7 Expert Tips for Captivating Engagement Photos in Chicago

blurry photo of the iconic Chicago Skyline at sunset during blur hour when the lights are bokeh and blurred during a Chicago engagement session

Chicago, the vibrant city along the shores of Lake Michigan, has endless possibilities. Especially when it comes to your engagement session. Chicago’s stunning skyline, iconic landmarks, and picturesque lakeshore provide the perfect backdrop. Whether you’re a local couple or just visiting, Chicago offers a ton of options for taking memorable engagement photos.

Don’t just take my word for it. Below are 7 tips that will help you create amazing memories (and images) that tell your story and stand out.

blurry photo of the iconic Chicago Skyline at sunset during blur hour when the lights are bokeh and blurred during a Chicago engagement session

Style and Fashion

First things first, because hello… what’s the vibe? What are we wearing? We’re talkin’ main character energy here, people. It’s time to bring it.

We’re not just talking about what you wear (we’ll get to that in a sec). We’re talking about setting the scene and creating a vibe that’s uniquely you. Are you going for an experience or a simple walk? Do you prefer a sunrise sailboat session on lake Michigan, or maybe just a stroll along the beach? I’d say my style is editorial meets documentary. Classic meets chic.

I typically send all my couples an engagement guide upon booking and there’s a whole section about this! This is the most fun (albeit stressful), IMO.

Couple laying down on a sailboat in Chicago holding glasses of Veuve Cliquot champagne while eating strawberries during their sunrise engagement session on Lake Michigan

To see more of this stunning Chicago sailboat engagement session, head here.

Best Time for Engagement Photos

Ah, timing, my friend: the secret sauce that turns good photos into great ones. Chicago experiences all four seasons in full force, each offering its own unique charm (truly). Some couples like to take their engagement photos in the same season they’re getting married in, typically a year before, while other couple prefer something totally different. The goal is to choose something that feels special, and also comfortable.

Besides the time of year, you’ll also want to consider the time of day for your shoot as well. Early morning or late afternoon light provides a soft, flattering glow that enhances your photos preventing harsh shadows. That’s always my favorite time of day to shoot.

Choosing the Perfect Chicago Location

When it comes to engagement photos in Chicago, the location options are limitless. Should you dive deep into pizza or the lake? Honestly, maybe a bit of both?

Start by considering the iconic landmarks that define the city. My favorite spots to stay dry and get a great view of the iconic Chicago skyline are on a sailboat in Lake Michigan, North Avenue Beach, Oak Street Beach, Lincoln Park, Milton Olive Park, or the Adler Planetarium. Growing up in Chicago has left me with a such an appreciation for the romance the skyline can add.

For a more stylish vibe, consider dressing to the nines and walking in and around (or shopping in) the Magnificent Mile to visit your favorite luxury stores. To brag, I also adore this idea.

For a classic Chicago vibe, head to the Navy Pier. With its panoramic views of the city and the serene waters of Lake Michigan, it’s an ideal spot for romantic shots against the backdrop of the city’s towering skyscrapers.

If you’re looking for a more natural setting, Lincoln Park provides a lush oasis in the heart of the city. The park’s picturesque gardens, tranquil ponds, and historic architecture offer endless opportunities for classic Chicago engagement photos.

Honestly, the options are as endless as pizza toppings. This particular section deserves its’ own blog post. More on that later.

Should You Bring Props?

Whether it’s popping a bottle of champagne, a special trip to Louis Vuitton or bringing along clear umbrellas (yes, it rains a lot in the Windy City), the right props can take your photos to the next level, adding depth and personality to the whole shoot.

Weather & Your Chicago Engagement Session

I jinxed it with the clear umbrella props, didn’t I? But listen. All I’m trying to say is all types of weather add a special unique ambiance to your session. So try to ditch checking your phone 60 times a day a week before your shoot. Flexibility is key in Chicago. It’s just important to be prepared, ya feel?

Embrace the Unexpected

One of the joys of taking engagement photos in Chicago is the element of surprise. Whether it’s stumbling upon a hidden gem in the city or capturing an unexpected moment, embrace the spontaneity. Grab a drink at a poppin’ bar or jump into lake Michigan if that’s what life calls for at the moment.


At the end of the day, it’s all about the memories you create. When I think back to my engagement photos with my husband 11 years ago (I know, I know, I’m aging myself), I think about how fun the whole experience was. Walking along the beach, playing cards, and meeting our families for pizza afterward. Of course the photos are important, but it’s the laughter, the love, and the experience shared with your partner that you’ll remember forever.

a black and white photo of a couple on a sailboat during their luxury sunrise engagement session drinking champagne and looking like vogue models.

Engagement photos should be an unforgettable experience in the best possible way, especially in a city like Chicago. Whether you choose to capture the city’s iconic landmarks, eat pizza, or hop on a sailboat, Chicago provides a stunning backdrop for celebrating your love. By choosing the perfect location, timing your shoot wisely, dressing the part, and embracing the unexpected, you’ll create timeless memories that you’ll cherish for a lifetime.

So, what are you waiting for? If this is your vibe, then I’m your girl. Contact me today to schedule your own unique session and we can brainstorm all the ideas that will tell your story. Let’s make some magic happen together.

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Vibe Check? You got it! 


The intersection of aesthetic and personality. Fueled by good light, wanderlust, and cookies. Chasing magic like I chase my kids; laughing always.

Whether I'm building legos or putting the final touches on your album design, it's always with intention and love. I believe life is too short not to live for today. My goal? To offer you the perspective of presence with my camera so you can sink into the moment.


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