When to Take Engagement Photos: A Seasonal Guide for Chicago Engagement Photoshoots

Trying to figure out when to take engagement photos might just be that tiny little detail in wedding planning that sends you over the edge, because let’s face it… You’re already probably super stressed, and now you have to figure out which season will give you the engagement photos that feel like you?? You’re literally just a girl!

Don’t worry, though. As your Chicago engagement photographer who loves anything that’s a little nontraditional and a little spunky, I’ve got you covered with what each of the seasons brings you for engagement photos, so that all you have to do is read this guide and say, “Oh, yeah. That’s the one that feels like us.” 

When to Take Engagement Photos in Chicago: The Breakdown by Season

Before we do a deep dive into each season, I’m gonna give you a little snippet of what each of the seasons is like for engagement photos, with a link that’ll take you right to that section. If you can’t tell, I’m all about making things easy for you, loves. 

• Winter engagement photos – these bring lots of snuggles, warm lighting, and cozy vibes. Also, they’re severely underrated. 
• Spring engagement photos – super romantic, super adorable. Every single time. 
• Summer engagement photos – if you love being outside together and contagious laughter… Yeah. Don’t pass up summer! 
• Fall engagement photos – these kinda make you feel like you’re in a Fleetwood Mac music video. And if you’re anything like me… You love that energy. 

Everything to Know About Taking Winter Engagement Photos in Chicago

As I said above, winter engagement photos? Criminally underrated. 

Winter is honestly one of the best times of the year and has so much character on its own, so don’t skip over it when you’re wondering when to take engagement photos. 

If you’re someone who hates the cold and you’re sitting there reading this like, “Immediately no,” just hear me out. Because Chicago has some insane indoor locations for engagement photos! I’m always down to pop into a little bar with the two of you and get some super editorial, dimly-lit pics, or even stand outside freezing my booty off while you two make snow angels and get in snowball fights. 

At the end of the day, winter engagement photos turn out super romantic every damn time, and if you’re the type of couple who wants something a little different and something a little soft… Let’s schedule your session for the wintertime, babes. 

Where to Take Winter Engagement Photos in Chicago 

Again, as a Chicago engagement photographer, I LOVE a good bar engagement session. Trivoli Tavern and Venteux always work for winter vibes, and don’t pass up city street photos and sneaking into hotel lobbies. 

You can also opt for taking them right at home, which I’m always obsessed with, as you can see here. 

When to Take Engagement Photos in Winter: The Best Time of Day

Winter sunsets hit different. The light being so strong itches something in my little photographer brain, and golden hour photos are a 10/10, every time. 

What to Wear for Winter Engagement Photos

Another reason that I love winter engagement photos is that you can get really creative with your outfits. This red fuzzy jacket + veil combo lives rent-free in my brain, but you can also go for something simple like a dress underneath a big coat so that you can just slip it off when you get to an indoor location. 

Everything to Know About Taking Spring Engagement Photos in Chicago

Spring is popular for engagement photos, and that’s for a good reason. Chicago in the spring?? It feels (and looks) like Heaven. The lighting is so soft and dreamy, the warmth makes everything feel giddy, and honestly, Chicago just looks SO gorgeous through the entire season.

If you’re someone who wants to run around in a field in a maxi dress and also bring a bouquet of your favorite flowers, spring just might be for you!! 

Where to Take Spring Engagement Photos in Chicago 

Okay, let’s be real, basically anywhere works for spring engagement photos. Fields, the city streets, you name it. One of my favorite places, though, will always be The Garfield Conservatory. The flowers that bloom in the spring?? Yeah, I’m completely and utterly obsessed. 

When to Take Engagement Photos in Spring: The Best Time of Day

Again, spring is so versatile that you could go out at any time of the day, and it would be picture-perfect. I will say, if you want to beat the crowds, though, early morning sessions work way better! 

What to Wear for Spring Engagement Photos

One thing to know about me is that I’m always gonna suggest a little bit of color, no matter when you take your engagement photos. Spring calls for pastel colors (with maybe some pops of bold hues!), and I’m obsessed with something like these Larroude heels paired with a white dress. 

Everything to Know About Taking Summer Engagement Photos in Chicago

If you’re one of my couples who loves all things bright and vibrant… One, I love you already. Two, summer is probably gonna be when you should take engagement photos, because the long days and the sunshine and the bold colors everywhere just create a combo that feels perfect for you. 

Summer in Chicago brings gorgeous temperatures and lots of color everywhere, and it’s something that really gets me. I’m obsessed with anything bright + fun, so if you’re leaning towards summer engagement photos… We’re gonna get along well, babes. 

Where to Take Summer Engagement Photos in Chicago 

Outdoor engagement photos in the summer just make sense, so if you’re looking for the best locations, I’ll always recommend somewhere like The Chicago Botanic Garden for lush greens or Chinatown if you really want to lean into the bright, neon feel of it all. 

When to Take Engagement Photos in Summer: The Best Time of Day

I’m a sucker for summer sunsets. Golden hour hits different in the summer, and if we plan your session to start just an hour or so before sunset, it’ll give us some dreamy light that feels like my personal version of Christmas morning. 

One thing to note here is that if you’re going to a public location, mornings will bring fewer crowds. So, if you’re one of those people who feels awkward taking pics in front of people and wonders how TF influencers survive in the world (I feel you), morningtime may be a better fit for you. 

What to Wear for Summer Engagement Photos

Surprise! I think you should wear something colorful for summer engagement photos. 

Seriously, though, summer gives you the chance to be vibrant, and any time that’s the case… I say take it. I may be biased as a Chicago engagement photographer since it makes your pictures fun and textured and sooo rich, but I also just love any kind of self-expression!! 

Everything to Know About Taking Fall Engagement Photos in Chicago

Now, fall in Chicago… It’s something really special. The brownstones and overall neutral hues of the city with fall colors on the leaves??? It gets me right in the heart every single time. If you don’t want to feel like you’re the main character in a coming-of-age movie twirling in falling leaves, that’s fine. If you do, though, you’re in luck. 

So if you’re all about cinnamon and sweaters and spooky season, let’s be best friends. And let’s also plan a fall engagement photoshoot, because if that all sounds like you, you should never, ever wonder when to take engagement photos. The answer is clear, babes. 

Where to Take Fall Engagement Photos in Chicago 

The University of Chicago Campus is 100% hands-down my favorite place for fall engagement photos in the city. The fall colors here feel like something I dreamt of that happened to come true every year, and it fits the vibes SO well. I also love that we can pop right over to Washington Park afterwards to soak up some more of that rich fall goodness. 

When to Take Engagement Photos in Fall: The Best Time of Day

Pretend like I haven’t answered sunset for almost all of the seasons because… You just HAVE to choose fall sunset engagement photos. The way the light hits is unmatched, and when it gets a little chilly, and you get a little snuggly… That’s my whole jam. 

What to Wear for Fall Engagement Photos

Trench coats and neutral colors (with a pop of red, probably) and fun accessories for fall engagement photos have my heart. I mean, just think about how chic you’d look in a plaid trench coat, some red Mary Jane heels, and maybe even a cute little red beret. Obsessed. 

How to Choose When to Take Engagement Photos

Still stuck? I get it. Because Chicago brings the vibes no matter what season we’re in. 

If you’re still wondering when to take engagement photos, here are a few more things to consider: 

• Your wedding date – let’s face it, your wedding planning timeline really makes a difference in when to take engagement photos. If you want to use them for your save the dates, you’re looking at needing to take them about 10-12 months before your wedding, so whichever season that falls in! 
• Your vibe – I mean, you obviously have to consider your vibe when you’re thinking about when to take engagement photos. If you’re bright and bubbly, summer is probably yours. If you’re a little moody, let’s shoot for winter!! 
• Any dates that are special to you – anniversaries or meeting dates can make your engagement shoot extra special, and I’m always here for a little bit of romance. 
• Your dream outfit – if you’re here, I’m gonna take a wild guess and say that you’re someone who cares about style. So, if you’ve had the perfect mini dress saved for far longer than you want to admit… Use that to guide when to take engagement photos!! You can also find TONS of outfit inspo for engagement photos here. 
• Your dream location – again, if you have a location that you pass all the time and dream about taking photos in, choose the season that fits the energy of that space. And if you need help looking for locations, this guide has you covered with the coolest ones. 

Wren and Rose Photography | Chicago Engagement Photographer

I’m all for helping you plan the session of your dreams, so if you want to talk it out, inquire right here and I’ll help you narrow down the BEST time for you to take engagement photos, then show up like your silly little third wheel and capture the cutest damn moments. 

Can’t wait to meet you, loves!!