How I Adjusted to Living in a Big City (on my 4th anniversary in Chicago)

chicago skyline, moving to chicago, moving to a city

Hey guys! I’m posting outside of my normal schedule because today is my anniversary of moving to Chicago!

July 26, 2014 I set off from college to move to Chicago. I moved from a town tucked away in corn fields to the 3rd largest city in the country. Here’s my tips if you’re thinking of taking the jump, some highs, some lows, and my overall journey I’ve had these past four years. Enjoy!

If you’re anything like me, you like to read and plan every big decision in your life. I like to know exactly what I’m getting into and exactly what to expect. That’s what I hope to do with this post if you’re like me. I wish I could be spontaneous and just jump into the deep end, but I can’t. Anxiety and stress rule my decisions. That makes traveling and moving incredibly difficult, but I manage. If that’s not you and you’re just reading to read and get more information before you move, hopefully this does that for you, too.

Long story put into a top 10 list:

  1. Take the leap and do it. You’ll surprise yourself with what you can accomplish outside of your comfort zone.
  2. Don’t let old Polish ladies park near your car.
  3. Make sure you have all parts of your bed when you move.
  4. Make sure you know how to get in and out of your apartment. Just in case, have food in your moving supplies for when/if you get held prisoner in your own apartment.
  5. Live with a random roommate, but make sure they’re compatible with your personality – it makes all the difference.
  6. Take time to walk around and explore. Learning about your new home is the best way to make it feel like home.
  7. Try new things! Try new foods! Shop at new stores! Embrace all of the new experiences.
  8. Research where you want to live ahead of time. Chicago has something like 77 community areas and around 200 neighborhoods. There are areas you want to live and areas you don’t want to live. It gets overwhelming, but if you can think of the qualities you want in your neighborhood, you can start narrowing it down.
  9. If you hate it, it’s only a year of your life (or shorter, dependent on how leasing works where you’re from). Anyone can do anything for a year. You won’t regret trying, but you will always wonder what would have happened if you did.
  10. HAVE FUN! EMBRACE IT! LOVE IT! Even if you hate it, you’re bound to love some part of it. The experience is only what you make of it. After the first week, I could have easily have said, “nope!” and moved back to familiarity…but I didn’t. I could have stayed hunkered in my apartment because I was scared of the big, bad city…but I didn’t. I could have not moved at all because of all of the negative media on crime in Chicago…but I didn’t. I’ve had the best experience because I allowed myself to do something new.


If you’ve read some of my previous posts, you know I’m from a small town. Spoiler alert: I’m working on a post related specifically to that. Until then, you’ll have to trust me. The “village” I grew up in was 450 people and I think it’s gone down since I’ve left. Something around ten towns made up my high school and it was still only 400 kids. I literally thought not knowing people in your school and especially your own class was something only portrayed in the movies. It wasn’t until I got to college/graduate school that I learned this was the farthest thing from the truth. Then I found out that there could be hundreds up to a thousand people in one graduating class. WHAT?! I graduated with 73 – mind. blowing.

Class of ’09 in an air conditioning-less gym, but whatever.


My graduate program was accelerated in some senses as it was one full year full of classes and one full year full of externships. I knew I wanted to leave my small town and experience something else. I was accepted into two placements to make up my year in Chicago. I knew ONE person (and her boyfriend) in the city. This was terrifying.

Chicago was still only 4 hours from home. There was a major airport that I could fly to see my mom (who moved to Florida). It was a city I always admired. I was so excited. I was in my 20’s and was going to be living in the middle of a huge city for some of the best years.

I spent countless hours researching neighborhoods, apartments, positives, and negatives of moving.

Chicago has a lot of negative media attention for crime. Yes, there are neighborhoods that you want to avoid and situations you want to avoid, but that’s in any city. Being observant and aware of your surroundings is obviously the number one thing. I was terrified for awhile walking around because of the preconceived notion I had in my mind about what city living is. Guess what? I survived and haven’t had one bad encounter.

I needed a roommate because rent in Chicago is expensive. I also wanted a roommate so I could have another friendly face that I could grow to know. Ready to hear the most sketchy thing next to a Craiglist ad? – yep, it’s a thing.

I’m pretty sure my “ad” read something about always having a fridge full of wine – cold. hard. truth.

I didn’t look too hard and found an incredible apartment that happened to be just a few minutes walk down the street from the only person I’d know. I took a weekend to look at the apartment and meet my potential roommate. She was super chill and laid back and I immediately fell in love (with both the apartment and the roommate). A few days later she got back to me and said that she wanted me to move in! Talk about aligning of the planets. The only downside was I couldn’t have my dog. Super bummer for all parties involved, but it let me have a year to grow used to the city without having to worry about her.

This chick was seriously one of the reasons my first year in Chicago was amazing and I didn’t just run home. She’d always invite me along to whatever was happening. She helped me figure out things like public transportation. She even continued wanting to live with me when I died on her bedroom floor the first night we drank together and puked in her mesh trash can. Then she got a boyfriend (now almost husband!) that randomly made us dessert and I was in heaven. For a random roommate, I could not have asked for anyone better.

Chicago Roommate, Moving to Chicago, Random Roommates, Moving to the City
Skinny, tan, cleavage… + the best first roommate in the city.

I absolutely suggest going the random roommate route. It really boosts your ability to talk to anyone and morph to all kinds of new environments. It gets you and out of your comfort zone and it was incredibly helpful for me!


Moving day – My cousin drove to my college to help me move. It was about 2.5/3 hours away and we packed all of my shit in two cars and set out on our way. We made it to Chicago just fine and all went well getting into the apartment. My roommate was out of town for the weekend, but no big deal at all, I was a big girl (I thought).

I wasn’t even at my apartment for a half an hour when a little old Polish woman that lived in my building backed right into my car. We were yelling at her backing up in slow motion, but her hard-of-hearing ears heard nothing. We expected it, we saw it happen, there was nothing we could do. Honestly, it was hilarious. My cousin then had to get in the car and finagle the woman’s vehicle out of the space she was trying to get out of. Welcome to Chicago!

I got all moved in, told my cousin goodbye, and started unpacking. It was about an hour in that I realized I was all by myself in a huge city for the first time. Oh hey, panic attack. I had one key, but I had no idea if it was for my apartment door, or the outside door, or some other random door I didn’t know about yet. That led me to being stuck in my apartment for a little over 24 hours with only tortilla chips to eat. I didn’t know how anything worked and my roommate wasn’t due home for a few days. In addition to that catastrophe, I had a sleep number bed that didn’t have the part to inflate. So I was a prisoner in my own apartment without a bed. It was a disaster.

I cried on my deflated bed on the floor my first night.

Moving to a city, Moving to Chicago, What to expect when moving
This was also a really sad part of my move.

My roommate finally came home and told me how to get in and out of the building without locking myself out. She took me to dinner and filled me with wine and I was OK again. Thanks, E!

Then came the time I had to go get groceries and other things to make me feel at home. I don’t think I’ve mentioned it yet, but I have anxiety. I have to have things planned out and know the steps to anything new that I’m doing. I searched the hell out of the grocery stores around me and read everything I could about them. Weird and not helpful to most, but I had to. I also, for the first time, had to walk to the grocery store and carry the groceries back. It was loud, it was a busy street and cross-section in the city. I was overwhelmed. I could only go one place per outing. I remember calling my mom and telling her I could only do small bits or the busyness and chaos overstimulated me.

I got everything done that I needed to and little by little I could go out and do things for longer. It seems unnecessary now, but it was a thing then. I don’t think I could have managed any other than the way I did it.

I finally got my bed to inflate, I got a bed frame, and I made my room a room. That helped 200% and I started to immediately feel better.

Moving to Chicago, New apartment, Making an apartment feel like home, Moving to the city
Check out that DIY night stand.


I remember the first time I had to meet my roommate somewhere that wasn’t walking distance. I hadn’t take the “El” (Chicago’s version of the subway) by myself yet and then had to walk from the stop to the bar. I had to have her spell it out step-by-step so I could get there. Then, I got on the wrong side so the train was going the wrong direction. I had to figure out how to get to the other side and then make sure I got off at the right stop. This was so new to me and being from a small town, I seriously thought I was going to be mugged. It was 7 pm…I was fine. And, I was only going 2 stops. I may have been over dramatic.

I got off the train and was looking at the map to figure out where the hell I was and how to get where I wanted to go. I guess I looked like a damsel in distress because security approached me and asked how they could help. I finally made it to the bar and thought I was going to throw up from my nerves. Then I proceeded to drink way too much and had the night described ending on E’s bedroom floor.

Picture Screenshot
Awful “Instagram editing” from a few years back – my bad


It was my first small conquer. From then on, I was able to navigate the city better. Most trips resulted in getting lost or not finding what I set out to find at all, but I was doing it! I felt very proud.

The next year consisted of meeting a ton of new people, making new friends, trying new experiences, and becoming extremely accustomed to city life. I have no idea how I ever survived without a grocery store two blocks from my apartment or having 25 restaurant choices in a four block radius. Don’t even get me started on delivery services for EVERYTHING. How do people not love living in a city like this?!

RELATED: Have you used DoorDash? Check it out & get money toward your first order. (reward perk > disclosure statement)

I got used to the sirens outside of my window, never being alone, and not knowing my neighbors. Silence and darkness became uncomfortable to me and I fell in love with a busy lifestyle.

Chicago Apartment View, Moving to Chicago, Chicago Apartments, Moving to a city
I loved sitting on my bed and looking at this outside of my window.

I miss the stars, I miss driving down country roads to clear my mind, and I miss my friends. That is expected. What I wasn’t prepared for, was Chicago becoming my new home in such a short amount of time. I fell in love with the city lifestyle. I fell in love with my boyfriend. I fell in love with the endless opportunities available to me. I felt like I was given the world. Everything I missed, I will always miss. The great thing is finding new experiences to match you where you are in your current life. I think that’s been the favorite thing I’ve learned since moving. Your past will always be a part of you, but you find what you need as you evolve and change.

Moving from my small town to a city with 3 million people in it was the best choice I ever made. I’m so thankful I was set up in life by my parents to have this opportunity. If I have one piece of advice, it’s go outside your comfort zone. Do what you don’t expect yourself to do or what others don’t expect you to do. You learn so much about yourself, your limits, and what you’re capable of. You really will surprise yourself.


I have now been in Chicago for 4 years. I have lived in three different apartments. The first one with E I lived in for one year, I lived by myself for one year, and then I moved in with my boyfriend. My dog has been with me for all but one of the years. I still live in the same neighborhood and just two streets north of the first place I lived. The second apartment I lived in, I was just one street north of the first apartment. Maybe it’s because I don’t like change, but I love my neighborhood. I’m glad I did the massive amounts of research. It’s convenient. It’s far enough outside of the downtown area, but close enough to get there in 15 minutes. There’s a ton of dining, bar, and activity options. Everything is in walking distance.

Chicago, Moving to a new city, Moving to a big city
Only friend I knew when I moved here

I began living here for my career, but I keep living here because I’ve made it one of my several “homes.” My career path has changed, but I’m still in love with the city. I often think where I would be if I didn’t jump off the high dive with a blindfold on. Everything would be so incredibly different. I don’t know for the better or for the worse, but it doesn’t matter to me. I’m so happy with how much I’ve grown, how independent I’ve become, and with the life I’ve made for myself.

RELATED: WHAT I’VE LEARNED: Starting to Travel

If you’re thinking about it. Stop. Stop thinking and do it. If you don’t like it, you can change your path. But if you don’t try, you’ll never know. Don’t be 50 and wondering what you could have done. Or, if you’re 50 and thinking, do it so you’re not 70 and wondering what you could have done.

Moving to Chicago, Moving to a city, making a big move
Photo by Violetta Photos – check her out if you’re near Chicago. Love her!

Have you made a decision like this? Are you thinking of making a decision like this? Tell me your story! I love these kinds of things!

5 Comments on “How I Adjusted to Living in a Big City (on my 4th anniversary in Chicago)

  1. Pingback: How I Made $89.01 My First Month Blogging – July 2018 Income Report – The Wandering Nobody

  2. Pingback: Sunshine Blogger Award 2018 – The Wandering Nobody

  3. Pingback: How I Made $89.01 My First Month Blogging – July 2018 Income Report – Wandering Nobody

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