Engagement Photoshoot Locations in Chicago: The Best Neighborhoods, Based on Your Vibe

In case no one has told you… Your Chicago engagement photoshoot doesn’t have to be a classic, traditional session where you stand in a pretty spot like a statue, fake smiling until your cheeks hurt. My favorite sessions, as a Chicago engagement photographer, are the ones that have some personality. The ones that are a little fun, a little unique, and make you say, “Oh yeah, this is SO us,” when you get your gallery back. 

Lucky for you, I know the best spots in Chicago to get pictures just like this. Because tradition? We don’t know her! 

I’m breaking down the best engagement photoshoot locations in Chicago for every type of couple: the artsy ones, the classic ones, and the ones who love all things nature. 

Chicago Engagement Photoshoot Locations For Funky, Artsy Couples

Okay, you love art, you dress in a way that everyone else probably finds a little funky, you spend your weekends at the record store, and you’re looking for an engagement photoshoot location that fits your energy. You’re in luck, because this is where Chicago thrives. 

The best engagement photoshoot idea for this type of couple is hitting Logan Square, Wicker Park, and then Pilsen. See my full guide to this kind of session right here. We’ll have to hop on the train to get from place to place, but that’s part of what makes it SO fun. And don’t get me started on subway engagement pictures because… They’re some of my faves!! 

Logan Square

Logan Square is filled with spaces that are gonna feel like a playground to you… Trust me. It has brick alleyways, colorful murals, and TONS of little stores that we’ll pop into for photos (but then you’ll probably end up buying something). 

It’s basically the visual equivalent of the inside of my brain, and it gives me the kind of photos that make me have to pause for a breath. 

Pilsen

For my art lovers, we absolutely have to hit Pilsen. There’s street art quite literally everywhere you look, plus a crazy view of the Chicago skyline that gets me everyyyy time. You’ll get date-night energy while also kinda feeling like you aren’t even in Chicago anymore, and I’m obsessed with the whole entire vibe. 

Wicker Park

Wicker Park has that neighborhood vibe that’s perfect for city street engagement photos that still feel unique. It’s like Logan Square in the sense that it has tons of little shops, funky walls, and artsy spaces, but it feels a little vintage, too. And the bar scene?? PERFECT for dive bar engagement photos that feel a little grungy. Gimme all of them!! 

Chicago Engagement Photoshoot Locations For Classic + Iconic Photos

If you’re the kind of couple who really loves all things Chicago and wants engagement photos that feel super cool and elevated, this is the section for you. You’ll find the architecture of my dreams (plus gold-plated designs that give us some really cool lighting) all around downtown Chicago, and these are the can’t-miss spots: 

Riverwalk

If you’ve stepped foot in Chicago a day in your life (or Googled it, if you’re coming in from out-of-town), you know Riverwalk. It’s basically one of the most iconic spots in the whole city, and for good reason. I mean, the skyline views are absolutely ridiculous. The Wrigley Building in the background makes for really cool, editorial shots, and the lighting on the water makes me giddy every single time I’m there!! 

The Board of Trade

Gold decor and city streets and tall columns make my heart beat a little fast, and if you’re the same way… The Board of Trade is basically the perfect spot for you. You get photos here that are equally editorial, magazine-style, but still really unique. Isn’t that kind of the best place to be in??

The Chicago Art Institute 

The Chicago Art Institute is forever one of my favorite engagement photoshoot locations in the whole city. The pictures turn out so damn cool every time I’m here, and it’s perfect for the couples who want something quiet that still screams, “Yeah, we’re the it-couple!!” 

Chicago Engagement Photoshoot Locations For the Nature-Loving Couple

Are you one of my get-out-in-nature-and-run-around-in-a-field type of gals? Love that for you. 

Don’t worry, Chicago has some fantastic spots for you too. The east side of Chicago is gonna be your dream come true if you love beach engagements, and there are also some conservatories that give garden energy in an edgy way, if you get what I mean. 

Conservatory Engagement Photoshoot Locations in Chicago

Lincoln Park Conservatory and Garfield Park Conservatory have my whole heart. Greenhouse vibes are perfect for summer engagement photos (especially for the people who love plants, flowers, and lush greenery. Love that for you). My favorite part, though? You can get really creative with your engagement photo outfits. Bold colors ALWAYS work here, and I’ll hype you up in them every time!! 

Northerly Island

Sunsets on Northerly Island are, like, pure magic. The way the light hits the water is insane, and you’re pretty much always totally alone here, so it gives that secluded feel that makes sessions feel more like a date and less like a photoshoot. 

North Avenue Beach 

Don’t let Chicago being a big city stop you from getting cinematic beach engagement photos, because North Avenue Beach?? It’s one of the best spots in the city. 

Engagement sessions here always feel really effortless, and there’s something about the juxtaposition of the beach and the city skyline that scratches my brain in all the right ways. I mean, just LOOK at these pics!! 

Wren and Rose | Chicago Engagement Photographer

Need some more ideas for your Chicago engagement photoshoot location? You know I’ve got you covered. Here are 10 more!! 

Whether there’s one spot that’s sticking out or you wanna hit, like, 5… I’m so down. Reach out right here, and let’s plan the most you-coded engagement session of all time, babes.