Chicago is my favorite city for engagement sessions—there, I said it!!

I’ve photographed couples at some of the most beautiful places in the world, but there’s something about Sweet Home Chicago that makes me fall in love with it all over again every single time. Yes, we have that iconic skyline, but we also have four beautiful seasons that completely transform the city every few months.

Most couples prefer the warmer months for their engagement photos, but I’m here to tell you—you can get beautiful portraits any time of year.

Below, I’m sharing my favorite engagement photo locations in Chicago, organized by season (along with real sessions for inspiration), so you can find a setting that feels exactly right for you.

Spring Engagement Photo Locations in Chicago

Spring in Chicago is fresh, soft, and full of movement (think flowy dresses, pastels, and crisp sunshine). It’s perfect for couples who love a light, romantic aesthetic.

If you time it right, we can catch blooming trees—lilacs, cherry blossoms, forsythia (!!). Truly magical.

Maggie Daley Park & Millennium Park

Chicago’s parks are second to none, and they really shine in the springtime. Timing is everything here—I keep a close eye on what the trees and flowers are doing as March and April progress so we can hit peak bloom.

Taylor and Will met me at Maggie Daley Park on the prettiest spring morning, and we caught everything just starting to bloom—it felt like the city waking up after winter.

Art Institute of Chicago

Did you know you can take photos inside the Art Institute of Chicago with just an admission ticket? No permit needed—which still feels wild to me.

Just keep in mind: no flash photography, no large bags/backpacks, and no flowers allowed inside.

It’s one of my favorite engagement photo locations in Chicago, especially as a backup for iffy weather. And if we step outside, the south gardens and Buckingham Fountain are right there.

Frankie and David’s session felt so timeless—like we were wandering through a painting one minute and chasing light outside the next.

The Lakefront

The lakefront is one of the most versatile engagement photo locations in Chicago, and it never disappoints.

Julia and Jeffrey brought their classic car and met me by Lake Michigan at sunset—we wandered along the beach, played in the water, and it honestly felt like a scene from a movie.

Summer Engagement Photo Locations in Chicago

Ahhh, summer in Chicago. You already know.

Summer sessions are all about warmth, golden light, and that effortless “we just spent the best day together” feeling.

North Avenue Beach

If you want skyline views with a relaxed vibe, this is easily one of the most iconic engagement photo locations in Chicago.

I LOVE suggesting sunrise sessions (HEAR ME OUT: the city is quiet, the water is calm, and the light is unreal). But if 4am isn’t your thing, golden hour is just as dreamy.

Maria and Quinn met me for a stroll through the Gold Coast before heading to the beach, and by sunset they were literally waltzing along the shoreline—pure magic.

Chicago Botanic Garden

I will never say no to a session at the Chicago Botanic Garden.

It’s stunning in every season, but especially lush in the summer. There is a permit required for photography, along with timed entry, and it does need to be arranged in advance—but it’s so worth it.

Dori and Eddy’s session felt like the dreamiest afternoon—just wandering through gardens, laughing, and chasing the prettiest pockets of light.

Adler Planetarium

“Planetarium Point” might be one of the most romantic spots in the city.

Sunset here gives you one of the best skyline views, hands down. (Pro tip: aim for a calm day—Chicago wind can be…aggressive.)

Adam and Kathleen danced along the lake with the skyline glowing behind them, and it was one of those sessions where everything just felt easy and joyful.

Autumn Engagement Photo Locations in Chicago

Fall in Chicago? Unreal.

Warm early fall days, changing leaves, crisp air—it’s cozy, colorful, and ridiculously romantic. No wonder it’s one of the most popular times for engagement photos in Chicago.

Field Museum Campus

This spot is such a hidden gem.

Behind the Field Museum, you get beautiful gardens, skyline views, the lakefront, and clean architectural lines all in one place.

Alison and Ty spent the most perfect October afternoon here—twirling, laughing, and completely surrounded by color. It’s one of those locations that just glows in the fall.

South Pond (Lincoln Park)

Yes, it’s popular—but there’s a reason.

If you go early (or even later in the season), you can still get that peaceful, colorful backdrop without the crowds.

Rachel and Matt met me on a chilly November afternoon, and we somehow had the whole boardwalk to ourselves. The colors were still so rich—it felt quiet and cozy in the best way.

Winter Engagement Photo Locations in Chicago

Okay, I’ll say it—I LOVE winter.

I know it can feel intimidating, but winter is one of the most underrated seasons for engagement photos in Chicago.

Chicago Cultural Center

If you love timeless architecture and soft, romantic light, this is one of the best indoor engagement photo locations in Chicago.

The marble, the details, the Tiffany dome—I will never get over it.

Sam and Charlie chose this spot on a cold, rainy January morning, and we were warm, dry, and completely wrapped up in this beautiful, quiet space.

Chicago Theater District (or Personal Spots)

Don’t be afraid to choose something personal.

Meghan and Domenic rented out a theater for their session (iconic), but this could also look like coffee at your favorite café, your apartment, or anywhere that feels like your everyday life together.

The best engagement photo locations in Chicago are often the ones that mean the most to you.

Union Station

Union Station is pure drama—in the best way.

The light bouncing off the marble, the architecture, the movement—it’s stunning, especially on a rainy day. It does require a permit ahead of time, but definitely worth the extra bit of effort.

Alexa and Alex chose this location for exactly that reason, and everything about their session felt classic and cinematic.

Final Thoughts on Choosing Your Engagement Photo Location in Chicago

When choosing a location, don’t just pick a spot because it’s trending, think about where you feel most like yourselves.

Is it grabbing coffee on a Saturday morning? Dressing up for a rooftop sunset? Walking by the lake? Sailing? Wandering through gardens?

There’s no “right” answer—just what feels like you.

And if you’re still not sure what fits yet… I’ve got you. I help all of my couples choose locations, timing, and overall direction so your session feels natural, easy, and completely true to who you are. I’ll also guide you through any permits or logistics along the way, so you don’t have to stress about the details.

If you’re planning your engagement photos in Chicago, I’d love to help you create something beautiful.