Congratulations on your engagement, this is SUCH an exciting time in your lives together!🤩 Your engagement marks the start of this next chapter of your lives together, which is why celebrating it with an engagement session is so important. Your relationship is unique. It’s always changing and always growing in ways you can’t even imagine until they happen. An engagement session is like a time capsule, a snapshot of what your relationship looks like now so that you can look back on the photos and reminisce on them for years and YEARS to come!! With how meaningful this moment in your lives is it’s only fitting that a lot of planning goes into making your engagement session in Chicago the best it can be. That’s why today we’re looking at my top 10 tips to plan your engagement session, let’s get into them!

A couple holding hands with one another smile at each other during their engagement session in Chicago with skyscrapers and the Chicago river behind them

1. Have Fun With It

For most couples their engagement session is going to be their very first time in front of the camera together. That can be a really stressful feeling to some, especially as there’s this person you’ve never met before taking photos of you and encouraging you to be loving on one another! Trust me though that these feelings are totally normal and something that I am very experienced at helping my couples work through. I’ll be guiding you through the session, giving you prompts to help you loosen up, and of course telling you where to put your hands if need be! And since we’re breaking the ice with this session, once we get to your wedding we’ll already feel like best friends so you’re ready to have the time of your LIFE in front of the camera on your wedding day!

What I want you to focus on for your Chicago engagement session is to simply enjoy yourselves and the love we’re here to celebrate! Focus on each other, how happy you are to be starting this new chapter with one another, how incredible it is that you two found one another, and how wonderful it’s going to be to spend the rest of your lives together.❤️ With that in mind the rest will take care of itself, with my help of course!

During an engagement session in Chicago a couple hold hands and smile at one another while walking on the roof of a parking garage with the city skyline behind them

2. Choose a Location

You seriously could NOT be in a better city than Chicago for your engagement session!! The Windy City is full of unique and incredible locations for your photos.✨ Whether you’re looking to have your photos taken somewhere iconic like the Tribune Tower or North Avenue Beach, or something more personal like your favorite bar or record store, there are so many different options in the city to choose from! When deciding on a location, talk things through with your partner. What do you both envision your photos to look like? Are you outdoors with the Chicago skyline behind you? Do you want something personal and intimate doing something the two of you love? Whatever it is, make sure you’re both on the same page when deciding on the location for your day! And if you need some recommendations to help you decide, fear not because I have TONS!!

A couple embrace one another and close their eyes as they're about to kiss while standing in a park in the fall with orange leaves in the trees and on the ground behind them

3. Permits and Permissions

With your engagement session taking place in Chicago there are going to likely be some permits and permissions that will have to be addressed for your session! While not a given for EVERY location, there are a lot in the city that require them! First off for permits most locations under the Chicago Park District umbrella like Lincoln Park Zoo are going to require photography permits. You’ll have to purchase these beforehand which is a pretty straightforward process, but a MUST in order to avoid any fines. If you’re wondering whether the location you have in mind requires a permit and aren’t sure where to look I’d be more than happy to help once we’re booked and planning!

Next we have permissions which apply to most restaurants, bars, and some stores that you may want to take photos in. Each business is different as are their views on photos in their establishment so you’ll want to call well in advance to the date of your session for their permission. I recommend that you reach out to the business rather than me since you are the customer and the one that loves their business SO much that you want to have your session in their space! To them I’m just a random photographer that they really could care less about. It’s important to note that some businesses will allow you to use their space but only on off hours, so before a bar opens to the public for example. Keep this in mind as we plan the other location(s) of your session!

During an engagement session in Chicago a woman looks back at a man and smiles while he smiles at her and holds her hand while they walk along a beach in front of the Chicago skyline

4. Make it About YOU

Speaking of making your Chicago engagement session personal, one thing I LOVE to recommend my couples is to find a way to make their session personal to them!! Try to think of an activity that you both love to do together that we can include as part of your engagement session. Whether it’s getting ice cream together, going thrifting at a shop near your house, or getting coffee together in the morning, some sort of activity that we can photograph can really take your engagement session to the next level! It helps you to loosen up as you’re doing something together that you love and that lets you focus on something aside from the camera. Not only that though, but it also makes your album feel SO personal as well as gives it more variety!

A couple standing in front of a median in the streets of downtown Chicago kiss one another while cars drive on either side of them during their engagement session

5. Try Out Your Makeup

An engagement session in Chicago is about the best possible chance you can get to do a trial run of your wedding makeup! Not only do you get to really see what your makeup is going to look like on your big day, but you’ll also get to see what it looks like in photographs. Oh and don’t forget the fact that you get to feel confident and look STUNNING for your photos!!

If you aren’t able to have your makeup artist do your makeup for your session, it’s no big deal. I still recommend you get your makeup done somewhere like Ulta or Sephora, but do something similar to what you normally have done there. You don’t want to try something completely new with an artist you’ve never worked with before! And if you’re feeling like treating yourself with a manicure for your engagement session, GO FOR IT! You should want to show off that beautiful new ring after all!!😍

3 photos side by side of a couple on a beach, the left is of them sitting in the sand and cuddling, the middle is of them holding hands while the woman smiles at the camera, the right is of the man lifting the woman in the air

6. What to Wear

I’ve said it before, and I’ll say it again, choose clothes that you not only look good in but FEEL good in as well. You should be equal parts stylish and comfortable so that you can really enjoy yourself during your engagement session! For my couples I’ll usually have them choose two separate outfits, one more casual one to start in and then something more formal to change into once we’re a little warmed up with one another. This lets you showcase multiple facets of your style to give your Chicago engagement session photos some more variety! With my warmer style of photography neutral colors and more earthy tones are my personal favorites. That being said, if we’re exploring the streets of Chicago then bolder pops of color can look incredible!

Make sure you and your partner’s outfits compliment one another. Clashing colors draw the focus away from you both which is not what we want, and matching can sometimes make it look like you morph into one mega person, also not what we want! For a more in depth style breakdown I actually have an engagement session style guide you can check out. And of course I am ALWAYS down to help my couples with any outfit questions they might have!!

2 photos side by side of a couple, the left is of a woman smiling at a camera while embracing a man who is looking down towards her, in the right photo they are both smiling at the camera

7. Break in Your Shoes

Going off of what to wear, one thing a lot of couples tend to overlook is their footwear for their session! Most people will buy new shoes and then maybe wear them once before their session. This always ends in disaster as their feet are SO sore the next day! If you have your trusty pair of shoes that you plan to wear for your session then you’re golden and have no need to worry. For those of you that are getting a fresh new pair though I cannot stress enough how you need to actually break them in before your session!! We’re going to be doing a fair bit of walking during your Chicago engagement session, I want you to be comfortable for it. Your feet and your photos will thank you for it!

During an engagement session in Chicago a man and woman hold hands while looking at one another and standing side by side in a parking garage

A woman smiles as a man hugs and kisses her from behind while on a sidewalk in Chicago during their engagement session

8. When to Have Your Chicago Engagement Session

Generally speaking it’s always a good idea to have your engagement session around 10 to 12 months out from your wedding date. Having your engagement session during the same season of your wedding is something I’m a HUGE fan of, especially if you plan on displaying your engagement photos on the day of your wedding. It makes it all feel so cohesive and well put together, but again that’s just my opinion!

If you’re looking to have your engagement session during a different season than your wedding you’re in luck, as EVERY season in Chicago is beautiful in its own right. Summer vibes in Chicago are immaculate, the fall is gorgeous especially when the leaves are changing colors, winter turns the city into a snow covered wonderland, and spring feels so freeing as the city comes back to life after the winter! One thing to keep in mind though as you plan out the date for your engagement session are your save the dates. If you do plan to use your engagement photos for your save the dates, those are usually sent out 6 to 8 months before the wedding, so be sure to give yourselves enough time to make it happen!

A man smiles at a woman as she holds his arm and smiles back while they stand atop a parking garage with the Chicago skyline behind them during their engagement session

9. Plan for the Weather

The week leading up to your engagement session I’m going to be watching the weather like a hawk, and you should be too! If temperatures are going to be cooler than expected we’ll need to plan out some layers. Is there supposed to be rain the day before our session? We may need to plan your footwear around the possibility of puddles or mud in some of Chicago’s parks. Remember, with Chicago being a part of the Midwest the weather can change at the drop of a hat, so always be on the lookout before your engagement session so you aren’t caught off guard!!

2 photos of a couple side by side, the left is of a man hugging a woman from behind while they smile at one another in front of the Chicago river, the right photo is of them in a similar pose while in front of a Chicago building

10. Make a Day of it!

Last and definitely not least on my guide to your engagement session in Chicago is to make a day out of your engagement session! Take the day off work if possible, or if not make sure that nothing else is on your schedules for after your session so that you can spend some quality time with one another. Whether it’s a date night out at your favorite restaurant, a drink at your favorite bar, or a stop at your favorite brewery, make the day about you and your engagement! I mean, you’re both already dressed up, and you’ve been loving on one another for the entirety of the session, you should be MORE than ready for a nice date night out with just the two of you!!❤️

A man smiles while sitting on a beach with a woman kneeling behind him and hugging him with Lake Michigan behind them

With this guide in hand you should be WELL on your way to planning out the perfect Chicago engagement session to celebrate and capture this next chapter in your adventure together!! If you’re looking for more wedding and engagement planning tips be sure to check out my blog, and if you’re ready to book me for your wedding, send me an inquiry through my contact page!