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Moving to Chicago: The Guide - Part 1: Your Bearings

Are you new to Chicago? Meeting people here confusing and stressful? If you are, I can relate to what you’re going though. Not only have I moved here recently, I’ve moved around a few times when I was younger (obviously, that makes me an expert) and if you’ve ever moved before, you know just how difficult it is to start over again. Getting to know your new neighborhood, what people wear, how they talk, making new friends and other little nuances can be a daunting task for some, no doubt. Take my friend for example: he recently got offered a job in Chicago and comes from a town in Missouri where the population is 429. No, that is not a typo, I didn’t miss any zeros: 429. His graduating class in high school was 22. Going to college was scary for him, think of being in a whole new city that is literally 6000 times bigger than his hometown!

So before he accepts the offer, he wants to know about Chicago. He’s asked me a ton of questions in his nervous frenzy and it sparked an idea that if he had questions, other people definitely do as well. Thus, this guide was born. A guide tailored to helping you adjust to the city of Chicago, but I think it can also give people moving to different areas a foundation to apply elsewhere as well. This guide will go over three parts of settling down in a new city: Your bearings, your finances and your social life.

Before starting, let me first say: welcome to this beautiful city so many of us call home now. You’ve probably read up about Chicago and different things about it, but if you haven’t gotten an outsiders perspective yet, this is my account. I moved here in June of 2015 knowing one person in the city which was a big change coming from being surrounded by my family and friends, but I was grateful to have at least one person to hangout with. To those of you who have bravely ventured to somewhere new all by yourself, I commend you and hope this guide helps. I’m still going through my own trials and tribulations and still have a lot to learn, but I’ve definitely made some progress! My hope for you reading this guide is that it helps you minimize the stress and frustration you might feel. Something like this would’ve definitely helped me, so let’s get started!

Part 1 - Your Bearings

Getting your bearings, or becoming familiar with your surroundings can be scary at first, but in no time you’ll become comfortable and relaxed. In this section, I take you through a few tips about getting around the city, Chicago’s main areas and the public transportation system.

Minimize Driving!

You will probably hear this often, but it’s worth repeating: If you don’t need to drive, I recommend you don’t. Strongly recommend. Chicago is one of America’s most walkable cities, meaning the city has made it easy to get around on foot and bike, so take advantage of this! Driving in Chicago means dealing with traffic, finding parking, angry drivers and potholes. If any of those would cause you a big problem, I recommend getting some good ole’ exercise and walking or biking! You pay more attention to signs and streets you’ve crossed, can find shortcuts and what areas to avoid. Try getting around without a GPS. It’s ok to get lost, just don’t venture too far!

Chicago’s Main Areas

Chicago was built on a grid system.  So, it's really easy to navigate going north, south, east and west.  Sure, there are a few diagonal streets, but once you realized Chicago blocks are like a box between streets, you'll get the hang of where you are.  While walking, you’ll start recognizing main streets like Milwaukee Ave., Damen Ave., North Ave., Chicago Ave., and Western Ave., etc. by seeing that there’s a ton of traffic, shops and life on these. These are the few streets around me that connect to all of the sub streets. Use these streets to relate to where you are or where you have to go. Using these as relative points will help give other people more information about where to go if you need help. And by knowing the main streets, you’ll have an idea of what area of Chicago you’re in. Every area has its own sort of style:

Lincoln Park/Lakeview

Upscale, preppy and most of the inhabitants are young professionals with well-paying jobs. Mostly people in their 20’s – late 30’s. It’s clean and safe but can be expensive as its right by the lake and in downtown.  Depaul University is at the heart of Lincoln Park on Lincoln Avenue. Wrigleyville, where the Chicago Cubs play at Wrigley is part of Lakeview.


North of Lakeview, Uptown used to be a really grungy place. In the past, Uptown was mostly an ethnic neighborhood, but now like much of Chicago, it has gentrified and nowadays you'll see Starbucks and Targets. Yet you will still see people from all walks of life, which makes Uptown an interesting and vibrant neighborhood. Old school bars like the Green Mill, where Al Capone and gang used to hang out during the Prohibition days are also common around here and definitely a fun part of Chicago.

Logan Square

Almost the opposite of Lincoln Park in terms of style. I hear this area used to be mostly Latinos about 10-15 years ago but because of recent rent hikes and gentrification, they have moved a little more northwest and young artists have taken their places. Some would describe it as ‘hipster’ and although it’s cheaper than Lincoln Park, the rent can run high. You’ll notice a lot of creativity and art everywhere here. Mostly a 20’s-30’s crowd here.

Wicker Park/Bucktown

Southeast of Logan Square by a couple blocks, but you can definitely notice a change. Wicker Park is a mix -- 60% Lincoln Park and 40% Logan Square. Not as yuppie but also not as hipster and prices can run high here too. Mostly a 20’s-30’s crowd here as well.

The Loop and River North

I don’t hang out here as much as I would like to, but from what I’ve noticed, it’s almost the same as Lincoln Park except it’s a little more of a party-ish area and more for tourists and consumers. There’s a ton of sight-seeing, shopping stores, clubs and dancing bars here. Same prices but a little older age range. Definitely a fun area to hang out in if you don’t mind the whole upscale atmosphere.

The Gold Coast

They don’t call it the ‘gold’ coast because it’s shiny, trust me. It’s super upscale and luxury is a given here. Most residents here are wealthy and older. In fact part of this area is called the Viagra Triangle (rich old men with young wife/girlfriends). I hear Oprah has a place here by the lake! There’s also lots of luxury clothing and jewelry stores, so bring a fat stack if you plan to shop here.  #Racks.

South and West Chicago

You’ve probably heard some not so good stories about these parts of Chicago and although some may be exaggerated, they do have some degree of truth to them. Be cautious of your surroundings and if you get a bad feeling in your gut, listen to it and turn around. The general rule of thumb is that the more south or west you go, the sketchier it gets. Specifically close to and south of highway 55 and also west of West Town until Oak Park.  

That said, there are some good spots on the south side. One of the up and coming neighborhoods is Pilsen - just south of UIC with an eclectic mix of students, artists, professionals and old schoolers, who are mostly long time Mexican immigrants. Easy to get to by the 'L', go to Pilsen for cheap drinks, unpretentious crowds and good Mexican food!

Another south side neighborhood that you might visit is Bridgeport. That is where the Chicago White Sox play. But good bars are few, especially if you are looking for a crowd at late night. Still, many people do choose to live here because it is a lot cheaper than the north side and conveniently near downtown and the 'L'.


Public transportation is yet another way to get around Chicago and definitely useful. Don’t be scared of the stories you may have heard about public transportation, it’s really not that bad. Just be mindful of your surroundings and know which stops to get off at. If you feel uncomfortable you can always move to the next car over or sit at the car with the operator.

I know when I first got here I was very confused and overwhelmed with all the different colors, numbers and routes you needed to know when taking the ‘L’, the metra or the bus, but have slowly figured it out. Let me speed up the process for you.

The “L”

Back in the 1940’s, there were no subways so the railroads were elevated like you see on Lake St. For short, people called it the “L” and the name’s stuck ever since. The L is a 24 hour train system (except the Purple Line Express to Downtown) that solely serves the downtown area. There is a train that comes from each direction and each train route meets at Grand Central Station in Chicago’s downtown Loop. The L has a color coded system and each color serves a different direction (for the most part) of the city. Refer to the route map on the CTA’s website to get a better look. Once you’ve figured out what route best serves you, you’ll need to figure out the cost. There’s a few ways to pay, here’s a quick overview:

Ventra Card – Meant for people who use the train frequently, a Ventra card is like the L’s debit card. You buy the Ventra card for $5 and can put money on it like a regular card. This is very convenient as you don’t need to continually pay for an individual pass and can just swipe at the gate and enter. Consider this method if you know you’ll be using the train a lot.

Individual Ventra Passes – If you know you’ll use the train rarely, this is the option for you. Near every gate, there will be vending machines which you can use cash or card to get individual passes. It’s $2.25 one-way regular fare but there are discounts available for disabled people, the elderly and students.

Special Passes – For one reason or the other, sometimes you might need to use the train continuously for a set period of time and then not as often or want to save money. For this option, there are passes you can buy in 1, 3, 7 and 30 day increments priced at $10, $20, $28, $33 and $100 respectively. You can also get a yearly pass if needed.

Once you’ve bought your pass, go ahead and swipe your card over the scanner and push through the gate. Follow the signs and wait for the train at your terminal. If you need help, there should be an operator by the gate there to help. The train shouldn’t take more than 10-15 minutes to arrive so just hangout till it does. After you’re on the train, pop a squat and admire the scenery. The beautiful concrete walls bring a tear to my eyes sometimes. There are also poles to grab onto in case you need to stand.  There will be announcements every stop as to where you are and what the next stop is and if you miss that, there’s also a map on the wall of every car giving the trains route. Sometimes you may need to transfer over to another line at a connection. Transfers are $0.25 at the transfer gate. When you reach your destination, go ahead and follow the signs out up the stairs and breathe some fresh air, you’ve survived!

The Bus

Taking the bus is another way to get around that may seem less desirable to some people but is actually very convenient. The bus system works with numbers, not colors. The same bus is assigned to a certain route. For example, bus 66 serves Chicago Ave. Find out the buses you need to take here and plan out your trip. If you’re a little nervous, don’t worry, you can always ask people at the bus stop or the bus driver for help. They don’t mind. Also keep in mind that not every bus goes all night, ask to make sure.   Once on the bus, you can pay $2.25 with cash or swipe your Ventra card since they also work for the bus system. Transfers are $0.25, so the pricing system is very similar to the L. Grab a seat if you can, otherwise there is space and handlebars to use for standing. The buses stop as select areas not more than a few blocks apart so if you need to get off another street, pull down the wire by the window when you get near where you need to get off to let the bus driver know ahead of time. Say your pleasantries and step off the bus…congratulations, you’ve made it!

If you want more information about the CTA and its fares, check this out. There’s also a Ventra app you can download to easily see your balance, transfer money into, etc. so look into that if convenient.

The Metra

This is another train system that serves the greater Chicago area, like the suburbs, to the city. Don’t confuse this with the L. They don’t use the Ventra system and are kind of old school in that they use tickets. Like the L, you can get special passes and discounts if needed. It’s quite a bit of detail to explain but there’s a handy info graphic you can look at. Go here and click the download link in the top right corner to get an overview of the fares and a map for the Metra. Generally, the further away you are from downtown, the more it costs to travel in but it’s only up to $10-ish one way, so that’s not too bad. The Metra is a little more safe and convenient than the L for those of you that have to commute for work.


Lastly, you can use Uber or Lyft. If you haven’t heard of Uber/Lyft, it’s basically a modernized taxi system. Individual people use their own cars to drive you to your destination using the Uber/Lyft app. Simply download the app, put the relevant financial information in and request an Uber/Lyft. The system then uses GPS to find your location and match you up with a driver to pick you up not more than 10 minutes away. It’s reliable, cheaper, faster than a taxi and very useful in big cities like Chicago. There’s also a rating system for drivers to assure you you’re not getting some random creepy stranger. Since I don’t live very close to the train line, I use this service quite a bit when I go out to Meet People Chicago events and it runs me $10-$20 total on average.

Try to explore all of these options and see which ones you work with best. In some cases, transportation can make or break your decision to stay or move. This will definitely take some trial and error, but don’t give up! You’ll make it, I believe in you ;).


Sam Amir | Superhost | Meet People Chicago 
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