20 Living in Chicago Pros and Cons

The city of Chicago has played an extensive role in the development of American culture, economics, and political history since its founding. It has also served as one of the primary Midwestern metropolis areas since the 1850s. Although French explorers arrived in the region in the late 17th century, the modern city was incorporated in 1837. It grew rapidly thanks to real estate speculation and the position that the city would serve for transcontinental transportation networks.

Even though the Great Chicago Fire in 1871 destroyed the central business district of the city, it would continue to grow through a combination of commerce, education, manufacturing, and eventually broadcasting. European immigrants flooded to the city between the 1890s and World War I, all becoming part of what would become an atmosphere where aggressive labor unions demanded high wages and offered sometimes violent strikes to get what they want.

Although Chicago suffered greatly when the steel industries and stockyards restructured, a focus on improved housing, public programs, and administrative work helped to promote a recovery. You will also discover that the independence and confidence that help this city become a leader on the global stage is still present when you live here.

These are the pros and cons of living in Chicago that you will want to know about before moving.

List of the Pros of Living in Chicago

1. It is easy to move around when you live in Chicago.
Chicago is a city that, for the most part, is a place where you can walk to your intended destination. Although there are a handful of neighborhoods where gang activities or crime would not make this feasible, you can access most areas of the downtown region of the inner city without difficulty. It is also home to the second-largest public transportation system in the United States, offering enough bus and rail options that you may not need to own a car. There is also an authorize bike sharing system that you can use in the city.

2. You have access to a central transportation hub for easy global travel.
If you love to travel around the world, then living in Chicago makes a lot of sense. With the access you have to O’Hare International Airport, you can travel nonstop to virtually any destination that you may wish to see one day. It is the second-busiest airport in the world, giving you access to regional flights (like Madison, WI) just as easily as you could fly to Tokyo or Prague. When you add in the Amtrak regional hub that is serviced through Central Station, you will discover that it is easy and affordable to go where you want.

3. Chicago sits on the shores of Lake Michigan.
Although Lake Michigan doesn’t provide an ocean beach, this body of water is one the largest of its type in the world. When there are warm summer days in the city, you can take a stroll along the lakefront to cool down whenever you want. There are festivals, barbecues, and parties happening throughout the year. Over 30 miles of beach are accessible in the city, with even more available if you have the means to own a boat.

You will find one of the landmarks of the city, Navy Pier, located along the beach as well. It extends 3,300 feet into the water, plus offers over 50 acres of parks, shops, restaurants, and attractions that bring 2 million people to the beach each year. It first opened to the public in 1916. It earned its name after World War I to honor the veterans who served, and then was even used as a training center for the Navy in World War II.

4. The sports culture in Chicago is world-class.
Chicago has earned the distinction of being named the Best Sports City in the United States a total of three times by the Sporting News. There are two MLB baseball teams to see (Cubs and White Sox), you can experience the NBA thanks to the Bulls, and hockey is represented by the Blackhawks. The Chicago Bears are the NFL team, where you will still hear about their 1985 Super Bowl win when visiting the bars in the city. Michael Jordan references are everywhere. You can also catch soccer in MLS by going out to Bridgeview to see the Chicago Fire or women’s soccer with the Red Stars.

5. Chicago is the Midwestern hub for U.S. culture.
You can spend weeks touring the various museums that are available in Chicago and never see the same exhibit twice. The variety of different places and opportunities is almost beyond compare in this city compared to other urban centers across the country. You have The Art Institute of Chicago, the Field Museum, and the interactive Museum of Science and Industry to go see for starters.

There is also the Adler Planetarium, the Chicago History Museum, and the Shedd Aquarium to tour. One of the unique benefit of living in this city is that you really can explore the entire world without ever leaving its borders. Just make sure that you know about whatever admission costs may apply because some locations can be quite expensive.

6. You will fall in love with the food that is available in Chicago.
The first thing that you must do after you start living in Chicago is to have a world-famous Chicago hot dog. With its combination of toppings and flavors with an all-beef frank, there isn’t a better option (arguably) available in the world today. Then you have all of the other city-style food options that are available, such as deep-dish pizza, Polish sausage dishes, Italian beef, gyros, butter-crust pizza, Jibarito, Chicago-style popcorn, and fantastic Italian restaurants dotted throughout.

You can have a great time visiting some of the city’s attractions, such as Millennium Park and the Aragon Ball Room, but it is even better when you have something tasty to munch on during your visit.

7. The architecture in Chicago is truly unique for a Midwestern city.
The city has a reputation for being a “laboratory” for architectural experimentation and innovation. You will find a unique combination of traditional, modern, Graystones, and skyscrapers all contributing to the experience. What is unique about Chicago is that the city is known more for its originality than something antique or specific, which means the melting pot of visual aesthetics is representative of the numerous cultures that you will find thriving in the 77 different neighborhoods that are available to you for settling down.

8. It is exceptionally easy to navigate the city streets if you get lost.
Getting lost in Chicago can happen, especially if you find yourself in a new neighborhood. If you know how the city numbers their streets, then you will be able to find your way back home with relative ease. There are eight city blocks per mile in the city, with 100 address numbers offered on each one. That means there are approximately 800 numbers per mile. The center of the street grid is Madison Street for the north/south and State Street for the east/west. By tracking the numbers and your street position, then you can always know how far you are from the center of town.

9. There are numerous starter homes available in the Chicago market today.
When you look at entry-level housing as its own category, Chicago is the second-largest market in the United States for supply of these homes. Although the median price of these properties is $295,000, with an average home value of $222,000, it is still more affordable to live here compared to a city like Los Angeles or New York. Even renting in the city is cheaper, with a one-bedroom apartment price $1,600 per month lower than LA and $1,200 less than in NYC. If your goal is to buy a home and stay there in a metro area for a while, then Chicago is one of the most affordable places for you to be.

10. You will find plenty of shopping opportunities available in Chicago.
This city has some serious style. Although some might not call it a first-rate shopping destination, you might change your mind after spending a day on the Miracle Mile. Michigan Avenue offers restaurants, high-rise malls, and numerous boutiques that mix with name-brand items and luxury goods for a unique experience.

That is only one of the places to explore with this advantage. Wrigleyville is where you will want to go to purchase the sports gear of your favorite team. Visiting Oak Street will allow you to find some designer-label options, with some stores tucked into old townhouses. There is also State Street to consider, which was the first shopping district in the city. Discount stores, affordable eating, and the largest Tiffany’s glass mosaic dome in the United States can be found there.

11. You can participate in the fun traditions that the city practices each year.
One of the most famous traditions that you will find in Chicago happens on St. Patrick’s Day each year. The city adds green dye to the Chicago River to let it flow green. This traditional began in 1962 and now draws over 400,000 people to experience it. You can grab a kayak and paddle in the light green waves underneath the bridges of the city if you wish.

The city also offers the most dance music festivals in the United States thanks to its invention of the house genre decades before. You will find the largest free outdoor food festival in the country when living in Chicago too, as well as a world-class blues festival that has free admission too.

12. Stores are open at all hours in the city if you need something.
It is not just the bars that are open late when you start living in Chicago. Everything is open at a time when most cities shut down for the night. Even if it is 3am, you can run down to the local grocery store to get that errand finished. There are Chinese or Mexican restaurants often right down the street that are still serving dinner (or an early breakfast). You can wander around if you want, have someone deliver the things that you need, and satisfy whatever craving you have.

It’s not just food and beverage locations either. There are open mic nights that extend well into the morning in Chicago’s cultural scene. You can play an obscure sport if you want. You can go dancing, binge movies at home, or take advantage of your preferred hobbies to create a wonderful and personalized experience when you call this city home.

List of the Cons of Living in Chicago

1. You will face a significant cost of living when you move to Chicago.
Chicago is one of the few places in the United States where even groceries are taxed (at a rate of 2.25%). There is also a 0.25% restaurant tax that you will pay if you purchase something ready-made to eat. You will face a combined 10.25% sales tax when you consider the local and state collections that occur on sales. The city also has the second-highest property taxes in the country as of 2019. You will need to consider all of these tax implications before you decide to move to the city to determine if you can afford it.

2. Crime is always something that comes to mind about Chicago.
The history of Chicago is one that is marked by the icons of Midwest crime, such as John Dillinger, Baby Face Nelson, and Al Capone. You can even find memorial markers to these men and others in certain places around the city. In recent years, the levels of murder happening in the city have dominated the news cycle. In 2016, nearly half of the national increase in homicides were due to the crime rate in the city.

There were 561 murders in the city in 2018, which is one of the most significant numbers in the country. That rate is still down significantly from 1992, when there were 943 in a city that had fewer people than it does today.

3. Traffic in Chicago can be very challenging at times.
The city only has seven mainline and four auxiliary highways that run through the city. Driving on the Dan Ryan or the Kennedy at rush hour can put you into standstill traffic for a considerable amount of time. You will need to plan for an extra hour (or two) when traveling to a specific destination in the city because it can take time to navigate the side streets when the highways are clogged. Drivers in the city lose 138 hours of productive time because of congestion, which is the third-worst rate in the United States as of 2018.

4. It can be an adjustment getting used to the city’s weather.
Chicago earns its nickname as the “Windy City.” The breeze can be downright brutal at times, depending on how the pressure systems move over the area with the presence of Lake Michigan. You will also experience the typical Midwestern seasons when living here, which means the summers are hot and humid, while the winters are cold and snowy. It is not unusual for temperature to get below zero with windchill ratings in the -30 during December and January. When summer comes, having temperature cross 100F is not unusual either.

5. The parking in Chicago is just as challenging as the traffic.
Although having a vehicle in Chicago can be an asset, it can also become a liability very quickly if you live or work somewhere that requires paid parking. Trying to find a spot can seem almost impossible. In the best-case scenario, you are going to need to become a parallel parking master to fit into the spots that are sometimes available. That’s why more residents, especially in the downtown center, use taxis or Uber because you can pay using your debit or credit card instead of carrying around a bunch of cash.

6. Your neighborhood defines you in Chicago.
The backbone of the city are the well-defined neighborhoods that make up the entire metropolis. Each offers its own set of culture, attractions, and personality to enjoy. Most residents settle into these areas and stay loyal to the specific segment where they live. On the North side, you will find an eclectic atmosphere that ranges from jazz to boutiques to baseball. Living on the West side will expose you to the city’s Mexican culture. The Downtown area is where all of the top attractions happen to be, while the South side features museums and monuments.

7. You will need to deal with the “dibs’ issue in the city.
Because Chicago is blessed with plenty of snow each year, you will find that street parking is limited thanks to an overall lack of driveway space. When residents clear out an area, then some feel like they have a right to continue using that spot indefinitely. That is how the “dibs” system gets its start. If you support this idea, then you’re entitled to the public space you clean out if you mark it properly. You will find lawn chairs, tables, and numerous other personal items blocking a parking spot in such a way. It can be fun from an outside perspective, but not necessarily so if someone calls the spot in front of your home.

8. The city has a lake, but you are going to be landlocked.
Lake Michigan can provide some relief to those who love a good beach. What you will not find available to you when living here are mountains or the ocean. You’re a good 2-3 days’ drive away from experiencing either option. If you like having these natural elements around, then you will find yourself sorely disappointed. The tallest point in the state of Illinois is called Charles Mound, which is 1,235 feet above sea level about 11 miles northeast of the small town of Galena.

A Final Observation About the Pros and Cons of Living in Chicago

Chicago is unique because it offers a small-town feel while still providing all of the benefits of a modern metropolis. People love their neighborhoods here, and will welcome you with open arms if you’re willing to contribute and support this local culture. It is one of the few cities where you can legitimately say that there is something for everyone. Most of the people are friendly, the crime isn’t as bad as it seems from the outside, and it is fairly easy to setup your life in a way that benefits you and your family.

The pros and cons of living in Chicago work to balance the job opportunities that are available with the safety of your family and the conditions to expect. There is an excellent public transportation system, which means many of the disadvantages don’t matter since others handle traffic and parking for you. If you dress for the cold, then you can manage it. When it gets hot, there is Lake Michigan to enjoy. Assuming that you can afford the experience, you will find this city is a special place to live.

Blog Post Author Credentials
Louise Gaille is the author of this post. She received her B.A. in Economics from the University of Washington. In addition to being a seasoned writer, Louise has almost a decade of experience in Banking and Finance. If you have any suggestions on how to make this post better, then go here to contact our team.