Chicago Engagement Sessions- Locations we LOVE!

I don’t try to hide it- I’m a country girl. I listen to strictly country music (unless it’s a serious dance bop then I’m all in…..Ride Wit Me may be one of my favorite songs ever…just saying). I live in the country. We drive trucks and grow corn in our backyard. Clearly, I never grew up north of I-80. But that doesn’t mean that I don’t LOVE to shoot in the city. It’s a whole new world for me and I can’t get enough. I get chills every time I drive in. And I do DRIVE in. I am most definitely not one of those central Illinois moms who is scared to drive in the city. Oh no- I LIVE for it. Bring it on people- get out of my way- I am not afraid of you:). If you know me- you know there’s no challenge I won’t accept- city driving included:). But I digress.

I shoot A LOT in the city. Easily 15-20 times year, which is kind of a lot for girl who lives 3 hours south. Many of my couples are choosing to get married in central Illinois- either the Champaign or Peoria area- because family is here, they grew up here, or frankly- it’s just way more affordable than getting married in Chicago! But a part of their lives are in the city. Maybe they grew up there. Maybe they live there now. I LOVE that we can capture part of their story in the city that means something to them!

I’ve shot many, many places in Chicago. But it’s a big city:). I haven’t even touched on some of them I absolutely want to shoot. First- I’m going to list the places I have (with some example photos) and why I love them!!! But keep reading til the end. There’s a list of places that I’m DYING TO SHOOT if someone would let me.

Before we dive in though- here’s some tips if you’re wanting engagement pictures in the city.

• Travel is a beast. I highly suggest we park our cars somewhere (hopefully free)- and then plan to invest in Ubers for the day. Ubers are the best way to get a lot of locations quickly without having to spend crazy amounts of money parking different places and trying to fight traffic on our own.

• Change of clothes- not worth it. If we’re shooting a bunch of locations in the city- it’s probably better to just stick to one outfit and rock it out! Unless you want to carry your change of clothes around in a bag and find a place to change- it’s often more trouble than it’s worth. Especially if we’re uber-ing! So it’s completely up to you but you won’t want to be dragging a huge garment bag all over the city, I promise:)

• Choose 2-3 favorite locations and we can make a plan around that! I also have some close combinations where we can park once, you can change in your car between locations, and we can get a nice variety of looks!

• Make sure we check what’s going on in the city:). One time, we scheduled an engagement session for Game 7 of the Blackhawks- RIGHT BY THE STADIUM. Not our best move. Another time, I scheduled a session the night of Obama’s acceptance speech. And another- we planned to meet smack dab in the middle of the Gay Pride parade going on. I’m clearly a magnet for these sorts of scheduling moves:). When planning, we need to make sure we are double checking for marathons and parades and games and presidential speeches and anything else that might slow down our evening….a lot.

• Weather: It is called ‘the Windy City’. It’s also not necessarily known for being the most sunny place on Earth- especially when we’re shooting in the middle of a bunch of skyscrapers. We will most definitely chase the sun if we can- but don’t feel disappointed if it’s not a bright sunny day on your session. The city is all about the energy- which is there sun or no sun!

Locations: There are a million places in the city to shoot. There’s a little bit of everything! We can absolutely plan your session strategically to hit the hot spots. We can hit places that scream CHICAGO! We can avoid places that scream Chicago! We can get full on city buildings, or we can do parks. We can be sports fans, or food fans. We can also choose a random block and then walk in a 3 block radius and find 800 amazing locations to shoot. That’s the beauty of the city. There are alleys and murals and doors and streets and subways and stairwells and so.many.places to shoot! Sometimes the best plan is to not have one:). But here’s a short list of locations I’ve shot and loved!! (remember to stay tuned to the end to read the places I WANT TO SHOOT if you’re game!)

1. a rooftop: There are many stores, hotels, restaurants, friends’ apartments that have rooftop access. It’s a great intimate way to get a view of the city behind you while not having to fight off a ton of people!! Love rooftop sessions!

2. Olive Park: located by Navy Pier- this park features a beautiful tree lined sidewalk that leads to a little concrete nook that overlooks the lake with the skyline behind you. It’s usually not that crowded, super dog friendly, and a great way to get some looks of ‘nature’ and ‘skyline’ in one shot. Bonus- it’s right across from Navy Pier- so we typically park at Navy Pier and get some shots there too. ( I feel like this a wine list…..Olive Park…pairs well with Navy Pier. I think I’m funny.)

3. Since we’re right by Navy Pier- let’s do Navy Pier. I love shooting here for the obvious- there’s some fun places outside with the Ferris wheel and other excitement along the little strip there. But I also love some of the more unthought of places. There’s a stairwell in the back that is AMAZING every time I shoot it. There’s the tall glass wall that is the entrance to the botanical/greenhouse thing. You can shoot inside the greenhouse no problem! The inside of Navy Pier is so cool- hanging lights and wood walls and just some really cool aesthetics. It’s definitely a fun place to shoot and gives you a lot of variety all in one!

4. Lincoln Park Zoo/the Honeycomb: One of the most popular engagement session sites is the Honeycomb located at Lincoln Park Zoo. I also LOVE this location for it’s incredible diversity in one spot. We park one place and can hit 4-5 different spots and looks without moving our cars!!! The honeycomb is a super cool structure with an amazing look of the skyline behind you. Check out #5 for the surrounding location ideas.

5. Amazing areas surrounding the honeycomb: There’s a beautiful grassy field that surrounds the honeycomb. We can take photos in this grass that makes you look like you’re smack dab in central Illinois- not a few hundred yards from the lakefront:). It’s beautiful all times of year!!! Also right by the honeycomb is a concrete structure building that has a cool archway, a series of arches above, and some pretty amazing concrete steps I love to shoot on. Right up those concrete steps is a pathway that always shoots so beautifully with a hint of the Chicago buildings in the back. It’s never failed me- and it’s definitely one of my favorites!

6. Oak Street Beach: After winding through Lincoln Park- you can access a walkway right from the same parking lot that walks you straight onto this beach. You can get a good view of the skyline and definitely some sand in your toes and walk all the way up to the water if you like! It’s great for a convenience factor as again- if we’re doing Lincoln Park area you don’t even have to move your car!

7. By going the opposite way by Lincoln Park Zoo- you can find this adorable little nook of amazingness. It’s like a tucked away little sanctuary with a pond and plants and it’s almost surreal- you DEFINITELY don’t feel like you’re in the city. It’s fun to shoot Lincoln Park Zoo- then walk to this little piece of paradise before heading to North Beach.

8. North Beach: This beach has some incredible views of the skyline. It’s a bit of a walk to get there (especially with Covid restrictions lately and beaches closed to parking)- but it’s worth it! We don’t even get down near the water- but shoot the steps, the grass, and the SKYLINE. SO amazing.

9. Montrose Beach: I discovered this area a few years ago when a family client of mine (who live in the city) suggested it for their family photos. I fell in love. It’s an amazing location for a great variety of looks and super easy and accessible. Montrose has street parking that’s pretty easy to find a space. You can start with the incredible skyline. It’s much further away- but it’s a pretty incredible view nonetheless. From there, you can shoot the bird sanctuary. Yep, you read that right. But it’s an amazing forrest area that is so beautiful year round!! (and again, such a different place from what you think of as ‘city’.). Then- just a little more of a walk and you’re on an adorable beach complete with this little colored vintage-y building and a ton of colorful boats and beach with zero depth water running right up to it. It’s so adorable. I’ve shot family sessions here at this little boat/beach area- but never engagement- so PLEASE be the first to let me:). The whole area is SO cute, so diverse, and one of the easiest places to access in Chicago in my opinion! **note- Covid shut down this beach for awhile:(. as did one weird bird infestation once!!! hahah! But it’s still one of my favorites!

10. Random city streets and sidewalks: Chicago is known for it’s traffic, it’s busy streets and sidewalks. I love shooting in the middle of streets (no joke). But I love the genuity of a city sidewalk for your engagement pics- and this can be done literally anywhere:)

11. Sports: What is a big city without its sports! If you’ve never looked into it- it’s a LOT of money to shoot inside stadiums and ballparks. A LOT. It’s cool as heck and if that’s your thing- let’s do it. I do feel like I need to come clean here that I AM NOT A CHICAGO FAN. St. Louis all the way baby. Cardinals and Blues have my heart. But I’ll still shoot your dumb photos. I’m totally kidding. We can make your sports pics work though without even getting in!

12. Your neighborhood: Chances are you aren’t going to be living in your neighborhood forever. I love when couples want to do their shoot in/around the neighborhood where they live. The restaurants they eat in. The bars they go to. Just a few passes around the block can really capture some incredible memories for you!

13. Bridgeport Art Center: I discovered this place when one of my couples booked their wedding there- and therefore wanted a few engagement photos here. We didn’t even go inside and I’m already in love. This little amazing outdoor area is accessible to anyone- it’s open air- but has this cool brick and chandeliers look to it!! It’s a perfect alternative if we’re a little unsure of rain/wind! Loved this area!

14. RANDOM places: if there’s one thing you’ll learn while working with me- it’s that I love the unexpected. I also get REALLY excited when I have an idea and I think it will be an adorable shot. Just go with it. I promise. I’m a little quirky, a lot of fun, and sometimes my crazy ideas pay off. How fun is this shot? And how Chicago is it:). There’s so many shots like this in Chicago I want to do!!!

15. JUST WALK: One of my absolute favorite Chicago engagement sessions came with NO plan. We met in their apartment. It was an easy place to meet. We decided to do a whole shoot in their apartment that was pretty much adorable- snuggling on the couch, having a pillow fight, in the kitchen. Then- we just started walking. We found fun walls, crossing the street, random bikes, this wall that maybe we used a little photoshop on to be funny, and so.much.more. I am in love with this engagement session still years later because of how genuine it is. I’m so guilty of being an over planner at times- but this session right here proved to me that especially in a city as exciting as Chicago- sometimes no plan IS a plan.

So there you have it- my list of places that I’ve shot engagement sessions in Chicago and loved. I still love all of these images so much and smiled the whole time I went back through galleries to make this blog! Any one of these locations, or a combination of them, would make for amazing engagement photos!

That being said- there’s quite a few more spots I’d LOVE to tackle for engagement photos! If you’re game- I am:)

1- HOT.DOG.CART. Chicago is KNOWN for it’s hot dogs. I have had dreams for almost 10 years now of shooting an engagement photo series of a couple eating a GIANT Chicago dog with ALLLLLL the toppings in a Lady and Tramp sort of style. Just one. Just one couple and I’ll shut up, I promise. :)

2- Millenium Park. An iconic part of Chicago- but will shoot so awesome. The Bean, the gardens, just all of it. A great place to shoot!

3- Museum Campus- there’s an amazing view of the skyline here as well. Not too much else to shoot here- so it’s a lot of work for a skyline pic- but it’s pretty incredible.

4- can I get some ice skaters??? Chicago has some ADORABLE outdoor ice skating rinks. There’s Maggie Daley ribbon which is super cute and right downtown. I also discovered this adorable pop up village last year called ‘Jack Frost’ with an outdoor ice skating rink and tons of opportunities for adorable photos. I was in love.

5- Salvage One- has a crazy cool 3d mural thing on the wall that says Chicago that would be epic to shoot in front of:)

6- segway tour. Just you two and two Segways heading down the sidewalks. This would be a total hoot.

7- Tribune building- I’ve shot weddings here and the lighting and buildings are just crazy cool. It’s right downtown so definitely we’d need to uber here- and there’s a million people- but it’s so cool!

Hopefully this helps my Chicago couples who are wanting to do some engagement pictures! I’m down for any of these ideas- and ALWAYS down for new ones too!! I can’t wait to spend an amazing day in the city with you!!!!

Love, Kara