Living in Chicago

Living in Chicago

Chicago, known for its stunning architecture, vibrant arts scene, and diverse neighborhoods, offers a dynamic urban lifestyle that attracts people from all walks of life. Whether you’re considering moving to the Windy City or just curious about what it’s like to live there, this guide provides an in-depth look at all aspects of life in Chicago, including housing, culture, dining, and more.

Chicago is the third-largest city in the United States, situated on the southwestern shore of Lake Michigan. It’s a city known for its bold skyline, which includes the Willis Tower (formerly known as the Sears Tower) and the neo-Gothic Tribune Tower. Chicago is a hub for finance, culture, commerce, industry, technology, telecommunications, and transportation, with one of the world’s largest and most diversified economies.

Chicago Neighborhoods

Chicago’s neighborhoods are as diverse as the city, each with unique character and charm. Lincoln Park is known for its sprawling park of the same name, offering a mix of historic homes, trendy boutiques, and a lively dining scene. Wicker Park is a hip, artistic neighborhood famous for its vibrant nightlife, eclectic shops, and a strong sense of community. The Loop, the central business district, is home to iconic attractions like Millennium Park, the Art Institute of Chicago, and many of the city’s skyscrapers. Located on the South Side, Hyde Park is home to the University of Chicago and the Museum of Science and Industry, boasting a rich history and a vibrant cultural scene. The Gold Coast is an affluent neighborhood known for its historic mansions, upscale shopping, and beautiful lakefront views.

Chicago Real Estate Market

The Chicago real estate market is diverse, catering to a wide range of budgets and preferences. There is something for everyone, from high-rise condos in the downtown area to historic single-family homes in neighborhoods like Lincoln Park and Hyde Park. The market is experiencing a mix of stability and growth. While some neighborhoods have seen significant appreciation, others offer more affordable options, making it possible for various demographics to find suitable housing.

The city's rich history also means many architecturally significant properties are available. Chicago real estate is relatively affordable compared to other major cities like New York and San Francisco. This makes it an attractive option for young professionals, families, and retirees looking to enjoy city life without the hefty price tag.


Chicago’s transportation infrastructure is one of the best in the country, making it easy to navigate the city and beyond. The Chicago Transit Authority (CTA) operates an extensive network of buses and trains (known as the “L”) that cover the city and many suburbs. The Metra commuter rail system also connects Chicago to its surrounding suburbs.

While owning a car is unnecessary due to the city’s robust public transit system, many residents choose to drive. The city is well-connected by major highways and has numerous parking facilities. Chicago is a bike-friendly city with an extensive network of bike lanes and the popular Divvy bike-sharing program. Chicago is served by two major airports, O’Hare International Airport, and Midway International Airport, providing numerous domestic and international flights.

Culture and Entertainment

Chicago is an artistic powerhouse, offering a wide range of activities and attractions. The Art Institute of Chicago, Field Museum, Museum of Science and Industry, and Shedd Aquarium are just a few of the world-class museums in the city. Chicago has a vibrant theater scene, with famous institutions like The Second City, Steppenwolf Theatre Company, and Broadway in Chicago.

The city is also a hub for music, particularly blues, jazz, and house music. Throughout the year, Chicago hosts numerous festivals, including the Chicago Blues Festival, Taste of Chicago, and the Chicago Air and Water Show. Chicago is a sports-loving city with teams in all major professional leagues, including the Bears (NFL), Cubs and White Sox (MLB), Bulls (NBA), and Blackhawks (NHL).

Dining and Nightlife

Chicago is a food lover’s paradise, with a diverse culinary scene that includes everything from deep-dish pizza and hot dogs to fine dining and international cuisine. Don’t miss trying Chicago’s famous deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs.

The city boasts numerous Michelin-starred restaurants, such as Alinea and Oriole. Explore the diverse flavors of Chicago’s many ethnic neighborhoods, including Chinatown, Pilsen (Mexican), and Devon Avenue (Indian). Chicago’s nightlife is lively and varied, with a wide range of bars, clubs, and live music venues. Popular nightlife areas include River North, Wicker Park, and the West Loop.

Outdoor Activities and Recreation

Despite being a bustling metropolis, Chicago offers plenty of opportunities for outdoor activities. The city is home to numerous parks and green spaces, the most famous being Grant Park, Lincoln Park, and Millennium Park, where you can find the iconic Cloud Gate sculpture (aka "The Bean").

The Lakefront Trail offers 18 miles of paths for walking, running, and biking along Lake Michigan, with beautiful views of the skyline. Chicago’s lakefront boasts several public beaches, including North Avenue Beach and Oak Street Beach, perfect for swimming and sunbathing in the summer. The city has numerous sports facilities, golf courses, and fitness centers, ensuring that residents can stay active year-round.


Chicago offers a wide range of shopping experiences, from high-end boutiques to unique local shops. The Magnificent Mile, this iconic stretch of Michigan Avenue, is home to various upscale shops, department stores, and luxury boutiques. State Street is a historic shopping district in The Loop, home to major retailers and flagship stores. Explore unique boutiques and independent shops in neighborhoods like Wicker Park, Bucktown, and Andersonville.

Cost of Living

While Chicago offers many amenities, it’s essential to consider the cost of living. Generally, Chicago's living costs are higher than the national average but are more affordable than those of other major cities like New York or San Francisco. As mentioned earlier, Chicago real estate offers a range of options for different budgets. Renting is common, especially for newcomers, but purchasing a home is a viable option for many due to relatively lower prices compared to other large cities.

Utilities and transportation costs in Chicago are in line with those in other major cities. Public transportation is affordable, and many residents find it cost-effective to use the CTA instead of owning a car. Food costs can vary widely depending on where you shop and dine.

Community and Lifestyle

Chicago is known for its strong sense of community and vibrant lifestyle. The city’s diverse population means there are numerous cultural festivals, community events, and neighborhood gatherings throughout the year. Chicagoans are known for their friendliness and pride in their city, creating a welcoming atmosphere for newcomers.

Embracing Life in the Windy City

Living in Chicago offers a unique blend of urban excitement and Midwestern charm. From its diverse neighborhoods and cultural attractions to its robust real estate market and world-class dining, the Windy City has something to offer everyone. Whether you’re drawn by the vibrant arts scene, the rich history, or the potential of the Chicago real estate market, this city is a place where you can truly find your niche.

Ready to explore the best of Chicago real estate? Contact The Kohler Group today for expert guidance and personalized service. Whether you're buying, selling, or investing, let their experienced team help you confidently navigate the Chicago real estate market. Get started on your real estate journey with The Kohler Group—your trusted partners in finding the perfect home in the Windy City.

A modern house with floor-to-ceiling windows and a pool.

Work With Us

The Jarnagin & the Kohler Group

With a combined experience of over 35 years, Rex Jarnagin and Kari Kohler stand as leaders in the real estate market, specializing in Chicago, Denver and Las Vegas. Recognized among the top 1% of agents nationwide, our success is driven by an unparalleled work ethic, intuitive nature, and seamless teamwork. Clients trust our expertise, resulting in tailored solutions and a remarkable sales volume exceeding $700 million. In this competitive market, experience matters, and we invite you to let our proven track record work for you.

Follow Us on Instagram