ENGAGEMENT
EXPERIENCE

THE

ENGAGEMENT PHOTOGRAPHER IN CHICAGO

ENGAGEMENT PHOTOGRAPHER IN CHiCAGO

As a Chicago wedding and engagement photographer with 10 years of experience in the industry, shooting over 250+ weddings, I have honed my skills to provide my couples with stunning and memorable portraits that will be cherished for a lifetime.

My personalized approach with every couple starts with taking the time to get to know you and understand your vision for your Chicago engagement photos. I believe that building a relationship with my clients is essential in capturing authentic and heartfelt moments. This allows me to create photographs that truly reflect the personalities and emotions of the couple and their loved ones.

Hi, I'm WINTERLYN

Reveal the genuine, unscripted beauty of your relationship.

As Chicago engagement photographers, our offerings are meticulously designed to elevate your love story into a timeless narrative, inspired by the spirit of storytelling. We believe that every couple has a unique tale waiting to unfold, and we strive to encapsulate the essence of your journey with artistry and passion. 

Every love story is unique and deserves to be captured with artistry and passion. As engagement photographers in Chicago, our services go beyond conventional photography – we're here to transform your special moments into timeless memories that will be cherished for a lifetime.

With a foundation in fine art, we bring a blend of creativity and passion to every frame of your Chicago engagement pictures, ensuring that your love story is not just preserved but celebrated in a way that is as unique as the bond you share. Join us on a journey where the ordinary becomes extraordinary, and your moments are transformed into timeless memories that will be cherished for generations to come.

A Journey in Love and Artistry

Chicago engagement photography

Kind wordS

 — Cindy and Dennis

The whole experience could not have been better because she made us feel comfortable. ”

Immerse yourselves in the enchanting world of our fine art wedding photography. Every frame is carefully composed, reflecting the elegance and timelessness of your love story. Through a blend of classical aesthetics and contemporary flair, we strive to create images that not only capture but also elevate the emotions of your special day.

With a foundation in fine art, we bring a blend of creativity and passion to every frame, ensuring that your love story is not just preserved but celebrated in a way that is as unique as the bond you share. Join us on a journey where the ordinary becomes extraordinary, and your moments are transformed into timeless memories that will be cherished for generations to come.

Chicago FINE ART WEDDINg photography



Imagine an intimate engagement session, not just as a prelude to your wedding day but as a celebration of the joy and excitement that defines your love story.

We strive to create an atmosphere where you feel free to be yourselves, resulting in photographs that not only freeze moments in time but also reveal the genuine, unscripted beauty of your relationship. It's about telling your story in a way that is as individual as your journey together, ensuring that every image becomes a cherished piece of the visual narrative that unfolds as you prepare for your wedding day.

Our commitment is to craft an engagement experience that not only captures but elevates the love and connection you share, creating images that will be treasured for a lifetime.

CHICAGO ENGAGEMENT PHOTOS

See our guide on how to plan your engagement session

Offered Services

The WP approach goes beyond traditional photography; it's about capturing the authentic essence of your unique connection.

Best Chicago Wedding Photographer

Consistently recognized for excellence, Winterlyn Photography has been named the best Chicago wedding photographer by Expertise for the last five consecutive years. In 2024, we were honored to be ranked as the number one wedding photographer in Chicago by Wedding Rule. We are also proud recipients of The Knot’s Best of the Knot Hall of Fame Award, celebrating our exceptional wedding photography and outstanding client experience. Additionally, we have been awarded the WeddingWire Couples' Choice Award in 2022 and 2023, a testament to the love and trust that our couples have placed in us.

adventurous 
well-traveled 
planning their next trip
playful
unapologetic 
thoughtful
wine enthusiasts
avid-readers  


adventurous 
well-traveled 
planning their next trip
playful
unapologetic 
thoughtful
wine enthusiasts
avid-readers
adventurous 
well-traveled 
planning their next trip
playful
unapologetic 
thoughtful
wine enthusiasts
avid-readers 


adventurous 
well-traveled 
planning their next trip
playful
unapologetic 
thoughtful
wine enthusiasts
avid-readers 

  


our clients are 

who we work with /

Our approach goes beyond traditional photography; it's about

capturing the authentic essence of your unique connection.

We adore our out-of-town couples and are delighted to welcome you to Chicago. At Winterlyn Photography, we focus on building a nurturing relationship with our couples so you can relax and comfortably express yourself at your engagement session.

We are delighted to offer travel services to provide the same seamless photography service for our wedding clients based in a different location or planning a destination wedding. We offer a complimentary engagement session when you book your wedding photography with us. 

THE PERFECT WAY TO REMEMBER the windy city

JETSETTERS

for the

Kahla & Brandon

from

It truly was a wonderful experience getting to work with her and I cannot recommend her enough.”

What people are saying

01/04

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Rebecca 

from

Winterlyn captured every moment and emotion and the photos are absolutely gorgeous.”

What people are saying

02/04

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Cindy & Dennis

from

The whole experience could not have been better because she made us feel comfortable. ”

What people are saying

03/04

View next

Samantha & Ben

from

From the moment we met Winterlyn, we knew she was the perfect one for our wedding.”

What people are saying

04/04

Your engagement portraits are more than just simple snapshots —they are a reflection of your relationship that deserves to be told with artistry and intention. Investing in professional photography means entrusting someone to capture the fleeting moments, the laughter, the tears, and the quiet glances that define your unique celebration. Our engagement sessions are meticulously crafted to provide a bespoke experience that reflects the essence of your love story. From the first consultation to the final delivery of your beautifully curated images, every step is designed to honor the significance of your day.

Our goal is to create a visual legacy that you and your loved ones will treasure for generations—a collection of images that not only document your love but also evoke the emotions and memories that will be felt long after. By choosing us to be a part of your engagement session, you are ensuring that your love story is captured in a way that is as timeless and beautiful as your relationship.

Capturing YOUR LOVE

begins here

Engagement photography is a joyful way to celebrate and share the beginning of your beautiful journey together. It captures the essence of who you are right now—the excitement, the anticipation, and the unique bond you share. These photos not only commemorate this special time in your lives but also serve as a timeless keepsake that you will cherish forever. While there will be countless memorable moments in your future, many will be rooted in the love and promise of this moment. So, take a moment to treasure it and preserve this chapter of your love story with images that will remind you of the joy and love you felt as you took this first step toward forever.

CREATE THE PERFECT CHICAGO ENGAGEMENT
SESSION

OUR GUIDE TO A PERFECT ENGAGEMENT SESSION

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