Chicago Proposal Photography

Planning a Proposal in Chicago?

Are you ready to propose in Chicago? Whether you’re visiting or calling The Windy City home, planning a proposal in Chicago and wanting to hire a proposal photographer in Chicago might feel a bit overwhelming. But it doesn’t have to be stressful, and you don’t have to do it alone. We’re here to help ease your fear of finding the best Chicago proposal photographer and planning your Chicago engagement photography.   

As trusted Chicago proposal photographers with over 20 years of experience and 750+ proposals captured, we specialize in turning your vision into reality — seamlessly planning, orchestrating, and photographing your “Yes!” We don’t just capture moments: We transform the most powerful memories of your life into breathtaking works of art that you and your fiancé will cherish forever. 

Why Hire a Proposal Photographer in Chicago?

Once a private moment, proposals are now just as cherished and shared as engagement and wedding photos.

✔ 75% of couples now hire a photographer to photograph their engagement in Chicago.
✔ Nearly half of proposals occur in public places — think iconic Chicago landmarks, scenic skyline spots, beaches, gardens, and parks.
✔ Intimate indoor Chicago proposals have become popular. We can help recommend the best private proposal locations in Chicago.

This is your once-in-a-lifetime moment. Whether you’re a meticulous planner or need a last-minute Chicago proposal photographer, we’re here to ensure your proposal is beautifully documented without any stress.

How much does photographing a proposal in Chicago cost?

The average price for Chicago proposal photography varies depending on whether customers value receiving simply proposal coverage or adding an additional portrait session following their proposal.

Many clients budget between $600 and $900, with most opting to invest $750.

You will sign a contract and remit a 50% retainer to secure your date and time. Your Remaining Balance is due once your images are ready for delivery. 

While a proposal coverage alone often delivers 25-50 photos, including the approach, proposal, detail photos of the ring, and a handful of quick portraits at the location where you got engaged, adding an additional 30 to 60-minute portrait session can equate to an additional 75-150 impactful images.

Post-proposal portrait Sessions offer a fun opportunity to create more memories incorporating additional locations, dynamic lighting, and a higher quantity of delivered images. These sessions result in some of our clients’ favorite memories, often doubling as save-the-dates, profile photos on social media, and artwork in our clients’ homes.  

Why trust Jason Kaczorowski Photography to photograph your proposal?

We are the OG Chicago proposal photographers.  

We’ve helped plan and capture more proposals in Chicago than any other photographer.

We deliver your proposal highlights within hours and your entire gallery the very next day!

✔ Two Decades of Experience.
✔ Hundreds of All 5/5 Star Reviews.
✔ Over 750 Proposals Planned & Photographed.
✔ Faster Delivery than any Photographer in Chicago.
✔ Piece of Mind. Back-Up Equipment. Back-Up Photographers.
✔ We Capture Moments that Captivate, Craft Striking, Timeless Portraits, and Sculpt Light into Art with Every Frame.

These are the moments in life that are worth investing in! Why risk the opportunity on someone still learning the art of properly photographing proposals? Proposals are spontaneous events — there are never any do-overs. This is a once-in-a-lifetime occasion. Don’t take chances on someone cancelling or not showing up on time to your proposal, missing the moment all together, or delivering anything less than amazing images of one of the most momentous moments in your life. We always carry back-up equipment and have a team of seven (7) photographers in case your photographer were ever sick, in an accident, or needed to quarantine.  

We’ve been photographing proposals in Chicago for twenty years and my team and I have helped orchestrate and photograph more than 750 proposals in Chicago and across the globe. 

We understand the importance of sharing the good news immediately, so we guarantee to send highlights within hours of your proposal and deliver your entire gallery within 24 hours.  Fact: We deliver photos faster than any other photographer in Chicago! 

Our passion, creative compositions, dynamic lighting, and dedication make our photos and customer service stand out.  

Don’t just take our word for it. Read what our customers are raving about!

My team and I have received hundreds of 5/5 Star ☆☆☆☆☆ / ☆☆☆☆☆ Reviews for our services across the internet. We invite you to read our online reviews on Google, WeddingWire, and The Knot.

Riley trusted me to photograph his proposal to Molly in December 2018. I captured their engagement session in the Fall of 2019 and then, due to several rescheduled dates due to COVID restrictions, their wedding in 2022 in Lake Geneva, Wisconsin.

Gavin trusted me to photograph his proposal in November 2019. He loved working together so much that he flew my team and I to the Riviera Maya to capture his engagement session and wedding to Hillary in Playa del Carmen, Mexico, in 2022.

Robby trusted me to photograph his proposal in July 2021 and his wedding to Erin in 2022. 

Mat trusted me to photograph his proposal in September 2023 and his wedding on top of Mount Rainier in Washington in 2024.

Juan trusted us to capture his proposal in May 2023, and then he flew my team and I to Pennsylvania in September 2024 to capture their sangeet, along with their wedding at The Franklin Institute in Philadelphia.

Ready to photograph your proposal in Chicago?

Let’s plan your dream proposal together! 

Complete our contact form below or drop us an email ✉ to start planning your proposal.

Just for reaching out, I will send you “The Art of Proposing: A Guide to Planning the Logistics for Asking the Biggest Question of Your Life.“