The Best Time for Fall Photos in Chicago: Choosing the Perfect Date

Everyone loves fall—the crisp air, the vibrant colors 🍁🍂, the cozy fashion, and of course, pumpkin spice everything. 🎃☕️ Now that September has officially started, it's basically fall in my book. And there's no better time than fall in Chicago for an outdoor photo session. Whether you've just gotten engaged, want to update your branding photos, are preparing for your family holiday cards, or maybe you’re expecting a new bundle of joy, fall is the perfect season to capture those special moments.

When you envision outdoor fall photos, you probably have a specific look in mind. You want to incorporate the rich colors of the leaves, some super cute cozy outfits, and maybe even a touch of golden light. But one thing most people don’t realize is how important timing is for your fall session. The date, weather, and your outfits all work hand in hand to bring your vision to life. Let me walk you through why timing matters and how to pick the perfect date for your fall photos.

Now, when I say timing, I’m not just talking about the time of day (though that’s still important). I’m mainly referring to the time of the fall season—whether it’s early, mid, or late fall. Each part of fall comes with its own unique weather conditions and distinct look. Hopefully, this blog will help you pick the perfect time for the fall session of your dreams.

Early Fall (September 10th-30th): Warm and Selective

If you’re looking to capture the early signs of fall, scheduling your session towards the beginning of the season can be a fantastic choice. During this time, the weather is still relatively warm, allowing you to embrace those lighter fall outfits—think cozy sweaters, boots, and maybe even a stylish hat—without the need for heavy jackets or scarves. This is perfect if you want that autumn feel without bundling up too much.

However, it’s important to remember that early fall is just the start of the season’s transformation. The leaves are only beginning to change, so you might have to be a bit more selective with your location to find those early pops of color. Some spots might still hold on to a bit of their summer greenery, while others may just start showing those warm fall hues. With careful planning and the right location, you can still capture that unmistakable fall vibe, giving your photos a unique and fresh feel that truly showcases the beginning of this beautiful season.

This period also offers a unique blend of late summer and early fall, which can add a special touch to your photos. Imagine combining the lush greenery of summer with the emerging fall tones—it's a subtle, beautiful transition that can make your session stand out. So, if you love the idea of an early fall session, you’ll be rewarded with images that capture the season’s first whispers, bringing together the best of both worlds.Mid-Fall (October): Peak Fall Vibes

Mid Fall (October): Peak Fall Vibes

By the time October rolls around, Chicago is totally in full fall mode. The city transforms into a kaleidoscope of vibrant reds, oranges, and yellows, making it easy to find that perfect fall backdrop just about anywhere you look. It’s the ideal time to get those classic autumn photos with all the gorgeous colors.

However, as the month goes on, the weather starts to cool down. You can still manage a photoshoot without a heavy coat, but layering up is definitely a good idea. Think cozy sweaters over cute tops, and maybe add a scarf or light jacket to keep warm. October has that quintessential fall vibe with its crisp air and stunning scenery, but be ready for a bit of a chill. If you’re planning a session with small kids, it might be smart to book your shoot earlier in the month to avoid the colder temperatures that can creep in as the days go by. That way, everyone can stay comfy and still enjoy the beauty of fall.

Late Fall (November): Crisp and Unpredictable

As you head into November, fall in Chicago starts to get a bit tricky. The temperatures drop a lot, and while you might still catch some colorful leaves early in the month, the later you wait, the more likely you are to see bare branches. This can all depend on how rainy it’s been and when the first snow arrives, as these can make the leaves drop sooner than you’d expect.

Even if the trees are bare, your fall photos can still turn out great. You can still rock those cute fall outfits you’ve been planning, but you might want to think about layering up. Depending on the weather, you might need to add scarves and coats to keep warm. It’s all about picking the right spot to match the more wintery look. Locations with cool architecture or urban vibes can still shine against a backdrop of bare branches. So, even though November’s weather can be a bit of a gamble, with the right planning and a little creativity, you can still capture beautiful moments that are unique to this season.

Don’t Forget About Daylight Saving Time

One more thing to keep in mind as you plan your fall photo session is daylight saving time. As the clocks turn back in early November, the amount of daylight available in the late afternoon decreases. If you’re hoping for that beautiful golden hour light, you’ll need to adjust your session time accordingly. The earlier sunset means you’ll want to plan for an earlier session to make the most of the natural light.

So as you can see timing your fall photo session in Chicago is key to capturing the perfect look. Whether you’re aiming for warm and colorful, or crisp and cozy, understanding how the date, weather, and outfits all work together will help you achieve your vision. And if you’re ready to capture the magic of fall with a mini session, I’d love to help you create some beautiful memories. Click this link ( JJP Fall Mini Session) to grab your spot with Janelle Jaqueline Photography and let’s make the most of this stunning season!