Creative imagery. Unique perspective. Documentary.

Best Chicago Engagement Photo Locations + 5 Tips for Amazing Pictures

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

Montrose Harbor Engagement Pictures

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

Lincoln Park Engagement Session

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

The 606 Trail

606 Trail Engagement Pictures

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

St. James Farm – Wheaton

St James Farm Engagement Pictures

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

Chicago Riverwalk

Chicago riverwalk Engagement Photographer

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

  1. 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.
  2. Choose Meaningful Locations
    Pick spots that reflect your relationship—where you first met, favorite date spots, or places with personal significance.
  3. Dress Comfortably & Stylishly
    Outfits should reflect your personality and complement the location. Layers, textures, and colors that pop on camera work best.
  4. Be Yourself
    Engagement photos are about connection. Laugh, play, and show your natural chemistry. Avoid stiff poses—we capture candid, real moments.
  5. 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.

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