Fall in Chicago is pure magic. The crisp air, warm golden light, and colorful foliage offer a romantic, cozy backdrop perfect for engagement photos. As an experienced wedding and engagement photographer based in this beautiful city, I’ve learned what it takes to plan a seamless and memorable fall engagement session. Here’s your complete guide, from what to wear, to fun prop ideas, to those essential location permits you don’t want to forget.

🍂 What to Wear: Dress for the Season and the Setting
Color Palette
Fall is all about earthy tones and rich, romantic hues. Think:

– Burgundy, rust, mustard yellow, deep green, and navy

– Cream, oatmeal, or camel for neutrals that pop against the foliage

Outfit Tips
– Coordinate, don’t match: Complement each other’s outfits without being too matchy-matchy. Choose tones in the same palette.

– Layer up: Chicago fall weather can be unpredictable. Incorporate cozy sweaters, scarves, and light jackets into your look—they not only keep you warm but add texture and visual interest.

– Avoid logos or busy patterns: These can be distracting. Stick to solid colors or subtle textures.

– Consider your footwear: We may be walking on trails, through grass, or over cobblestones, so wear something stylish and practical.

Pro Wardrobe Tip
Bring a second outfit! Start with a casual look (chunky knits, denim, boots) and then transition to a more romantic or elegant style (flowy dress, blazer, heeled boots). It gives you visual variety and lets your personalities shine.

🍁 Props to Personalize Your Session
Props can add personality and story to your engagement photos. Here are some fall-friendly favorites:

– Blanket or quilt: Perfect for sitting poses or cozying up together. Choose a plaid or neutral-colored one for a classic fall vibe.

– Mini pumpkins or florals: Cute, seasonal, and great for flat lays with your rings.

– Hot drinks: Bring mugs of cider or coffee—adorable for candid sips.

– Your dog (or pet): Fur babies are always welcome in my shoots—just bring treats and a helper if possible!

– Save-the-Date signs: If you’re planning to use your photos for announcements, consider incorporating a simple sign or chalkboard.

📸 Best Chicago Locations (and Their Permit Requirements)
Fall in Chicago is breathtaking, and there are endless spots to choose from. Here are some of my go-to favorites:

Lincoln Park South Pond / Nature Boardwalk
– Why: Dramatic skyline views, golden reeds, and a romantic boardwalk.

– Permit required: Yes. Apply via the Chicago Park District.

North Avenue Beach (Skyline Backdrop)
– Why: Epic city views, especially during golden hour.

– Permit required: Yes, through the Chicago Park District.

Garfield Park Conservatory
– Why: A stunning indoor backup if the weather turns. Lush greenery year-round.

– Permit required: Yes, with fees depending on size and duration.

Lurie Garden at Millennium Park
– Why: Prairie grasses and skyline views—it’s urban meets natural.

– Permit required: Yes, via the Millennium Park Office.

The Morton Arboretum (Lisle, Suburb)
– Why: Arguably the most stunning fall foliage in the region.

– Permit required: Yes, and they’re strict on time slots and group size.

Humboldt Park or Ping Tom Memorial Park
– Why: Hidden gems with bridges, water, and fewer crowds.

– Permit required: Often yes. Check with the Park District for the latest.

🎯 Pro Planning Tips
– Book early: Fall dates fill quickly—especially weekends.

– Time it right: Aim for mid-October when foliage peaks.

– Check the sunset: Plan your session for golden hour, usually 1.5–2 hours before sunset.

– Bring extras: Hand warmers, tissues, a lint roller, and water can save the day.

– Stay flexible: Weather can be unpredictable. I always keep rain dates on standby.

Final Thoughts
Your engagement session should be fun, stress-free, and as unique as your love story. With a little planning and a great photographer (hi, that’s me! 👋), fall in Chicago offers the perfect canvas for memories you’ll cherish forever. Whether you’re cuddled up on a park bench or laughing through the wind on the lakefront, your photos will capture not just the beauty of the season—but the start of your forever.

Let’s plan your dream shoot. Reach out early to snag those peak fall dates! 🍁📷