Ah, fall family photo season — also known as the great race against the leaves, the weather, and everyone else trying to get their holiday cards out on time. 🍂 Every year, as soon as that first cool morning hits, my inbox fills up with families ready to capture those golden tones, cozy sweaters, and the annual “how did they grow this much already?” moments. If you’re ready to embrace the coziest time of year, Chicago fall family photos are one of the best ways to usher in the holiday season.

This is my third year photographing this sweet family, and it’s always such a joy to see how much their boys have grown and how their personalities have exploded. They live near Humboldt Park and love exploring the neighborhood, so it’s the perfect backdrop. Between the pretty leaves and the familiar spots that feel like “them,” it’s become our go-to place to make memories and capture their updated family photos.

As a Greater Chicago family photographer, I can tell you that fall is the season for updated portraits—and for good reason. Between the vibrant colors, crisp air, and the excuse to buy a new chunky-knit cardigan, it’s basically Mother Nature’s photo studio.

If you’re starting to think about family photos (or those elusive holiday cards that somehow sneak up every year), here’s everything you need to know to plan your fall session like a pro . . . and actually enjoy it.

Everything You Need to Know About Chicago Fall Family Photos 

(and those priceless holiday cards we have every intention of sending out…)

1. When Should We Book Our Fall Family Session?

Fall sessions (September through November) book up fast—like, pumpkin-spice-latte-in-August fast. I usually fill up by early September, which surprises a lot of people! If you know you want those golden leaves or a few holiday card-worthy shots, the best time to reach out is late summer.

The earlier you book, the better your chances of snagging that perfect time slot when everyone’s schedule aligns. Because we all know once school, sports, and work commitments ramp up, family calendars start looking like advanced Sudoku puzzles.

2. Where Should We Do Our Family Photos in Chicago?

The best thing is that fall in Chicago gives you options for family photos.

Some families love choosing a location that means something to them, like Humboldt Park. Others want a woodsy preserve, a lakeside view, or even a cozy in-home session surrounded by pumpkin-scented candles and toddlers in footie pajamas (precious!).

My advice? Choose a spot that feels like you. And don’t stress about chasing the “perfect” backdrop. The best images are always about connection, not coordinates.

3. What Should We Wear for Chicago Fall Family Photos?

This is the #1 question I get every season. (Understandably! Fall outfits can go from Pinterest-perfect to plaid-overload real quick.)

Here are a few quick tips:

• Think texture, not matching. Mix knits, corduroy, denim, or soft cotton layers instead of everyone wearing the same color.
  
• Stay neutral with pops of color. Rust, mustard, olive, navy, and cream photograph beautifully and complement fall foliage without clashing. They also flow easily into the winter holiday season.
  
• Comfort is key. If your kiddo hates that scratchy sweater or can’t walk in those fancy shoes, it’ll show. Cozy and confident beats stiff and styled every time.
  
• Don’t forget movement. Dresses or flowy tops with a little swish catch the light beautifully when you’re walking, twirling, or snuggling up.

And if wardrobe panic sets in, don’t worry: I am happy to be your sounding board to pull things together with zero stress (and minimal Target runs). Take a picture and show me what you’re considering. More than likely, you already have what you need in your closets and just need a fresh pair of eyes. (But I won’t tell if you decide you need to splurge on a new ‘fit that makes you feel good. 😉)

4. How Do We Get Photos in Time for Holiday Cards?

This one’s all about timing and communication.

If you’re dreaming of sending cards before December 15th, book your session for no later than mid-November. That gives enough time for editing, gallery delivery, and designing those perfect cards without resorting to a midnight drugstore photo kiosk moment (we’ve all been there).

Once your photos are ready, I can share some printing and design insights to make the process ridiculously easy. Because no one needs another “upload, crop, panic, repeat” situation in their life.

Pro tip: choose a favorite family portrait and a few candid shots for your card layout. Those giggly, in-between moments are always the ones people comment on the most.

5. How to Actually Send Out Holiday Cards (Without Losing Your Sanity)

You’ve got your photos, you’ve picked your design… now comes the part that usually leads to a flurry of group texts, outdated addresses, and “Wait, did we send one to Aunt Linda last year?”

Here’s how to make it painless:

Start gathering addresses early.

• Share easy-peasy Google Forms (especially with family).  
  If you wait until your cards arrive, you’ll end up handwriting envelopes at 11 p.m. with a cup of cold cocoa and mild regret. A quick Google Form or a shared spreadsheet link sent to family and friends can do the trick (and you’ll have everyone’s details updated for next year, too). 
  
• Use your phone like the modern miracle it is.
  Snap a photo of return envelopes as they come in throughout the year and save them in a “Holiday Addresses” album. When it’s time to order cards, you can easily check spellings and zip codes without digging through drawers.
  
• Leverage online address books.
  Sites like Minted, Postable, Paper Culture, and Mailbook allow you to upload addresses directly into your account. Or, send out the link to friends and family; it’ll compile addresses for you, and voila! You’re set. Some even print and mail the cards for you (so you can officially skip licking envelopes this year).

When to send out holiday cards:

If you’re a stickler for tradition, aim for the first two weeks of December. If your cards are more “Happy New Year!” than “Merry Christmas,” you can send them through early January—bonus points for taking the pressure off.

**Remember: no one on your list is grading you on punctuality. They’re just happy to see your smiling faces and growing kids show up in their mailbox.

6. What If the Weather Doesn’t Cooperate?

Welcome to Chicago, where fall can mean 80° and sunny or 45° and misty all in the same week.

Here’s the good news: soft overcast light? Photographer’s dream. It’s flattering, even, and gives those fall colors extra richness.

If we get true downpours or gusty wind, we’ll reschedule. I always build some flexibility into my fall calendar for exactly that reason.

7. How Can We Make the Session Fun (Especially for the Kids)?

Priceless family photos come when everyone’s relaxed and just… being themselves.

I always tell parents: let the kids lead for a bit. Let them run, explore, or show me their favorite silly face. Those genuine smiles, the ones that come right after the giggle or the chase, are what you’ll want to remember.

Bring snacks, maybe a favorite toy, and keep expectations light. We’ll get those mantle-worthy shots and the goofy, real ones that remind you exactly who your family is right now.

8. What’s the Secret to Stress-Free Fall Photos?

A little planning, a little flexibility, and a whole lot of letting go.

Book early, pick a location that feels “happy” for your family, wear what makes you comfortable, and let the session unfold naturally. I’ll handle the rest: guiding, directing, and capturing all the in-between magic that makes your family yours.

Ready to Book Your Fall Family Session?

Whether you’re planning your first family session or your fifth, fall is the perfect time to capture those cozy, joy-filled, leaf-crunching moments (and maybe even check “holiday cards” off your to-do list before December hits).

If you’re catching this post a little too late for a session, don’t fret! Reach out to see if I have any late fall or early winter availability (New Year’s cards are fun!), or snag a spot for spring family photos. Don’t miss out on family memories just because fall is full.