Your engagement session is more than a photoshoot it’s a celebration of the season you’re in and the love you share. These images will become keepsakes, showing the joy and anticipation leading up to your wedding. In a city as vibrant as Chicago, the backdrops are endless, from lakefront sunsets to iconic architecture. At Engagement Photography in Chicago, I guide couples through planning sessions that feel relaxed, personal, and authentic.

Choosing the Right Time

The time of day sets the tone for your photos. In Chicago, golden hour (just after sunrise or before sunset) is magical, casting a warm glow over the skyline or lakefront. Morning sessions are quieter and often perfect for couples who want a calm, intimate vibe. In winter, consider early afternoon since the sun sets quickly.

Plan ahead if you want multiple looks or locations—full sessions (about an hour) give us time to change outfits and explore, while mini sessions (20–30 minutes) are ideal for quick, focused storytelling. Always keep an eye on the forecast. A cloudy day or a touch of rain can add a romantic, moody atmosphere you’ll love looking back on.

Outfits That Feel Like You

The best photos happen when you feel comfortable. Choose outfits that reflect your style and let you move freely whether that’s a flowing dress, crisp button-down, or cozy sweater. Stick to complementary colors rather than matching exactly. Soft neutrals and earth tones look timeless against Chicago’s urban and natural backdrops.

Bring one or two outfits if you’d like variety. Think of it like a date night wardrobe: a casual look for relaxed moments, and a slightly dressier option for portraits. Layers like jackets or scarves add texture and keep you warm if Chicago’s breeze shows up.

Working with Chicago Weather

Weather here is full of surprises, but it doesn’t have to stop your session. Summer can bring sudden showers, winter calls for layering, and spring winds can sweep in off the lake. If rain is forecast, we can embrace it with umbrellas for a playful mood, or move to a cozy café or indoor landmark. Some of my favorite romantic rainy wedding photos have come from unexpected weather—it often creates the most unforgettable memories.

Choosing Locations with Meaning

Chicago is rich with stunning settings for engagement photos:

• Lakefront beauty: North Avenue Beach, Promontory Point, and Evanston’s Grosse Point Lighthouse offer sweeping lake views and soft natural light.
• Garden charm: The Lincoln Park Conservatory or the Bahá’í Temple gardens in Wilmette add timeless elegance.
• Urban icons: Union Station, the Art Institute steps, or a rooftop with skyline views give your photos a classic city feel.
• Hidden gems: Street murals in Wicker Park, your favorite café, or even a quiet corner of your neighborhood park bring personal meaning to your images.

For more inspiration, see my guide to Chicago engagement photo locations.

Tips for a Stress-Free Session

• Plan ahead: We’ll talk about your vision and must-have shots before the session, so everything flows easily.
• Stay playful: Walk, dance, laugh, and let your personalities shine. The first 10 minutes are just a warm-up after that, the real magic begins.
• Trust the process: I’ll guide you gently when needed, but the most beautiful photos often come when you forget the camera is even there.
• Add personal touches: Bring props, pets, or meaningful details that reflect your story. Sessions should feel like you, not a staged production.

Conclusion

Your engagement session is the beginning of your wedding story. It’s a chance to celebrate who you are right now and create images that will carry meaning for years to come. With thoughtful planning, a bit of flexibility, and the vibrant energy of Chicago as your backdrop, your photos will be as genuine and timeless as your love.