Why October Is Pure Magic for Family Photos in Chicago

Let’s play a little game. Close your eyes and picture your perfect family photo. Are there crunchy leaves beneath your boots, golden sun warming your cheeks, and your kids laughing while wrapped in cozy layers? Ah yes… that’s October in Chicago.

If you’ve ever tried to schedule holiday portraits or family photos in November or (gasp) December, you’ve probably felt the stress bubble up. The weather? Unpredictable. The light? Practically nonexistent after 4pm. And your kids? Somehow more restless than relaxed.

That’s why I always tell my clients: if there’s a sweet spot for luxury family portraits in Chicago, it’s October. Let me show you why.

Real Talk: Fall Photo Season Is Not Just “Pumpkin Spice and Pretty Leaves”

Trust me, I get it. You’re juggling school drop offs, a full work calendar, cramming soccer practices between dinner and bedtime, and trying to remember what actually goes in a lunchbox (spoiler alert: it’s not a banana and a granola bar for the third day in a row).

Carving out time for family photos feels a lot like squeezing into jeans with no stretch. It’s not easy. But here’s my promise to you: I’ve built Michele Taylor Photography to make your session feel less like a chore and more like a memory you’ll love living through.

And October? It gives me a head start in making that magic happen.

Why October Is Actually the Best Month for Your Family Photography Session

Let’s dig into the very real, very practical reasons I recommend October for families who want relaxed, stunning portraits that actually get printed (and not just lost in camera-roll purgatory).

1. That Glorious, Glowing Fall Light

Look, I could photograph families in stadium lighting and still make it work, but give me October’s golden hour? Game over.

• Earlier sunsets mean I can schedule sessions around your toddler’s bedtime, and still capture dreamy, warm light that flatters literally everyone.
• The sun is lower in the sky, so the light hugs instead of harshes – think soft shadows and cozy warmth, not squinting or shiny foreheads.
• Even cloudy days in fall have a certain glow that summer just can’t compete with.

2. Chicago’s Fall Colors? Gorgeous AND Underrated

If you’ve never experienced Lincoln Park in October, add it to your bucket list. Chicago puts on a show that rivals East Coast leaf peeping, and you don’t have to leave the neighborhood to find it.

• South Pond in Lincoln Park, Winnemac Park, Montrose Harbor – our public spaces turn into golden wonderlands.
• Vibrant leaves set against cozy neutral outfits = chef’s kiss.
• It’s not just pretty, it adds depth, warmth, and texture to every image.

3. Comfort-First Wardrobes That Still Look Fabulous

Let’s be honest: no one wants to be freezing in a sundress or melting in long sleeves. October lets us play in that sweet spot where style meets sanity.

• Layers look polished and photograph beautifully: think soft knits, warm tones, structured jackets.
• Nobody’s overheating, nobody’s shivering. Everyone’s feeling (and looking) good.

4. The Calm Before the Holiday Storm

This one’s for the planners. Booking in October gives you what every mom wants: more time and less stress around the holidays.

• Your photos will be edited, curated, and ready to go well before the printing deadlines hit.
• That means less scrambling for the perfect card photo, and more time sipping whatever’s in your favorite holiday mug.
• Plus, you’ll actually have room on your calendar to enjoy the season instead of navigating a photo-related meltdown mid-November.

Spoiler: Your Kids Don’t Have to Be Perfect for the Photos to Be Perfect

So many busy moms tell me, “I’ve been meaning to book… but I’m waiting for a weekend when the kids aren’t all over the place.”

Friend. That weekend may never come. But here’s what I’ve learned, after years of photographing wild toddlers, squirmy siblings, and reluctant dads.

The best images? Rarely planned. They come in moments of laughter, weird faces, playful interaction. And fall gives us the perfect setting where kids can explore freely, wrapped in cozy clothes, bubbles of breath in chilly air.

Don’t wait for perfection. We’ll capture the beauty of right now.

Let’s Make Your October Session Happen

October fills up fast – like, early-bird-gets-the-good-light kind of fast. Whether you’re dreaming of heirloom albums or that one iconic shot for your holiday cards, now’s the time.

At Michele Taylor Photography, I’ll walk you through every detail:

• What to wear (without needing a stylist or three Target runs)
• How to prep kids (without bribes, but maybe some snacks)
• Posing that doesn’t feel like posing
• Artwork and albums that actually live in your home, not in a drawer

You deserve a session that feels as good as the photos look. October makes it easier – but spots are limited.

Ready to snag one? Contact me today to book your family’s fall session in Chicago or book your session online. Let’s create images you love living with.