For those considering living in Chicago, this vibrant and diverse city has some unique perks and challenges. Chicago is much more than just deep-dish pizza and towering skyscrapers. It offers a diverse culture scene and is notorious for its snowy winter months. So, is Chicago a good place to live?
Whether you’re moving to the Windy City or you’re a local curious about what others think, here’s a breakdown of the key pros and cons of living in Chicago.
Chicago’s art and culture options are second to none. The Art Institute of Chicago consistently ranks among the best museums in the world and features everything from classic paintings to contemporary exhibitions. Beyond museums, locals enjoy live theater in the bustling downtown Loop area, standout performances at the Chicago Symphony Orchestra, and comedy shows at iconic venues like The Second City. Chicago’s deep cultural roots mean there’s always a gallery to visit, a play to see, or a street mural to admire.
Chicago’s food scene is one of its shiniest gems. Sure, deep-dish pizza from Giordano’s and Chicago-style hot dogs are iconic staples, but the city is so much more than its stereotypes. With more than 7,300 restaurants, including seven AAA Diamond-rated establishments, 26 Michelin-starred spots, and 40 James Beard Award-winning restaurants, Chicago is an unmatched culinary destination. From Michelin-starred fine dining to global cuisine representing dozens of cultures, there’s something for every palate. Must-trys include Italian beef sandwiches, hearty Polish pierogis, and upscale dining along Randolph Street’s famed Restaurant Row.
Chicago boasts one of the most comprehensive public transportation systems in the United States, making it incredibly easy to navigate the city for work or leisure. The Chicago Transit Authority (CTA) operates the iconic "L" train — short for "elevated" — along with an extensive bus network, ensuring seamless travel across the city. Beyond the CTA, the Metra Rail system extends this accessibility to the suburbs. Additionally, Chicago’s two major international airports, O'Hare and Midway, are easily accessible by train, offering convenient connections for both domestic and international travel.
Chicago didn’t just build skyscrapers — it redefined them. The high-rise buildings designed by architects like Ludwig Mies van der Rohe and Frank Lloyd Wright are celebrated worldwide. Structures like the Willis Tower (formerly Sears Tower) or the modernist Aqua Tower are constant reminders that Chicago stands at the forefront of design and ingenuity. Take an architecture river cruise to learn the stories behind the buildings, or simply enjoy a sunset stroll through Millennium Park to appreciate its beauty.
Did you know? Oak Park, IL, a Chicago suburb, has the highest concentration of buildings and homes designed by Frank Lloyd Wright.
Sports fans will feel right at home in Chicago. Whether you’re a die-hard fan of the Cubs, the White Sox, or both, the city boasts historic ballparks and massive fan bases. Wrigleyville could even become your next home, offering Cubs aficionados a front seat to all the action. Share your pride for the Chicago Bears in football, or rally behind the Bulls in a captivating basketball match. There’s no off-season for professional sports here, and you’ll find camaraderie and excitement at local sports bars, stadiums, or street celebrations.
If there’s one thing you’ll hear about living in Chicago, it’s the winters — and they live up to the reputation. With temperatures frequently dipping below freezing and wind chills earning it the nickname “The Windy City,” Chicago’s winters can be brutal. Snowstorms and icy sidewalks are common, making good winter gear a necessity. On the bright side, Chicagoans know how to enjoy the colder months, with activities like skating at Maggie Daley Park or visiting festive holiday markets.
Living in Chicago comes at a cost. The average home value is $297,772, and rent averages $1,983 —slightly lower than the national average of $2,060, and still more affordable than cities like New York or San Francisco. However, property taxes and utility bills, especially heating costs during the winters, can add up quickly. Additionally, Chicago has one of the highest sales tax rates in the country, with a combined state and local rate of 10.25%. While this revenue helps fund city services, it's an important consideration for those keeping a close eye on their budget.
Like any major city, Chicago struggles with heavy traffic, especially during rush hour. Highways such as the I-90/94 often face paralyzing gridlock. Public transportation does alleviate some of this pressure, however, owning a car in the city comes with its own set of challenges, including high parking costs and lack of public parking. Despite efficient public transit in various parts of the city, driving can be a test of patience due to notorious traffic hold-ups, particularly in areas like the Loop and River North.
Chicago’s stunning Lake Michigan shoreline is a natural treasure, offering beaches and parks that locals love. But if you’re craving mountain hikes or dense forests, you’ll need to leave the city. Unlike cities that blend urban living with abundant access to natural landscapes, Chicago’s flat terrain and lack of close-in wilderness might not appeal to outdoor enthusiasts. However, nearby destinations like Indiana Dunes National Park provide a reprieve from city life, and a quick road trip can take you to nature-rich spots across the Midwest.
Check out homes for sale along the Lake Michigan shoreline
Air quality in Chicago can vary, particularly during the summer months when smog levels rise. Heavy car traffic and industrial zones contribute to this issue. While the city continues to improve its sustainability efforts, air pollution and waste management remain ongoing challenges. These issues could be bothersome depending on where you live within the city. If you're looking to buy a home in Chicago, you can review air pollution, among other climate risk data, on for sale listings to see what risks are most prevalent in your area.
Ready to take the next step? Once you’ve explored homes for sale or rentals in Chicago, connect with a local real estate agent, to help find your next home.
*Rental and home price data from February 2025
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