Living in Chicago: The Pros and Cons


There’s a lot to love about living in Chicago, IL. But it’s not all roses and sunshine. In this blog post, we’ll explore some of the pros and cons of living in Chicago. Whether you’re thinking about moving to the Windy City or you’re already a resident, this blog post is for you.

The Pros of Living in Chicago

chicago skyline

1. Opportunity (Work)

There are a number of advantages to living in Chicago, but perpaps the greatest thing about the Second City is the sheer volume of possibilities, especially if you’re looking for business or employment opportunities. First of all, Chicago is home to a large number of Fortune 500 companies, which means there are plenty of job opportunities for advancement. 

2. Cultural activities

There are so many amazing things to do in Chicago. The city is home to world class architecture and some of the world’s most famous museums, including the Art Institute of Chicago, the Field Museum and the Shedd Aquarium.  There’s always something going on in Chicago. 

3. Outdoor activities

One of the best things about living in Chicago is that there is always something to do outside no matter what time of year it is. In the summer, you can enjoy biking or jogging along Lake Michigan, sunbathing on one of the city’s many beaches, or exploring one of the many parks or neighborhoods. And in winter, you can go ice skating at Millennium Park or take a walk down Michigan Avenue to see all of the holiday lights. Lincoln Park zoo is a great, free zoo for families.

4. Walkability

The city is incredibly walkable. Walking is great for exploring neighborhoods. You get to experience the vibe of the area and see things you wouldn’t otherwise notice from a car. And Chicago is one of the handful major cities in the country where you don’t need to own a car in the big city. One of the most popular things to do is take a nighttime walk along the Chicago river. 

5. Food scene

Chicago residents take their food seriously, and for good reason. The city has countless Michelin-starred restaurants, as well as more casual dining options to suit every taste and budget. From deep dish pizza and Italian beef to world-class sushi, from Polish to Chinese or Mexican restaurants, there’s great food for everyone in one of Chicago. 

6. Public transportation

Public transportation system in Chicago is excellent, with the city’s ‘L’ train system being one of the largest and most efficient in the world. The Chicago Transit Authority (CTA) runs 24/7 in downtown and nearby neighborhoods, contrary to Southern California where public transportation is a hit or miss.

7. Sports culture

Chicago is a sports city and home to numerous professional sports teams. The Windy City is known for its enthusiastic fans, sports bars and strong sporting traditions. From Chicago Cubs to Chicago Bears, there’s a team for everyone to root for in Chicago.

The Cons of Living in Chicago

chicago winter

1. Weather

Of course, there are also some drawbacks to living in Chicago. The most obvious one is the weather—the winters can be long and cold, and the summers can be hot and humid. Every year, temperatures dip below freezing and the wind chill makes it feel even colder. As the days grow shorter and the nights longer in the winter months, most people find that living becomes quite difficult when it starts getting dark and gloomy around 4 pm. The gloominess settles over everything, making it feel like the weight of the world is bearing down on us.

2. Cost of living

Compared to other cities in Illinois and the Midwest, the cost of living in the Second City is pretty high. Chicago’s housing costs are notoriously high compared to other cities. It is one of the most expensive cities in the United States and definitely not affordable. Living in Chicago and enjoying it to the fullest can be a challenge for many people. 

3. Traffic

Chicago has some of the worst traffic in the country. It can be a nightmare during rush hour, so if you’re commuting from the suburbs it may take you longer than you think to get into the city each day. It’s not uncommon for your commute to take an hour or more just to get from one side of town to the other.

4. Taxes

Chicago has some of the highest taxes in America. If you’re a resident of the Windy City, you’re probably all too familiar with the high cost of living here. From housing costs to the price of a cup of coffee, everything seems to be just a little bit more expensive in Chicago than in other parts of the country. It has perhaps the highest property tax in the nation. 

5. High crime rate

The days of Al Capone are gone but the third largest city is home to many street gangs and big city problems. Crime rates are relatively high in some parts of the city, so it’s important to be aware of your surroundings at all times. 


Chicago is truly a great place to live, work, run a Chicago web design company, and raise a family—but it’s not for everyone. Sure, there are some downsides to living here—but there are upsides too. At the end of the day, it all comes down to what you’re looking for in a city and whether or not Chicago offers what you need. 

Picture of Chris Granat

Chris Granat

Chris is the founder and lead web designer at Flamingo Agency, a Chicago web design firm.