How-to Guide: Living in Chicago


You made the move. You’re no longer a Chicago visitor but instead a full-fledged Chicagoan. Now it’s time to start acting like one. There’s always a learning curve when you move to a new city. You have to learn to navigate public transit, find the best hot spots, learn basic etiquette and figure out which parts of the city to avoid. Chicago is a major city with lots of little quirks. You can learn by trial and error as you go, or you can follow our advice on everything from the best Chicago life hacks to things you should never say if you want to pass as a real Chicagoan.

Chicago Life Hacks

When you’re new to Chicago, it can seem intimidating or frustrating to do everyday tasks. Getting from point A to point B can be quite the ordeal when you aren’t familiar with the city, but it doesn’t have to be so difficult. Here are some of our favorite simple life hacks to help you jump right in to Chicago city living:

  • Get a Ventra Card. Unless you enjoy white-knuckling it through the Chicago traffic and squeezing your car into an impossibly small spot, you’ll likely rely on public transit to get to and from work and around town. The Ventra card saves you time and money. Buy an unlimited monthly pass, add it to your Ventra card and you can buzz around town as easily as touching your Ventra Card to the reader on buses or at train stations. If you don’t use public transit enough to warrant the monthly pass, add money to pay as you go with the Ventra Card.
  • Rework your schedule to avoid busy times on the train. Your workday ends at 5pm. Guess what? So does everyone else’s — or at least that’s how it will feel when you have to cram into the train with all of your fellow Chicagoans. It can get quite uncomfortable. If possible, rearrange your schedule so you can get on the train earlier or later. Ask for some wiggle room in your work schedule, or tackle some errands close to the office after work before you head home. This can help reduce the number of people you share the train with.
  • Learn the Pedway system. You probably already noticed our trains are overhead instead of underground. What you may not know is that we have an intricate system of underground tunnels in the downtown area. It’s a great way to get around to several retail locations, different CTA stations, even City Hall, all without dodging traffic or trudging through piles of snow. Give yourself time to learn the system, though. It’s easy to get lost if you don’t know where you’re going.
  • Don’t leave the house unless you’re prepared for drastic weather changes. Chicago weather can be unpredictable. One minute you’re freezing. The next you’re sweating and trying to peel off layers. If your plans for the day will keep you away from home for several hours, be prepared for whatever comes your way. Wear layers, or pack a bag with a change of clothes. And keep a few backup umbrellas on hand. The wind can do a number on an umbrella around here.


Worst Intersections in Chicago

We can’t lie: driving in Chicago is no picnic. Let’s just say not all drivers are considerate. You’ll get cut off. You’ll have to fight (almost to the death) for a parking spot. And you’ll discover intersections that look like a bunch of drunken college kids designed them after a night of partying.

Knowing which intersections are worst is half the battle. If you can’t avoid them completely, you’ll at least be able to mentally prepare for the stress and confusion they may cause — and the long wait from all of the backed up traffic. Here are a few of the worst:

    • Damen, Milwaukee and North Avenues: What could possibly go wrong with three streets converging into one intersection? That must have been what the planners said when they designed many of the intersections in Chicago. Damen, Milwaukee and North is one with a bad reputation. With six corners, you have cars, pedestrians and cyclists going every which way, all hoping to make it through the intersection in one piece. Pedestrians at this Wicker Park intersection are known to cross outside the crosswalks, and traffic is regularly backed up in all directions. You’ll need to meditate or pour yourself a drink once you make it through this intersection and to the safety of your new Chicago apartment.


    • South Chicago, 79th and Stony Island: Not only is this another three-street intersection, beams from overhead entrance and exit ramps add to the challenge. You don’t have a wide field of vision to see oncoming traffic. If you’re turning left, hold your breath and hope for the best.


    • Irving Park, Milwaukee and Cicero: Yet another six-corner intersection, this one also makes the list of worst intersections. With lots of shopping centers and side streets nearby, it’s not easy to get through this intersection without mumbling some not-so-nice words under your breath.


    • Belmont and Kedzie: It may only be a two-street intersection, but Belmont and Kedzie is no walk in the park. This intersection rests below the Kennedy underpass. The lighting is bad. Concrete posts are everywhere. In short, visibility at this intersection is horrible. Watch for cars entering and exiting the expressway if you must use this intersection.


Whether walking, driving or cycling, these intersections are dangerous and often difficult to navigate. Here are a few others that make the worst intersection list:

  • Cicero and I-55
  • Halsted, Fullerton and Lincoln
  • Western, Diversey and Elston
  • Cicero and Chicago
  • Cicero and Madison
  • Dearborn and Ontario

Things You Won’t Hear a Chicagoan Say

Some things are better left unsaid, mainly because they will instantly brand you as an out-of-towner. If you want to sound like a true Chicagoan, you should avoid certain statements. Chicagoans tend to have strong opinions on some matters, and they’ll let you know if you say something they don’t like.


Without further ado, here are statements you’ll never hear from the mouth of a Chicagoan:

  • “We should hang out at Navy Pier. It’s my favorite spot.”
  • “Parking is never a problem in Chicago.”
  • “No, really. You take this parking spot. I’ll just look for another one.”
  • “It’s so cheap to go to a Cubs game.”
  • “I don’t think I’m going to drink at the Cubs game.”
  • “Chicago elected officials are the best!”
  • “Can you hold the mustard on my hot dog? I prefer ketchup.”
  • “This L car smells amazing!”
  • “Michigan Avenue is full of great deals.”
  • “Winter in Chicago isn’t so bad.”
  • “I can’t wait for winter.”
  • “Winter is my favorite season.”
  • “Michael Jordan had an okay career.”
  • “Should we head to the ‘burbs to party tonight?”
  • “I love all the lakefront roller bladers.”
  • “Rush hour really isn’t that bad.”
  • “The drivers here are so considerate.”
  • “The cyclists here follow all the traffic rules. I never see them running red lights.”
  • “Sox. Cubs. They’re both fine teams. Who really cares which one you support?”
  • “It’s Willis Tower now.”
  • “St. Patrick’s Day really isn’t a big deal around here.”

Things That Out-of-Towners Don’t Understand About Chicago

Once you’re here, you’ll learn the ins and outs of Chicago life fairly quickly. But that doesn’t mean your friends and family will understand what it’s like to live here. Be prepared to explain a few things when you have out-of-towners visit. Here are a few of the things Chicagoans have to explain to outsiders:

    • The Loop is not the place to see or be seen. Especially after 7pm. Bars and restaurants close early — usually before midnight. The true gems aren’t in the city center anyway. The same goes for Navy Pier. It’s not a place that Chicagoans go. It’s a tourist spot. End of story.
    • The Cubs aren’t the only team in Chicago. Sure, Wrigley Stadium is a treasure, but the White Sox have die-hard fans just like the Cubs. In fact, Chicagoans are pretty divided and aren’t afraid to fight for their team — sometimes physically. If you look back to the 2005 World Series winner, it’s not the Cubs. The Sox brought home that title. We’re fine with you cheering for either team, but please don’t forget there are two.
    • Wrigleyville is a great place to party, even if the Cubs lose. Go to the area around Wrigley Field — especially on game day — and you’re sure to find a party. Most establishments in this area are a lot cheaper than places downtown, which means you can stretch your party budget. Take your out-of-town guests to Wrigleyville when they want cheap drinks and a party atmosphere.
    • If you truly want to experience Chicago, come in the summer. Winters here are brutal. The lake effect means we get a lot of snow. And it lasts a LONG time, basically Halloween to St. Paddy’s Day. It doesn’t bring everything to a screeching halt, but there is a distinct difference between Summer Chicago and Winter Chicago. The streets come alive in the summer, and the city is full of people, fun festivals and warm weather activities.
    • It’s still the Sears Tower. It doesn’t matter what the official name is. You won’t hear a Chicagoan refer to this iconic building as the Willis Tower. To us, it will forever be called the Sears Tower.
    • We don’t say “Lake Michigan,” “Chi-town,” or “the Windy City” to describe Chicago. Around here, we simply refer to Lake Michigan as The Lake. And calling Chicago “Chi-town” or “the Windy City” is a sure way to identify yourself as an out-of-towner. On a side note, the Windy City nickname doesn’t come from the weather. It actually refers to all the hot air from the blowhard politicians that like to call Chicago home.
    • Parking is a sore subject and not easy to find. Expect to pay a lot to park. And that’s if you’re lucky enough to find a spot where you’re allowed to park without a permit that is anywhere close to your destination. As much as Chicago has to offer, ample, easy-to-find parking at an affordable price is not one of them. And you will get ticketed or towed if you don’t obey the parking rules.


    • People from the suburbs often say they’re from Chicago even though they’re from, well, the ‘burbs. When you’re out at the bar having drinks and you meet your soulmate, don’t forget to calculate how much that cab ride is going to cost you to get back from whatever suburb she’s actually from.
    • Watch out for bikes. No, seriously. They don’t always follow traffic rules. Whether you’re driving or walking, you may experience a close encounter with a bicyclist speeding along, weaving in and out of traffic.
    • Bars close at 2am…or 4am…or 5am. What? It’s true. Last call is not always last call if you head to one of the late-night bars that serves alcohol until 4am. And on the weekends, those bars may stay open until 5am. You can thank the special liquor licenses for giving you more time to make poor decisions.
    • Housing is actually affordable here, especially compared to other major cities. The average rent in Chicago in November of 2015 was $1,653, according to Zillow. The median home value is $200,300 if you prefer the homeowner route. Either way, you can find an affordable place in Chicago.


Unspoken Rules of Living in Chicago

You’re getting the hang of this living-in-Chicago thing. You know how to get around town. You’ve found a few favorite spots, made some friends and tried some local restaurants. But do you know how to act like a true Chicagoan? As nice as we are here, we do have some expectations.

To avoid rubbing your fellow Chicago residents the wrong way, make sure you follow these rules of living in Chicago:

    • Be courteous when walking down the sidewalk. If you’re on your own, don’t walk right down the middle or wander in an unpredictable path. If you’re with friends, don’t take up the whole sidewalk, making it nearly impossible for anyone to pass. Most of us need to be somewhere on time, or we simply walk at a fast pace. We’ll get cranky if we get stuck behind you. We probably won’t say anything, but we’ll definitely be thinking not-so-nice things about you. We may even give you a look.
    • Know how to use the escalators. It doesn’t seem difficult. The stairs move for you. You simply go along for the ride, right? Wrong! Sure, the moving aspect helps you along the way, but we expect you to walk up those escalators, folks. If you insist on standing still and letting the escalator do all the work, please, please, please stand to the right so that the rest of us can walk up the left side.
    • Ride courteously. If you brave the streets of Chicago on a bicycle, please follow traffic rules. Remember those horrible intersections we discussed? They become so much worse when a cyclist decides to run a red light or weave in and out of traffic. Even on the less dangerous streets, it’s always best to follow the rules of the road. You’ll significantly improve your chances of arriving at your destination in one piece, and you’ll make the drivers around you a lot happier.
    • Pick a team. Cubs or Sox. We won’t hold your decision against you (unless you choose the wrong team), but you must decide. And you must stay loyal to said team until your dying day. It’s in the rule book.
    • Learn to make good recommendations. When people find out you live in Chicago, they’ll start asking you for all sorts of recommendations. What’s a good restaurant downtown? Where’s the best place to listen to live blues? How do I get around in downtown Chicago? If you’re going to represent our city, you need a solid response to all of those appeals for recommendations. Sending people to chain restaurants, touristy spots or generally bad places makes the whole city look bad.
    • Find out about your ward and alderman. Don’t have a clue what a ward or an alderman is? Find out. It’s important. Contacting your alderman is one way to share your concerns. Sure, you may not get much of a response. Chicago elected officials aren’t exactly popular, but it’s still important to be involved (or at least know who represents you).
    • Stop calling it Chi-Town. Or the Windy City. Just don’t. It’s Chicago, plain and simple. You just sound like you’re trying too hard or don’t know what you’re talking about when you use either nickname.
    • Don’t bash our heroes. Michael Jordan will always be the greatest. The Bears always have a chance. Everyone knows who Ditka is. Please don’t argue with us on these points. While we’re at it, don’t even suggest any city could trump Chicago. Saying Chicago is like a mini-New York is not a compliment. If you claim that New York (or any city for that matter) is better than Chicago, you might as well start packing your bags and make plans to move there. We’ll defend the greatness of our city every time.
    • Don’t ruin a Chicago-style hot dog with ketchup. In fact, it’s not even a Chicago-style hot dog once you put ketchup on it. You won’t be chased out of the city by pitch-fork-wielding Chicagoans if you ask for ketchup, but be prepared to catch flack for the request. Mustard is the acceptable condiment on a Chicago-style hot dog. Give it a try the Chicago way just once, even if you don’t think you like mustard.


  • Invest in some serious winter gear. We’re not joking when we say the winters are brutal. Don’t wait until the worst weather hits. Get the best parka you can find, along with a collection of waterproof boots, hats and gloves. You’ll use them for more months of the year than you’ll want to admit. And learn to layer. Even the best winter coat can’t keep the chill out completely.


Rites of Passage to Become a True Chicagoan

You have a Chicago address, but are you a true Chicagoan? Some might argue you have to go through a few rites of passage to truly claim the title. If you’re not quite sure whether or not you’re a true Chicagoan, consider these Chicago rites of passage as your checklist for joining the club:

  • You successfully navigate the Pedway and don’t get lost once. Bonus points if you do it without a map.
  • You successfully navigate a multi-leg CTA trip — bus, bus, L, for example. And it didn’t take you all day.
  • You argue with a cab driver when you pull out a credit care to pay. It’s your legal right to pay with a credit card, but that won’t stop many cab drivers from doing whatever they can to convince you not to use your plastic. If you plan to pay for cab fare with a credit card, be prepared to stand your ground.
  • You use the names for the highways instead of their numbers. I-290 is the Eisenhower. I-90 is the Kennedy. I-55 is the Stevenson. You get the point.
  • You’ve had to claim your car at Chicago Auto Impound. Bonus points if the words “Lincoln Towing” make you quiver. The tow zone signs are no joke. It’s okay. We all learned the hard way.
  • You call out a suburbanite on his claim to be a Chicagoan when we all know he didn’t earn that title.
  • You’ve seen someone urinate — or worse — on the L. Just don’t let yourself be that person. No one wants to be that person.
  • You have a favorite hot dog stand. You order your hot dogs Chicago-style with the works. You don’t use ketchup.
  • You order your Italian beef dipped. Wet is the way to go.
  • You declare your allegiance for either the Sox or the Cubs and you stick with it. If you choose to cheer for the Cubs, this means you must continue supporting them even when they lose. And also, be prepared for them to lose. A lot.
  • You claim “dibs” on a parking spot in winter with a chair or other large object. Hey, all’s fair in love and parking spots…or something like that.
  • You’ve argued with someone over the practice of calling “dibs” for parking. It’s a yearly debate once the snowflakes start swirling. If you haven’t noticed, we Chicagoans are divided on several issues.
  • You give directions to a tourist, and you actually know what you’re talking about.
  • You’ve had a run-in with the Old Navy preacher. If you don’t know what we’re talking about, head to the State Street Old Navy so you can check this one off your list now.
  • You learn to appreciate Jeppson’s Malört. It’s a Chicago-made beskbrännvin. It’s basically wormwood-based Swedish schnapps. If you didn’t know that before we explained it, this is still on your must-do list before you can claim the Chicagoan title. Buy your bottle at Binny’s for extra Chicagoan points.
  • You stop wondering if you’re a true Chicagoan.

Don’t worry. It takes time to accomplish every rite of passage. This is one thing you can’t rush.

Things That Will Happen Once You Move to Chicago

Part of moving to Chicago is all of the potential for adventure. You never know what will happen. It’s part of what appeals to Chicagoans, but there are certain things that are bound to happen to you eventually once you take up residence in Chicago.

You may not be able to avoid them, but knowing about them at least prepares you for the following things that will happen when you move to Chicago:

    • You will change your definition of “shorts weather.” As your first Chicago winter winds down and spring seems like a possibility, 40 degrees seems balmy and worthy of throwing on your best pair of shorts.
    • You will learn to start asking people specifically where they are from when they claim to live in Chicago, because, as we covered, many of those suburbanites who like to party with us will claim Chicago as their home, even if they live over an hour away.
    • You will get used to all of the corrupt politicians. It’s pretty common here. What can we say? It can’t all be sunshine and roses.
    • You will master parallel parking, assuming you own a vehicle. If you refuse to parallel park in some pretty tight spots, you’ll spend your entire day looking for parking.
    • You will defend your team, whether you choose to root for the Cubs or the Sox, because that’s what we do. We live and die for our teams. And we’re not afraid to tell fans of the other team that they are wrong.
    • You will base decisions about everything from job offers to dates on the commute time or the proximity to an L stop. Something or someone has to be seriously worth it if it’s not near the L.
    • You will learn that life — and work and school — goes on even during a blizzard. Have we mentioned how brutal the winters are? Chicagoans keep going, snow or not. But trust us, there will be snow. A lot of it. Do you have your parka yet?
    • You will gain weight in the winter. It all goes back to the cold and snow. Life may go on, but all those summer activities that kept you active aren’t possible in the winter. Hit the gym twice as hard, or just accept that winter and weight gain go together in Chicago.
    • You will fall in love with architecture. Or you’ll at least marvel at our beautiful skyline. The architecture here is pretty amazing.
    • You will become a pizza aficionado. You will know the difference between stuffed deep dish and thin crust. You will explain what makes Chicago’s pizza so great to all of your non-Chicago friends.


    • You will quickly learn what goes on a Chicago-style hot dog. We’ve already covered that ketchup is in no way involved.
    • You will grow to appreciate just how clean Chicago is compared to other large cities.
    • You will learn to love public transit. It’s so much better than battling for a parking spot.
    • You will start defining people by the Chicago neighborhood they live in. It may be stereotyping, but many of our neighborhoods have very distinct vibes, and the people who live there often fit that mold to some degree.
    • You will quickly learn and understand the grid system that is the basis of Chicago. It all starts at Madison and State Streets, which is the center of the grid. As you move away in any direction, each block goes up by 100. It actually makes it quite easy to navigate, that is if you could remove all of the traffic, pedestrians and cyclists in your way.
    • You will learn that Chicago has beaches. You can only use them a few months each year, but we do have them. And Lake Michigan is almost like an ocean.


What’s Coming Up in Chicago in 2016

There’s no shortage of entertainment in Chicago. Even in the cold winter months you’ll find a variety of warm indoor activities. Art festivals, street fairs, beer fests, food showcases, cultural fairs, theatrical productions and world-class music are a few of the categories of activities you’ll find in Chicago throughout the year.

It’s impossible to cover all of the events, but here are a few highlights in 2016:

    • Chicago Restaurant Week, January 22 to February 4, 2016: It’s called Chicago Restaurant Week, but you actually get two weeks to enjoy special prix fixe menus at hundreds of amazing restaurants. It’s a great way to try some new eateries so you can work on that list of recommendations for out-of-towners.


    • Blue Man Group, February 4 to April 10, 2016: Experience all of the special effects, comedy and music in a new Blue Man Group show at the Briar Street Theatre.
    • Chicago Theatre Week, February 11 to 21, 2016: Chicago Theatre Week fires up just after Chicago Restaurant Week winds down. Explore the wide range of theatrical offerings in Chicago with more than 100 productions offering special pricing for the event.
    • Chicago Polar Plunge, March 6, 2016: What better way to embrace the Chicago cold than to willingly wade into the frigid waters of Lake Michigan in March? This annual North Avenue Beach event is a fundraiser for Special Olympics Chicago, so the frostbite is totally worth it. If you don’t feel like braving the Polar Plunge just yet, watch from the beach.
    • St. Patrick’s Day Parade and River Dying, March 12, 2016: We know St. Patrick’s Day does not fall on the 12th, but in Chicago, the parade always happens on Saturday. You may have heard we take our St. Paddy’s day celebration very seriously, so we always party on the weekend. If the 17th doesn’t fall on a Saturday, we celebrate the Saturday before. This is an event you need to experience. Watch the river flow green, and stick around for the parade at noon with more activities afterwards.
    • Baconfest Chicago, April 30 to May 1, 2016: The name says it all. Top chefs from Chicago create their best bacon dishes and drinks. If you love bacon, and who doesn’t, you’ll want to add this to your list.


    • Chicago Critics Film Festival, May 20 – 26, 2016: Held at Music Box Theatre, this film festival is completely created and curated by film critics. Check it out if you like flicks.
    • Wright Plus, May 21, 2016: If you’re intrigued by architecture or history, check out the Wright Plus walk, featuring tours of homes designed by Frank Lloyd Wright and his colleagues from Prairie School. It’s your chance to go inside these innovative buildings.
    • 57th Street Art Fair, June 4 – 5, 2016: Explore original art at this free festival, which is the oldest juried art fair in Chicago. You’ll find lots of other art fairs throughout the summer all over Chicago. It’s a great way to discover new artists. Support the talent you discover, and decorate the walls of your new Chicago pad at the same time. If you love art, you’ll feel right at home in Chicago.
    • Chicago Blues Festival, June 10 – 12, 2016: Grant Park fills with some of the best blues musicians during the Chicago Blues Festival. Plan to continue the party at local bars and clubs.
    • Taste of Chicago, July 6 – 10, 2016: Enjoy food from 33 restaurants, sit in the wine garden, drink in the beer hall and enjoy live music.
    • Lollapalooza, July 29 – 31, 2016: You can’t talk about Chicago events without mentioning Lollapalooza. Everyone has heard of it, even those who aren’t fans of alternative rock, punk rock, heavy metal and hip hop. Enjoy music and activities over three days at Grant Park.


  • Chicago Air and Water Show, August 20 – 21, 2016: Enjoy daring displays in the sky and on water with parachuting, jets, water skiing and boat jumping. It all happens near the North Avenue Beach.
  • Christkindlmarket, November 20 to December 24, 2016: This open-air Christmas market makes you feel like you were transported to Germany. Daley Plaza fills with vendors selling traditional European-style gifts, art and other items, along with German food and drink to keep you satisfied. You’ll also hear choirs and carolers to create the Christmas feeling.
  • Thanksgiving Parade, November 24, 2016: Watch as giant balloons, marching bands and floats make their way up State Street on Thanksgiving Day.

Welcome Home

There it is. The complete guide to being a true Chicagoan. We know it’s a lot to take in, so we’ll give you a break if you mutter the occasional “Chi-Town” or forget to walk up the escalators. Share your Chicago experiences with us, and share this guide!