20+ Pros & Cons of Living in Chicago To Know Before Moving

Looking to move to Chicago? Well, you’ll want to know about these pros & cons of living in Chicago before spending your precious time and energy!

Chicago, the Windy City, is a place that has captured many hearts of many with its vibrant culture, rich history, and stunning architecture.

From its world-renowned food scene to its bustling downtown, Chicago offers a unique blend of urban excitement and Midwestern charm. 

Like any major city, it also comes with its fair share of challenges. If you’re considering making Chicago your new home, this comprehensive guide will explore the many facets of living in this dynamic city.

So whether you’re searching for studio apartments in Chicago or homes for sale, read on to find out what life is like living in Chicago!

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Pros of Living in Chicago

Pro #1: Vibrant Arts and Culture Scene

Chicago is a haven for art enthusiasts, boasting prestigious museums like the Art Institute of Chicago, which houses over 300,000 artworks. 

The city’s thriving theater scene includes over 200 venues, such as the Goodman Theatre and Steppenwolf Theatre Company. 

Chicago also hosts renowned art fairs and festivals, including the Chicago Jazz Festival and the Hyde Park Jazz Festival, attracting musicians from around the world.

Fun fact: The arts and culture sector in Illinois state represents 3.7% of the state’s GDP and supports 224,102 million jobs. (source)

Iconic structures like the Willis Tower and John Hancock Center add to its artistic allure as well!

🖼️ Explore these top-rated Chicago Arts & Culture tours!

Pro #2: Hot Sports and Entertainment Scene

If you enjoy sports, music, or nightlife, Chicago offers endless entertainment. 

The city is a sports lover’s paradise with major league teams like the Bears (NFL), Bulls (NBA), Cubs (MLB), and Blackhawks (NHL). Historic venues like Wrigley Field and Soldier Field provide dynamic energy. 

Chicago also boasts world-class theater at Steppenwolf and Goodman Theatre. Music lovers can enjoy blues and jazz at venues like House of Blues and Buddy Guy’s Legends. 

The nightlife in River North and Wicker Park is legendary, with multifaceted bars, clubs, and lounges.

Pro #3: Famous Skyline and Architecture

Chicago, the birthplace of modern architecture, boasts one of the world’s most iconic skylines. After the Great Chicago Fire of 1871, the city pioneered steel and glass skyscrapers, creating a visually stunning landscape that influences global design. 

Iconic buildings include the Willis Tower, John Hancock Center, and the Equitable Building. Beyond skyscrapers, Chicago features masterpieces by renowned architects like Frank Lloyd Wright and Ludwig Mies van der Rohe.Architectural tours, including the famous Chicago Architecture River Cruise, provide an in-depth look at the city’s architectural marvels.

Pro #4: Amazing Food Scene

Photo credits: Pequod’s Pizza

Chicago is a culinary haven for food enthusiasts, highlighted by famous dishes like deep-dish pizza and Chicago-style hot dogs. 

Beyond these classics, the city’s diverse culinary scene caters to all tastes and budgets, from Michelin-starred restaurants to local food trucks. 

Ethnic neighborhoods like Chinatown and Little Italy serve authentic international cuisines. Food festivals like Taste of Chicago celebrate the city’s culinary diversity. 

Additionally, Chicago’s thriving craft beer scene features numerous breweries and pubs offering locally brewed selections.

🍕 Explore the best food in Chicago with these guided food tours!

Pro #5: Great Public Transport

Chicago’s public transportation, ranked among the nation’s finest, appeals to urban dwellers seeking car-free living. Operated by the Chicago Transit Authority (CTA), it’s the second-largest system, linking neighborhoods and suburbs via buses and trains. 

The iconic “L” train system, featuring elevated tracks, offers skyline views. Metra commuter trains connect the city to suburbs, while Amtrak serves intercity routes. With extensive bus, train, and bike lane networks, living in Chicago sans car is seamless.

Fun Fact: In 2022, total CTA ridership reached 243.5 million bus and train rides. (source)

With apps and real-time tracking, navigating public transport is user-friendly, making daily commuting or exploring the city a breeze.

Plus, Chicago is known for its pedestrian-friendly neighborhoods, with many amenities and attractions within walking distance.

Pro #6: Cheaper than living in New York City

While living in a major city can be expensive, Chicago offers a more affordable alternative to cities like New York.

The cost of living in Chicago is lower, especially when it comes to housing. According to data from the Council for Community and Economic Research, the overall cost of living in Chicago is about 23% lower than in New York City.

Did you know: The average cost of a one-bedroom apartment in the city center is $3,789.87 in New York City, compared to $2,251.24 in Chicago? (source)

In Chicago, your dollar stretches further, whether for rent, dining, or entertainment. Enjoy an urban lifestyle with top-notch amenities at a fraction of the cost of other major cities. 

This affordability appeals to young professionals, families, and retirees, ensuring a high quality of life without financial strain.

Pro #7: The City is Beautiful

Chicago’s beauty shines through its skyline, lakefront, and parks, inviting residents and visitors to embrace the outdoors. 

With a mix of historic and modern architecture, the city boasts 18 miles of public beaches like North Avenue Beach and Oak Street Beach, perfect for relaxation or a stroll. Grant Park and Millennium Park offer stunning skyline views and host outdoor events. 

Chicago features over 580 parks and 26 miles of lakefront trails for biking or leisurely walks. From Millennium Park’s gardens to Alfred Caldwell Lily Pool, the city’s public spaces offer an urban relaxation.

Pro #8: The People

Chicagoans embody Midwestern hospitality, fostering a strong sense of community. The city’s diverse population brings together people from various backgrounds and cultures. 

Tight-knit neighborhoods, local businesses, and community events cultivate belonging. From cheering for the home team to supporting local artists, Chicagoans take pride in their city and each other. 

Their warmth and welcoming nature make living in Chicago fulfilling. It’s not just the place but also the people that make Chicago special, instantly making you feel at home.

Pro #9: Chicago is a Transport Hub

A key transportation hub in the heart of the United States, Chicago features O’Hare International Airport, one of the world’s busiest. With non-stop flights to every continent, the airport constantly adds new routes and boasts recent renovations for improved efficiency. 

The city’s extensive public transit system, including CTA buses and “L” trains, connects neighborhoods and suburbs. Metra commuter trains and Pace suburban buses extend public transportation options. 

Chicago’s strategic location at the intersection of major interstates facilitates easy access to other regions by car.

Pro #10: Diversity

Chicago’s diversity is a key strength, evident in its incredibly varied neighborhoods rich in cultures and traditions from around the globe. 

Chinatown, Little Italy, Pilsen, German Village, Swedishtown, and Greektown showcase the city’s history through festivals, eateries, and cultural centers, offering experiences you shouldn’t miss. 

The dense cultural mix can make you feel like you’ve traveled the world in just a few blocks. This diversity extends to the economy, fueling creativity and innovation, making Chicago a bustling place to live with abundant job opportunities.

Pro #11: Rich History and Heritage

Chicago’s history reflects its dynamic and multicultural population. Regarded as the birthplace of urban blues, the city influenced jazz and blues scenes, with venues like Buddy Guy’s Legends and Kingston Mines preserving the musical legacy. 

For classical music enthusiasts, the Chicago Symphony Orchestra and downtown Theater District offer top-notch concerts. Beyond music, events like the Great Chicago Fire and World’s Columbian Exposition have left indelible marks on the city and the nation. 

Museums and architectural landmarks like the Art Institute of Chicago and The Field Museum showcase Chicago’s innovation and social change. 

Whether exploring museums, historic districts, or attending festivals, Chicago’s rich history and heritage captivates residents and visitors alike, enhancing the city’s allure as a fascinating place to live, work, and explore.

Cons of Living in Chicago

Con #1: Crime is a Problem

Chicago struggles with crime in certain neighborhoods, and there are about 30.6 crimes per 1.000 residents in Chicago, which is pretty much a concern for residents and potential newcomers.

The city has faced challenges with gang violence, shootings, and other criminal activities. While efforts are being made to address these issues through law enforcement and community programs, crime rates in some areas remain high.

Surely 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.

Just note that crime is not evenly distributed across the city, and many neighborhoods are considered safe and family-friendly. 

Con #2: Traffic is Always Bad

Chicago’s busy streets and highways are frequently congested, particularly during rush hours, causing delays and frustration for drivers. Traffic jams not only add stress but also worsen air quality. 

Although public transportation exists, its convenience varies based on location and destination. 

The city has introduced buses, trains, and bike lanes to ease congestion. However, heavy traffic should be anticipated when planning travel in and around Chicago.

Con #3: Brutal Winters

Living in Chicago means enduring 3-4 months of harsh winter, with temperatures averaging -3°C. The cold, heavy snowfall and biting winds pose significant challenges. 

Sub-zero temperatures, exacerbated by wind chill and lake-effect snow, are common. Brutal winters disrupt daily life, causing commuting issues and higher heating bills. 

Snowstorms can halt transportation and close schools. While some enjoy winter activities, others find the season arduous. Consider these factors before choosing Chicago as your home.

Con #4: High Sales Taxes

Living in Chicago means facing a hefty financial burden due to high sales taxes. In 2023, the combined sales tax rate reached 10.25%, among the nation’s highest, comprising a 6.25% state sales tax and various local taxes. 

This impacts everyday purchases, quickly accumulating costs for residents.

While sales tax revenue supports vital services, it can strain tight budgets or those aiming to minimize expenses. Consider this aspect before committing to Chicago living.

Con #5: Poor Air Quality

Like other major cities, Chicago grapples with air pollution due to industrial and transportation sources. The metropolitan area ranks as one of the most polluted regions. 

This poses health risks, especially for those with respiratory conditions like asthma, and hampers outdoor enjoyment. While efforts are underway to mitigate pollution, it remains a pressing concern for residents and environmentalists.

Con #6: Parking is Terrible

Parking in Chicago is frustrating and time-consuming due to dense population and limited spaces. Downtown options exist but are often unavailable or costly on weekends. 

Complex regulations, permit needs, and high fees exacerbate the issue. In some neighborhoods, finding parking is time-intensive, with violations leading to hefty fines. 

This situation can deter car-dependent individuals and influence decisions on living, working, and commuting in the city.

So if you’re driving into the city, carpooling with friends or family gives you a better chance of finding parking!

Con #7: High Cost of Living

Chicago, though more affordable than New York, still boasts a relatively high cost of living as a major metropolitan area. Expenses, from housing to groceries and transportation, can quickly accumulate. 

The median home price exceeds the national average, and renting in desirable neighborhoods ranges from $1,300 to $2,284. 

While salaries in certain industries may be higher, the overall cost of living can strain budgets, particularly for newcomers or those on fixed incomes. 

It’s essential to consider the financial implications of living in Chicago and plan accordingly to make the most of what the city has to offer.

🕵🏻‍♂️ See how Chicago compares with Seattle

Con #8: The City is Flat

Chicago’s flat terrain, governed by a grid system originating in the historic Loop, lacks the varied topography found in other cities, disappointing avid hikers, mountain bikers, and climbers. 

However, this flatness facilitates easy walking and biking, making the city accessible. While the lakefront and parks offer outdoor enjoyment, Chicago’s overall terrain may disappoint those craving rugged landscapes.

Con #9: Concrete Jungle

Chicago’s urban landscape, dominated by towering skyscrapers and bustling streets, can feel overwhelming, lacking green spaces that provide solace and connection to nature. 

While renowned for its architecture, the concrete jungle may induce a sense of confinement. For those yearning for open spaces and fresh air, Chicago’s dense urban environment might be excessive. 

Despite scattered parks and green areas, they may not suffice for those seeking a more natural setting.

Con #10: Not for Those Who Don’t Like the Hustle and Bustle

Chicago’s bustling atmosphere, characterized by crowded streets, lively nightlife, and a fast-paced lifestyle, is both energetic and exciting. While this lively energy appeals to many, it may overwhelm those seeking a quieter, more laid-back lifestyle. 

The noise, crowds, and relentless pace can be stressful, making Chicago less appealing to those who value tranquility. If you prefer a peaceful environment, Chicago’s constant activity may be a significant drawback to consider.

Con #11: High Property Taxes

Chicago’s property taxes rank among the nation’s highest, posing a significant burden for potential homeowners. The average tax rate exceeds the national average and varies by neighborhood and property value. 

This may influence your purchasing decision and necessitate careful budgeting. Consulting a local real estate expert is crucial to grasp the full implications of property taxes in your preferred area.

Con #12: School System Challenges

While Chicago hosts excellent schools, especially in affluent areas, the public school system confronts challenges that may worry relocating families. 

Funding disparities result in varying quality, with some schools lacking essential resources. Researching school districts, including private and charter options, is a must for families prioritizing education. 

Navigating the complex system may demand additional time and effort to find the best fit for your children. Make sure you prioritize research if education is vital for your family’s needs.

Con #13: Economic Disparities

In Chicago, some neighborhoods are doing really well, while others are struggling with money and don’t have enough resources. 

This affects things like healthcare, schools, jobs, and safety. Before moving there, it’s important to know which neighborhoods are which, because it could affect where you live and work. 

Even though Chicago has a lot of cultural richness and growth opportunities, the city’s social and economic challenges must be taken into account.

Understanding both the advantages and drawbacks is essential to determine if Chicago is the right city for you or not.

If you’ve determined to check out Chicago, make sure you take a peek at our picks of the best Italian, ramen, sushi, and brunch spots in Chicago!