Best Time for Outdoor Family Photos in Chicago Area - Expert Tips
After 18 years of photographing families in the Chicagoland area, I can tell you that one of my most successful sessions happened on a spring evening in May at Cantigny - and it wasn't during the popular fall season that everyone books.
The best time of year for outdoor family photos in the Chicago area, in my opinion, is spring and early summer (May through early June), followed by early fall (September through mid-October). While everyone thinks fall is ideal, spring offers less crowded locations, more flexible scheduling, and beautiful blooming backdrops without the stress of cold weather affecting young children.
Let me break down exactly what I've learned about timing outdoor family sessions in our unpredictable Chicago climate.
Cantigny in Wheaton in the spring
Why Spring Is the Most Overlooked Season for Family Photos
Spring is hands down my favorite time to photograph families. Everything is blooming, you get gorgeous, fresh green backdrops, and we have the place to ourselves most of the time.
I did a sunset session at Cantigny in May with one of my favorite families - we had the entire location to ourselves, everything was blooming, and the lighting was perfect. Spring isn't as busy at Cantigny, so there's no one there to work around.
Here's what makes spring sessions work so well:
Weather that cooperates: Not too hot, not too cold - perfect for keeping everyone comfortable
Faster turnaround times: I'm not as busy in spring, so I can get your photos edited much quicker
More scheduling flexibility: During the spring months, I see 6-15 families per month versus up to 100 families in three months during fall
Creative freedom: Less volume means I have more time to be creative with your session
The blooming flowers and fresh spring colors look completely different than fall photos, giving you something unique for your walls.
Cantigny in Wheaton in the Spring
Fall Photo Sessions: What You Need to Know Before Booking
I love fall photography, but there are real challenges that families don't always consider when booking those popular late October sessions.
The biggest mistake I see? Families booking late October sessions with babies or toddlers. A cold baby is an unhappy baby, and you can't reason with a six-month-old about staying outside when it's 40 degrees. I always flag this because I'd rather you have a happy, smiling baby than book when the leaves are supposedly at their peak.
Here's the reality about fall sessions:
Limited flexibility: I'm at set locations on set days, usually seeing 5-8 families per day on weekends
Unpredictable weather: The timing of peak leaves isn't as predictable anymore with our changing climate
Busier locations: Everyone books fall photos, so we're sharing space with other families and visitors
If you have older kids (6-7 and up) who can handle cooler temperatures, fall can be beautiful. Just plan accordingly and book early. I typically send out an email to everyone on my email list in late July or early August with my fall availability.
Summer and Winter: When They Work Best for Your Family
Summer works great if you have school-age or college-aged children and want maximum scheduling flexibility. The key is avoiding that harsh midday sun - I always schedule early morning or later in the day sessions. I like to be as close to sunrise or sunset as I can get!
Winter can be magical at the right locations. Veterans Acres in Crystal Lake has tall pine trees that look stunning year-round, even with snow. Pine trees never lose their needles, so it's one of the few outdoor locations I can honestly say looks good in any season.
For summer sessions, I love locations like Independence Grove in Lake County with mature trees providing natural shade. Winter sessions work best when it's cold but not windy - wind is the biggest enemy for any outdoor shoot.
Independence Grove in Libertyville during the Summer
Weather Factors That Make or Break Your Photo Session
Here's something most people don't realize: it's not the heat or cold that ruins outdoor photos - it's wind. Wind can make or break a photo shoot faster than anything else.
I can photograph in winter just fine if it's not windy. But 20-mile-per-hour winds at 75 degrees? Miserable. Your hair's in your face the entire time.
The other major factor is timing. I always avoid high noon when the sun is highest in the sky, directly overhead. During busy fall seasons when I have sessions all day, I schedule my lunch break during this time because the lighting is unflattering.
I always aim for early morning or later sessions. Those sunrise and sunset slots book up fastest, especially in fall, but there's a reason they're ideal.
Best Chicagoland Area Locations by Season
After 18 years, I have my go-to spots that work beautifully depending on the season, all across Chicago and the Suburbs:
Year-round locations:
Veterans Acres in Crystal Lake (those pine trees are magical in any season)
My studio in Algonquin with Town Park out back (indoor/outdoor flexibility)
Garfield Park Conservatory in Chicago (it is like being outdoors, but inside)
Spring and summer favorites:
Cantigny in Wheaton (I buy a yearly permit here)
St. James Farm in Warrenville
Independence Grove in Libertyville
South Pond in Chicago
Chicago Riverwalk for urban looks
Naperville Riverwalk
Downtown Geneva
Fabyan in Geneva
Winnemac Park in Chicago
Fall Favorites:
South Pond in Chicago
Chicago Riverwalk
Veterans Acres in Crystal Lake
Schweitzer Woods in West Dundee
Montrose Bird Sanctuary (a little oasis inside Chicago)
Independence Grove in Lake County
Leroy Oakes in St.Charles
Fabyan in Geneva
Winter Favorites:
Veterans Acres in Crystal Lake (those pine trees are magical in any season)
My studio in Algonquin with Town Park out back (indoor/outdoor flexibility)
Garfield Park Conservatory in Chicago (an individual permit is required)
Lincoln Park Conservatory in Chicago (an individual permit is required)
My Clients’ homes, especially when decorated for the holidays!
Pilcher Park Nature Center in Joliet (individual permit required)
I handle all the permit requirements for locations in DuPage and Lake County. Some of the most beautiful spots require permits, and I've got the yearly ones covered for the locations I use most.
Veterans Acres in Crystal Lake during the Winter
Insider Tips for Choosing Your Ideal Photo Session Timing
What makes working with me different is that I know all the events happening in most areas. I've had 18 years of experience navigating Chicago-area events, and my calendar is full of "do not book" alerts for marathons (Yes, I am looking at you Chicago Marathon), festivals, and celebrations that could shut down locations.
The last thing you want is booking a session at the Chicago Riverwalk only to find out Chicago's been shut down for festivities and the bridges are all up.
Here's my honest recommendation: consider spring or early summer. You're not stressed about getting photos done quickly for holidays. Kids aren't already overwhelmed with back-to-school schedules. And I have way more flexibility to work with your family's specific needs, especially if you have college-aged kids.
Weeknight sessions often produce better results because locations are emptier, and we have more freedom to move around. I understand everyone wants weekends, but if you can swing a weeknight, you'll get a much more relaxed experience.
During spring, I can go wherever. During fall, I'm locked into specific locations on specific days because of the volume of families I'm seeing. This flexibility makes all the difference when planning the perfect outdoor family photos in the Chicago area.
Ready to schedule your family photo session during the perfect season for your family? Let me know what time of year you're considering, and I'll help you choose the ideal timing and location based on what works best for your family's needs and comfort.
You can check out my family pricing and reach out to directly book me!