Proposal Photography

Whether you are visiting The Windy City for the first time or are a Chicago native, planning a proposal in Chicago might seem overwhelming, especially if you’re considering hiring a professional photographer to photograph your proposal.

I offer complimentary consultations to help you plan your proposal in Chicago. I will help you orchestrate the perfect proposal and photograph the moment your partner says “I Do”.

I have photographed countless marriage proposals throughout Illinois. My favorite locations to photograph wedding proposals in Chicago is along the lakefront in front of the magnificent Chicago skyline.

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

Contact Me and I will send you “The Art of Proposing: A Gentleman’s Guide to Planning the Logistics for Asking the Biggest Question of Your Life” just for inquiring!

Jason Kaczorowski

Your Proposal Includes

• Proposal Planning Consultations
• Pre-Proposal Waiting Time
• Candid Proposal Photography
• Post-Proposal Portrait Session
• Full Resolution Digital Files
• Guaranteed 48 Hour Delivery


75-90 Minutes
60-75 Minutes
30-45 Minutes


90-105 Minutes
75-90 Minutes
45-60 Minutes

I provide more time for weekend proposals to prepare for increased traffic, added time to park and pedestrian interference during portraits. Therefore I arrive earlier than anticipated and allow more time for relaxed portraits following your proposal.