Chicago: City vs. Suburbs

We consider ourselves to be Midwest gals through and through and are so happy to call this area home. We’re all about that hometown pride here on the blog, so when a reader asked us to talk about what why we live where we live, we thought it would be fun to dedicate a post to the topic!

We both grew up in a southwest suburb of Chicago… in Orland Park. While neither of us has called Orland home for many years, we still visit the area to see family and Bridget heads there for work every day (fun fact: Bridget teaches at the high school where we both went!). Growing up, we’d both “go downtown” pretty often with our families. The city of Chicago is about a 40-minute drive from Orland and it was always a treat to head to Chicago for back to school shopping, summer days, or Christmas festivities. 

Today, Casey lives in the heart of Chicago and Bridget now calls a western suburb home. So why do we live where we live? And are we planning to stay there for the long haul? We each break it down for ya…

Casey – City Girl

Why I live where I live

After college, Finn and I moved around the midwest as I pursued my career in TV. We lived in Wisconsin for a few years, and then headed to St. Louis for a couple more. But I was always so eager to get a job in Chicago to head back home. My entire family lives in Chicago (my mom, dad, and 3 siblings), so I wanted to settle down here to be close to them. 

Chicago is divided into neighborhoods and each one is incredibly different. We live in “East Village” which is technically Ukrainian Village. It’s only about a block away from Wicker Park, which is our favorite neighborhood in all of the city. We chose to live here because it’s close to the blue line (a train we use to get to work), close to the heart of the city, close to the highway, and close to sooooo many amazing restaurants and shops.

What I love about living in the city

I’m close to just about everything! Every kind of cuisine you could imagine, so many fun things to do, and so much diversity. I walk around my neighborhood and it’s such a mix of people, which is refreshing for a girl who grew up in a mostly white upper-middle-class area. 

On any Saturday, Finn and I can walk out our door and just see where the day takes us…all on foot (or bike!). The ease of being able to get around is really awesome, and we rarely have to use our car. 

And you guys have heard me rave all about our favorite food & drink in this city from this post, but I must mention it again. There is always a new restaurant to check out, a cuisine to try, and happy hour to attend! Living in the city truly is a hell of a lot of fun.

What I don’t love about living in the city

I absolutely love love love our condo and I believe we have done so much to turn this 2-bedroom, 2-bathroom place into a space that feels like it’s truly home. But I’d be lying if I didn’t admit that we could use a bit more room. A backyard and some grass sounds pretty heavenly, especially on nice days! And while we adore all of our neighbors, it can sometimes feel like you’re on top of one another. You feel bad having people over and being loud when there are other people in the building to consider.

Also, running errands in the city takes about 10x longer than in the suburbs. We will usually drive for errand days and getting around can be a bear. Not to mention parking can be a challenge in some places. Whenever I’m out by Bridget’s house, I feel like I can get so many errands done in no time at all!

My favorite things to do/eat/see

I really broke down our favorite restaurants and cafes in this post, so instead, I’ll highlight the things I like to do and see in Chicago. Before I started blogging full-time, all of my day jobs were located in downtown Chicago. I love the feeling of being in the heart of the city with the hustle and bustle of people heading to work. My commute always involved a stroll on the Chicago River and it truly is just so gorgeous. If you ever come visit Chicago, please take an Architectural boat tour ride. Yes, it’s touristy…but it’s a magical way to see the city. 

Because we live west of the city, we don’t go to the lakefront as often as I’d like to. But it is beautiful, especially in the summertime. Riding bikes on the lakefront is a great way to spend an afternoon! Over the summer, it feels like there’s a festival every single weekend and we are always heading to those to shop, listen to music, and eat from food trucks! I also hit up the Wicker Park Farmer’s Market every Sunday with my mom.

Our plans for the future

While I love living in the city of Chicago, I don’t see us living here forever. We have no immediate plans to move and have decided to not discuss it until our family is larger than the 2 of us. Right now our condo isn’t huge, but it’s more than enough for just Finn & I. If kids are ever in the picture, I would love to have more space and a yard (& maybe a dog too!).

But my mom, brothers, and sister all live in the city, and I don’t want to go far from any of them. If we did move to the suburbs, I’d probably head to the area where Bridget lives so we could be close to her! Plus, it’s an amazing suburb that is a close commute to the city for work (which would be ideal for Finn’s job). But I’ll let Bridget tell you more about why she lives where she lives…

Bridget – Suburb Girl

Why I live where I live

Like Casey mentioned, I live in a western suburb about 15-20 minutes from downtown Chicago and we LOVE it. Matt and I chose to live here because it’s a great community with amazing schools, its a 15-minute commute to work, and it’s close to both of our parents (and families!). We loved our old neighborhood too, which is only about a mile from where we live now, but didn’t love the schools as much… plus we needed a little more space with a baby on the way at the time.

What I love about living in the suburbs of ChicagoWhat I love about living in the suburbs of chicago

We especially love our current location because we can actually walk to the town’s “downtown” and enjoy the neighborhood on foot. Our options to eat, drink or explore are not nearly as generous as Casey’s neighborhood in the city, but it is nice to have some options walkable since that isn’t always a luxury that comes with living in a suburb. We also love our neighborhood and neighbors because it’s such a tight-knit community. There are organized events on the block throughout the year and people are always out and about. We LOVE that and will probably love it more when Ben is older and can play outside. We also love that this suburb is close to downtown Chicago. I can hop in the car and get to my sister’s place in the city in less than 20 minutes (as long as it’s not rush-hour!).

What I don’t love about living in the suburbs of Chicago

Honestly, there isn’t a ton that I don’t love about living in the suburbs. I guess I would say taxes if I had to name something. Haha, I officially sound OLD! But our town’s taxes are a bit on the higher side, so if I had to name something — it would be that!

My favorite things to do/eat/see

We love our town’s downtown area, mostly because we can walk to it and enjoy dinner, drinks, or whatever event the town is hosting (craft shows, parades, festivals, etc.). Matt and I don’t necessarily go out of our way to try new restaurants or hit up a new happy hour because honestly, we’re happy eating at McDonald’s (don’t judge). But we do walk downtown and grab food, ice cream, and have even done a few “progressive dinners”. This is where we stop at several different restaurants for a small bite and then move on to the next one. It’s nothing fancy, but it’s always fun!

Our plans for the future

We definitely plan on staying in this area (and probably this house!) to raise our family. We are obsessed with our tight-knit neighborhood and our location. We have such sweet neighbors and love that there are always kids outside playing, people outside walking their dogs, and young families moving in. As Ben grows up and starts making friends, we will probably appreciate this even more. Plus, we live 2 blocks away from Ben’s grammar school and middle school so we are very excited that he can walk there someday! Overall, we love everything about our little slice of suburbia.

What about you? Do you live in the suburbs or the city? We’d love to hear what you love about where you live!


The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.