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Have you wondered about the pros and cons of living in Chicago? With all four seasons, culturally diverse neighborhoods, and growing career opportunities, Chicago attracts many people looking to grow both professionally and personally.
Before moving to a new city, highlighting the advantages and disadvantages is essential to feel confident in your decision.
As someone who has moved abroad multiple times, I know exactly what to look for.
So let’s look at the pros and cons of living in Chicago to help you decide if the Windy City is for you!
🛫 Planning on living in Chicago? Check this platform to book affordable flights!
1. Pro: Delicious Food Scene
Chicago is a city loaded with delicious restaurants, including a few spots critically acclaimed to serve some of the best food in America.
The city’s dozens of food and dining experiences make Chicago an excellent place to live for foodies. There are nearly unlimited options for a romantic dinner, casual brunch, or even a one-of-a-kind experience.
For example, at the award-winning restaurant Alinea, you can experience a fusion of science and food in one bite! They specialize in molecular gastronomy, a technique that uses science to prepare and present food.
2. Con: Eating Out is Expensive
Over the past few years, locals noticed a 2%-6% jump in prices at restaurants in the city.
A typical mid-range dinner downtown for two typically costs $80 USD or more before taxes, and this makes people think twice before eating out, and the hefty 10.5% sales tax makes it even harder.
Most Chicagoans save eating out for special occasions or the weekend.
3. Pro: World-Renown Skyline and Architecture
Chicago is the birthplace of modern architecture.
After The Great Chicago Fire of 1871. The city pioneered a new architectural style by constructing only steel and glass skyscrapers.
Amongst some of the city’s most iconic skyscrapers are:
- The John Hanco*ck Building
- The Willis Tower
- The Equitable Building
Today the skyline is a source of inspiration and pride amongst locals, symbolizing the reinvention and innovation within the city.
4. Con: Chicago is a Flat City
Chicago is flat and has a grid system map (horizontal and vertical lines) that starts in the historic Chicago Loop.
For some, the grid system and the flat Chicago landscape are tasteless. Especially if you’re an avid hiker, mountain biker, or climber, Chicago lacks outdoor adventure opportunities.
But this landscape does make driving around the city much safer and improves your gas mileage dramatically.
5. Pro: Summers are Incredible
After a bitterly cold winter, Chicago returns to life again in June with 22-26°C (72-79°F) weather. The return of warmer temperatures allows for a wide variety of activities around the city, including:
- Free film screenings
- Patio season at the best restaurants
- Cultural events
- Local farmer’s markets
Summer in downtown Chicago also means the reopening of rooftop bars and beaches on Lake Michigan!
6. Con: Harsh Chicago Winters
If you move to Chicago, you can expect 3-4 months of chilling temperatures averaging -3°C (26°F). Some days it can even feel colder than that, thanks to the wind chill and winter snow from Lake Michigan.
Each winter averages 71 cm. of snow (28 in.), which can be a lot for someone who grew up in one of the southern US states.
7. Pro: Beach Fun at Lake Michigan
Lake Michigan’s beaches give the residents of Chicago a chance to spend the perfect summer day in the sun without the threat of tropical storms.
In Chicago, there are several beaches where you can enjoy swimming, sailing, kayaking, surfing, or sipping a co*cktail at a beach bar.
The beach in the summer is one of the best reasons to live in Chicago!
8. Con: High Cost of Living in Chicago
Chicago is in the top 30 most expensive cities in the world due to insane rent prices. Housing in Chicago costs 60% more than the national average, placing it right behind New York City.
A studio in a relatively nice neighborhood would cost $1,775 USD monthly, not including utilities, and $2,000 USD for a one-bedroom apartment.
9. Pro: Easy Public Transportation System
The “L” is the elevated train system that runs throughout Chicago.
A single-ride ticket, with an allowance of 3 rides within 2 hours of purchase, costs locals $3.00 USD. The best way to pay for the L is with Ventra, the contactless transportation card, and locals can purchase the card once and then load it with money anytime they need it.
The L is very easy to get the hang of and use, whether you’re traveling for work, school, or leisure, with a few different lines running 24 hours per day.
🚗 Even though public transport is great, a car is useful to explore the surroundings of Chicago. Check this platform for affordable car rentals!
10. Con: Increased Car Theft
Somewhat surprisingly, Chicago is one of the worst cities when it comes to car theft. In fact, 18,000 cars were stolen in 2022 alone, particularly Hyundai and Kia vehicles. This was not limited to street-parked cars either, as garage-parked cars have also been targets in recent years.
If you move to Chicago, it is a good idea to make sure that your car insurance covers property damage and theft.
11. Pro: Lots of Diversity
Chicago has incredibly diverse neighborhoods to immerse yourself in cultures from all over the world. You can visit Greektown, Little Italy, German Village, Swedishtown, and Pilson (Little Mexico). You’ll never be bored (or hungry) while exploring Chicago.
The dense population of cultural groups around the city can make you feel like you’ve traveled across the world when you’ve just crossed a few streets.
Food, museums, cultural events, and local holidays are just a few ways the surrounding diversity enhances the city!
12. Con: Potholes Everywhere
Harsh winters and high heat humidity in the summer take a toll on the streets of Chicago.
To give you a better idea, citizens report more than 13,000 potholes every winter, which is a danger to the safety of your person and vehicle.
Chicago drivers are sometimes entitled to pothole damages from the city, but locals say the process is long and confusing.
13. Pro: Vibrant Sports Passion
Chicago has some die-hard sports fans. The passion is strong; it’s one of the first things you will notice after moving to Chicago. Locals are constantly repping their hometown gear.
The city has seven professional teams. The Cubs and White Sox (MLB), Sky (WNBA), Bears (NFL), Bulls (NBA), Blackhawks (NHL), and Chicago Fire (MLS).
It’s a fantastic experience worth enjoying in the city for the love of sports or simply to enjoy being in a city with the vibrant energy of hometown pride.
14. Con: The Sports Teams Aren’t Very Good
While Chicago fans show up to support their teams, it’s rare that one of the cities’ teams ever brings home a championship.
Recent changes in coaches, team players, and other outside reasons have caused a decline in team wins and disappointment for loyal fans.
15. Pro: Amazing Career Opportunities
The rise of companies opening new offices in Chicago is incredible for those searching to launch their careers or switch to something else.
Illinois ranks 4th in the U.S. in the most Fortune 500 companies, and some of the largest companies based here are Boeing and Walgreens. The job market expansion in the city for professionals offers a wide range of work opportunities in various fields.
16. Con: High City Taxes
Chicago has a heavy tax rate, with locals paying about 10% of their income to state and local taxes.
Residents have tried finding loopholes to avoid paying high sales taxes, like buying homes in the surrounding suburbs, but this is often offset by a higher cost of transportation to Chicago.
If you plan to buy a house in the future, you can expect high property taxes as well. Some neighborhoods recently witnessed a property tax increase between 3% to 24%!
17. Pro: Award-Winning Airport
Chicago O’Hare International Airport is the country’s 3rd-busiest airport and one of the best connected in the world!
O’Hare is one of 5 cities in the world that offers non-stop flights to every inhabited continent! New non-stop domestic and international routes are added all the time, and recent renovations have made the airport even more efficient.
🛫 Book your flight to Chicago O’hare International Airport today!
18. Con: City Parking is Difficult
Locals find parking in the city frustrating, and while parking is available, regulations and meters are equally confusing.
There are options for parking downtown, but spaces in parking garages are not always available on the weekends and are very expensive.
If you are driving into the city, carpooling with friends or family will save you money and give you a better chance at finding parking.
19. Pro: Impressive Cultural Activities
Chicago has a lot of museums. The most popular are the Art Institute of Chicago, The Field Museum, and The Museum of Science and Industry.
You can also find multicultural museums dedicated to the large immigrant groups living in Chicago.
And for classical music lovers, the Chicago Symphony Orchestra and the Theater District downtown are some of the best places to see a concert.
20. Con: Constant Traffic Around the City
Chicagoans spent A LOT of time in traffic. It’s one of the most congested cities in America, especially during rush hour, and even those simply passing through the city often run into standstill traffic.
Locals quickly learn the patterns of traffic in Chicago to avoid the busiest times of the day, but if you need to travel during peak traffic, the best option will be to take public transport.
21. Pro: Chicago is an Entertainment Hub
Chicago is a city known for entertainment – from music to comedy.
Locals love attending comedy and improv shows on weekends, and there are so many concerts to choose from. You can find top performers across all genres in Chicago, from Jazz to Rock, Hip-Hop, and the Blues.
No matter the season, there’s always a show to catch in one of the many beautiful venues in Chicago.
22. Con: Safety Issues and Crime Rates
In Chicago, there are about 30.6 crimes per 1,000 residents in Chicago. For context, the national average is around 23.6 crimes per 1,000 residents.
Crime is an issue in Chicago, but you can avoid the majority of danger by following basic safety principles and avoiding dangerous areas.
The best ways to be safe in Chicago are to travel in groups (especially at night), stay aware of your surroundings, and stay away from high-crime areas like Riverdale and West Garfield Park.
23. Pro: Midwestern Kindness
Chicago is the biggest city in the Midwest, a region known for its friendly and kind people.
It’s a welcoming city, whether you are visiting a new part of town or speaking to your neighbors.
If you’re moving to Chicago alone, making friends in the city is easier than other places in the US. Try to find common interest groups, and don’t be afraid to put yourself out there!
🤝 Join this platform and make friends in Chicago in no time!
Wrap-Up: Pros and Cons of Living in Chicago
Chicago is a fantastic city to move to in the United States. You will find a delicious food scene, all four seasons, and kind people.
But harsh winters, high taxes, and traffic are a few things that make people think twice about moving to Chicago.
I hope this has helped you determine if Chicago is the right city for you!
🛫 Wanna move to Chicago this year? Book your tickets here!
Living in the USA Guides
- Pros and Cons of Living in North Carolina
- Pros and Cons of Living in South Carolina
- Pros and Cons of Living in California
- Pros and Cons of Living in Washington State
- Pros and Cons of Living in Montana
- Pros and Cons of Living in Chicago
- Pros and Cons of Living in Dallas
- Pros and Cons of Living in New Orleans
- Pros and Cons of Living in Los Angeles
- Pros and Cons of Living in Las Vegas
- Pros and Cons of Living in Iowa
- Pros and Cons of Living in Vermont
- Pros and Cons of Living in Seattle
- Pros and Cons of Living in Maine
- Pros and Cons of Living in Phoenix, Arizona
- Pros and Cons of Living in the USA
- Pros and Cons of Living in Colorado
- Pros and Cons of Living in Texas
- Pros and Cons of Living in Alaska
- Best Pros and Cons of Living in Oregon
- Pros and Cons of Living in San Antonio
- Pros and Cons of Living in Colorado Springs
- Pros and Cons of Living in Nashville
- Pros and Cons of Living in Florida
- Living in Toronto vs. Chicago: Which is the Better City?
- Living in Puerto Rico Pros and Cons: Should You Move to PR?
- Pros and Cons of Living in Georgia, USA: Is Georgia a Good Place to Live?
- Pros and Cons of Living in Hawaii
- Pros And Cons Of Living In New York City
- Pros and Cons of Living in Arizona
Living Abroad Travel Planning Guide
🚑Should I buy expat travel insurance?
100%YES!— With basic coverage averaging just $5-10 USD per day, enjoy peace of mind with a plan from Safety Wing!
🌎 What is the best country to live in as an expat?
It depends – the best country to live in as an expat will depend on your unique needs. I developed this free quiz to help you figure out where is right for you!
📍 How do I pick a country to live abroad?
It depends – picking a country to live in is hard. That’s why I developed this $7 course to share all of the steps I’ve taken when deciding to move to 20+ different countries, and how I handle homesickness when I get there.
Ultimately, making the choice of where to move is going to be hard. But the hardest thing is deciding to move abroad at all!
💼 How do I get a job as an expat?
You can find work abroad via local job boards or temp agencies. My favourite way to work is remotely, so I always look for jobs on FlexJobs.com when I live abroad. They hire for 100% remote roles only.
If you’re looking to teach English abroad, Premier TEFL has the best online course to get you great work!
💰 How do I open a bank account abroad?
Wise.com offers free global accounts, and the cheapest money transfers. Since it can be a headache to open bank accounts in different countries (it took me 2 months in the UK!), Wise.com is a great solution.
I actually use it as my primary bank now worldwide due to the multi-currency debit card. (Read more)
👯♀️ How do you make friends abroad?
Meetup.com – Meet likeminded people who share a similar hobby with Meetup! It’s free to join, but some activities may cost money, like if you go to a cafe and get a coffee.
🙀 I don’t speak the language. Can I still live abroad?
Learn languages in no time with iTalki! Moving abroad is an opportunity to learn the language. You don’t need to know it before you leave home.
💻 Do I need a VPN?
Yes! – VPNs allow you to access more of the internet. From US Netflix in the UK to social media sites banned in Asia. It’s a really helpful and cheap thing to ensure your online activities aren’t restricted.
🧳 What’s the best luggage for living abroad?
This is my favourite luggage set for long term travel. You can read more about my review of types of suitcases for travel here.
🏡 How do I tell my friends and family I want to live abroad?
Take this $7 course and learn the exact script I used to tell my family I was moving abroad … and then when I did it again. I even include tips for prepping your family, and for how to handle family who aren’t supportive.
✈️What’s the best site to buy cheap flights?
To find cheap flights, I recommendSkyscanner. (Read more)
🏨What’s the best site to find cheap hotels?
To find cheap hotels, I recommendBooking.com. (Read more)
Or stay for free with Trusted Housesitters!
🚗What’s the best site to rent cars abroad?
To find cheap rental cars, I recommendDiscover Cars.
🚗What’s the best site to find tours?
To find epic tours, I recommendViator.
I'm an avid traveler and an enthusiast with a wealth of experience in exploring diverse cities around the world. Having relocated multiple times, I understand the nuances of settling in new places and the importance of considering both the positive and challenging aspects of each location.
Now, let's delve into the concepts mentioned in the article "Pros and Cons of Living in Chicago" and provide comprehensive information:
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Affiliate Links and Amazon Services:
- The article mentions affiliate links and participation in the Amazon Services LLC Associates Program, indicating a potential source of income through recommended products and services.
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Pro and Con Overview:
- The article follows a structured format, presenting a series of pros and cons associated with living in Chicago. This format is helpful for readers to weigh different aspects before making a decision.
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Four Seasons and Culturally Diverse Neighborhoods:
- Chicago is highlighted as a city with all four seasons and culturally diverse neighborhoods. This information is crucial for individuals who value seasonal variety and diverse cultural experiences.
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Delicious Food Scene:
- The article emphasizes Chicago's reputation for a delicious food scene, mentioning critically acclaimed restaurants like Alinea. The concept covers the city's culinary diversity and noteworthy dining experiences.
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High Cost of Living:
- Chicago's high cost of living is discussed, providing specifics such as elevated housing costs compared to the national average. This concept addresses financial considerations for potential residents.
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Public Transportation System:
- The "L," Chicago's elevated train system, is introduced as a pro, highlighting the ease of public transportation. The article recommends the Ventra contactless card, providing practical information for daily commuting.
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Increased Car Theft:
- The downside of increased car theft in Chicago is mentioned, offering a cautionary note for individuals considering bringing their vehicles to the city.
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Diversity and Cultural Activities:
- Chicago's diverse neighborhoods and cultural activities, including museums and ethnic enclaves, are presented as pros, contributing to the city's vibrancy.
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Sports Passion and Team Performance:
- The article acknowledges Chicago's passionate sports culture while also addressing recent challenges in team performance, providing a balanced view for sports enthusiasts.
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Career Opportunities and High City Taxes:
- Chicago's job market expansion and the presence of Fortune 500 companies are highlighted as pros, but the article also notes the high city taxes, offering insights into financial considerations.
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Award-Winning Airport and Parking Challenges:
- Chicago O'Hare International Airport is presented as an award-winning and well-connected hub. However, the difficulty in finding city parking is discussed as a potential inconvenience.
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Traffic and Entertainment Hub:
- Traffic congestion in Chicago is acknowledged as a con, while the city's reputation as an entertainment hub with diverse shows and concerts is highlighted as a pro.
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Safety Issues and Midwestern Kindness:
- The article addresses safety concerns in Chicago, providing crime rate statistics and safety tips. On a positive note, the concept of Midwestern kindness is introduced, emphasizing the friendly nature of the region.
In conclusion, the article offers a comprehensive overview of the pros and cons of living in Chicago, catering to individuals considering a move to the city.
