One of my favorite places for engagement sessions has to be the iconic & historic city of Chicago. While I am based in Indiana, I often venture to the Windy City to document my couples & their love stories in the one of a kind city. There’s SO much that I love about Chicago, & so many locations throughout it that make for excellent backdrops for an engagement session. With that in mind we’re going to go over everything you need to know to plan your own engagement session in the city. From the early steps & decision making, to finding the best location for your session, we’ll be talking about it all. So let’s get into it!
Planning Your Chicago Engagement Session
While not as in depth as planning your full wedding day, there is still quite a bit of planning that goes into crafting your engagement session. There’s a few key things to keep in mind throughout the planning process which we’ll take a look at first, after which we’ll check out 10 of my favorite locations throughout Chicago that are perfect for an engagement session!
The Feel of Your Session
First & foremost you’ll want to start planning your Chicago engagement session by deciding how you want your photos to feel. Are you envisioning a more upscale & classy vibe? Something a little more casual & carefree? Do you want to keep things cozy & simple? There’s no wrong answer here, but there are a LOT of different ways to go about crafting your ideal engagement session. The important thing to keep in mind is that this is YOUR engagement session. You, your love, & your story are at the heart of this event. With that in mind try to imagine the session that best fits you & your one of a kind relationship. There are many different areas that will affect the feel of your session, the first one being…
Where to Have your Session
One of the most impactful decisions you’ll make in terms of the look & feel of your engagement session in Chicago is where you end up deciding to have said session. Chicago has a seemingly endless supply of fantastic locations to choose from, & we’ll be taking a look at some of my favorites later. The important thing to note now is no matter what you’re looking for as a setting for your session, Chicago undoubtedly has it! From natural oases, to cozy shops, high end bars & restaurants, historic buildings bursting with character, the list really goes on indefinitely. I could write about my favorite 100 locations in Chicago & we’d still just be scratching the surface of what this city has to offer!
A huge benefit of having your engagement session in Chicago is that so many of these incredible locations are all in close proximity to one another. This means that if you’re having trouble deciding on a single setting for your engagement session you’ll more than likely be able to fit multiple into your day with minimal effort. Just another one of the MANY reasons to choose the Windy City for your engagement session.
When to Have Your Session
The next factor to consider when planning your engagement session in Chicago is when to actually have your session. This is a two parter, what time of day & then which season to have your session.
What Time to Have Your Session
In terms of what time of day to have your session, it largely depends on where your session is. For instance, with an outdoor session I’d recommend either a sunrise or sunset session for the best lighting, & you may want to go for the sunrise option to avoid the crowds at more popular locations. On the flipside, some indoor locations will only allow you in during certain hours which can limit the timeframe of your session. Once you have your location(s) decided on, your photographer will help you to iron out the timeline of your engagement session (don’t worry, we’ll talk about booking your photographer in just a little bit!)
What Season to Have Your Session
In terms of what season to have your engagement session in, Chicago makes a pretty good argument for each of its seasons!
- Summertime is when the city is most vibrant & bustling making the city feel truly alive, but it’s also a very busy time of year.
- Fall is cooler & slightly less busy, & in the parks of Chicago you can enjoy the fall colors as the leaves change if you time things right.
- Winter is when Chicago becomes a winter wonderland, & is often the least popular time for tourism throughout Chicago which can make things easier if you’re willing to brave the cold.
- Spring is when the city starts to bloom, & while it can be on the rainy side this can also lead to your photos having an extra layer of emotional depth if you’re up to do a bit of dancing in the rain.
Knowing this, the choice is ultimately yours for what season you choose to have your session in. Keep in mind that these photos are likely what you’ll be using for your save the dates, wedding invites, & potentially some décor around your wedding venue. In that case then, do you want your photos to match the season of your wedding, or be on the complete opposite side of the spectrum for some variety? The season of your engagement session also heavily impacts how your session will look & feel, both due to the setting & what you’re wearing for the session. Speaking of which!
What to Wear for Your Session
What should you wear for your engagement session in Chicago? The Windy City has a prominent reputation for having some unpredictable weather, as is pretty standard for the Midwest. Days where it’s below freezing in October, 70 degree days in August, 80 degree days in April, & the occasional polar vortex in the winter only begin to describe the wide array of temperatures & weather conditions that could take place during your session. With that in mind it’s important to plan ahead for your session, as while we may not know the exact weather of your day until it’s upon us, we at least have a rough idea of what we’ll be dealing with.
I always recommend my couples have at least two outfits in mind for their engagement session, typically something more formal & then something more casual. Choosing these outfits is a task that I help ALL of my clients with. We’ll go through color palettes based on your season & location(s), layering options, accessory options, & things to avoid like strong patterns or matching colors.
Finding the right outfit for your session can sometimes help you to narrow down which season you want to have your engagement session in as well. If you both have some epic winter coats that you’re obsessed with you may opt to brave the Chicago winter to show them off. Or maybe you’re both more into the sunny beach vibes of summer, in which case we can definitely make that a reality for your session. Whichever outfits you end up choosing just make sure they’re true to you, & if you plan on getting new clothes or shoes for your session make sure they fit & are broken in beforehand!
Booking Your Photographer
It wouldn’t be an engagement session without a photographer, literally! Choosing a photographer is one of the most important decisions that you’ll be making for your engagement session, as their style determines much of the look & feel of your photos. More than that though, you’ll want to find & choose a photographer who you actually enjoy & want to be around. This is because many times the photographer for your engagement session will also be the photographer for your wedding day. I always recommend having the same photographer for both as it gives you all a chance to get to know one another & get any initial awkwardness out of the way early!
10 of My Favorite Locations in Chicago for an Engagement Session
With all of that out of the way, it’s time we take a look at 10 of my favorite locations for engagement sessions throughout Chicago! As I mentioned earlier, there are practically endless locations & settings to choose from here in Chicago. That’s to say that even if there isn’t a location on this list that immediately jumps out to you it doesn’t mean you can’t find it in Chicago. This is more to give you an idea of my all time favs in the city, & show you what makes them some of the best so that when you’re deciding on your engagement session location you know what to look for.
1. Milton Lee Olive Park
First on our list is the stunning Milton Lee Olive Park, a true natural oasis on the shores of Lake Michigan. This small but impressively gorgeous park offers one of THE best views of the Chicago skyline the city has to offer, making it a phenomenal choice for an engagement session. The park is in the center of Chicago’s lakefront, sandwiched in between the iconic Navy Pier & the popular Ohio Street Beach. The location of Milton Lee Olive Park also means that it is incredibly easy to access many of the other top locations in Chicago, some of which we’ll be covering later here on this list.
This is one of the more popular locations throughout the city, though the crowds can be avoided if you opt for a sunrise session. Ultimately though, if you’re looking for a more natural setting with epic city views mixed in then this is the spot for you.
2. In The Loop
The literal heart of Chicago, The Loop is home to some of the most impressive & inspiring views you’ll find in the city. Named after the “loop” of CTA public transit trains that are in the center of the city, this neighborhood of Chicago is where the majority of Chicago’s big businesses are found as well as some of its most iconic & historic buildings. One such building is a favorite of mine to get photos in front of, which is the Chicago Board of Trade. This building epitomizes what is so great about this area of Chicago.
The towering structure acts as a breathtaking & epic backdrop for your session, & that feeling of these massive skyscrapers towering above you is something truly remarkable no matter how many times you’ve experienced it. The central location of the loop means that practically everything is close by, though you may have to battle some traffic to get there, on foot or via car!
Another aspect to consider when booking your photographer, in addition to their photography style & whether or not you get along with them, is whether or not they’re able to document your engagement session in Chicago. Are they local to the area? Are they a destination photographer (like myself!), who is well versed in all the intricacies of the Windy City? Having someone who knows the city well, knows whether or not you need a permit for certain locations, & can help you to make planning & last minute decisions for your session is crucial for your experience. That’s why I recommend either a local photographer or an experienced destination photographer for your session.
3. North Avenue Beach
Heading north to Chicago’s Lincoln Park neighborhood we have the wonderful North Avenue Beach, our next engagement session location option. This beach offers one of, if not THE most popular views of the Chicago skyline. Its popularity is well justified, as the views of the towering buildings of Chicago with the waters of Lake Michigan beneath them create a gorgeous setting for your engagement session no matter the season. The only issue is that this beauty comes with the cost of it being one of the busiest spots in Chicago, making it hard to have your session feel like an intimate moment between the two of you. This can be avoided by having a sunrise session though, & those are absolutely breathtaking here! Finally, this spot is nearby the beautiful Lincoln Park, which can act as an easy to access second location for your session.
4. Michigan Avenue
Next up is Michigan Avenue, one of the most important & centralized streets of Chicago. While some of you may know this as the Magnificent Mile, Michigan Avenue has a LOT more going for it than its fantastic shopping options. My favorite aspect of Michigan Avenue is south of the Mag Mile, & that is the DuSable Bridge. This iconic bridge crosses the Chicago River & offers some of the coolest & most impressive views in all of Chicago. The clearing of the river gives space for you to experience the towering skyscrapers around you in a way that feels truly out of this world. It’s one of the many locations you can find on Michigan Avenue that offer a feel to your engagement session that is 100% unique and authentic to Chicago.
5. Your Favorite Bar, Brewery, or Restaurant
Chicago is teeming with an array of bars, breweries, & restaurants, each with their own distinct style & charm to them. These businesses are the driving force behind the spirit of Chicago, & incorporating them into your engagement session is something I always recommend as an indoor option! There are practically an infinite amount to choose from, & just as much variety when it comes to their settings. As an example, for Abby & Christian’s engagement session we made a stop at The Palmer House which had the best high end, classy vibes for our photos. This is just one of the many different styles of establishments to choose from throughout Chicago. If you’re set on this experience but aren’t sure on what business would suit your vision best I have a TON of recommendations for you!
6. Union Station
One of the most photographed interior locations throughout Chicago, Union Station offers a setting for your engagement session that is almost too good to pass up. Just blocks away from the Chicago Board of Trade Building, this train station is an integral piece of Chicago’s history & features some of the most breathtaking architecture in the city. The building’s overwhelming sense of history & impressive scale combine with natural lighting thanks to the massive skylight to create the ideal indoor setting for your engagement photos. The close proximity to The Loop also makes it simple to include multiple other locations into your session.
7. Chicago Cultural Center
Another building with a rich history & a jaw dropping interior is the Chicago Cultural Center. Found on South Michigan Avenue, just across the street from Millennium Park, this phenomenal building features immensely beautiful interior design. There is a lot to love about the Cultural Center, but the best part has to be the famous Tiffany Glass Dome. This massive centerpiece of the building is remarkably beautiful, & with the surrounding interior equally as gorgeous & cared for to maintain its original beauty, this space is a must consider for any couple looking to include a beautiful piece of Chicago’s history into their engagement session.
8. The Art Institute of Chicago
Just south of the Cultural Center is none other than The Art Institute of Chicago. The art institute is a lovely location for an engagement session for a number of reasons. The first is that there is no photography permit required to take photos within the institute. As long as you don’t disturb other visitors during your session you’re free to use any & all of the beautifully unique art exhibits as backdrops for your session.
The next reason I love The Art Institute for an engagement session is that it’s beauty extends to the exterior of the building thanks to their immaculate gardens, which help give your session some variety without the need to travel anywhere. If you are looking to get even more variety into your session though, the central location of the Art Institute of Chicago makes it an ideal location for your engagement session as you can get to practically any other location you want for the other portion of your session.
9. Your Favorite Neighborhood
I absolutely love when my couples make their engagement session personal to them & their love story, & one way many couples do this in Chicago is by having part of their session in their favorite neighborhood! It can be the neighborhood you live in now, the one you had your first date in, the one you love to frequent the most, or even one you’ve been itching to check out for a while now. Having your engagement session in one of the many different neighborhoods that make up Chicago is a great way to really capture the spirit of the city in your photos. Whether it’s the Fulton Market District, Wicker Park, Wrigleyville, or one of the many others, these unique neighborhoods are what make Chicago the city that it is, & as such are a great option for your engagement session here in this one of a kind city.
10. Chicago Riverwalk
Last on our list is the lovely Chicago Riverwalk. Don’t write this one off just because it’s at the end of the list, because the Chicago Riverwalk really does have a TON going for it in terms of a location for your engagement session. Its centralized location offers easy access to tons of other locations, some we’ve already talked about like Michigan Avenue & Milton Lee Olive Park. The Riverwalk also provides a different view of the city that’s hard to come by. It’s so cool seeing the Chicago River up close & personal while the massive buildings of the city tower overhead. It’s a great place to either start off or finish your engagement session here in Chicago!
There you have it, all the ins & outs of planning your own engagement session in the Windy City of Chicago! As I said earlier, there’s a lot of planning that goes into these sessions & more potential locations to choose from that make listing them all out in text form practically impossible. Luckily that’s where your discovery call comes into play. If you’re interested in booking me for your wedding & engagement session in Chicago be sure to send me an inquiry through my contact page. Together we’ll iron out all the details of your session to make sure you have THE best time possible here in Chicago!
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