Find the Best Chicago Proposal Photographer

Let’s capture your perfect proposal

  • done8,000+ Surprise Proposals Captured
  • doneEasy, Hassle-Free Booking Process
  • doneHand-Picked, Local Photographers
  • doneBeautiful, Professional Photos Guaranteed

Since 2013, Flytographer has captured thousands of surprise proposal photos. Discover the perfect locations in the Windy City for Chicago proposal photography such as the iconic architecture along the Chicago Riverwalk, a romantic stroll through Millennium Park, or views of the Chicago skyline at North Avenue Beach. Choose from our top-rated, professional photographers below and we’ll take care of the rest!

Find My Photographer

How to Book a Proposal Photographer in Chicago

Whether you’d prefer an intimate moment, or dream of a wild, romantic gesture when you pop the big question, our photographers will bring your vision to life and ensure your surprise proposal is beautifully documented.

1. Find Your Secret Photographer

Choose from our community of highly-vetted, Chicago proposal photographers.

2. Create the Perfect Game Plan

Choose one of our go-to proposal tactics, or customize your own. Learn more.

3. Capture the “Yes!”

Share your vision with your photographer and communicate with them directly to plan every detail.

4. Receive Your Photos

Your online gallery will be sent within 5 days of your shoot – ready for you to download and share.

Choose Your Chicago Proposal Photographer

Our professional photographers are all vetted, hand-picked and highly rated. They LOVE their city and their clients, and are passionate about capturing life’s special moments. From romantic getaways to marriage proposals to family memories, they are here to capture the beauty of it all.

Select a date to view available photographers below.

Danielle
(22)

I am a Chicago-based photographer who loves traveling, animals, coffee, and taking as many pictures as I possibly can! My style is candid, but I can also set up a great posed shot when needed. I love bright colors, dreamy atmospheres, and a couple who loves to laugh and have fun with each other! I think that always makes for the best photos.
Brigette
(8)

I am obsessed with exploring our globe with my camera in hand. I love the color purple, crazy hats, funk music, and all things outdoors! My photography style is candid, in the moment, and has a strong emphasis on showcasing the landscape and location we are in. I stick to natural colors with a hint of vibrancy and color.
Amanda
(84)

I'm Amanda and I am beyond excited you have found me, my work, and are considering me to capture your adventure! I am an avid hiker, jeep beeper, craft beer nerd, and most days you can find me planning a trip around a live concert. My photography style is all about capturing who YOU are, by keeping it relaxed, casual, and authentic. Being outdoors inspires my photography style, and I hope that it inspires you as well. You can find my work featured on "Wandering Weddings", "Wedventure Magazine", and "Photobug Community".
Brandon
(32)

I am a dedicated and enthusiastic photographer that has an eye for aesthetics, details, and editing. Through my photography I try to encapsulate the moment and the person authentically. My style of photography ranges from bright and airy to dark and dramatic, depending on the feeling I chose to capture. I have shot for red carpet events, local businesses and was featured in the Just Water Mother's Day campaign. I have also started a blog where I showcase much of my work as I collaborate with different brands.
Maurice
(22)

I’d describe my photography style as the perfect blend of editorial, photojournalistic, and documentary approaches. My goal as an artist is to tell a story that feels true to you—capturing candid emotions and genuine moments while delivering images that are both timeless and stylish. I strive to create definitive portraits that showcase who you are in that moment, with a touch of artistic flair.
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Perfect Locations to Propose in Chicago, Illinois

Beautifully capture your love story at one of these best places to propose in Chicago below – curated by our local Chicago photographers – or choose your own custom route.

Most Booked

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Chicago Riverwalk

Iconic architecture

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North Avenue Beach

City skyline

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North Avenue Beach & Lincoln Park

Epic views

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Family Favourite

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Lincoln Park

Gardens and sculpture

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The Bean at Millennium Park

Public art

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Iconic Sights

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Millennium Park & Chicago Riverwalk

Urban stroll

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Top Chicago Proposal Photoshoot Locations

"Easiest service I ever came across. The options of photographer with examples of their work made it easy to choose the style and time domain I wanted. The communication once the booking was complete was on point and the planning leading up to the event was perfect. This website made my engagement extra special!"

— Matt L
Book a Photographer

Chicago Proposal Packages & Pricing

Capture the YES!
30 minutes
$425 USD

20 Photos

1 Location

Digital Files Included

Capture:

checkThe build-up and anticipation

checkThe actual proposal moment

Capture the Memory
60 minutes
$525 USD

35 Photos

1-2 Locations

Digital Files Included

Capture:

checkThe build-up and anticipation

checkThe actual proposal moment

checkCelebratory moments afterwards

Most Popular

Capture the Glow
90 minutes
$690 USD

50 Photos

Multiple Locations

Digital Files Included

Capture:

checkThe build-up and anticipation

checkThe actual proposal moment

checkCelebratory moments afterwards

checkPosed portraits + candid interactions

Capture the Love
2 hours
$815 USD

65 Photos

Multiple Locations

Digital Files Included

Capture:

checkThe build-up and anticipation

checkThe actual proposal moment

checkCelebratory moments afterwards

checkPosed portraits + candid interactions

checkMore hidden gems of Chicago

Chicago Proposal Photo Shoot Reviews

“ Oh my goodness. Hired Amanda to capture our engagement… I don’t know how she did it but she captured every emotion so completely, looking at the photos brings me right back.❤️ Amanda is very warm and personable. She will make you feel comfortable from the moment your session starts. She does a great job balancing your requests/preferences with her expert knowledge to capture your moments in the best way. ”

“ Maurice did a great job for our proposal shoot! He was helpful in planning this moment from day one. He was timely and professional throughout the entire process. Everyone we have shown the photos to were blown away! I highly recommend using his services!! ”

Maurice in Chicago
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“ Maurice's preparation and ability to go the extra mile made this proposal shoot possible. Thank you so much for helping me capture this once-in-a-lifetime experience! ”

Maurice in Chicago
location_on Custom Route

“ Brandon was extremely helpful in the planning of my proposal. He was very easy to work with and the pictures he took were incredible. He captured her reaction perfectly and we couldn’t be happier with the way everything turned out. ”

Brandon in Chicago
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Frequently Asked Questions

What are some proposal tactics to choose from?

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  • Friendly Tourist: Your Flytographer, posing as a friendly tourist, will offer to take a photo of you and your partner.
  • Vacation Cover: Let your partner know that you’ve booked a regular couple’s photo shoot so you can prepare for the photo shoot together without suspicion.
  • Fly on the Wall: Your photographer will remain hidden for the actual proposal. While this allows for an intimate moment, it is the most risky as passersby could interrupt your shot.
  • Customized: We are happy to adjust these scenarios if you have another idea in mind for how you would like your proposal to go!

Will I be connected with my proposal photographer directly?

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Yes! Immediately after you book your Flytographer in Chicago, you will be connected via email to begin the proposal planning process together and create the perfect plan. You can choose from one of the above proposal scenarios, or share another idea, and ask them any specific questions you might have leading up. Your photographer will be able to share their favourite tips on how to plan your Chicago proposal.

What is the difference between a proposal and engagement shoot?

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Your proposal photo shoot with us in Chicago would involve your Flytographer capturing the moment when you get down on one knee to surprise your partner with a marriage proposal. After the big moment in a proposal photo shoot, you can transition to taking engagement photos if you choose a longer session.

Engagement photo shoots with us would take place after the proposal moment (when you are already engaged) and involve capturing your newly engaged bliss. If you are already engaged, you can book a normal engagement session rather than a proposal photo shoot.

How much does a proposal photographer cost in Chicago?

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Our proposal package pricing starts at $425 USD for a 30-minute shoot. Easily book a trusted, local photographer in Chicago. We'll organize all the details and share our expert tips to ensure your proposal in Chicago goes perfectly. Make the moment last a lifetime with beautiful photos to reflect on together, relive the memories, and share with friends and family when you return home.

How much are engagement photos in Chicago?

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If you have already popped the question and are just looking for Chicago engagement photos, our regular engagement photography portrait sessions start at $325 USD. See all pricing here.

Does Flytographer do wedding photography?

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We do not offer wedding photography; however, we can capture the moments leading up to and after the big day. While we can’t capture wedding photos in Chicago, we can capture surprise proposals, engagement photos, pre-wedding trips, bachelorettes, bachelor parties, honeymoon trips, anniversary photos, and more!

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