Chicago Proposal Photography



Need help planning your proposal in Chicago?

Whether you are visiting The Windy City or are a native, planning on proposing in Chicago might seem a little overwhelming.

I ease anxieties by helping plan, orchestrate, and photograph picture-perfect proposals in Chicago.  

I have helped plan and photograph over 500 proposals in Chicago, along with the greatest destinations throughout the world, and would be honored to capture your “Yes!” 

Should I hire a photographer to photograph my proposal?

What once was an intimate moment has become something couples are capturing and sharing as much as their engagement pics and wedding photos.

According to The Knot’s 2017 Jewelry & Engagement Study which surveyed more than 14,000 engaged or recently married people across the US — 47% of couples hired a photographer to capture the special moment. Today, that number is closer to a whopping 75%. 

45% of proposals occur in a public place such as a scenic spot, garden, park or zoo — signifying a shift away from the typical private proposal.

If you’re a super planner, or are trying to conjure together a last-minute proposal while on vacation in Chicago, I can help plan and photograph the perfect proposal for you.

Where is the best spot to propose in Chicago?

According to The Knot, the top three spots people said they’d prefer to get engaged were (1) on vacation (2) at the site of your first date (3) or at a landmark. Perhaps that’s why so many contact our studio to photograph their proposal while visiting Chicago on vacation.

If you’ve never been to The Windy City before and are looking for the best locations to pop the question in Chicago, I will help plan and photograph the perfect proposal for you. Check out my list of the Top 15 Locations to Propose in Chicago or get inspired by more than 200 proposals that we’ve recently captured in our Proposal Highlights

Popular Chicago proposal locations include the Chicago Riverwalk, the Alfred Caldwell Lily Pool located in Lincoln Park, The South Pond Pavilion at the Nature Boardwalk at Lincoln Park Zoo, The Chicago Theater, the Garden of the Phoenix Japanese Garden in Jackson Park’s Osaka Garden, The Adler Planetarium, along with the entire Chicago Museum Campus overlooking the Chicago Skyline.

If there’s rain or snow in the forecast, I can always help secure a permit for an indoor location such as The Rookery. This historic Chicago icon from 1888 was designed by famed Chicago architects Daniel Burnham and John Root and reimagined by Frank Lloyd Wright in 1905.

It doesn’t matter if it’s raining on your proposal, a Winter proposal, a Spring proposal, a Summer Proposal, a Fall Proposal, a Sunrise proposal, a Sunset proposal or even a Surprise proposal in front of family & friends at your favorite restaurant, my team and I have photographed proposals in every season, climate and location imaginable.

How much does it cost to photograph my proposal in Chicago and what is included?


• Planning & Creative Consultation
• Location Recommendations
• Permit Acquisitions
• The Art of Proposing Guide
• Pre-Proposal Consultation

• Early Arrival & Wait Time
• Candid, Coached or Selfie Approach
• Image Selection and Correction
• Same Day Highlights
• Online Highlight Gallery
• Social Media Highlights

• Full Resolution Digital Files
• Digital Download Gallery
• Guaranteed 72 Hour Delivery
• 100% Rebate Toward Wedding

Proposal Photography


Option to Add

30 Minute Portrait Session

60 Minute Portrait Session

90 Minute Portrait Session


Why trust Jason Kaczorowski Photography to photograph your proposal?

These are the moments in life that are worth investing in!

Don’t take chances on someone still learning the craft of properly photographing a proposal. Proposals are spontaneous events and there’s 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!   

I’ve been photographing proposals for more than 14 years and capturing weddings for two decades. I have personally photographed over 250 proposals and more than 750 weddings since 2005, and my team and I have photographed over 500 proposals. 

I work with a dedicated team of Associate Photographers so if I am personally already unavailable or already booked for your date, I can always assign the honor of capturing your “Yes!” to one of my trusted photographers.

I will always work with you every step of the way in planning your proposal and will be the one processing and perfecting your images so they share the same quality and consistency you admire about my portfolio. 

I’m so confident that you will love working with me that I will photograph your proposal for free. That’s right! I will rebate the entire amount of your Proposal Photography and apply it toward your wedding photography if choose to trust my team and I to capture your big day too.  

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

Gavin trusted me to photograph his proposal in November of 2019 and 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 of 2021 and then photograph his wedding to Erin in 2022. 

In fact, more than half the weddings we photograph are from our previous proposal clients! 

Plus, my team and I have received hundreds of all 5/5 Star Reviews across the internet for our serices. We invite you to read our reviews on Google, WeddingWire and The Knot.

Contact Me today to start planning your proposal and I will send you “The Art of Proposing: A Guide to Planning the Logistics for Asking the Biggest Question of Your Life” just for reaching out.

Proposal Inquiry

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