Making the move from New York City to Chicago is a big decision. While both cities are iconic urban powerhouses in their own right, they offer vastly different experiences. From the way locals handle winter to how neighborhoods feel, here’s a detailed look at what to expect when transitioning to life in the Windy City.

Embracing Chicago Weather

In Chicago, you’ll experience the full force of all four seasons. Unlike NYC’s ocean-driven weather patterns, Chicago’s climate is shaped by its central location and proximity to Lake Michigan. Summers are hot and perfect for lakefront adventures, while winters bring heavy snowfall, icy streets, and bitter cold. Spring tends to be wet, and fall is often blustery but beautiful. The cold here lingers longer than in New York, but the city is well-prepared—warming stations are readily available, and landlords are legally required to keep homes heated to at least 63 degrees.

Getting Around the City

Chicago boasts the second-largest public transit system in the U.S. The CTA’s iconic “L” trains snake across the city, connecting the urban core with surrounding neighborhoods. Buses fill in the gaps for areas not directly served by train lines. During warmer months, water taxis along the Chicago River offer a scenic commute, and Divvy, the city’s bike-sharing program, makes cycling a fun and viable option. While New Yorkers often rely exclusively on public transit, many Chicagoans also drive—though be warned, traffic jams on the expressways can rival NYC’s worst.

Understanding Chicago Taxes

Taxes in Chicago differ in structure compared to NYC. Illinois has a flat 4.95% income tax rate, and the city sales tax tops out around 10.25%, including state and local portions. Property taxes, however, are significantly higher than in New York—averaging around 2.32%. While New Yorkers are familiar with city income taxes and lower property taxes, Chicago flips this script. On the upside, there’s no additional city income tax like NYC’s extra 3.876% on higher earners.

Exploring Real Estate Options

Chicago offers diverse housing choices ranging from historic row homes and brick bungalows to sleek, modern high-rises and converted lofts. Following the housing crash in 2008, prices gradually recovered before cooling in recent years. It’s not uncommon to find two-bedroom condos in the $200K range, while luxury properties can exceed $10 million. Compared to NYC, Chicago’s real estate offers more space for less money, making homeownership more accessible.

Living It Up in the Windy City

Chicago’s entertainment scene is a major draw. From Michelin-starred restaurants to quirky neighborhood cafés and vibrant nightlife, there’s something for every taste. Along the 20-mile Lake Michigan shoreline, residents enjoy beaches, trails, and stunning skyline views. The city is also home to world-class museums, a free zoo, and major league sports teams—including the Cubs, White Sox, Bulls, Bears, and Blackhawks—keeping the city buzzing year-round.

The Cost of Living Advantage

One of the most attractive aspects of Chicago living is affordability. A two-bedroom apartment might rent for as little as $1,400, significantly cheaper than NYC prices. The city’s median income sits around $68,000, lower than New York’s, but your money stretches further. Housing, food, transportation, and leisure activities all tend to cost less. Economists estimate that a single person could cover basic expenses with an annual income of about $48,000.

Career Opportunities and Key Industries

Chicago’s job market is solid, especially for those in transportation, logistics, finance, healthcare, education, and manufacturing. The city has long been a hub for blue-collar workers and union-backed jobs. With railroads, trucking, and shipping channels converging in the Midwest, the city remains a national transportation center. Its publishing industry ranks second only to NYC, and the financial sector continues to grow with institutions like the Federal Reserve Bank and Chicago Mercantile Exchange.

Let Movers Not Shakers help you transition smoothly from the Big Apple to the Windy City. As expert New York to Chicago movers, we specialize in long-distance relocations that are efficient, eco-friendly, and stress-free. Whether you’re moving a studio apartment or an entire household, our team ensures your belongings arrive safely and on time.

Contact us today to get a personalized quote and make your Chicago move the easiest part of your new adventure!