A wedding day should feel lived in, not directed.
With over a decade photographing Chicago celebrations, I approach each event with calm awareness, knowing when to step in, when to step back, and how to keep the day moving while preserving the emotion within it. What you receive are photographs that feel as natural as the memories themselves.
Rooted in documentary storytelling and guided with refined editorial direction, my work has been featured in Loverly, Chicago Style Weddings, and Modern Luxury Weddings Chicago. The result is imagery that feels effortless. Allowing you to remain present while every moment is intentionally preserved.
Chicago Wedding Photographer
Who Makes You Feel
Comfortable, Seen, and Present.
Chicago Illinois Wedding Photographer
Winterlyn Stebner
I’m Winterlyn — a Chicago Wedding Photographer. After more than a decade photographing weddings across Chicago, I’ve come to understand that beautiful images are rarely created by chance, they come from a day that feels steady, considered, and cared for.
I work closely with planners and families to anticipate timing, guide portraits with intention, and step back when moments deserve space, allowing the celebration to unfold naturally without interruption.
Couples often tell me they felt unusually at ease. Not because nothing unexpected happened, but because someone was quietly prepared for it.
The photographs are simply the record of a day they were fully present for.
Meet Winterlyn
Founder + Lead Photographer
Florian & Ashley
The Rookery
“Our experiance with Winterlyn was amazing! She was so good at making us feel relaxed. We love the pictures she took; can’t recommend highly enough!”
Amanda & Chad
Union League Club
"Winterlyn and her team are so incredibly talented. Our photos are jaw-dropping! She has a true knack for capturing those special moments."
Jamie & Connor
Michigan Shores Club
“We felt confident in choosing Winterlyn and our experience confirmed!! Winterlyn’s passion for what she does translates to photos that are special and memorable. ”
Ways to collaborate
Photography Experiences
Destinations
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Weddings
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Engagements
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Best Chicago Wedding Photographer
Winterlyn Photography has been consistently recognized among Chicago's finest. For five consecutive years, we've been named one of the Best Wedding Photographers in Chicago by Expertise.
In 2024 / 2025, we were honored to be ranked the #1 Wedding Photographer in Chicago by Wedding Rule and recognized among the Top 10 by Wezoree. Our work has also earned a place in The Knot's Hall of Fame, alongside WeddingWire Couples' Choice Awards in 2022, 2023, and 2024.
These honors reflect the trust our couples place in us and the stories we're privileged to preserve with care, artistry, and intention.
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Miltevia & Jay
Congress Hotel
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The Langham Hotel
Hannah & Nate
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Bethany & Craig
RPM Events
CHICAGO WEDDINGs
real weddings, Real moments
The Armour House, with its timeless elegance, provides a picturesque setting for your wedding, blending romance and historic charm seamlessly.
The Armour House in lake Forest
FEATURED VENUE:
I take on a limited number of weddings each year to ensure a deeply personalized experience. If you’re planning a wedding in Chicago or the Midwest and want photography that feels intentional, supportive, and emotionally true to your day, I’d love to hear about what you’re imagining.
Start The Conversation
If This Feels Like What You’ve Been Looking For
Request Availability
Each proposal is tailored to reflect the scale, pace, and priorities of your celebration.
To begin, share a few details below. I personally review every inquiry and will be in touch with next steps if your date and vision align. I’ll be in touch within 48 business hours.
Inquire & Connect with WP
A Personal Reply
Within 24 Hours
A Customized
Proposal
Let's Connect
No bots here-just me. You'll receive a warm, thoughtful response from me within one business day, so be sure to check your inbox (and spam folder, just in case)
Once I learn more about your day. I'll send over a tailored proposal that reflects your vision, timeline, and photography priorities-because
no two weddings are the same.
If it feels like a great fit, we'll schedule a Zoom call to talk more about your day. I'll answer all your questions and share how I approach wedding photography with care and intention.
The Experience & Investment
Over the past 11 years, I've had the privilege of documenting love stories all across Chicago and beyond. My approach is intentional, artistic, and deeply rooted in storytelling because your photos should feel like you.
Most couples invest between 8,900 and 12,500
for full-day wedding coverage.
• Two photographers (8-12 hours)
• Engagement session or welcome shoot
• Heirloom albums
View a full wedding gallery
