A couple kiss one another while taking engagement photos in their winter clothes, behind them is the Chicago River and many different buildings of the Loop

Winter Engagement Photos in Downtown Chicago | Rachel and Keenan

Summer may be just around the corner, but that doesn’t mean I can’t daydream a bit about this past winter season and how magical it was! One of the highlights from this time was Rachel and Keenan’s engagement session in downtown Chicago. I honestly hope that winter engagement sessions in Chicago start becoming more of a thing, as I honestly would love to have more reasons to take photos while strolling through my favorite city! Check out the highlights from Rachel and Keenan’s session and who knows, maybe it’ll make you want to have your photos taken next winter in the Windy City.

A couple wearing winter coats kiss one another while standing next to the Wrigley Building in Chicago looking out over the Chicago River
A couple wearing winter clothing smile at the camera while the woman rests her hand on the man's chest showing off her engagement ring as they stand in front of the Chicago River

The Perfect Spots for Winter Engagement Photos in Chicago

There’s a LOT to love about Rachel and Keenan’s engagement session in downtown Chicago, first of course being these two amazing people themselves! They share a fun loving, lighthearted love for one another that is just SO much fun to document. When you put a love like that in a city like Chicago you end up with a session that feels like a Hallmark Movie in the Windy City. It was as if each photo told a different part of their love story, and every location was important to their journey together.

We were able to include some of my all time favorite locations for engagement photos in Chicago for their session as well as a special stop for Rachel and Keenan. We started things off at the Wrigley Building looking out over the Chicago River. From there we headed down Michigan Avenue and made our way to the iconic Chicago Theatre. Then it was back up to The Riverwalk where we made a stop outside of their favorite restaurant, Smith & Wollensky, before winding up back at the Wrigley Building for the finale!

A couple kiss one another while taking engagement photos in their winter clothes, behind them is the Chicago River and many different buildings of the Loop
A woman smiles while a man holds and kisses her on the cheek as they stand next to the Wrigley Building in Chicago wearing stylish winter coats for their engagement photos
A man and woman kiss one another while standing next to the Wrigley Building in Chicago, the woman's hand has an engagement ring on it and is resting on the man's cheek
Photo of a couple kissing while wearing their winter coats at the Wrigley Building in Chicago, behind them is the Chicago River, on the woman's hand is an engagement ring
A couple wearing winter coats kiss outside of a building in Chicago decorated for the holidays with nutcrackers and holiday greenery
A couple kiss while standing outside of a store in Chicago that is decorated for the holidays
A woman smiles over her shoulder towards a man as he hugs her from behind while the two stand in front of a large Christmas tree, the woman is wearing an engagement ring and they both are in their winter coats for these engagement photos
Detail photo of a woman's hand with an engagement ring on it holding the hands of a man who is hugging her from behind
A couple wearing stylish winter coats walk hand in hand along a sidewalk outside a large Macy's store in Chicago that is decorated for the Holidays
A couple walk hand in hand amongst a crowded sidewalk in Chicago outside of a Macy's store that is decorated for the Holidays
A woman smiles over her shoulder towards the camera while holding hands with a man as they walk down a sidewalk outside a Macy's in Chicago, ahead of them is the Chicago Theatre
A couple hug one another and look across a street towards the large sign for the Chicago Theatre
Photo of a couple in their winter coats kissing one another for an engagement photo, behind them is the sign for the Chicago Theatre across the street
A woman wearing a white winter coat smiles while holding hands with a man as they stand on a sidewalk in Chicago
A couple kiss one another while in their winter coats standing in front of the Chicago River as they have their engagement photos taken
A woman is lifted in the air by a man as the two hug and smile at one another while standing on the River Walk next to the Chicago River
Black and white photo of a couple next to the Chicago River, the woman is smiling as the man holds her in the air while they hug
A couple wearing their winter coats dance with one another while at the Wrigley Building in Chicago, behind them is a large well lit Christmas tree
A woman smiles at a man as he holds her face while the two stand outside of the Wrigley Building in Chicago, behind them is a large Christmas tree

Planning Your Engagement Session

Engagement sessions like Rachel and Keenan’s don’t just happen out of nowhere, there’s a lot of planning that goes into them! From choosing when and where to have the session, to deciding what to wear, as well as who your photographer is going to be, there’s a TON to consider! Thankfully Chicago is one of the best places to plan an engagement session for a few reasons. 

A couple kiss one another while in their winter coats as they stand on a median on a street in Chicago
A couple kiss as the man lifts the woman in the air while standing on a median in a street of Chicago

For starters there’s no shortage of amazing locations for photos to choose from, both inside and out! Chicago also has a ton of cool and talented photographers such as myself that would LOVE to be a part of your journey. I do strongly encourage booking the same photographer for both your wedding and engagement as there are SO many benefits to doing so. If you’ve been enjoying my photos from Rachel and Keenan’s winter engagement, and you’d like to have me document your engagement and/or wedding, be sure to send me an inquiry today! I’d love nothing more than to be a part of your journey and document these moments for you to look back on and relive for years to come!

A couple hold hands and walk across a street in Chicago together as they smile over their shoulders and look back towards the camera
A couple kiss one another while standing on a sidewalk in Chicago on a rainy winter day

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About Jayde 

Docu-torial Photographer

I'm a Chicago wedding photographer with a passion for people, candid moments, authenticity, and golden hour. I document weddings with a ferocity for the real moments that matter on a wedding day: the moments you lived with the people you love. With 200+ weddings under my belt, I use my expertise to guide my clients to feel comfortable and confident so their images feel like them. 

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