Chicago Proposal Photography

Chicago Proposal Photographer

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 the best 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 while 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. 

Where to propose in Chicago

We invite you to explore our curated list of the Top 15 Places to Propose in Chicago to get inspiration for Where to Propose in Chicago.

If you’re looking for one of the most unique and lavish locations that we’ve photographed proposals in Chicago, check out Connor’s proposal aboard a luxury yacht cruising along the Chicago River. When it comes to opulent proposal locations in Chicago, few are as enchanting as proposing at the Grainger Hall of Gems inside the iconic Field Museum. If the Chicago Skyline is on your list of locations to propose, we suggest the Adler Planetarium, North Avenue Beach, Milton Lee Olive Park and The South Pond Bridge in Lincoln Park, which offer amazing city views. If you’re looking for a location perched high above the city, consider a private rooftop proposal in Chicago at a spot such as the LondonHouse hotel or boutique Ambassador Chicago. What if rain or snow is in the forecast and you need an indoor location to propose in Chicago? We’ve got you! The Garfield Park Conservatory and Lincoln Park Conservatory can each be utilized with a nominal photo permit fee and reservation from the Chicago Park District. Equally, the Art Institute of Chicago makes a wonderful indoor location to get engaged, though we recommend purchasing a Museum Membership and proposing during Member Hours (10–11 a.m. Monday-Sunday; excluding Tuesdays) as the museum is less crowded and can feel more intimate. 

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.

2025 Proposal Trends

According to The Knot 2025 Real Weddings Study “Professional proposal photography is on the rise, with 25% of proposers hiring a photographer — a significant increase from previous years”.

Over half of the people proposing felt pressure to plan a highly unique proposal, with the majority of proposers reporting planning for one to three months in advance. (TheKnot.com)

 According to Statistic.com, December is the most popular month for an engagement with a proposal rate of 19 percent.

The Houston Chronicle reports, “58% of proposers feel pressured to create a highly unique and shareable proposal experience,” which is in part due to the popularity of Instagram and TikTok.

Vogue encourages proposers to, “resist the urge to follow fleeting engagement fads; your wedding proposal deserves to be as one-of-a-kind as your love”.

Brides.com recommends, “When searching for proposal ideas, make sure to think about your partner and their personality. For example, while you may want to pronounce your love for them in front of all of your family and friends, they may be a more private person and prefer that such a moment is kept between the two of you. On the other hand, they may be someone who loves the spotlight and envisions a dramatic, over-the-top moment that’s done in a public setting.”

How much does photographing a proposal in Chicago cost?

The average price for Chicago proposal photography varies depending on whether customers value receiving simple 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 by 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.  

Our Chicago proposal packages begin at $600 and include all coordination, your proposal, portraits following your “Yes!” and your full resolutions Digital Files which you’re always invited to share with family and friends.

We also offer the option to add additional time to your portrait session if you value receiving more photos, utilizing more locations, and adding dynamic lighting techniques to bring out our creativity and make your portraits pop with bold colors and vibrant intensity. 

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 while Crafting Striking, Timeless Portraits and Sculpting Light into Art with Every Frame.

This is a once-in-a-lifetime occasion. Don’t take chances on someone canceling or not showing up on time to your proposal, missing the moment together, or delivering anything less than amazing images of one of the most momentous moments in your life. We always carry backup equipment and have a team of seven (7) photographers in case your photographer is ever sick, in an accident, or needs to quarantine.  

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. We invite you to explore thousands of Chicago proposal photos at https://jasonkaczorowski.com/proposal-highlights/ and explore our list of the Top 15 Places to Propose in Chicago. https://jasonkaczorowski.com/proposals/claire-connor/

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 in Chicago.

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.“

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