Chicago Engagement Photographer

Hi! 🙋‍♀️ Here at Flytographer, we easily connect people with trusted photographers for fun photo shoots and have captured over three million memories worldwide. 🌎 The magic of Flytographer is both the experience and the photos. Explore the city with a fun, talented photographer and get wall-worthy photos to relive your trip, forever! 🖼 Today we’re going a step further than “just” wall-worthy and diving into engagement-announcement-worthy! Get excited, Chicago engagement photography tips, tricks and other photo-related details coming your way in 3, 2, 1… 🚦

TLDR

• Engagement photo locations in Chicago — sharing our top three recommendations for engagement photo locations in Chicago, showing off you and that iconic skyline.
• What to wear for your Chicago engagement — everyone wants to look beautiful for their engagement shoot, but Chicago weather isn’t known for its subtlety… we’ve got ideas that’ll make sure you’re covered (pun intended)!
• Choosing your photographer — having a connection to your photographer isn’t a requisite, but it is a fun bonus when you find commonalities, and/or their photos speak to you in a special kind of way.
• Chicago engagement posing tips — being in front of the camera can feel a little (or a lot) awkward, but that doesn’t mean that will translate in your photos. 
• Tips for your surprise proposal — if you’re here because you’re hoping to be engaged, but aren’t yet, we’re talking to you, too! Sharing some great proposal tips here in the Windy City.

Photo: Amanda in Chicago for Flytographer. Jared and partner capture memories in Chicago with a proposal photoshoot along the Chicago Riverwalk.

Engagement photo locations in Chicago

The third 3️⃣ most populous city in the United States, Chicago, Illinois, has one of America’s most beautiful cityscapes and is an ideal backdrop for engagement photos! 📸 Having an engagement session in Chicago is great for a variety of reasons, and we can’t wait to share with you some of our favourite locations to make your Chicago shoot super successful and extremely pretty!

Top tip: When choosing the perfect engagement location, consider your partner’s preferences and personal details to make the moment truly special and tailored to them. ❤️

Photo: Flytographer in Chicago. Robby and partner capture memories in Chicago with a proposal photoshoot in Lincoln Park.

1. Chicago Riverwalk

Perhaps the most iconic activity in downtown Chicago, the Chicago Riverwalk is a pedestrian pathway 🚶‍♀️ with water and city views, connecting you to some of the best restaurants and eateries. With its passing bridges, greenspaces, and excellent people-watching areas, we love the Chicago Riverwalk. Engagement photos here in Chicago will give you gorgeous, dramatic and unique images with your love no matter the season! 🤗 

Photo: Amanda in Chicago for Flytographer. Jas and partner capture memories in Chicago with a proposal photoshoot along the Chicago Riverwalk.

2. Lincoln Park

Lincoln Park is a neighbourhood on Chicago’s North Side. The beautiful grounds are home to sculptures and manicured gardens, all while featuring jaw-dropping architectural details 😍 with hints of Chicago’s beautiful skyline in the background (namely the iconic Willis—formerly Sears—Tower). Be sure to check out this route for something special, romantic and a bit different. 👍

Photo: Flytographer in Chicago. Mark and partner capture memories in Chicago with a proposal photoshoot in Lincoln Park.

3. North Avenue Beach

North Avenue Beach has epic views of the Chicago city skyline 🏙 along the boardwalk—a favourite for engagement (and proposal) shoots. North Avenue Beach means landing photos where the water meets the sky, and the photos here are out of this world! 👌

Photo: Francisco in Chicago for Flytographer. Cat and partner capture memories in Chicago with a proposal photoshoot along North Avenue Beach.

What to wear for your Chicago engagement

Ok! Now that we’ve shared our favourite engagement photography locations, let’s talk clothes in Chicagoland. 💃 Everyone wants to look beautiful for their engagement shoot, but Chicago weather isn’t known for being subtle and mild. 😉 We recommend you plan some different options as the weather here can be hit-or-miss! Bringing layers to your shoot is a good idea—removing a layer in the summer or adding one (or more 😜) in the fall and winter months can be helpful. (Temperatures peak in July with highs around 28° C/80° F and drop in January to -6° C/20° F. 🥶)

Want more specific inspo about what to wear? How about summery casual? Cute and cool! This classy peacoat below is a perfect solution when you want to be warm and look simultaneously chic, fitting right in here in the Windy City. Do you have visions of keeping things elegant? Dress up! This classy vibe below is a win-win for your engagement shoot. In our photography experience, we recommend going with something that helps you both look and feel good—that’s the key to having fun and pulling off amazing photos! 💞 Looking for more engagement photo outfit ideas? Your local Chicago Flytographer will be able to provide you with some tips & recommendations!

Photo: Amanda in Chicago for Flytographer. Jenna and partner capture memories in Chicago with a couples photoshoot along North Avenue Beach.

Photo: Flytographer in Chicago. Morgan and partner capture memories in Chicago with a couples photoshoot along the Chicago Riverwalk.

Choosing your photographer

While we’re on the topic of shopping (of sorts)—let’s talk about choosing the right Chicago engagement photographer for your shoot! 📷 We have a stellar team of pros in Chicago—be sure to check out their profiles, photos and a bit about each of them. Connecting with your photographer isn’t a requirement, but it is a fun bonus when you either have something in common, and/or their photos speak to you in a special kind of way. ⭐️

Photo: Danielle in Chicago for Flytographer. Justin and partner capture memories in Chicago with an engagement photoshoot along the Chicago Riverwalk.

Chicago Engagement Posing Tips

Ok, you’ve selected your location/route, your photographer, and you know what to wear. Wahoo! It’s picture time. Being in front of the camera can feel a little awkward, 😬 but that doesn’t mean awkwardness will translate in your photos! Lean into your partner, and trust that professional Chicago engagement photographer behind the camera. Want some tips for prep to put your mind at ease? Your wish is our command!

• Holding hands & walking 👫 is a tried-and-true, classic “pose” that gives your antsy body motion. You can change pace, face toward or away from the camera and show off your full body looks alongside those great Chicago backgrounds.
• The dip kiss 💋 is romantic and playful. This is a fun one to practice in advance, so you feel like you’ve got some synchronization and relaxation in your graceful elegance. Hot stuff! ❤️‍🔥
• We couldn’t talk about your engagement love story without this portrait photography staple: show off that ring! 💍 You’ll want to rest your left hand with that beautiful ring against your partner’s arm, chest or back, and let your photographer capture your shiny new jewel!

Photo: Flytographer in Chicago. Zena and partner capture memories in Chicago with a couples photoshoot along the Chicago Riverwalk.

Photo: Flytographer in Chicago. Kelsie and partner capture memories in Chicago with an anniversary photoshoot from the Planetarium to the Buckingham Fountain.

Photo: Amanda in Chicago for Flytographer. Price and partner capture memories in Chicago with a couples photoshoot in River Point Park.

Tips for your surprise proposal

If you’re here because you’re hoping to be engaged, but aren’t yet… we’re talking to you, too! Surprise proposals in Chicago are incredible, wonderful and soooooo romantic! If you’re looking for the best photographer to capture the job, you’ve come to the right place. Flytographer’s Chicago engagement photographers can’t wait to make your dream proposal happen. 🙌

Need some extra prep? We’ve got plenty of helpful tips on mistakes to avoid when you propose! You’ve got this! 😎

Photo: Flytographer in Chicago. Jack and partner capture memories in Chicago with a proposal photoshoot on North Avenue Beach.

Capturing Engagement Memories in Chicago

Photo sessions are our love language here at Flytographer, and we absolutely adore capturing engagement photos prior to your big day 💒 (#weddingday)! Although that special day can’t be beaten, engagement photos are an ideal way to announce your upcoming nuptials with family and friends, not to mention pretty perfect for wedding announcements. 💌 Whether you’re from Chicago or visiting for the first time (or fifth), taking engagement photos in the Windy City is magical. ❣️

See you soon! 👋