Chicago Wedding Photographer Blog

8 Surprise Chicago Proposal Ideas

8 Surprise Chicago Proposal Ideas

Stuart popped the big question last week…and he somehow managed to keep it all under wraps from Jessica! As a Chicago proposal photographer, I was able to lend my experience in helping Stuart with a few Chicago proposal ideas! I thought it might be fun to scroll through their proposal photos while sharing some proposal tips!

Here are 8 Chicago proposal ideas to help anyone in planning a proposal!

1. A Good Alibi – Every good proposal needs a good story. You can’t have your partner showing up wearing sweatpants! It was Saturday bunch with friends. If you need help with a good alibi for your proposal – send us a message and we can help!

chicago proposal ideas photos riverwalk

2. A good location: Stuart wanted this particular spot. He loved the view and this location became the anchor for the rest of his plans!

chicago proposal ideas photos riverwalk

3. Hire a professional photographer: Stuart knew that he wanted epic photos from his special moment. A flood of emotions came over them and Jessica was so glad Stuart had hired me to capture it all!

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4. Make her go WOW! Let’s just say…she LOVED her ring!

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Needless to say…they were both so excited to be engaged!

chicago proposal ideas photographer riverwalk

5. Take Photos Afterwards: Hiring a professional photographer means you will have more photos together after the proposal! Look at the sheer joy on the both of their faces!

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Number 6 of our Chicago proposal ideas: Have a Surprise #2! As we were taking photos along the riverwalk, Stuart’s surprise #2 was gathering in the rooftop space of Gibson’s Italia. You can see the rooftop space in this photo below

chicago proposal ideas pictures riverwalk

It was my job as their Chicago proposal photographer to get them to Gibson’s Italia on time…without her knowing what I was doing!

surprise chicago proposal ideas photos riverwalk

7. Have a party! Waiting in Gibson’s Italia were all of their closest friends and family from all over the country!

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Gibson’s Italia rooftop has the most amazing view of the Chicago River! That first bridge in the background is the bridge where Stuart proposed!

engagement chicago proposal ideas photos Gibsons Italiaengagement chicago proposal ideas photos Gibsons Italia

8. A Group Photo: We made sure to get a group photo of everyone who came to help commemorate the moment! (yet another great reason to have a professional photographer at your proposal!)

engagement chicago proposal ideas photos Gibsons Italia

Congrats again Stuart + Jessica! Your proposal was perfect! Jessica: I loved capturing all your emotions through it all. Great job Stuart on all your wonderful Chicago proposal ideas! You did it! Hope these photos help bring you back one of the happiest days of your lives!

with love,

your Chicago proposal photographer,

Kenny Nakai

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Chicago Wedding Photographer

312-298-9721

3334 N Avers Ave #2

Chicago, IL 60618