Finding the perfect location for your engagement session can make all the difference in creating beautiful, authentic, and memorable images. At Lilly Photography, we specialize in creative engagement portraits in Chicago, blending natural moments with stunning backdrops to capture your connection.
Here are some of our favorite spots and tips to make your session effortless and fun.
Top Chicago Engagement Photo Locations
Montrose Harbor

A favorite for couples who love waterfront views and city skyline backgrounds. Golden hour here creates soft, romantic light that enhances every shot.
Lincoln Park South Pond

The pond, bridges, and lush greenery offer a serene environment for candid, natural moments. Perfect for both playful and intimate photos.
The 606 Trail

Urban charm meets greenery. This elevated trail provides city views, murals, and unique angles for modern, creative portraits.
St. James Farm – Wheaton

A hidden gem for couples who enjoy nature. Rolling fields, trees, and open skies create a dreamy, storybook backdrop.
Chicago Riverwalk

Iconic city views combined with bridges and reflections make this ideal for couples who want dynamic, urban engagement photos.
5 Tips for Amazing Engagement Photos
- Schedule Around Golden Hour
For soft, flattering light, we recommend shooting 2 hours before sunset. The light creates warmth and depth, making your images timeless. - Choose Meaningful Locations
Pick spots that reflect your relationship—where you first met, favorite date spots, or places with personal significance. - Dress Comfortably & Stylishly
Outfits should reflect your personality and complement the location. Layers, textures, and colors that pop on camera work best. - Be Yourself
Engagement photos are about connection. Laugh, play, and show your natural chemistry. Avoid stiff poses—we capture candid, real moments. - Plan for Weather & Season
Chicago can be unpredictable. Have a backup plan for rain, and consider seasonal landscapes like fall foliage, winter snow, or spring blooms.
Why Couples Love Lilly Photography
We specialize in documentary-style engagement photography, capturing the real, unscripted moments that tell your story. Each session is designed to be relaxed, fun, and reflective of your relationship.
Check out our engagement photography portfolio to see couples at these locations and more.
Let’s Capture Your Engagement Story
Ready to plan your Chicago engagement session? Contact Lilly Photography to schedule a fun, creative, and authentic session that reflects your love story.
