the proposal
proposal for
Megan & Josh
Wedding Date
Aug 30th, 2026
prepared by
Winterlyn Photography LLC
Proposal
Client
Hello,
Thank you for sharing your vision and story with me. I am both honored and delighted that you are considering working with me. I invite you to view the collections below. Each has been tailored to fit your needs while staying true to the timeless sophistication I weave into all aspects of my work.
Watch this short video for a personal welcome and an inside look at what you’ll find in your custom proposal.
Your wedding photography experience with me begins long before the day itself. From the very first message, my goal is to make this process feel effortless, warm, intentional, and entirely centered on you.
Every email, every call, every timeline edit is crafted to ensure that when your wedding day arrives, you can simply live it. I’ll be there to guide you naturally, calm the nerves, and quietly create the kind of photographs that don’t just look beautiful but they feel like your day.
the core of my work
A Curated, Connection Based Approach
Winterlyn Stebner
a note from
Hello! I’m Winterlyn, a Chicago-based wedding photographer who values connection, intention, and timeless style. My approach is rooted in the belief that your wedding day isn’t just an event to photograph, it’s a story to live in, feel, and remember. I want you to show up and be together, while I quietly (or playfully) weave through the day capturing those genuine moments.
From our first call you’ll experience a process designed for ease: thoughtful planning + helpful resources + clear communication so you feel confident and excited. Many couples share how they “felt completely at ease in front of the camera,” or how I “made the entire process smooth and enjoyable.” On your wedding day I’ll be present, calm, and ready. Handling the logistics, fixing details you’ll never think about, and staying ready for the moments you will.
After the big “I do,” you’ll receive your images quicker than expected. Your gallery will tell a full story, laughter, tears, confetti, portraits, details, candid fun — so you feel like you’re reliving the day. And when your friends and family open your photos they’ll feel like they were there too. One couple told me, “The investment in Winterlyn Photography was, without a doubt, one of the best decisions we made for our wedding." My promise to you: a meaningful experience, beautiful imagery, and a legacy of love captured. If that sounds like what you’re looking for, I’d be honored to document your day.
Holding A Reverence For Real Emotions
After more than a decade photographing weddings across Chicago, I’ve learned that the difference between good photography and unforgettable imagery lies in connection. I take the time to truly know my couples to understand your personalities, your comfort levels, and what matters most to you.
Capturing All With An Editorial Essence
This allows me to anticipate moments before they happen, to document genuine emotion, and to create photographs that reflect your story, not a template. My couples often tell me that working with me felt like being photographed by a friend who just happens to be an expert in lighting, posing, and timing.
peruse the portfolio →
providing
Curated Collections
Tailored based on our discussion and with more adjustments available — the below options are designed to fit your needs and encompass your full vision.
prioritizing
Connections and Emotions
Your connection to the moment and to this beautiful love that you’ve found will translate into impactful photographs that capture the genuine emotions of these memories.
rendering
Fine Art Heirlooms
Custom-order an elegant record of your legacy — from fine art prints to luxury linen albums. Like this, your legacy will be passed down, remembered and loved for generations.
Winterlyn is pure behind the camera. Every single photo is breathtaking.
Beyond her incredible talent, Winterlyn made us feel so comfortable and cared for. She’s calm, kind, and such a reassuring presence on a whirlwind day. She truly feels like a close friend and I’m so glad she got to witness our love story.
— Bethany & Craig
magic
Honor Moment Embody Romance Capture Your Most Iconic Memories
THE EXPECTATION
My approach blends editorial artistry with candid storytelling. I pay attention to how light moves through a room, how fabric falls, and how your laughter changes when you look at each other. I balance composition and spontaneity, guiding when needed, stepping back when the moment unfolds naturally.
The result is a timeless collection of images that are as elegant as they are emotional. Photos that will still take your breath away decades from now.
the
and
Weekend
Coverage
Designed for couples with destination weddings, multi-day events, or luxury-level celebrations who want every detail documented and presented in a beautifully crafted format.
TOTAL INVESTMENT — $11,500 USD
Up to 12 hours of wedding day coverage with two professional photographers
Up to 2 hours of rehearsal-dinner coverage the night before
Priority editing and fast gallery delivery for a truly elevated experience
Engagement session with styling guidance and location planning.
12 × 12 custom-designed heirloom wedding album
Two 8 × 8 parent albums.
Custom Album Design Session.
Private online gallery with high-resolution images & print rights.
Full Story
Coverage
Our most requested offering. Perfect for couples who want the full narrative — from preparation through reception and value heirloom quality in prints and albums.
TOTAL INVESTMENT — $8,500 USD
Up to 10 hours of wedding day coverage with two professional photographers
Engagement session with styling guidance and location planning.
Personalized photography timeline consultation.
A 10×10 custom wedding album to beautifully preserve your story
Timeline and vendor coordination support to seamlessly integrate photography into your schedule
Private online gallery with high-resolution images & print rights.
Signature
Coverage
This collection is highly customizable, allowing you to tailor your experience with thoughtful add-ons such as a second photographer, additional coverage hours, or a handcrafted wedding album designed to preserve your day beautifully.
TOTAL INVESTMENT — 6,800 USD
Up to 8 hours of wedding day coverage with two professional photographers
Custom-designed online gallery with high-resolution downloads
Detailed timeline creation and pre-wedding consult to ensure every special moment is captured
A stress-free, refined experience tailored to your celebration
Additional Hourly Coverage
STARTS AT $650
Heirloom Albums
STARTS AT $1600 plus tax
A LA CARTE OFFERINGS
Engagement Session
STARTS AT $900 USD
Transportation
OFFICIANT
CALLIGRAPHY
Invitations
Tablescapes Event Rentals
The Festive Frog
Arcana Vintage Rentals
Hall's Rental Chicago
Windy City Linen
JEMMs Are Forever Rentals
RENTALS
WEDDING DRESS
CAKES
Windy City Glam
Rare Bird Beauty
Nicki Rouge Enterprises
Feeling Pretty
Elegance By Kim
Marissa Flood Makeup
HAIR & MAKEUP
Toast & Jam
The DJ Firm
Indigo Band Chicago
Luniks Entertainment
Modern Love DJs
Connexion Band
Yazz Events
DJ & BANDS
My Chef Catering
Catering With Elegance
Boka Catering
Chic Chef Catering
Hearty Boys
Tasty Catering
Cocina Fusion
CATERING
With Love productions
Karen Louise Documentaries
Katie Doyle Films
Oakhouse Wedding Films
Ariel Hall Creative
Wynn Films
ViDEOGRAPHY
Lavender Field Florist
Cresco Stems
MJM Occasions
Flowers for Dreams
Atmosphere Events Group
Xo Design Co
Branching Out Chicago
Bella Flora
FLORAL DESIGNERS
Cheers! Chicago Events
Stasia K. Events
Event Shoppe Chicago
WediCity
Urban Allure Events
Bweddings Planner
Ohana Events
WEDDING PLANNERS
Over the years, we've learned the important role quality vendors play in creating a stress-free wedding day. We've worked with many of the vendors below and we can't recommend them enough! This is not a paid list - we chose these vendors for both the quality of their work as well as their professionalism on the actual wedding day.
WHO WILL MAKE YOUR DAY INCREDIBLE
Vendors
That in-the-moment feeling will be captured in photographs
"If you’re looking to work with a kind soul, who will answer all your questions and requests with kindness and understanding, take beautiful pictures, and do it all with skill, speed, and proficiency, then we highly recommend Winterlyn!"
— O & L, The Rookery
like these.
WHAT CAN WE EXPECT DURING THE WEDDING PLANNING PROCESS?
frequently asked questions →
As your photographer, I will make every effort to contribute to a seamless experience. Much of this comes down to full and easy communication with you, and partnering with your planner to coordinate as needed. I’ll build an organic photography timeline that is conducive to your experience, enhancing each moment rather than taking away from your enjoyment.
CLOSE
WILL YOU POSE OR DIRECT US WHILE YOU DOCUMENT OUR WEDDING?
My approach is a delicate mix of photojournalism and editorial, with an emphasis on the moment. I can sense when you’re carrying tension or feeling anxious, and will provide pointers to help you ease into the moment for naturally beautiful photos. You can expect careful guidance, simple posing, and encouragement to just be yourself.
CLOSE
IN YOUR OPINION, WHAT MAKES A BEAUTIFUL PHOTOGRAPH?
An incredible photo is the one that you find yourself returning to with fondness throughout your life. So, I would say that the best wedding photographs are more than timing, posing, backgrounds, and lighting. A large part of creating a beautiful photo is capturing the real moments so you can look back and feel genuinely immersed in this time of celebration.
CLOSE
WHEN ALL IS SAID AND DONE, HOW WILL WE RECEIVE OUR GALLERY?
You’ll receive a complete collection of professionally edited photographs in a private online gallery. Each image will be carefully edited to enhance the beauty of the moment while remaining true to your lived experience. These can be downloaded, shared and printed with ease.
CLOSE
HOW DO WE BOOK OUR DATE(S) WITH YOU?
Reach out, and I’ll send booking materials with your preferred collection. You can officially book your date(s) with a signed contract and service retainer.
CLOSE
LET'S BEGIN
You deserve a photographer who sees the full picture, not just the timeline, but the emotion and meaning woven through every hour of your day. My promise is to document your story with care, artistry, and heart. When you open your gallery, you won’t just see how beautiful your wedding looked — you’ll feel how it felt to live it. That’s the legacy I want to create for you.
To ensure that your date is fully reserved, please email me with your preferred collection and any other notes. Last, but not least, allow me to express my sincere gratitude. I look forward to hopefully working together.
Tell The Story
of a
Lifetime
BOOK your consultaion →
proposal for
Annette & Phillip
Wedding Date
April 25, 2026
prepared by
Winterlyn Photography LLC