What’s a Good Month to Schedule Family Photos?

October 14, 2022

We adore living in a state that has four seasons. Our favorite thing about it is that no matter what, there’s always variety in terms of what the climate of our amazing city can offer in terms of wardrobe choices. Today we are going to talk about all four seasons and the advantages for having family photos taken in each.

When you’re contemplating having your family portraits taken, a good thing to think about is which season you’d prefer. Begin with the end in mind. Does your home décor have yellow or orange tones where fall photos would look good? Is your vibe more coastal where summer photos by the lakeshore would look perfect? Perhaps you have softer, more muted tones in your home where spring photos would suit you best. Of course, winter pictures are gorgeous with all that snow and neutral enough that it would fit most any décor.


Fall is the most popular time of year to get family photos taken in Chicago. But is it right for you?

Earlier sunsets can be helpful for families with small children who have earlier bedtimes. You can still get that beautiful light and no cranky children. Bonus!

Autumn family photo at the Chicago Riverwalk in September
Autumn family photo at the Chicago Riverwalk in September
September family photos in Chicago
September at the Wrigley Building
October family photo session at Winnemac Park
Chicago family photos in October

It’s important to know that scheduling can be difficult in the fall because there are only about two weeks in the year when those leaves look as good as they do and those coveted spots book up fast, with our VIP families securing the best dates as far out as July.

A caution about fall sinus infections and viruses

One thing to remember is that during this time of year, there is often viruses going around daycares and schools so if you may miss your session. It’s not uncommon with little ones to have lingering runny noses, HFM or even sinus infections due to fall allergies. Cranky, sick kiddos don’t make for great photos! Rolling the dice to do a family photo session during flu season can require a reschedule at a time when the weather is cooling rapidly.

Chicago family photos in October

Finally, popular locations often get very busy with other photographers and their families. Keep that in mind if you have your heart set on a public park for your location, especially if you don’t have a lot of weekend availability in your schedules.

Early November is really on the cusp of being autumn-like, but often quite cold already so cozy-up with lots of layers!


Winter is the least popular season for family photos but we love the magical beauty of winter for a few reasons. Often, you have the whole park to yourselves. The quiet of winter makes for little distractions as well.

The simple colors of winter when framed in a photo fit easily into homes. Tan grasses and simple branches (versus the yellow-green leaves of deciduous trees) and of course the white snow are easy to match with the tones of the décor in modern day homes. Finally, Chicago under a blanket of snow is simply beautiful. The focus really is on the family rather than on a backdrop of leaves.

november family photos in Chicago
While technically November is autumn, from a photo perspective its cold enough to be considered winter!
These two little girls had so much fun during their November family session.

The sun is lower in the sky this time of year giving off an ethereal, dreamy quality of light than what you’d find the rest of the year. Winter clothing offers fun accessory possibilities: adorable peacoats with scarves, cute boots and warm mittens.

Chicago family photos in December – a perfect shot to frame in the living room!

We love winter because it’s perfect for candid photographs. It’s fun to play around in the snow with your family. Build a snowman or have a snowball fight. These activities will all make for excellent, real photos you’ll treasure forever.

Magical unique Chicago family photos in February

Winter sessions can be a bit briefer than sessions at other times of the year due to the cold. This can be advantageous if you have a partner with little patience for photos or children who lose interest. Either way, one of our skilled photographers will work quickly to get the photos you will love.

Magical unique Chicago family photos in December
Christmas tree Chicago family photos in December

In addition to layering up in cozy clothing, families often bring along a big thermos of hot cocoa to sip on after their photo session. Hand warmers that have been activated a bit further in advance are a great option to put in coat pockets to keep children ready for some outdoor fun.


It’s easy to find available dates on your photographer’s calendar as spring is not as popular as summer or fall. Depending on what your family is involved in spring could be an easier time of year to find the time to schedule family photos rather than summer or fall.

In early spring, layered clothing is essential this time of year because the temps can swing dramatically, but the good thing is that layers look fabulous in photos!

An adorable photo from a Chicago family session in March
A photo from a documentary family photo session in May
A May family photo session at the beach

Spring photos at the beach are amazing because there are no crowds and parking is a piece of cake!

May is great for uncrowded beaches and easy parking
April family photo session
April family photo session
This adorable family chose May for their family photo session
The Wrigley Building is a favorite spring family photo location. This one was in May.
Towards the latter part of May, its often warm enough to start wearing lighter clothing.
A beach family photo session in May
August summer family photo session in Chicago
By early June, a lot of greenery is available, though its still not so humid.
A family with excited children during their June family photo session

Although the weather is usually comfortable and the kids are so happy to be outside playing again. We recommend bringing along some cute rain boots for children to splash in any puddles they find at the end of the session. They will be so happy having this fun and authentic photos like these are some of our client favorites.


Summer is a close second to fall for family photos. The weather is usually nice, especially if you are open to early morning of evening sunsets. Wildflowers are abundant in the summer lending for beautiful backgrounds in your photos. The easy-breezy feeling of summer is perfect for laid-back styles like maxi skirts, bare feet, and sundresses. Extended family may be in town visiting during this time of year so you may be able to get some photos with Grandma and Grandpa too!

July summer family photo session in Chicago
August summer afternoon family photo session at the Chicago Riverwalk
July summer family photo session in Chicago
July summer family photo session in Chicago at Winnemac Park
August summer family photo session in Chicago
July summer morning family photo session in Chicago at Winnemac Park
August summer family photo session in Chicago
August summer afternoon family photo session in Chicago

The days are long in the summertime so if you have little ones who have early bedtimes it might be near impossible to schedule a sunset session. We recommend morning sessions for kiddos who aren’t great at pushing bedtime off. Cranky children even with beautiful light will still be cranky children. Well-rested, happy children are better every time.

August summer family photo session in Chicago
August summer morning family photo session in Chicago at Giddings Plaza in Lincoln Square
August summer family photo session in Chicago
August summer morning family photo session in Chicago at Giddings Plaza in Lincoln Square


If you always have your family photos taken in the same season, we urge you to try others. It just might surprise you and end up producing your new favorite photos! Whatever season you decide is perfect for your family photos, we are here for you!

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