Five Festive Chicago Holiday Engagement Photo Ideas

Winter Wonderland Inspiration for Your Engagement Photos

Well, apparently we are skipping fall and going straight to winter this year in Chicago. With the snow on the ground today, I wanted to share a few ideas with those of you looking to incorporate winter and the holiday season into your engagement photos. Read all the way through for style tips and how to stay warm!

Winter engagement photo in Chicago


Christmas Tree Farm

I’ve been DYING to do a shoot like this for years, so take this as one very big hint, wink and nudge. Personally, I’ve always been an artificial Christmas tree girl, but the idea of going to a farm and picking your perfect holiday tree sounds incredibly romantic. Imagine: Snow covered trees. Cozy coats, scarves, hats and boots. Hot cocoa in your hands. Walking along the rows of trees together with a vintage sled in tow. Strung lights overhead. Maybe a snowball fight occurs. Maybe there’s a fire pit and s’mores. What’s not to love about this idea?!


Snow Covered Forest

My favorite place to be during the winter is out in the absolute middle of nowhere. Think places where the snow is still pure and white with no footsteps to be seen. There are beautiful places in the nearby Chicago suburbs that will give you all the walking in a winter wonderland vibes without having to travel too far. As much as I love the city, I love the simple beauty found in nature even more. With a wintry white backdrop, think about wearing bright colors that will pop vividly in photos. We’ll walk along the snow covered hills, through rows of pine trees, and capture icy pink sunset skies. 

^^Imagine this but with snow!

Downtown Holiday Decor

Chicago during December is truly one of the happiest times of the year. There is no shortage of Christmas trees, holiday garland and magical lights throughout the city. Even the Chicago Theater sign can read “Happy Holidays!”. Take advantage of this! I highly recommend scheduling city shoots for the mornings and weekdays to avoid the shoppers and crowds. And don’t forget you can always bring your own holiday spirit with you! Steve’s Flower Market made this wearable garland shown below. We styled it as if it were a shawl and later used in the background.

Cozy Coffee Shops & Bars

When the weather is cold, it’s a great idea to plan an indoor stop. A cozy coffee shop can do just the trick to warm up your spirits. Order a hot drink and find a cozy place to sit together. Given that you’ll likely be wearing coats and scarves for outdoor photos, it will be a nice change to loose the layers and have a different look. If you have a coffee shop or bar in mind, always call them ahead of time and ask if it’s okay to take photos. Most of the time as long as you plan to order drinks, it will be fine, but they may recommend that you come at a less busy time of day. 

Ice Skating Rink

There’s no shortage of ice skating rinks available during the winter season in Chicago and it can lead to some very fun photos. If you have your own skates, bring them. If not, plan to arrive plenty early to rent. This is a popular winter activity, especially around the holidays, so best to plan this for a time or day that’s not busy. 

Winter Engagement Session Attire Tips: 

Assuming it’s a cold winter day in Chicago, you’ll want to plan your outfit around your outerwear first and foremost. Avoid the bulky parkas and puffer coats. Yes, they might be warm, but they don’t photograph well and you’ll end up looking like a marshmallow. Your coats will essentially be your outfits, so pick a style that flatters your figure and makes you feel great. Elizabeth and Ashish completely nailed it with their outerwear choices. The bright pop of red is an instant show stopper and it fits her perfectly. Ashish’s gray tweed coat adds instant texture and dimension in photos. The two balance each other perfectly. 

Winter engagement photo in Chicago by Lake Michigan with the skyline in the background.

A few other suggestions: Yes, it’s going to be cold. Wear what you need to feel comfortable. An extra pair of socks goes a long way. Leggings under your jeans can do the trick. Have hand warmers ready in your pockets for when you need a little relief. Bring gloves to wear to in between shots. Keep a cozy blanket on hand to wrap around each other when the time is right. Bring a thermos filled with hot coffee or hot chocolate (spike it with some whisky while we’re at it!). Plan for some indoor stops, if only to take a break from the cold. My number one priority is to make sure it’s a fun and comfortable experience. If any of my ideas sound dreamy to you, reach out! I’d love to do some winter shoots this year and capture the magic of the season. Cheers!


Have a question?

Reach out to Ashley today and let's start planning the perfect photography experience for your wedding, boudoir or portrait session.

Email: ashley@artistrieco.com