Chicago Winter Engagement Session Tips + Locations

Chicago winters may be chilly, but they’re also some of the most magical months for engagement photos. For this reason, I wanted to share Chicago winter engagement session tips as well as suggested locations in case you nplan to celebrate your engagement anywhere between November and February! Over the years, I’ve had the joy of capturing couples in the middle of downtown snowfalls, tucked into cozy corners of the city, and surrounded by that crisp winter glow you only get this time of year.

If you’re dreaming of a session this season, I’m sharing some of my favorite Chicago winter engagement photo locations, plus tips to make your shoot feel comfortable (and fun!) even when the temperatures drop. Thinking of braving the cold for unforgettable photos? These winter engagement session tips and locations are for you. For more examples of sessions in my portfolio, click here.

Chicago Winter Photo Location Suggestion #1: Cloud Gate (The Bean)

Cloud Gate (a.k.a. The Bean) is usually packed in the summertime, but winter changes everything. When a snowstorm rolls in, the crowds disappear and suddenly you’ve got one of Chicago’s most iconic spots almost to yourselves. With snowflakes falling around you, the Bean’s reflection turns into something magical — a mix of city lights, snowy skies, and that unforgettable skyline. It’s a backdrop you truly can’t find anywhere else, which is why Cloud Gate is always one of my top picks for winter engagement photos.

Chicago Winter Location Suggestion #2: Millennium Square

Another beautiful spot in Millennium Park is Millennium Square. The mix of striking architecture, glowing city lights, and open space creates such a romantic backdrop for engagement photos. Whether you’re walking hand in hand or cozying up together, the energy of the city adds an extra layer of magic to your photos here.

Winter Chicago Location Suggestion #3 : South Rose Garden

In the warmer months, the South Rose Garden is overflowing with colorful blooms — but don’t overlook it in the winter. When the trees and bushes are dusted with snow, the garden transforms into a quiet, romantic walkway that photographs beautifully. Just a short stroll from Millennium Park and closer to Buckingham Fountain, it’s one of those hidden gems that feels just as dreamy in the colder months as it does in summer.

Winter Engagement Photo Outfits Tips

One of the first things couples ask me when planning a winter session is: what should we wear? The secret is simple—layers! Chicago weather can change quickly, so having warm outer layers is key. Bring a cozy coat (or even a blanket!) to warm up between locations, or to wrap up in for a few sweet photos.

Shoes are another big one—choose something that will actually keep your feet warm and let you move around in the snow. Waterproof boots are always a good idea, and if you’d like, you can bring an extra pair of “photo shoes” to swap into once we’re on location. Since it’s harder to do full outfit changes in the winter, I usually recommend planning one main outfit and switching up your look with a jacket, scarf, or accessory.

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More Tips for Winter Engagement Sessions

Here are a few extra tips to help you feel comfortable and confident during your session:

• Go waterproof with your makeup. Cold winds and watery eyes are no match for waterproof mascara and setting spray!
• Bring a friend. Having someone tag along to hold coats, shoes, or even a warm drink makes everything so much easier.
• Plan for earlier timing. Winter daylight is short! Since I shoot with natural light, sessions often need to start as early as 2:30–3:30 pm. (It’s worth sneaking out of work a little early for these photos!)
• Focus on the reason you’re here. At the end of the day, this isn’t about the cold—it’s about the two of you. You’re getting married, and that’s something to celebrate, snowflakes and all. Winter sessions are some of my favorites, and I know you’ll love them too.

Chicago Wedding Photographer

Working with an engagement photographer who has plenty of experience shooting outdoors in the winter can make all the difference in your experience. I’m based right here in Chicago and have photographed countless sessions in every season — so I know the best winter photo locations, how to time your shoot for the prettiest light, and little tips to keep you comfortable (and having fun!) even when it’s cold.

I’d love to help you plan your winter engagement session. ❄️✨ If you’re wondering where to take photos, what to wear, or how to prepare for Chicago’s unpredictable weather, reach out here and we’ll start planning your own winter wonderland session.