Ten Best Chicago locations for engagement photos.

Reading Time: 8 minutes

Known for its impressive architecture what follows are a few of my favorite iconic Chicago spots that inspire me. If Chicago has a special place in your heart, it’s worth considering one of these locations for engagement photos that you will cherish for years to come. If you have your own unique vision for your engagement photos awesome! You can make your engagement a new adventure, or a celebration of your favorite spots.

If you have a favorite place in Chicago you would love to be photographed at tell us in the Facebook comments box at the bottom of this page.

1. The Chicago Theatre

Jason and Daniel met me for this portrait right at dusk so we got the marquee lights in the scene.

Just a few blocks from the Bean is the Chicago Theatre on State Street. Built-in 1921 the landmark theatre is drop-dead gorgeous inside and out.  If you can combine your engagement portrait with tickets to a fun show you’ve got yourself a super fun engagement date.

For photographers keep in mind that sign is so huge you’ll need to position your couples across the street to get all the letters in the photo and the marquee lights do not come on until dusk.

2. The Bean | Millenium Park

To get an uncrowded portrait at everyone’s favorite sculpture the Bean in Millenium Park meet your photographer super early. Or start your engagement session at dusk during the summer for a gorgeous inky blue lit-up cityscape.

One of the loveliest feelings about doing it early is you get the feeling that you have the city all to yourself! For architecture nerds, the Bean was inspired by liquid mercury according to Wikipedia.

Jessica & Scott met me at 6 am on a Sunday to create this classic Bean portrait with empty city streets. This put a strong Alfred Hitchcock noir film feel to their portraits.

This photo session can be paired with photos walking down Michigan Avenue, in front of the famous Art Institute lions and using the super romantic stone sculptures and lush dark green ivy in the South Garden.

An ideal date afterward is to take in the Chicago Symphony Orchestra which is just across the street on Michigan Avenue and a landmark all on its own, or you can take in some art right inside the Chicago Art Institute which I cover in more detail further down this page.

3. Montrose Beach

If you love being outside at the lake during the summer and find the water and sand inspiring then Montrose Beach is for you. It boasts incredible views of the Chicago skyline too.

Here you can stroll down tree-lined pathways, step over to the beach and put your toes in the sand, or walk out onto the docks for a nautical feel. In the summer you’ll find fields of lush grass that are accented by a delicate but unkempt tree-line that gives the location a natural, casual feel.

Even though you’re in the middle of the city, you’ll feel like you’ve stepped miles away.

Phil and Jessie horsing around at Montrose Beach.

If you’re a playful couple trying out some piggyback action is a classic. Being able to just play around and have fun will make your photos feel super personal and real.

On the shore, you can observe the waters of Lake Michigan with the gorgeous downtown architecture of Chicago rising in the distance. Along the water, the details on the boats provide pops of color as they gently rock in the waves. Its variety of backdrops and textures, as well as the great views of the skyline, make Montrose Harbor and Beach a fantastic spot for Chicago engagement photography.

If you switch it up and get a bit sultry esp. at sundown we can make a very different photo.

Here Jessie grabs Phil with a 1950s style Jessica Rabbit hey come here you!

And finally the last Montrose beach photo I want to show you is one that’s all about mood and true friendship. I’ll admit we got lucky with the reddish-orange night sky. The evening was so gentle and warm we gave up the need to talk for and chilled out for what seemed forever.

I love a good silhouette. To me, this one looks wall-worthy!

4. The Art Institute

The Art Institute of Chicago is one of the city’s cultural prizes, a masterpiece collection of artwork housed in a stunning building that makes a fantastic location for a date and your engagement shoot.

More importantly, it was the setting for a super memorable scene from the beloved Chicago film Ferris Bueller’s Day Off. If you haven’t seen it yet I super recommend it.

Learning to appreciate beauty and art together has to be healthy for a relationship. Finding your favorite artists and then sharing what you love about the work with one another and allowing them to inspire your life and your love for one another makes the Chicago Art Institute my absolute favorite spot for warm indoor engagement photos.

I can’t think of a more interesting date than a stroll through the Chicago Art Institute.

The original building, constructed in 1893 for the World Columbian Exposition, was designed in a grand beaux-arts style of smooth, solid walls and impressive archways, giving it an old-world feeling of regality. The entrance is guarded by two lion sculptures, each one weighing over two tons. Time has turned its copper forms a fascinating combination of blue and green.

In the Art Institute garden, you’ll find a wonderland of geometric shapes, classical planters, and ivy-covered walls that will inspire you for a creative session. In the fall, you’ll be treated to a spectacular display of colors as the ivy turns red against the walls and the yellow leaves of the trees.


Max and Liz steal a smooch 1/2 way down the grand spiral staircase at the Chicago Art Institute.

Other perfect photo spots inside the museum are in front of the Rothko Collection which is super colorful and just huge! The modern wing is reached by a bridge that also makes an excellent place to shoot with its clean angles. The building displays vertical lines that meet the roof at a perfect right angle, a spectacular sight.

5. Fulton Market | West Loop

I consider Fulton Market my backyard since our studio is located here. It was formerly a meat-packing, warehouse, and industrial district so it’s got a strong post-industrial feeling to its buildings and alleys.

Andrew & Caitlin get toy-sized in front of everyone’s favorite giant yellow door.

Think rusted iron, abandoned rail yards and graffiti-covered abandoned warehouses. After your photo session, there are plenty of fantastic restaurants and art galleries to take in which are in themselves great spots for photos so take your photographer.

Kasia & Trevor keep one another warm on one of the little side streets near our studio in the West Loop. It was so cold that day we had to keep jumping back into the car to warm up!

I love going on adventures with my couples where we discover an area together and make the best use of it for portraits. We found this Cubs logo painted onto the side of an abandoned warehouse in the West Loop and immediately knew what do do with it!

If you’re a Chicago Cubs baseball fan this spot is definitely for you.

6. Union Station

I love Union Station because it’s super romantic and the architecture is classic. The trick here or any other busy public space is to ignore the other people and let your photographer find a way to separate you from the crowd. We can do that with flash, motion blur or just the way we compose the photo.

This photo was inspired by the famous V-Day sailor photo in Times Square that we all know and love.

With all it’s marble, stone and vaulted ceilings it’s hard to not get caught up in the moment at Union Station. Built-in 1925 it is the hub for all of Illinois METRA train lines just begging to be explored. If you want photos inside the station they require a permit. If you love train travel it may be worth it. One loophole is they permit photography without a permit if you purchase a ticket which leads me to my fun engagement adventure suggestion. Just grab some Ravinia Festival tickets and pack a lawn blanket and a dinner basket!

Union Station has a massive set of Corinthian columns outside their Canal Street entrance.

7. Wicker Park | Logan Square

Repurposing marketing messages for art is probably the coolest thing you can do for your engagement photos. Here we appropriated the @properties signage in front of their Damen Ave office.

Instant Instagram -able portrait check!

The Damen Blue Line CTA stop is right in the heart of Wicker Park and steps away from Big Star Tacos. After dinner surprise your partner with tickets to some awesome live music at Subterranean music venue which is one of the great remaining classic nightspots left since the mass gentrification of the area.

Joshua and Keri make their music under the Damen CTA stop. Some photos just look classic in B&W.

What a lot of people don’t realize is that Wicker Park has as a park and it’s gorgeous in the summertime. Here Marc and Brittany snuggle up on the same bench they met for their first date making their engagement portrait personal.

Wicker Park is surprisingly lush for a city location and the perfect setting for a spring or summer portrait.

Heading up along Milwaukee Avenue towards Logan Square you will find the vintage postcard inspired mural ‘Greetings From Chicago‘ painted by artists Victor Ving (a former graffiti artist from New York City) and photographer Lisa Beggs.

Logan Square has some nice spots for portraits including this giant mural on Milwaukee Ave.

If you love to color there are dozens of amazing building scale graffiti installations in almost every neighborhood. Check out this Instagram feed for the very latest and plan your engagement shoot!

8. Chicago CTA

If you use the Chicago CTA then you might have a soft spot in your heart for a particular station stop and there are at least a dozen ways to create a romantic portrait using the trains with a train vibe.

Tell your photographer to print out a hardcopy of the CTA photography policy from their website because many station managers aren’t familiar with it and they will get up in your grill. Diplomacy and respect work best in these situations. Remember that for the most part they’re just doing their jobs and trying to keep idiots (not you the other folks of course!) off the tracks.

CTA stations are a perfect setting for a romantic portrait but please for the love of Christ stay on the inside of those blue lines!

I’m going to include two wedding photos here because I feel they can be accomplished easily for engagement photos as well and I’ve always loved them.

Francie and David used the CTA Brown Line to get from their hotel to their reception venue.

Here we mixed silly with dramatic using an ultra-wide lens to create a super fun composition for Francie and David. Not shown are the 30 or so passengers behind us who were cheering up a storm!

The brown line platform at Quincy is the best old school Chicago wrought red iron station. Originally constructed in 1897 it is perhaps the oldest surviving stop in the L system.

9. North Avenue | Fullerton Beach

Exhale. These photos are all about relaxing into the moment and capturing the warm summer sunlight.

If you love water and skyline then the downtown beaches are for you. These portraits are best in the evening as the sun gets low. For the best portrait find the sea wall off Fullerton beach and head out as far as you can.

10. LaSalle Street Bridge | Top of Michigan Avenue

Alan and Tina enjoy a Chicago sunset groove on the LaSalle Street Bridge.

The rusty red wrought iron bridges of Chicago provide an old world beauty that is totally unique to our city. You can pair this spot with all the gorgeous stone steps surrounding the Vietnam Veterans Fountain, the Chicago Riverwalk and the top of Michigan Ave by the Wrigley Building (a favorite for weddings but why not for engagements?!)

If you have a favorite place in Chicago you would love to be photographed at tell us in the Facebook comments box at the bottom of this page.

Jake Miller

Photographer, printmaker, jiu jitsu hippie, pyromaniac, science nerd, obsessive personality, dog nut, no inner-monologue. I'm a recovered addict and my life is dedicated to preventing domestic violence. Almond cookies are my Kryptonite what's yours?