The Pros and Cons of Living in Chicago

So you’ve packed your bags and want to move to the Midwest? Here’s a list of pros and cons of living in Chicago for considering before you make your big move. 

Chicago is at the heart of the many cultural and economic movements that shaped the U.S.A as we know it today. From the glitz and glamour of the jazz age to the manufacturing powerhouse of the Chicago stockyard, this city has seen and done it all. Let’s start with the pros of living in Chicago first.

The Pros of Living Chicago

1. The History

Since its founding in 1781, the city of Chicago has played a pivotal role in the story of North America. What started as a small trading post at the mouth of the Chicago River has now become one of the most internationally renowned major U.S cities to date. 

Jean Baptiste Point Du Sable established the first permanent settlement in the area in the 1770s. Chicago then incorporated as a city in 1837. In the feverish height of American westward expansion during the 1800s, the Midwest proved to be an essential trading point as the settlers moved inland. 

The growing number of traders and travelers moving through Chicago set its place as the crossroads of U.S trade across the continent. Even up until today, 50% of the U.S national rail freight still passes through Chicago every single day.

2. The Architecture

Did you know that Chicago once housed the tallest building in the world?

The Home Insurance Building, finished in 1885, is considered the Father of the Skyscraper. It towered ten stories over the city at 138 feet high, which was undoubtedly a novel concept.

The city is known for being the center of innovative and experimental architectural concepts. After the Great Fire of Chicago devastated the entire city in 1871, architects and engineers worked closely together to use the real estate that was left available – the sky. This moment of ingenuity gave birth to the “Age of Skyscrapers.” Take a walk along the Loop, and you’ll see monoliths like the Sears Tower or the NEMA dominating the Chicago skyline.

Go to any city in the world, and you’re bound to see a skyscraper peeking through the clouds. The advances in engineering and architecture born out of necessity in the Windy City have made all that possible today.

3. The Sports

Competitive sport seems to be a way of life around here. Chicago is incredibly proud of its hometown heroes, and Sporting News magazine has named it “Best Sports City” thrice, most recently being awarded in 2010.

Chicago is one in only ten U.S cities to have teams playing for all major American professional team sports (Baseball, Hockey, Football, Basketball, Soccer). There is no doubt that the sports fans you meet in Chicago will be some of the most loyal and passionate fans you will ever find. With that kind of support, it’s no wonder that their teams are no strangers to bringing home the hardware.

From home runs at Wrigley Field to slam dunks at the United Centre, there’s always an exciting sports event to look forward to all-year-round. And of course, Chicago also gave the world one of the most celebrated professional sports franchises of all time – The Chicago Bulls!

Chicago's Wrigley Field
Wrigley Field – Photo by Heather Maguire on Unsplash

4. The culture & arts

Many cultural movements of the 20th century had its roots in Chicago. The stories of Chicago gangsters like Al Capone live on forever through movies and books until today. 

Jazz music first went international in Chicago, when the original jazz musicians from New Orleans in the south migrated north to the Midwest for employment opportunities in the manufacturing and meatpacking industries. You can spend an evening watching some cool cats playing and singing the blues at the aptly named House of Blues Chicago.

The Art Institute of Chicago, one of the oldest and largest art museums in the U.S, is home to a world-renowned collection of art pieces from artists such as George Seurat and Grant Woods. Tourists flock all year round to visit Millenium park, taking pictures with the iconic silver sculpture called “Cloud Gate” – or also known affectionately by the locals as “The Bean.” 

The Auditorium Theatre on Ida B. Wells Drive has staged thousands of shows since it first opened in 1889. It remains the oldest surviving theatre in Chicago, built into an existing building called the Auditorium Building. Designed and engineered by Louis Sullivan and Dankmar Adler, the Auditorium Building incorporated a hotel, offices, and retail spaces alongside the theatre. It was one of the first public buildings in the world to use modern technology such as electric lighting and air-conditioning!

With hundreds of theatres and live music venues running events almost daily, you’ll find something you’d enjoy watching in Chicago.

5. The food

The many food options available in Chicago are a testament to the diverse and multicultural flavors of the city. Whatever cuisine you crave, there’s always a place you can find to satiate your hunger. There is no question about the quality of food you can get from xiao long bao in Chinatown to a bowl of delicious ramen in Wicker Park. If you’re looking for something a little more local – there are plenty of eateries all around the city serving up some delightful Chicago favorites like the Italian Beef Sandwich, Chicago Hotdogs, Rainbow Cones, and of course who can forget – the world-famous Chicago Deep Dish pizza. The best part? Most of these restaurants open way past midnight. Perfect for a late-night post-bar bite on your way home. 

6. The shopping

Take a walk downtown through the Magnificent Mile, where luxurious designer brands and independent boutiques alike entice you with their perfectly curated storefronts and window displays. Chicago truly is a shopper’s paradise, with the Magnificent Mile alone boasting over 450 individual retailers and three vertical shopping centers. If you’re not interested in luxury retail, vintage shopping at the Randolph Street Market is available as well, with cool, rare finds waiting for you almost every weekend. 

7. The beach

Yes, Chicago has beaches! The entire 43km shoreline around the massive lake Michigan is entirely human-made. On hot summer days, locals and tourists alike head to the beaches to cool off and enjoy some sun, sand, and sea. Although it’s not exactly a holiday in the Caribbean – with 24 beaches to choose from up and down the Lake Michigan coastline, you can find your little slice of summertime paradise in Chicago. 

8. The connectivity

Home to the sixth-busiest airport in the world, Chicago O’Hare International Airport sees seventy-five million passengers going through its gates every year. Chicago O’Hare International serves over 2400 planes flying to 60 different destinations daily. This worldwide connectivity ensures that Chicago can get you where you need to go with ease. But, Chicago’s public transit infrastructure is also one of the best in the world. 

The CTA (Chicago Transit Authority) ferries close to five hundred million Chicagoans by bus and train around the city every year. The efficient public transit system helps get its people to work, and keeps Chicago’s economy going strong. An extensive bus and train network allows commuters to reach every corner of the city at an affordable price. There are also taxis, Uber/Lyft, and hire cars if you don’t feel like sharing your commute with others. 

Alternatively, the Pedway (Downtown Pedestrian Walkway System) is a series of walkable underground tunnels and overhead bridges that link over 40 blocks across a span of 5 miles right in the heart of the CBD. It’s especially useful during the harsh winter months to get around town without battling the cold weather!

The Cons of Living in Chicago

1. The weather

The winters in Chicago can get harsh. Brutally harsh. An average temperature of 17.2 degrees Fahrenheit during the winter months – just reading that would be enough to make your bones shiver. The lowest ever recorded temperature was in 1985, at -16.6 degrees below zero. The average annual snowfall in Chicago is relatively unchanged at 36 inches and snow is always well into the meteorological spring months. So expect to really enjoy your summers while they last!

2. The traffic

If you actually do find yourself owning a car in Chicago – there’s a high chance you won’t get to enjoy using it half the time. Chicago is known for having huge traffic jams that almost double your commute. This is before the nightmare that is finding parking in the city. It’s a game of cat and mouse trying to find a suitable parking spot for your car – and when you do find one, your time and gas wasted trying to find it far outweighs the benefit of driving to your destination. On average, drivers in Chicago spend more on parking than any other U.S city. Public transport remains a more efficient and cost-effective option for getting around the city.

3. The high cost of living

Being a bustling city home to over 8 million people, Chicago’s average cost of living is over 23% higher than the national U.S average. It ranks 29th out of 477 major cities in the world for the cost of living. Be prepared to fork out more for real estate taxes if you buy property, as Illinoisans pay out the second-highest real estate taxes in the U.S, at average more than 2% of the home’s value.

If you have a car, you’ll end up chucking a nice part of your salary out for high vehicle insurance and liability costs. Grocery taxes of 2.5% are enforced in Chicago, and it is one of the few U.S cities to actually have such a tax enforced.

4. The crime

The violent crime rate in Chicago is 164% higher than the national U.S average. Since the era of the mobsters of the 1920s like John Dillinger and Al Capone, Chicago has been a hotbed for gang activity, with an estimated 100,000 active gang members across 60 groups in the city alone this date. 

A long history of public corruption has also reduced trust in local government. An FBI operation in the 80’s called Operation Greylord – considered to be one of the most successful operations in FBI history – indicted over 150 government officials, including judges and police officers. They were convicted of charges such as racketeering, drug trafficking, fraud, and bribery. 

4. The “dibs”

The heavy snowfall that Chicago gets every year results in a lack of driveway space, and because of that, the already limited street parking is further reduced due to the heavy blanket of snow. Residents in the neighborhoods get around this issue by shoveling a parking spot in the common driveway, thus calling “dibs” on it for the rest of the season. This can happen even if it was right in front of your house. Lawn chairs, sunbeds, and all manner of random furniture will be used to mark the spaces that they will use. This form of entitlement to public space isn’t necessarily bad if you take the effort to clean out inches of heavy snow and mark a spot for your car, but if things get nasty – this can result in a severe neighborly dispute that may go on for a while. 

The Verdict

So there you have it, these are the pros and cons of living in Chicago. There are many other factors to consider, but these are just a few of the examples to start. 

Ultimately you decide to find a side of Chicago you like the best and as with any other city in the world – you probably just need to live with the best and worst of it. It’s exactly the same with people too! Find your balance, don’t be afraid to step out of your comfort zone, and always be happy wherever you choose to be.

Alan Behrens
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