Chicago Winter Engagement Session - Maddie and Sam
Photographing a Chicago Winter Engagement Session
Chicago’s historic architecture, soft winter light, and a nearly empty cityscape made for a perfect engagement session with Maddie and Sam. While many couples dream of a warm-weather shoot, winter engagement sessions have a charm of their own—especially when you’re drawn to the classic beauty of downtown Chicago.
Winter Vibes & Iconic Locations
Maddie and Sam’s engagement session took place in February, right in the heart of downtown Chicago. Their love for the city’s historic buildings led us to some of the most stunning architectural backdrops:
The Chicago Cultural Center – Not only is this a breathtaking location, but it also allowed us to warm up indoors while capturing the couple surrounded by intricate mosaics, grand staircases, and of course the Tiffany Dome.
The Art Institute of Chicago – The stately front steps provided the perfect setting for classic, timeless portraits.
Millennium Park & The Bean – Sam was eager to include one of Chicago’s most famous landmarks in their session, and thanks to the cold weekday afternoon, we had the area nearly to ourselves.
A Private Moment in the City
One of the unexpected perks of a winter session? Fewer crowds. Chicago is always buzzing with energy, but on this chilly weekday, it felt as if the city belonged to Maddie and Sam. Walking through Millennium Park and Washington Street with only a handful of people around created an intimate, almost cinematic feel to their session.
Overcoming the Winter Chill
With temperatures on the colder side, we made sure to keep things moving to keep Maddie and Sam comfortable. They dressed for the weather in a classy and elegant way. The soft, overcast sky provided beautifully flattering light, adding to the romantic winter atmosphere. We even took a quick break inside a nearby Starbucks to warm up before heading back out for more portraits.
Favorite Moments & Cityscapes
One of my favorite parts of the session was capturing views down Washington Street from Millennium Park. The mix of city lights, the elevated train, and the soft winter light made for an incredible urban backdrop. The combination of Maddie and Sam’s natural chemistry and the quiet, wintry city created some of my favorite engagement images of the session.
Winter Engagement Sessions – A Hidden Gem
If you’re considering a winter engagement session, let this be proof that cold weather doesn’t mean sacrificing beautiful photos! With the right locations, elegant outfits, and a little movement to stay warm, winter sessions can be just as stunning—if not more—than their warmer counterparts.
Looking to schedule your own engagement session? Let’s create something magical together, no matter the season. Reach out to J. Brown Photography to start planning your Chicago engagement session today!
