Chicago is a city unlike any other, which is why so many couples choose to celebrate their engagement here in the Windy City. Whether you two met here, you love to visit Chicago, or you’ve always wanted to check it out, this city holds something special for everyone. This magic, and the abundance of it, really shines when I consider how many incredible locations and settings I’ve documented during my engagement sessions here. Thinking about this is what’s led to this article, and I’m so excited to share with you some of my favorite ideas for documentary style engagement photos throughout Chicago!
Deciding Where to Have Your Engagement Photos Taken in Chicago
A quick point I want to make before we really dig in here is how to decide where to have your engagement photos taken in Chicago. I’m not exaggerating when I say there are endless options here, the 20 below just barely scratch the surface of it all! Knowing this, something I always recommend my couples do is to try and make their session unique to them. Whether that’s through a sentimental location, an activity you both love to do, or something you’ve always wanted to try together, making your session true to you is the best way to make your photos feel like, well, you!
As you read through the options below, consider how they fit into your life and your love story. Even if none of the options on this list are what you’re looking for, you may still find some inspiration for the engagement session that fits you best.
1. One of Chicago’s Bars or Breweries
Chicago is a city bursting with charm, and one of the most apparent displays of this is through our unique bars and breweries. From classic dive bars like the Old Town Ale House, to spaces like Trivoli Tavern that exude vintage elegance, Chicago has something for everyone. Another personal favorite of mine is Maria’s Packaged Goods and Community Bar, though there are hundreds of options in the city, and that doesn’t even take into account the different breweries like off color, Hop Butcher, and so many more. Whether you both love a nice cold beer, or just enjoy the ambiance of the setting, Chicago’s many bars and breweries make for fantastic options for engagement photos.
A Quick Note: I recommend calling ahead prior to your session to make sure the business of your choice is ok with you having your photos taken there. Sometimes they’ll even allow you to come in early before any other patrons show up. It does help to hear from a couple that loves their space SO much that they want to include it in their engagement photos rather than a photographer who they feel just wants it as a backdrop though!
2. A Thrift or Record Store
Another set of businesses that really showcase the unique and varied style of Chicago are the thrift stores and record stores! If you live for the thrift, or both love to sort through record crates looking for your favorite albums, this is such a fun way to make your engagement photos in Chicago unique to you. Iconic spots like the Reckless Records in Wicker Park have been providing a stellar space for vinyl heads and fans of music in general for years. For vintage lovers, while you do need a reservation for photos here, the wonderful Salvage One is one of THE coolest spots in the city for photos.
There are tons of other options to choose from throughout the city for both record stores and thrift stores, so be sure to look around to find the one that fits your style best! Also, much like above, I recommend reaching out to the store prior to your session to make sure having your photos taken is cool with them.
3. Your Favorite Bookstore
For the avid readers out there, there’s no better way to celebrate your engagement with photos at one of the many incredible book stores of Chicago. Take Lauren and Kevin’s engagement session at Volumes Bookcafe for instance. The setting and the activity itself both lend themselves SO well to the flow of an engagement session, and you might just go home with your new favorite book that’ll now always remind you of this time! Another favorite location of mine in the city is Open Books Pilsen, but as you might have guessed there are a ton fabulous bookstores throughout Chicago to choose from.
4. With the CTA Trains
Whether you currently live here, or you’ve spent a good amount of time in Chicago, chances are you have some memories of being on the CTA Trains together. Heading home from date nights, going out to meet up with friends, using them to get home after a concert, they’re an integral background part of your lives and in turn your love story. This makes them an excellent candidate for inclusion into your engagement photos as they directly tie into your story here in Chicago, plus their abundance makes it incredibly simple to include into part of the session!
5. At the Chicago Cultural Center
One of my go to indoor locations for engagement photos, the Chicago Cultural Center is an iconic space of the Windy City. Found just across from Millennium Park on Michigan Avenue, the Cultural Center is a great option for photos for a number of reasons. First is its location, which allows you to easily get to many other phenomenal spots in Chicago with ease for your session. The center also has no admission fee or permits for photography which is a huge plus. Finally is the interior architecture. Marble staircases, gorgeous mosaics, and two incredible stained glass domes all set the stage for an engagement session unlike any other. Check out Alexandria and Miles’ photos for a closer look at this wonderful space.
6. The Stunning Fourth Presbyterian Church
One of the most distinct buildings found in downtown Chicago, the Fourth Presbyterian Church on Michigan Avenue features some wonderful gothic architecture that is SO much fun to work with. It’s a wonderful setting for photos, and with it being on the northern end of the Magnificent Mile there are plenty of other locations nearby for additional photos like Oak Street Beach, Navy Pier, and the Mag Mile itself.
7. In Your Home
One of THE best ways to make sure your engagement photos really feel like you is to have them taken in the comfort of your own home. I love this option either for the start or the end of an engagement session as it allows my couples to really relax and enjoy themselves in the space they’re most comfortable in. Whether you spend the entire session in your home, or only part of it, this is a realllllly fun option that I love documenting. You can even include an activity into your in-home session like making pasta or salsa together to really spice things up.
8. A Roller Skating Rink
A surefire way to make your engagement photos feel like you, and have even more fun in the process, is to include an activity you both love to do into your session. There are so many fun ways to go about this, but one I’ve always wanted to document is an engagement session at a roller rink! It’s the perfect setting for documentary style photography, and most roller rink spaces include arcades and other activities that you can include into the session as well!
9. Local Theaters
Whether you love a night out at the movies, or you love to go to plays and musicals together, including your local theater into your engagement session can be a really great option. My couple Mia and Matt included The Logan Theatre into their engagement session and it was a wonderful time. This is a great way to end an engagement session as you can then have yourselves a little date night at the theater after spending the afternoon together loving on one another.
10. Sunset at Horner Park
There’s nothing like a good sunset for engagement photos, and in my opinion there’s no place better for this in Chicago than Horner Park. Cassie and George’s engagement session is a wonderful example of this. The stunning park and the beautiful golden lighting from the sun all come together to create a space that really lets you enjoy one another and this incredible moment in your relationship.
11. Share a Pie at Bettie’s Chicago
If you love a retro diner vibe as much as me then Bettie’s Chicago has to be on your list for potential engagement photo locations. In addition to the 1950’s aesthetic of the space, they also offer classes and date night event options that make for a great part of your engagement session!
12. Hammocking on the Lakeshore Path
The Lakeshore Path that runs along Lake Michigan offers so many stunning views and relaxing settings throughout it that all make for amazing locations for engagement photos in Chicago. Strolling along the path itself is a ton of fun, but you can take things to the next level by hammocking along the path like Laura and John did for their engagement photos. The path itself can get pretty crowded, so this is a great option to give yourselves a little bit of space while still enjoying the serene lakefront and views of Chicago.
13. At Your Local Library
Your local library can be an amazing setting for an engagement session. Whether you love to go here together looking for new books to read, or just to enjoy the space, it can bring that extra level of personal feel to your photos. Sometimes you can take things even further though, like my couple Bridget and Brian. They had their engagement photos taken at the library of Loyola, where they would eventually celebrate their wedding which made it all the more special!
14. Sunrise in Downtown Chicago
Sunset often gets most of the attention when it comes to photos, but the golden hour of sunrise deserves just as much praise in my opinion! A huge benefit of a sunrise session is that there are far fewer people out and about, which makes things all the more intimate for your photos. This is even true in the heart of downtown Chicago. Sunrises in the heart of the city are incredible. It feels as though you have the entire city to yourselves, and having the golden glow of the sun reflecting and shining through the buildings is absolutely breathtaking.
15. At the Art Institute
Another iconic space of Chicago, the Art Institute is a favorite of mine for engagement photos and wedding portraits alike. Like the Cultural Center, the Art Institute does not require a photography permit for photos, but you are required to pay the entrance fee. That’s a small price to pay though for the opportunity of having the institute as the backdrop for your photos. Stunning architecture, incredible art throughout, and the gorgeous outdoor gardens all set the scene for an unforgettable session unlike anything else in the city. Check out Connie and Steve’s session for a closer look at this space!
16. A Beloved Coffee Shop
Need a little pick me up to get your engagement session started? Why not grab a cup of coffee from one of the wonderful coffee shops throughout Chicago and include it into your engagement photos? Spaces like Dark Matter Coffee don’t just give you great coffee to get the day started, they also have a stellar space that is SO much fun to work with for photos.
17. The Majestic Campus of the University of Chicago
One of the most beautiful campuses in the city, the University of Chicago is a phenomenal option for engagement photos. Whether you’re alumni, currently attending, or just love natural beauty and astounding architecture, it’s a space of endless opportunities for photos. The mixture of contemporary and gothic architecture provides a ton of variety, made all the more wonderful by the natural beauty of the parks on campus. While the campus is a good ways south of the heart of Chicago, the close proximity to the lakefront gives you plenty of options to also include into your engagement photos.
18. Your Favorite Neighborhood
A huge part of what makes Chicago such an incredible city are its divers and distinct neighborhoods. Including these neighborhoods into your session isn’t just a great way to make your session feel more personal to you, but it also gives your photos that authentic Chicago feel to them. Whether it’s the neighborhood you live in now, the one where you met, or where you two love to head for date night, I love this option for engagement sessions here in the city!
19. While on a Vintage Boat Cruising the Chicago River
One of the more unique experiences available in Chicago, cruising along the river on a rental boat can be an amazing way to make your engagement photos SO much fun. There are plenty of rental companies such as the Chicago Boat Company that have great personal boat rental options. Imagine riding along the river together, skyscrapers towering above as the sun begins to set, a truly romantic way to end your engagement session!
20. In a Pottery Studio
Any fans of Ghost here? This is such a fun activity to celebrate your engagement with, whether you already have experience with pottery, or you’ve been wanting to take a class together for a while now. The best part is that after your session you’ll have a brand new piece of pottery for your home that will always remind you of this moment in your love story.
Planning the Other Details of Your Engagement Session
There’s more to an engagement session than just planning the location and activity you’ll be doing, a LOT more. That’s why I put together a guide on how to prep for your engagement session to help you through some of the other important details of it. I also love helping my couples plan their session firsthand, so if you’d rather have someone to work through ALL the aspects of planning your engagement photos with you be sure to send me an inquiry through my contact page!
