do you pick out the best things to say and the best moments to reminisce on? We want to help you! Check out our guide to find out!
Your proposal speech is one of the biggest speeches of your entire life, why would you not have something prepared? Do you know where to start when creating a speech that is so deep and personal? It's essential you know all the right things to say when you get down on one knee. It can be hard to know what to say to your partner on such a special and momentous occasion. Visions wants to make sure that you know exactly what to say and we have a whole guide to help you out. Check it out!

Chicago Unique Venue Proposals

18 Pins
A private string quartet, a candlelit venue, and the two of you surrounded by winter’s quiet beauty. The perfect Chicago proposal—intimate, unforgettable, and straight out of a dream.
When you put less effort into the proposal it will show and it's not a great look. The proposal is THE moment, it's what she has been waiting for. The after party is not what she has been dreaming of for months. Nor will it be the question everyone asks...Did he throw you an after party?? The number one asked question is "HOW DID HE PROPOSE?" Put your effort into the propsoal and add a fun after party for the cherry on top.
Your proposal is a reason to celebrate! But, by bringing the party in too soon, it takes away from the magic of the initial proposal moment.  A private proposal allows you both to enjoy the moment without all eyes on you.

Chicago Luxury Hotel Proposals

15 Pins
A proposal after party may be your perfect way to celebrate your proposal right after. But there may be a reason not to. There is a very clear and obvious reason why a proposal after party may not be the best choice for you and your bride. She is not a big fan of being the center of attention and is extremely private.
More isn't always merrier, read more on the reasons we believe you should keep the proposal private. We’re not suggesting excluding your family entirely. However, there are far better ways to include all of your loved ones without subjecting your girlfriend to a room full of people staring at her during one of the most intimate moments of her life.
You have to pull out all the stops to get down on bended knee and the spotlight is on you, what you have planned, what you came up with and of course when you proposed. | Golden Hours

Chicago Rooftop Proposals

21 Pins
When you get down on bended knee there are certain things you want to say, we understand how hard it is to get the important stuff out while not getting tongue-tied. When you propose, it's important to keep it short and sweet, but still sentimental and meaningful. So, how do you pick out the best things to say and the best moments to reminisce on? We want to help you! Check out our guide to find out!
Confused about what to say at your proposal? Most men will typically wing it and hope for the best. That definitely is not what she is expecting or wants.Remember! You have to tailor your proposal to her, what is it about her that you love so much, how does she make your life better? Not every woman is the same, actually, every woman is very different.That's the beauty of proposing! You get to create a speech that's unique to your love story and your special journey.
Lexi-David LondonHouse Proposal in Chicago, IL, US Janet D Photography beautifully captured Lexi-David LondonHouse Proposal. Event Info Location: Chicago, IL, US Event Date:  Jun 19, 2019 Client Info Client Orientation: Hetero Client Names: David Gust & Lexi Schultz Album Story – Lexi-David LondonHouse Proposal  Lexi thought the couple was on their way to meet with David’s […] The post Lexi-David LondonHouse Proposal in Chicago, IL, US appeared first on AisleMemories.

Chicago Intimate Outdoor Proposals

78 Pins
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Kicked off day ONE of 2025 this morning with the amazing Dr. Edie Wadsworth for Made for More! 🎉 Her wisdom was exactly what I needed to hear today. 🙌 Already downloading her book All the Pretty Things because I can’t wait to dive in (yes, I’m officially adding it to my 2025 book list 📚 because why not?!) Let’s do this! 💥 #MadeForMore #AllThePrettyThings #2025ReadingGoals #GrowthMindset
black and white photograph of people sitting at tables in a restaurant with candles on the table
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
a man and woman kissing in front of a christmas tree
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
black and white photograph of a woman holding her hand up to her mouth with the city lights in the background
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
a man and woman standing next to each other in front of a cityscape
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
a man and woman holding hands while standing on a roof top with candles in the background
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
a man and woman kissing in front of the city lights
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
a man and woman kissing on top of a building with candles in front of them
Rain or shine, this proposal at the Ambassador Chicago was nothing short of magical! 🌧️ Natalia thought she was simply going out for drinks with friends, but little did she know, she was about to walk into a fog of romance. Surrounded by the soft glow of candles and the twinkle of city lights, the moment was nothing less than perfect. ✨ It was a scene that felt like something straight out of a dream—intimate, romantic, and unforgettable. As they stepped into this new chapter, their love was ...
This may contain: the year in review is here
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✨ Wrapping up 2024 with gratitude and excitement! ✨ To all the incredible couples who trusted us with your proposals this year: THANK YOU. 💍 It’s been such an honor to help bring your vision to life and celebrate this unforgettable moment with you. A huge shoutout to the amazing vendors and venues—both new partners and longtime favorites—who made every detail extraordinary. We couldn’t do it without you! Wishing everyone a happy and love-filled New Year as we look forward to all the love s...
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Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
Calling All Besties! You know your girl deserves a proposal straight out of her dreams, and it’s time to make it happen. Her partner might have the ring, but let’s be real—they need a little extra help to pull off something truly epic. That’s where a proposal planner (and you, the ultimate wingwoman) come in. 💁‍♀️ From florists to photographers, and every tiny detail in between, a planner takes the stress out of the equation. We’re talking logistics, timing, and even those “what if it rain...
💍 Imagine this: Your bestie has been dreaming of the perfect proposal since the moment she learned what Pinterest was. She's dropping hints like they're confetti, and her partner is overwhelmed by options. Enter you—the real MVP—who knows that calling in a proposal planner is the ultimate move. Trust me, this isn't just a step; it's a whole leap into Best Friend of the Year territory. 🌟 Hiring a proposal planner isn’t just about making things easier (though, let’s be real, avoiding the stres...
💍 Imagine this: Your bestie has been dreaming of the perfect proposal since the moment she learned what Pinterest was. She's dropping hints like they're confetti, and her partner is overwhelmed by options. Enter you—the real MVP—who knows that calling in a proposal planner is the ultimate move. Trust me, this isn't just a step; it's a whole leap into Best Friend of the Year territory. 🌟 Hiring a proposal planner isn’t just about making things easier (though, let’s be real, avoiding the stres...