5 Ways to Make Your Engagement Session More You — Plus Our Favorite Chicago Locations


Your engagement session is more than a photoshoot—it’s a celebration of your story, your connection, and the little things that make your relationship yours. Whether you’re dreaming of something cozy and casual or bold and cinematic, here are 5 ways to make your engagement session feel personal, fun, and true to you. Plus, we’re sharing some of our favorite spots around Chicago to bring it all to life.a Heading

Urban street photography sequence showing a couple walking past historic architecture.
Panoramic sequence of a kayak journey across calm waters under cloudy skies.
Street scene showing people walking along an urban sidewalk with parked cars.

1. Bring Your Favorite Food

Sharing a slice of pizza, sipping coffee, popping champagne—it’s those little moments that create the best memories (and the most relaxed, candid photos). Think: a deep-dish picnic from Lou Malnati’s or coffee from your go-to neighborhood café.


Perfect Chicago spots for this:


Friends enjoying drinks together at sunset on a rocky beach.
Black and white photo sequence of people dining at a casual restaurant.
Couple enjoying a casual meal together at an outdoor restaurant patio.
Couple in formal attire sitting together on a rooftop with brick buildings in the background.
Candid sequence of friends laughing together in a modern space with city lights visible.
Evening gathering at a rustic outdoor venue with string lights and wooden beams.

2. Choose a Meaningful Location

Is there a spot that means something to your relationship? Maybe it’s where you had your first date, the park you always walk through, or the lakefront you love to visit. Choosing a location with meaning adds depth to your photos—and makes you feel more at ease.


Some of our go-to Chicago engagement photo locations:


Golden hour engagement photos with city skyline and sunflare in background.
Romantic evening scene in front of Chicago Theatre with illuminated marquee lights.
Street scene in downtown Chicago with pedestrians and urban architecture.
Playful couple running through city streets at dusk wearing matching dark outfits.
Urban engagement photoshoot with city skyline and modern architecture in the background.
Wide angle cityscape view of Chicago's downtown streets and skyscrapers.

3. Bring Two Outfits (and Play with Color!)

We always recommend bringing two looks: one casual and one a little dressier. This gives you a mix of relaxed and elevated vibes—and helps tell a fuller story of who you are together.


Don't be afraid to play with color! Earthy tones, muted jewel shades, soft neutrals, or even a bold pop can photograph beautifully against Chicago’s mix of architecture and nature.


Need outfit inspo? We’ve got a Pinterest board full of ideas saved for you 👉 Couple Outfit Ideas

4. Practice Your First Dance

Whether you're already choreographing or just want a romantic spin in the middle of the street, moving together in front of the camera brings out so much genuine emotion—and helps you feel more comfortable for the big day.


Where to try it:


A couple poses playfully in a park with golden sunlight and city skyline in background.
A romantic couple embraces and laughs together on a sandy beach at sunset.
A couple walks hand in hand along a windswept beach with dramatic waves.
A couple shares a joyful moment under string lights in an urban setting at dusk.
A couple dances together on a city street with modern high-rise buildings in the background.
Beach engagement photoshoot with waves and sand at sunset.

5. Share Your Vision With Us

We love when couples share their Pinterest boards, mood inspo, or even just a few favorite photos. It helps us understand your vibe so we can create something that's not just beautiful—but completely yours.

A couple explores a lush indoor conservatory filled with tropical plants and palm trees.
A romantic moment shared at an upscale bar with vintage newspaper decor.
A couple enjoys a romantic moment in a small yellow pedal boat on dark waters.
Frozen Chicago River with boats trapped in ice beneath city bridges and buildings.
A playful proposal moment captured in a tropical greenhouse setting.
A couple sits on modern black steps in an elegant architectural setting.

Want to Book an Engagement Session in Chicago?


We offer standalone engagement sessions or you can add one to any of our wedding photography packages. We help with planning, outfits, location scouting—you name it. Just fill out the contact form on our website and we’ll get back to you with all the details.

Let’s make some magic in this city we love.