Oh Chicago! The one-of-a-kind city home of summer street fests, deep-dish pizza, and a plethora of stunning and iconic locations is perfect for your engagement session. Whether you’re a Chicago native or this is your first time in the Windy City there are a TON of details to consider when planning out your engagement photos in the city.
From locations, time of day, season, permits, what to wear, and more we’re covering it all. So strap in, grab yourself a nice cup of coffee, and get ready to know everything you need to know to get the best engagement photos in Chicago!
Believe it or not, you CAN have your engagement photos taken during any time of the year in Chicago. I know you might be concerned about having your session in the winter being in the Midwest, but trust me there are some huge benefits to having a winter session here in the Windy City. Ultimately it comes down to the style and vibe you want for your photos and the experience you’re looking to have for your session. This is something you and your partner will have to decide on together and be on the same page about, so read through the benefits of the seasons below to get an idea as to what would work best for you!
For a full-on magical feel to the city of Chicago look to the springtime for your engagement photos in the city! After the long cold winter months, the city and everyone in it are just about ready to burst. Once the weather starts to warm up and the greenery of the city starts to bloom Chicago starts to really come alive. People are out and about enjoying themselves, businesses start to open their patios, and the city’s nature areas start to bloom bringing such a feeling of life and beauty to your photos.
The most popular time in the city, and for good reason, is the summertime. All the blooming of the greenery and adventurous spirit of the Chicago residents are in full swing come summer. From the seemingly weekly street fests and constantly bustling restaurant patios, to the parks and beaches where residents flock to enjoy themselves and take in their surroundings. This is Chicago at its liveliest! If you love the vibe and feel of a bustling city, and the warmth of the summer, and aren’t afraid to have your engagement photos around some potential onlookers, the summer of Chicago is for you.
While Chicago is a huge and vast city that doesn’t mean that it doesn’t take advantage of the fall time colors. The parks of the city become stunningly beautiful in the fall with the change of colors, and the colder temperatures allow for some fun options for your outfits. It is worth noting that Chicago being in the Midwest can lead to some unexpected and abnormally cold temps for the fall, so if you do plan to have your engagement photos in this season bring some layers and keep an eye on the forecast!
I know what you’re thinking, “the Windy City in the winter is going to be FREEZING, why would I want my engagement session then?” Let me tell you, while it is true that Chicago winters are cold, they also make for some of the most beautiful and scenic opportunities for engagement photos. The magic of a fresh snowfall in the city is something you have to see to get the full experience of its beauty. Capturing that look and feel for your session is SO much fun and instantly makes braving the cold worth it. Plus we can always dip into a bar or restaurant for some photos and a break from the cold making the session even more fun and more of an adventure.
Knowing what season you’re going to have your engagement photos taken in Chicago is only part of the process, you also have to decide on the right time of day for your session! Similar to season this one depends highly on your preference and what style of lighting you want for your photos. The other factor that you have to consider though is the specific location of your session as some are better suited for different times of the day. We’ll go over the different times of day next and how to work with each followed by some of my FAV locations in the city and which times are best for them!
Let’s talk about your session at the start of the day, when the sun is rising over the waters of Lake Michigan creating an epic yet dreamy look for your Chicago engagement photos. Sunrise sessions are great for many reasons. The obvious one is the sheer beauty that comes along with sunrise in Chicago, but the other is the lack of crowds. How many people are around during your session is something we’ll cover later, but if you’re keen on avoiding onlookers an early morning sunrise session is the best bet for you.
It comes as no surprise with just how massive Chicago is that you’re going to come across a ton of other people depending on the time of day and season. Crowds during an engagement session aren’t necessarily a bad thing, but they are something you have to be aware of and prepare for. It’s up to you whether you want to have as few people present for your engagement photos in Chicago or if you’re fine with onlookers being present at the moment. Let’s take a look at how to make each option work and go over what makes each special in their own way!
Giving a similar vibe and feel to the sunrise session, but with the sun casting its golden rays through the towering buildings of Chicago, sunset is another beautiful time to take your engagement photos. Depending on your location you can get some INSANE light coming through and reflecting off the buildings of Chicago giving you an amazing backdrop for your photos. It is important to note that with a sunset session, it’s much more likely for other people to be around during your session, depending on your location. Especially on a warm day, EVERYONE is going to want to be out and about in the city!
Another important note before we go on is that Sunrise and Sunset offer the best possible lighting for your engagement photos. Midday and nighttime sessions can be great, but they offer their own set of challenges which we’ll cover. With sunrise and sunset sessions though the light from the sun isn’t too harsh yet and it makes capturing some really beautiful images of you and your love so much simpler.
A midday session is when the light is at its most intense. This means that we’ll have to work around this in order for your photos to not be washed out with all the bright light. Luckily this is very doable in Chicago, so if you were hoping for a midday session for your engagement photos you’re in luck! We can use the abundance of buildings in Chicago as shade spots for your session, and we can even go in some of the buildings of the city for some indoor photos. Check out this Engagement Session in Lincoln Park for Inspiration!
Last but not least we have night time sessions! Night time in Chicago is honestly jaw dropping with all of the buildings lit up and the city hustling and bustling even late into the night. I LOVE embracing Chicago’s nightlife in an engagement session, and shooting after dark in a city like Chicago is definitely a fun way to go if that’s the vibe that you’re going for!
Your engagement session often can feel a little overwhelming. It’s often one of, if not the very first time the two of you will be having professional photos taken of yourselves with a focus on your love for one another and your relationship. This understandably leads to feelings of anxiousness and nervousness, which is why it’s sometimes a good idea to avoid times and places with tons of people present. Even with the size of Chicago this is still possible to do and can lead to a much more intimate feel and experience for your engagement photos. If you plan on avoiding the crowds of Chicago, plan to have your session at a less popular location(s), during sunrise or off hours of that location, or have your session on a weekday.
On the flipside, having your engagement session embracing the crowds of Chicago can actually be a ton of fun in its own right! The hustle and bustle of the city is something Chicago is known for and is an aspect that can be a ton of fun to capture in your engagement photos. Whether it’s at North Ave Beach during sunset or heading into downtown Chicago for some photos in the center of the city, you can create some incredible experiences even with crowds present. Having people around and watching during your session can actually act as a confidence boost to some, people are ALWAYS cheering on my couples during their engagement sessions which is such a fun part of engagement photos in Chicago.
To give you a little location inspiration for your engagement photos in Chicago let’s take a look at 11 of my favorite spots in the city!
Chicago is known for its diverse neighborhoods, each with its unique charm and character. You can capture the essence of the city by choosing a neighborhood that holds special meaning to you and your relationship. Whether it's the vibrant street art in Pilsen, the historic buildings in Lincoln Park, or the bustling atmosphere of Wicker Park, the neighborhoods of Chicago offer unique backdrops for memorable engagement photos. The neighborhoods are really great for sessions at any time of day!
For an iconic and romantic spot for your engagement photos, North Avenue Beach is a hard location to beat in the city of Chicago! With incredible views of the city and Lake Michigan combined with the sandy shores of the beach and the walking path along the lake there is SO much to work with for your session! If you’re thinking North Avenue Beach might be the place for you, check out my full guide to engagement sessions at North Avenue Beach! I prefer engagement sessions at North Avenue Beach during sunrise or sunset.
The Lincoln Park Boardwalk runs along the shores of North Pond and provides a scenic setting with stunning views of the Chicago skyline. The serene atmosphere and lush greenery make it an ideal spot for a romantic spot for engagement photos in nature while still being in Chicago. It’s important to note that a photography permit through the Lincoln Park Conservatory is required.
Choosing a favorite Chicago bar can add a personal touch to your engagement photos. It allows you to showcase their favorite hangout spot in the city or a place with sentimental value. Additionally, capturing candid moments while enjoying drinks or playing games can create a relaxed and intimate vibe for your photos. Really any time of day works for having a session at your favorite bar or restaurant, there are some bars though that will have you come in before they open to ensure our session doesn't interrupt patrons experiences.
Chicago's beaches, such as Oak Street Beach or Montrose Beach, offer a unique setting with the lakefront as the backdrop. The sandy shores, crashing waves, and the city skyline create a perfect blend of natural beauty and urban elements for stunning engagement photos in Chicago. Because of harsh lighting conditions with the sun so high and the water reflecting, the hours around sunrise and sunset are best for sessions at Chicago's beaches.
Museum Campus is a picturesque location in Chicago that includes iconic attractions like the Field Museum, Shedd Aquarium, and Adler Planetarium. The blend of lush greenery, architectural marvels, and lake views provide varied and diverse options for capturing beautiful engagement photos.
Chicago's Riverwalk along the Chicago River offers a charming and vibrant urban backdrop for your engagement photos. The picturesque bridges, scenic river views, and the lively atmosphere of restaurants and cafes make it a popular choice for engagement sessions with that trademark Windy City feel to them!
The Bird Sanctuary at Montrose Point is a true hidden gem of Chicago with an incredibly peaceful and naturally beautiful environment. It's an excellent spot for nature lovers looking to have a unique engagement session with serene surroundings as well as a gorgeous view of the Chicago skyline. Sunrise and sunset are best for this beautiful lake side location.
The Art Institute of Chicago is one of the most renowned art museums in the world. Its iconic architecture and stunning collection of art offer an elegant and sophisticated backdrop for engagement photos in Chicago. It’s easily one of my favorite locations in the city for photography sessions and the fact that no permit is required just makes it that much better!
Chicago's Chinatown offers a vibrant and culturally rich atmosphere. The colorful buildings, traditional Chinese architecture, and decorative elements create a unique and visually appealing setting for engagement photos in Chicago with some of the most distinct characters you’ll find in a Chicago neighborhood.
Salvage One is a vintage event space with an eclectic collection of salvaged architectural elements and antiques. It's a popular choice for couples seeking a rustic and unconventional backdrop for their engagement photos in Chicago. The unique and artistic ambiance of the venue can add a touch of next level vintage charm to the photos. It’s important to note that you’ll have to call ahead to book and there is a fee to have your session here, but it is VERY much worth it!
Chicago is a city filled to the BRIM with incredible locations, big and small, that are perfect for engagement photos. It would be literally impossible to list each and every one off here for you. In case none of the previous locations really do it for you, or you want something more personal, here are a few more general ideas to get your brain flowing! Navy Pier, West Loop, Little Italy, one of the street fests. Coffee shops can be great as they offer a cozy and unique atmosphere. We can go to your favorite one or try one you’ve always been wanting to. Your favorite restaurant is also an awesome option that can give your album a TON of personality. For inspiration check out this engagement session at the Alderman!
Lastly, your favorite stores you like to frequent can be a ton of fun too. Whether it’s a record store, thrift shop, or somewhere else the two of you love to go, adding this bit of personality to your session is always a fun option!
Chicago being as dense and populated as it means that many locations will have different requirements when it comes to photography permits. When booking with me I’ll not only be able to help guide you through choosing a location in Chicago for your engagement photos, but also help get any of the necessary permits filled out. While not every location requires a photography permit there are a lot that do so this research is crucial.
One other thing to note is if you plan to have your engagement session at your favorite bar or restaurant you'll have to call ahead of time to plan out the session. Most locations will require you to come during off hours to keep things simple both for them and for you. I also recommend that my couples reach out to these locations instead of me as the restaurant or bar knows you or at least appreciates you as their customer. They'll be much more likely to let us use the space if they hear from the people that LOVE their space rather than the random photographer wanting to borrow it for a photoshoot.
There are a lot of different factors you’ll want to consider when planning out what to wear for your engagement photos in Chicago! From the vibe of the photos you want, the weather you’ll be dealing with, complimenting your partner, and more. Let’s go over all the different aspects you’ll want to consider before deciding on your outfits!
First and foremost you’ll want to decide what kind of vibe you want for your photos as your outfit will play a HUGE part in it. Do you want to feel classy and sophisticated? Laid back and relaxed? Comfy and Cozy? Figure out what feel you want for your engagement photos in Chicago so that you can start to plan your outfits around that feeling. You’ll want to keep your season, time of day, and location in mind as well to make sure everything fits together. If you’re looking to wear your favorite cozy sweaters, a summer beach session isn’t really going to work!
This one is SUPER important! It doesn’t matter how good your outfit looks, if you’re uncomfortable in it it is going to show in your photos. You won’t enjoy your session anywhere close to as much as you should, and you’ll be paying the price for days to come! We’re going to be walking and moving around a good bit during your session, so comfort is key. Break your shoes in if they’re new, wear your clothes to make sure they fit and are comfortable, and wear your entire outfit at once to make sure you really like the look of it all together. I can’t stress enough just how much being comfortable during your engagement session in Chicago will improve your photos!
For my engagement sessions, I will typically have my couples choose 2 separate outfits. I do this for a number of reasons, the two biggest being that it gives your album a greater sense of variety and it lets you showcase more of yourself and your style! Be sure that when you are choosing both outfits for your engagement photos in Chicago you follow the previous steps to make sure both outfits fit your style, match the weather we’ll have, are comfortable to wear, and compliment your partner’s outfits.
When it comes to weather in Chicago you really have to be ready for anything, and I MEAN anything! Being in the Midwest means that the weather in Chicago can change at the drop of a hat. Snow can happen in the fall and spring, it can be sunny and 50 degrees in the winter, or raining cats and dogs when the forecast said it would be clear a couple of days ago. Keeping an eye on the forecast all the way up to the time of your Chicago engagement photos is key in making sure you’re prepared for the day. Plan your outfits around what the weather is typically like for your season, then plan out some layers to either add or remove in case the temperatures vary!
Though matching outfits can be cute and campy, it's not the 90s anymore, so choosing outfits that complement each other over matching is typically the way to go! Matching outfits can blur your bodies together in images, and end up actually being distracting for the viewer. Complimentary outfits are outfits that have a similar color palette, so the clothing looks good together, but, still has enough of a difference so that the viewers' eyes can still see a distinct difference between your body shapes.
Most couples like to have their engagement session during the same season of the year that their wedding would be in, but really as far out as you would like! Many couples use their engagement photos for their save-the-dates, and by industry standards, you would want to have your save-the-dates out within 8-12 months of your wedding day. With a couple of weeks turnaround time from your session, having your session about a year out from your wedding day is a great time to take your engagement photos!
Why SHOULDN’T you have your engagement photos taken in Chicago? Seriously though there are SO many reasons to have your engagement session in Chicago! Some we’ve already covered already like the incredible locations and the different experiences the seasons provide. Outside of that though Chicago is a one-of-a-kind city with so much personality and charm to it. From its people to the food to the distinct neighborhoods of the city, to its bars and nightlife, it is literally bursting with character! This means that not only are you set to have a next-level engagement session, but you can also make a weekend of your trip and really experience all there is to love about Chicago!
Chicago is a city built on commuters, and while the traffic can be a bit of a headache at times, there is a wide array of parking options for each location throughout the city. There are parking garages all throughout the city that you can use, though those are typically a little more pricey. The app SpotHero is a great alternative that gives you access to tons of parking spots all throughout the city, usually for lower rates than typical parking garages. Lastly, street parking is also available but sometimes hard to come by. Whether it’s free or pay by the hour, street parking is usually the first to be taken up, but if you can snag a spot it’s usually the closest option to your location!
Having two separate outfits for your Chicago engagement photos means that you’ll have to change between the two at one point during our session. This can be easier at some locations than others. For instance, at locations like a coffee shop, restaurant, or other places with a public restroom it can be very simple. Changing in your car is another option although somewhat less private and a little cramped. That’s why for my engagement sessions I like to bring a changing tent for my clients to use for ease of mind!