Holiday family portraits are one of those traditions that seems simple until you’re actually trying to execute one — coordinating schedules, wrangling outfits, managing kids who have opinions about everything, and hoping the light cooperates. Done well, a holiday family portrait session produces images that go on walls, get turned into cards, and become the annual visual record of how much everyone has changed. Done poorly, it’s a stressful hour you’d rather not repeat.
Here’s how I approach holiday family portrait sessions in Chicago, and what you can do to make yours as smooth as possible.
When to book your holiday family portraits
If you want your images in time for holiday cards, you need them delivered by mid-November at the latest — which means booking your session in September or early October at the latest. Fall is my busiest season by a significant margin, and weekend dates in October fill months in advance. If you’re reading this in September thinking “I should probably get on this,” you’re right. Book now.
For families who miss the fall window, a winter session in December or January can be just as beautiful — particularly if there’s snow on the ground — and the images work perfectly for New Year’s cards or simply as a winter portrait without the holiday card pressure.
Best locations for holiday family portraits in Chicago
For fall sessions, the options are extensive — Chicago’s tree canopy turns in a way that rivals anywhere in the country. A few locations that photograph consistently well in fall: Winnemac Park for north side families, Lurie Gardens for a more architectural backdrop with seasonal plantings, and Northerly Island for families who want open sky and lakefront views. For suburban families, neighborhood parks and tree-lined streets often produce the most personal and beautiful results.
For a complete overview of Chicago-area family photo locations by season, see the full locations guide.
What to wear for holiday family portraits
The most common mistake is over-coordinating — everyone in matching red sweaters, or a color scheme so rigid that nobody looks like themselves. A much better approach: choose a general palette (warm tones, neutrals, jewel tones) and let each person interpret it in their own way. The images look cohesive without looking like a catalog shoot.
Avoid busy prints and loud logos, which distract from faces. Textures — knits, denim, layered fabrics — tend to photograph beautifully in fall light. For the full wardrobe guide with seasonal suggestions, see What to Wear for Family Photos.
Managing kids during holiday portrait sessions
Young kids and formal portrait sessions are not a natural combination, and the harder you try to force it, the more it shows. A few things that help: schedule around nap times, bring snacks, keep expectations loose, and don’t tell kids that today is a Very Important Photo Day. Kids who’ve been told forty times to be on their best behavior tend to arrive stressed and perform accordingly.
My approach is to work with kids where they are — if they want to run, we photograph them running. If they’re shy, we give them time to warm up. The best holiday portraits almost never come from the moments when everyone was perfectly posed. For more prep tips, see How to Prepare Your Family for a Photo Shoot.
Holiday mini sessions vs. full sessions
I offer both full family portrait sessions and holiday mini sessions in the fall. Mini sessions are shorter (typically 20–30 minutes), at a fixed location, and priced lower — they’re a good fit for families who primarily need holiday card images and have relatively cooperative kids. Full sessions are better for families who want a more varied gallery, have multiple kids or extended family, or want flexibility on location and timing.
Ready to book your holiday family portraits?
Fall dates fill quickly — don’t wait until October to reach out. Get in touch here and let’s find a date that works.
FAQs
When should I book holiday family portraits in Chicago?
September or early October for fall sessions. October and November weekends fill months in advance. If you want images for holiday cards, you need them by mid-November.
What’s the best time of day for fall family portraits?
Late afternoon — the hour or two before sunset — produces the warmest, most flattering light in fall. Early morning works well too. Avoid midday when the light is flat and overhead.
Do you offer holiday mini sessions?
Yes. I offer mini sessions in the fall at select locations. Reach out for current availability and pricing.
What if the weather is bad on our session day?
I monitor the forecast closely and will reach out in advance if conditions look uncertain. We can reschedule, move to the studio, or in many cases shoot in overcast conditions — which often produce beautiful, soft light.
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