Planning your engagement session can feel overwhelming. What vibe are you going for? Where should you take pictures? What should you wear? And are there specific things to consider when taking photos in the city? Chances are you're looking to your wedding photographer to help answer these questions — that’s where I come in! I've put together this comprehensive guide to help you feel confident and prepared, covering everything from location recommendations to outfit ideas. Before we dive in, here are a few key things to consider:

When should you schedule your session?

Many couples plan their engagement session with save-the-dates in mind. These are typically sent out 6-12 months before your wedding day. Keep in mind that engagement galleries are typically delivered within two weeks, so factor that into your timeline. If you're not in a rush, I recommend scheduling your session during the warmer months (May through October) for beautiful lighting, scenery and weather.

Tip: for the best experience, I recommend avoiding the city on/around holidays or during large events (Lolapalooza, etc); foot traffic is heavy and transportation & parking can be tricky – something to keep in mind as you are picking your date!

What is your vision for the session?

Do you imagine your session feeling formal, relaxed, romantic, playful — or maybe a mix of all of these? Defining your vibe is key to choosing the right location.

A few things to consider: Is your wedding in the city, and do you want your engagement photos to echo that? If so, downtown Chicago offers stunning backdrops to capture that urban energy. On the other hand, if your wedding is already in the city, you might want to switch it up and opt for a more natural setting with greenery and open landscapes. The good news? Chicago has countless incredible locations to fit any vision!

Below, I’ve rounded up my favorite spots for engagement photos in and around the city. Keep in mind that the final time of day we schedule will depend on your chosen location for the best lighting possible.

Engagement Session Location Ideas

The Art Institute of Chicago

Elegant, timeless, and undeniably iconic, the Art Institute offers endless photo opportunities, making it a fantastic choice for a formal and classy engagement session — especially during the winter months.

As an LBP couple, you’ll enjoy complimentary admission through my membership and exclusive early access to the galleries an hour before they open to the general public, allowing us to capture beautiful moments without the crowds.

Tip: The Art Institute has restrictions on what can be brought into the galleries (large bags, etc.. However, you can pack personal items and outfit changes and take advantage of the complimentary coat check at entry.

Lincoln Park Nature Boardwalk

I love this location for its foliage, especially in the summer when the wildflowers are in bloom. It’s the best of both worlds because not only do you have greenery, but it also offers skyline views. The Nature Boardwalk is a great option for a more casual, relaxed vibe.

Tip: Parking near the Nature Boardwalk can be tricky; Stockton Drive is often packed with cars so I recommend parking along Clark Street parallel to the park, where street parking is more readily available.

Grant Park

Grant Park is a breathtaking location for engagement sessions, offering a perfect blend of nature and city elegance. With the iconic Buckingham Fountain as a centerpiece, lush gardens, and sweeping views of the Chicago skyline, it provides a timeless and sophisticated backdrop. Whether you're envisioning a classic, formal feel or a romantic stroll through beautifully manicured landscapes, Grant Park delivers a refined setting that feels effortlessly grand.

Tip: before choosing this location, check and see if there will be any events happening in the park on your date – this is a busy area for festivals and events in the summer.

Olive Park

Olive Park is a hidden gem for engagement sessions, offering a stunning mix of Chicago’s skyline and the serene beauty of Lake Michigan. Its signature tree-lined path creates a dreamy, intimate feel, while the overlook structure—suspended above the water—adds a unique and breathtaking touch. With its close proximity to Navy Pier and Ohio Street Beach, this small yet picturesque park provides a perfect mix of urban and natural scenery. Sunset sessions here are especially magical, with golden light reflecting off the lake and cityscape, creating an effortlessly romantic and glowy atmosphere.

See more from this featured gallery in my portfolio.

Tip: this location can be tricky in the summer with crowds – if this is the location you have your heart set on, it is recommended to do a weeknight where there will be less foot traffic.

Gilson Park Beach

Gilson Park Beach is my personal favorite location for engagement sessions, offering a serene and dreamy escape from the city. Unlike urban settings, this Wilmette gem features soft sand dunes with tall, wispy grasses that create an ethereal, romantic atmosphere. The beach itself provides a clean, minimalist backdrop, allowing the focus to remain entirely on the couple. For the most beautiful, glowing light, sessions here should take place in the evening before sunset, when the golden hues enhance the natural beauty of the landscape and create effortlessly stunning images.

See more from this featured gallery in my portfolio.

North Avenue Beach

North Avenue Beach is an iconic Chicago location for engagement sessions, offering breathtaking skyline views and a striking mix of city and water. Its defining feature is the jetty that extends into Lake Michigan, providing a dramatic and high-impact backdrop with the skyline rising behind it. Whether capturing romantic moments along the water’s edge or standing against the vast cityscape, this location is perfect for couples looking for a bold yet timeless setting. The mix of lakefront serenity and urban energy makes North Avenue Beach a standout choice for engagement photos.

The Wrigley Building

One of the most popular engagement session locations in the city, the area surrounding The Wrigley Building is undeniably iconic. With stunning views of the Chicago River and skyline, it offers a timeless and elegant backdrop. The building’s intricate gold doors and charming skybridge also provide beautiful, refined settings for portraits. Its popularity also means it’s one of the busiest spots for portraits, but with the right timing, it’s well worth it for the breathtaking photos! This location naturally lends itself to a more formal and sophisticated vibe, perfect for couples looking for a classic and polished look.

Tip: Weeknights or Sunday evenings are usually less busy with Saturday being the busiest with tourists and wedding parties.

Museum Campus

Museum Campus is a breathtaking location for engagement sessions, offering a mix of grand architecture, lush greenery, and stunning city views. Because of its size and variety, I recommend choosing this as the sole location for a session to fully take advantage of all it has to offer. The Field Museum’s iconic columns and stately stairs provide an elegant, timeless backdrop, while the nearby gardens with tall grasses and wildflowers add a soft, romantic touch—especially in the summer. Further down, the outdoor area surrounding Adler Planetarium offers sweeping, unobstructed views of the full Chicago skyline and Lake Michigan, creating epic, high-impact portraits.

Additional Location Considerations

While I’ve shared a list of recommended locations, it’s important to know that these are suggestions of some popular locations. I love getting creative with my couples and am always open to exploring new ideas. Whether it's a stroll through Chicago’s charming tree-lined neighborhoods, capturing intimate moments at their apartment, or at their favorite bar, the possibilities are endless. Ultimately, I want your engagement session to reflect who you are as a couple, and I’m here to help make that vision come to life!

Outfit Planning

As a light and airy photographer, I advise my couples to stick to neutral palettes (think whites, light blues, pastels for her and whites, tans, greys, black or navy for him). The key is to coordinate with each other without being too matchy-matchy.

Another consideration is the type of fabric you wear. For instance, loose, flowy dresses and skirts gives us room to play in posing and can create an ethereal, romantic look. Alternatively, something more form fitting can feel chic and modern.

For the ultimate timeless look, I recommend avoiding anything overly trendy so when you look back at your photos 20 years from now, it’s not the first thing you notice. In a similar spirit, sticking to solid colors eliminates distractions (however, I have had couples choose subtle paterns, as pictured above, that were fantastic!). One thing to definitely avoid is fine/small, repeating patterns, which can produce a distortion effect in digital photography known as morié.

Because this is a special occation, I always recommend dressing up, but ultimately you should choose outfits that make you feel special, yet like yourselves. If you plan on doing an outfit change during your session, you could use the second look as something more fun and casual to create some variety in your gallery. Or you could go with two dressier outfits, you do you!

Lastly, as you are selecting your outfits and are in need of a second opinion, you can always send me photos!

Session Preparation & Additional Considerations

• Dogs: If you're bringing your dog to the session, I recommend taking them on a long walk earlier in the day to help burn off some energy so they’re more relaxed for the session. Be sure to bring their favorite squeaky toy and plenty of treats to grab their attention when needed! I also suggest bringing along a trusted family member or friend to help manage your pet while we focus on photos of just the two of you.
• Ring Cleaning: To ensure your ring looks its best in photos, give it a good cleaning before the session—we’ll be getting some beautiful “bling” shots! Inspiration Images: If you have any must-have photos or inspiration shots in mind, please send them to me at least a week before your session. This gives me plenty of time to plan and make sure we capture everything you’re hoping for.
• Shoes: Engagement sessions often involve quite a bit of walking, so I recommend bringing a comfortable pair of shoes for walking between shots. This is especially helpful for larger locations like Museum Campus, where we’ll be covering a lot of ground!
• Parking: Make sure to give yourselves plenty of time to find parking! Creating a parking plan ahead of time will help eliminate stress and allow us to focus on enjoying the session.
• Outfit Changes: If you’re planning on doing an outfit change during the session, please let me know ahead of time so I can plan shots accordingly. This also allows us to coordinate when and where the change will take place. For locations without nearby restrooms, I bring a pop-up tent to make the process more comfortable and convenient.
• Personal Items: These can be a wonderful way to add a unique touch to your session and make it even more meaningful. Whether it’s a favorite beverage, a boquet of flowers, a cozy blanket, a keepsake or something else that’s significant to you as a couple, feel free to bring it along! These little details can help tell your story and make your photos even more personal and memorable.

I hope this guide helps you feel more prepared and excited for your engagement session! Remember, this time is all about celebrating your love and the unique connection you share. Whether we’re capturing intimate moments in a quiet garden or enjoying the vibrant city backdrop, my goal is to create photos that feel just as special and authentic as your relationship. If you have any questions or ideas, feel free to reach out—I can’t wait to create beautiful memories with you!