9 True Things Small Town People Have Asked Me About Life In Chicago


I currently live in a small town after spending ten years of my life in the third largest city in the country. This move is temporary, as I wanted to “experience small town life” after being in a big city for all of my adult life. Chicago is only three hours away and easily accessed from this small-town location by train, by car, or even by plane, and yet there are quite a few people who haven’t even explored 5 miles outside of the town they’re from.

I’m not kidding.

The city is shrouded in mystery to them and yet they could easily find the answers for themselves if they so choose. But they don’t.

Over the past few months, here is a completely true account of things people have said to me or asked me when they find out I’m recently from Chicago.

1. “Oh wow, did you live downtown?!”

The answer to this is yes and no – My first year I lived downtown because I didn’t know any better and my college had living quarters there. After a year, I smartened up and became a “True Chicagoan” and moved to one of the many neighborhoods. I am very familiar with Portage Park, Wicker Park, and Uptown.

Most Chicagoans merely work downtown. Yes, I know certain Loop neighborhoods are becoming more popular to live in again, but the truth is not everyone can afford a place there. Anywhere outside of downtown is usually cheaper. And why would you live downtown? Many places there in my experience closea bit earlier than other neighborhoods.

2. “So you didn’t actually live in Chicago then?”

I don’t know how this is such a difficult one to understand, but “downtown” isn’t the entirety of any city. Chicago especially is known to be a city of neighborhoods – from North Side to South Side, there are many different types of neighborhoods of any walk of life you can imagine. Chicago is full of 234 square miles of vibrancy, culture, and things to do. And if you spend long enough in any one neighborhood, it starts to feel like a small town.

3. “Are you kidding me?! Chicago is SO BIG! How is it like a small town?!”

Each neighborhood is like it’s own small city, at least in my perspective. You generally have a shopping district, a residential area, and any other amentities you need within a few short blocks like a grocery store, a post office, a library, etc. If you tend to frequent places and become a regular, like any other town people eventually know you by name and are excited to see you.

Secondly, if you have lived somewhere long enough, you are bound to know people all over the city and run into them in random places, like say, the Wilson red line stop. It goes something like this:

“Oh hey buddy! What are you doing up here? I usually see you in Wicker Park!”

“Hey! I’m just up here, running some errands. My girlfriend actually lives in Andersonville. Why are you up here?”

“Just coming up to visit my old favorite Thai place.”

“Cool, OK – see you around the neighborhood!” 

I know Chicagoans can get weird about leaving their designated neighborhoods as if trucking across the city were some huge ordeal (this largely depends on the weather) but it’s not uncommon to be in any other neighborhood across the city at any time. Public transit exists and runs often enough.

4. “Wait, you didn’t have a car in Chicago for ten years?! How did you get around?”

The nice thing about Chicago is that you don’t need a car if you don’t want one. Many born-and-bred Chicagoans do have a car, but for me, it wasn’t worth it. Why put yourself through the hassle of buying a city sticker once a year, paying car insurance, paying gas prices well over $4 a gallon, dealing with car repairs (hello potholes!), not to mention paying for parking nearly everywhere (remember the whole parking meter debacle?), and then the parking tickets if you’re only about five minutes late getting back to your car. Public transit costs $100 a month for unlimited rides on a bus or train, any time of day or night and got me anywhere I wanted to go.

The large majority of my friends didn’t own a car in the city and didn’t want to. I actually knew people from the city who never even bothered to do driver’s training. What is typically a rite of passage for most people anywhere else, I knew a number of people in Chicago who never bothered to get a driver’s license.

5. “I couldn’t imagine not having a car and not going anywhere you wanted to at any time of day. I used to wait for a bus that ran once an hour in (insert random small Midwest city) and I couldn’t stand it.”

Although we complain constantly about the timeliness of the CTA, most of the bus routes aren’t all that bad, with many being a 5-15 minute wait. The BusTracker has been a huge help in many instances, even if sometimes you have been waiting for the bus that’s five minutes away for ten minutes. This isn’t always the case, but it happens often enough. 

Again, public transit can get you pretty much anywhere you need to go. If need be, do the car-share deal combined with your CTA pass and you can drive all over! Cabs are also usually plentiful unless it’s New Year’s Eve or Halloween night or if there is some giant Cubs game, so you’re pretty much never stuck. This is why if you prefer to be out late, your best bet is to live off of a train line with nightowl service like the red line or blue line which are both 24-hours.

6. “But weren’t you scared to walk around the city at night? Isn’t Chicago super-violent?”

Short answer: No, I wasn’t scared to walk around at night. You pick and choose which neighborhoods you want to be in. If you’re going to be in a slightly rough-around-the-edges neighborhood at night, go with a friend or have them meet you. You also learn to walk very quickly. Don’t look scared, be aware and walk with a purpose. Also, don’t look at your phone.

About the violence thing: no matter how “safe” any neighborhood claims to be, it’s still the third largest city in the country. Use your best judgment. I’ve been robbed at gunpoint in perfectly “safe” neighborhoods and on the contrary, I have been completely fine at night for many years in a neighborhood where hearing gunshots was the norm. Don’t fall for the hype of how “safe” any area of the city may be even if you’ve “done your research”. There have been broad daylight shootings on Michigan Avenue.

The truth is, when you let your guard down is when things are more likely to happen to you. And people looking to steal anything like to go to nicer neighborhoods to take from people who have more money. I actually felt safer in sketchier neighborhoods because of this.

Let’s put it this way: I’m actually more scared of driving down open highway around here at 80 miles per hour than I am of walking around Chicago at night.

7. “Ah, Chicago! Expensive town!”

No, not really. You have to know where to look.

You can choose whether Chicago is ridiculously expensive or affordable. If you want to live on the Gold Coast, of course you will be paying far more. If you are content to live say, in Avondale — your options are a lot better.

I once did the math on how much it would be to live a similar life in this small town versus living in Chicago, and I honestly came to the conclusion that Chicago was only slightly more expensive by about $75 a month. Add in the fact that out here I will always need a car, insurance, a car repair fund, and I will likely have to drive about 45 miles one-way to a job worth even having plus gas costs. Take that into account and you’re already in the red.

Chicago is one of the more affordable cities in the nation and that’s been talked about time and time again in articles computing the cost of living index of cities nationwide. If you want to go spend your money on going out every night, or grabbing a latte from the coffee shop every morning, those costs will add up quickly. Just because something is available for you to buy doesn’t mean you should buy it. It’s common sense.

I’ve also found that you do indeed make far more money in Chicago. Even what people in this small town consider a “crappy retail job” Chicago paid me far more than in the same position out here. I’m talking like, a $6 wage difference. No joke. And there are plenty jobs to go around in Chicago, despite it’s competitiveness. In a small town, if your local mall isn’t hiring you have to do the 90-mile round trip commute just to break even.

8. “Oh, I’ve been to Chicago! We always shop on Michigan Avenue!”

Speaking of malls…. the Magnificent Mile (dudes, not the “Miracle Mile” like some of you have said, wrong city.) is basically one big giant mall.

This is why you think Chicago is expensive.

If you only want to stay downtown, why not check out State Street? Even better, there are plentiful local boutiques in Wicker Park or in Lakeview near the Belmont and Clark, or some really great shopping options in Andersonville. There are many things you’re missing out on simply because you feel the need to not stray away from downtown. Do some research on the city before you go and you will find gems.

9. “My aunt lives in Chicago! Oh where does she live? She lives in Tinley Park!”

I hate to break it to you lady, but your aunt does not live in Chicago. She lives in Chicagoland.

This is something else that’s weirdly confusing to people. You do realize that Tinley Park is 30 miles away from Chicago? (At least according to Google Maps, I’ve never been there.) The suburbs of Chicago are not Chicago, period. Any Chicagoan will tell you this.

Furthermore, I have hardly been to any of the suburbs in the ten years I’ve lived there because everything I need is within city limits. Why go to the suburbs unless someone’s family that you know is out there and it’s some holiday? Do you really need to go to an Applebee’s?

While I realize that much more of the nation is relegated to small towns and suburban life, there’s no reason to be intimidated by a big city. Perhaps the people I’ve chatted with are just excited to talk about “city life”. And if you love your small town, then good for you! It’s all about preference and we should live where we all want to live. Seriously – no sarcasm intended.

If you’re a small-towner lusting for big city life like I once was, don’t let anyone talk you out of experiencing it even if you only stay for a short time. But if there is one thing you take away from my perspective here, let it be this…no one who lives in Chicago goes to hang out at Navy Pier.