A guide to help you imagine a picture-perfect winter engagement session in Chicago.

All photography by Artistrie Co.

There’s something truly magical, cozy and romantic about winters in the Windy City. Chicago’s iconic skyline and frozen lakefront provides the perfect canvas for love to unfold against a backdrop of urban sophistication and winter whimsy. In this article, I’ll explore nine ideas to infuse your winter engagement photoshoot in Chicago with romance, creativity, and personal touches. From iconic landmarks draped in snow to cozy moments that defy the cold, let’s embark on a visual journey through the dreamiest settings the city has to offer, ensuring your engagement photos are not just memorable but a testament to the enchantment of love for wintertime.

For more inspiration, please read my Ultimate Guide to Winter Engagement Photos in Chicago.

01: Take it Indoors

Think outside the box and consider visiting at least one indoor location to give yourselves a reprieve from the cold. Chicago has so many beautiful locations worth considering! Be photographed amongst the greatest works of art at the Art Institute of Chicago, enjoy Frank Llyod Wright’s iconic architecture at The Rookery, pretend it’s summer at the Garfield Park Conservatory, or simply visit your favorite restaurant, bar or a cozy coffee shop. If you’d like to work together, I’ll be happy to collaborate with you to create the perfect plan for your photos!

Related: Chic Indoor Chicago Engagement Location Ideas

02: Wear Cozy Coats & Winter Fashions

Anyone else watch the cheesy holiday movies purely for the winter fashion inspo? Take this as your sign to buy all the adorable knits and outerwear. From jewel-toned coats to chic boots and cozy winter accessories, I absolutely adore winter fashions. 

When it comes to your engagement photos, layering your wardrobe adds dimension and visual interest. Winter is the perfect season to play into this and have a killer look.

03: Sprinkle In Holiday Decor

Now, if you actually want to feel like you are living in a holiday movie, take advantage of all the beautiful decor found throughout Chicago. Throughout downtown in December and all of the city’s unique neighborhoods, there is no shortage of holiday trees, wreaths, garland, twinkling lights, ornaments and beyond found outdoors. 

Now, if you’re looking to take it inside, find a holiday pop up bar or restaurant that goes ALL out for the holidays. And I mean ALL out. Think: Hundreds of ornaments dangling from the ceiling, Christmas lights galore, everything wrapped like a present. The more gowdy, the better (ya know, if that’s your thing).

04: Enjoy Minimal Crowds

One of the best reasons to take engagement photos in the winter around Chicago is the small crowds. Some of the most popular photo locations in Chicago will be completely empty in the winter. Whereas in the summer and fall, you’d be one of dozens of people taking photos at the same spot, but in the winter, you’ll have the best locations all to yourself. 

05: Embrace Staying Close

Yes, it will be chilly, but magic happens when my couples embrace the weather, hold each other close and have fun. Consider it to be an opportunity to be super sweet and up close and personal with one another the entire session.

A few bonus tips to help you stay warm (in addition to the snuggles):

Hand warmers that you can keep in your pockets, an extra layer of socks on your feet, a thermos filled with hot chocolate or coffee (spiked with Bailey’s or Peppermint Schnapps optional), a wool blanket to wrap around each other that can double as a photo accessory, hats & gloves and taking breaks to thaw out in the heated car or indoors.

06: Watch Unbeatable Sunsets Along Lake Michigan

I’ve photographed sunsets along Lake Michigan for over 15 years and I promise you my favorite skies have always happened in the winter. Something about the icy cold air results in vibrant, unforgettably pink skies that reflect off the frozen water. Yes, the wind and cold can be fierce, so we work quickly and efficiently, but I promise you will absolutely love the results.

07: Consider Winter Activities

Consider embracing the time of year and include your favorite winter activities into your engagement session. This could be ice skating, visiting a Christmas tree farm (seriously – this idea is SO cute), walking through a winter wonderland, cozying up on the couch at home with hot cocoas in hand, visiting your favorite museums and art galleries, building a snowy bonfire outside and roasting marshmallows for s’mores or even having a wintery picnic. There’s such a beautiful serenity to this time of year. Take advantage of the parts that make it so special.

08: Wear Colorful Outfits

While I know a lot of my couples stick to neutral tones for engagement photos, I absolutely adore color! If you love color too, winter is a perfect time to show off your favorite hues. Your wardrobe will pop vividly amongst the snow, ice and frozen Chicago.

09: Showcase the Beautiful Fallen Snow

Bright white fresh fallen snow photographs beautifully and we only have it for such a short period of time each year. By embracing the snow, I promise your engagement photos will be incredibly unique. While we can’t always plan for the perfect snow, when it happens, it’s something that’s truly special.

If you are hoping to schedule an engagement session this winter in Chicago or the surrounding midwest area, I’d love to hear from you! I truly love this time of year for photos and can’t wait to collaborate with you soon. Visit the Contact Page on my website for more information or visit my Engagement Session Portfolio here.

Related: 62 Inspiring Ideas for Your Chicago Engagement Photos