Chicago, often called The Windy City, is known for its deep-dish pizza, iconic skyline and lively city life. It’s a place that attracts people looking for energy, culture and a true urban experience.

Being the birthplace of the very first skyscraper, Chicago has greatly influenced architecture around the world. At the same time, like many big cities, it also offers plenty of natural beauty to enjoy.

So, is Chicago a good place to live? With its 18.5-mile lakefront trail and more than 600 parks, the city is perfect for people who love the outdoors and for urban explorers planning a long-distance move.

It’s easy to see why so many people choose to move to Chicago. Over the years, STI Moving & Storage has proudly helped countless clients settle into this great city.

Here’s our guide to moving to Chicago.

#1. The Chicago Lifestyle

So, what’s life in Chicago really like? With nearly three million people, it’s the third-largest city in the U.S. Living here gives you the best of both worlds — the fast pace of a big city mixed with the friendly charm of the Midwest.

Whether you’re into exploring different cultures and foods or spending time in parks and outdoor spaces, Chicago has plenty to offer. If you’re new here, it might feel a bit overwhelming to meet people at first but the city has lots of social events that make it easier to connect with others who share your interests.

From fitness classes and volunteer work to bar crawls and sports leagues, there are plenty of chances to meet new people and make friends. Living in Chicago is all about exploring — you just need to take that first step.

#2. Chicago’s Climate and Weather

If you like cold winters and hot summers, you’ll probably enjoy Chicago’s mix of seasons. Summers can be warm and humid, while winters are often snowy and chilly. The city also earned the nickname “The Windy City” because of its breezy and unpredictable weather.

  • Summers are hot and humid, with July and August usually reaching highs of about 82°F and lows around 62°F; during heat waves, it can climb into the mid-90s or even hit 100°F;
  • Chicago winters are cold and windy, with January and February temperatures often ranging between 12°F and 31°F;
  • Spring and autumn usually bring milder days, with temperatures between 40°F and 60°F.

Most days come with a light breeze (around 10–12 mph); the wind often makes it feel colder in winter or hotter in summer than the actual temperature.

Chicago gets about 36 inches of rain and 21 inches of snow each year, with the heaviest rainfall usually happening in June and July.

#3. The Cost of Living in Chicago

The cost of living is an important thing to think about before moving to Chicago. From housing and rent to groceries and daily expenses, there are many costs to keep in mind when deciding to settle in the Windy City.

Housing

As of February 22, 2023, the average cost of a home in Chicago is about $190.28 per square foot — though prices differ from one neighborhood to another. In the past year, the typical home sold in the city was around 50 years old and about 1,476 square feet in size.

The higher housing costs in Chicago come from several factors. One main reason is the limited supply of homes, which leads to more competition among buyers and pushes prices up.

On top of that, Chicago’s strong economy, great location and rich cultural attractions make the city appealing, which also drives up the demand for housing.

Low interest rates and other economic factors have also made it easier for people to buy homes, even with the higher housing prices.

Taxes

One appealing part of Chicago’s tax system is that there’s no state income tax. This means more of your income stays with you instead of going to the government.

There are still property taxes but they’re lower than in many other big cities, which makes them easier on homeowners. The city also provides different tax credits and exemptions, like the Homeowners’ Exemption for owner-occupied houses, which helps reduce the overall tax load.

Living Wage

The average cost of living in Chicago is about $63,251 a year, which is more than 23% higher than the national average. This is affected by many things, like the salaries employers pay, the type of career you choose and the cost of buying or renting a home or apartment.

However, living in Chicago still costs less than in New York or Los Angeles. With an average yearly salary of about $73,800, it’s very possible to enjoy a comfortable lifestyle.

#4. Exploring Chicago Neighborhoods

Back in 1830, surveyor James Thompson created the first map of Chicago. He divided the city into three main areas based on where the Chicago River meets — the North Side, West Side and South Side.

Since becoming a city in 1837, Chicago has grown in every direction, adding nearby areas and reaching all the way to the shore of Lake Michigan.

The Loop

The Loop is Chicago’s main business district and one of the city’s 77 official community areas. It’s a hub for both business and culture, bordered by the Chicago River on the west and north, Lake Michigan on the east and Roosevelt Road on the south.

It’s where you’ll find City Hall along with many popular attractions like museums, parks, theaters and shopping areas. The Loop is also a lively part of Chicago with several colleges, including the Art Institute of Chicago, the University of Chicago and Columbia College Chicago.

The North Side

Chicago’s North Side has a mix of homes, cultural spots, shops and entertainment. It’s also home to several wealthy neighborhoods, including Wicker Park, Lakeview and Lincoln Park.

This part of the city is popular for its wide variety of restaurants, boutique shops and busy nightlife. Some of Chicago’s most famous attractions are here too, like Navy Pier, Lincoln Park Zoo and the Magnificent Mile.

As Chicago shifted from factory jobs to technology and modern businesses, the North Side grew into a busy hub for this “new economy.” It’s also home to the famous Chicago Cubs, who play at historic Wrigley Field in Lakeview.

The West Side

Chicago’s West Side is often called the city’s melting pot because of its mix of cultures. Here, you’ll find the Garfield Park Conservatory, the historic Garfield Park Lagoons and Museum Campus West. This area also highlights cultural spots like the National Museum of Mexican Art, the Peggy Notebaert Nature Museum and the Adler Planetarium.

Besides the museums, the West Side has lots of entertainment. Wicker Park is full of bars and restaurants for a fun night out, while East Garfield Park is well known for its jazz spots.

Sports and entertainment fans can catch games and events at the United Center Arena. For outdoor fun, nature lovers can enjoy the Chicago River, Douglas Park or sledding at Wilson Park, whether it’s summer or winter.

The South Side

From the busy shops and restaurants in Hyde Park to the lively nightlife in Bronzeville, Chicago’s South Side offers something for everyone to enjoy.

The South Side has plenty of public parks, gardens, museums and landmarks. Highlights include the Museum of Science and Industry, the DuSable Museum of African American History, the Pullman Historic District and the Frederick C. Robie House. For shopping, you’ll find lots of options along State Street and at the Chicago Ridge Mall.

For music and nightlife, the South Side has plenty of clubs and bars, or you can catch a show at the Riviera Theatre. When it comes to food, you’ll find everything from classic Italian in Little Italy to top-notch Asian dishes in Chinatown.

The South Side also has many unique neighborhoods, each with its own character — from the quiet residential streets of Beverly to the lively energy of Woodlawn.

#5. Navigating Public Transportation

Chicago’s public transit includes CTA buses and trains, Metra commuter trains, and Pace buses that serve the suburbs.

  • The CTA ‘L’ Trains: This is the busiest transit system in the Midwest, carrying about 1.7 million rides each day; it’s the backbone of the city’s transit, linking both commuters and visitors to downtown, neighborhoods, and the far north, south, east, and west sides;
  • The Metra Commuter Rail System: It has eight lines connecting Chicago with its suburbs. Pace suburban buses reach even farther, serving more than 700 communities across six counties in northern Illinois;
  • Bicycle Riders: The Divvy bike-sharing program has about 5,800 bikes and 580 stations across the city. It also connects with CTA routes, making it easy to combine biking with bus or train rides. There are also plenty of bike paths for both leisure and commuting, giving riders easy access to parks, workplaces and other destinations.

#6. Chicago’s Job Market Opportunities

According to We Will Chicago, the city has the most diverse economy in the country, with no single industry making up more than 14% of it.

Chicago also has the second-highest number of Fortune 500 companies which is one of the many reasons it’s considered a strong business hub.

A few of these are highlighted here:

  • Chicago is home to more Transportation, Distribution & Logistics (TDL) companies than any other city in the U.S.; since 2010, more than 200 TDL start-ups have been launched; this industry includes not only trucking and rail freight but also funding for research and development of advanced autonomous vehicles;
  • Chicago is ranked among the top ten U.S. cities for its Life Sciences and Healthcare sector, with many well-known scientists and biologists based here; in the past three years, the city has also seen the biggest jump in venture capital funding for life sciences;
  • Because of its wide range of economic resources, the Chicago tech sector is thriving. It serves both TDL companies and Fortune 500 firms. With more than 12,300 businesses employing over 344,000 people, its strength is also shown by the fact that it produces the second-highest number of computer science degrees in the U.S.

#7. Chicago’s Crime Rates

When looking at crime rates, it’s important to know that the numbers don’t always show the full picture. Even though Chicago’s crime stats may seem high, the city is still safer than 9% of U.S. cities.

It was not listed in Neighborhood Scout’s 2022 Top 100 Most Dangerous Cities report. For murder rates, it ranks seventh in the country, behind cities such as St. Louis, New Orleans and Baltimore. So, is Chicago really a dangerous place?

One thing to understand about Chicago’s high crime rate is that violent crimes — like homicide, rape and robbery — make up more of the city’s crime than property crimes, such as burglary, arson or car theft.

But like any big city, the risk of crime depends on your situation and the neighborhood you live in. According to statistics, the chances of being a victim of violent crime in your area are 1 in 103.

#8. Retirement in Chicago

Chicago’s Area Agency on Aging works to make sure seniors enjoy a good quality of life. Eligible seniors can get benefits through more than 70 programs and they can also take part in free activities at the city’s senior centers.

Seniors can also choose from many living options in the city, including upscale independent and assisted living communities. Chicago is home to top hospitals like Northwestern Memorial Hospital, the University of Chicago Medical Center and Lurie Children’s Hospital, giving retirees access to excellent medical care.

#9. Quality Education in Chicago

Whether you’re interested in public or private schools, K–12 or higher education, Chicago is a strong place to find quality learning opportunities.

Chicago Public Schools

Chicago is well known for its strong education system. Public schooling has been a focus in the city for more than 100 years.

The Chicago Public Schools (CPS) system is the third-largest district in the U.S., serving over 400,000 students in 612 schools. CPS promotes a culture of excellence, aiming to support every student’s success and prepare them for college and future careers.

The district’s wide curriculum helps students get a balanced education in subjects like arts, language, science, math, social studies and physical education. About 63% of Chicago public school students go on to higher education.

Chicago Private Schools

Private schools in Chicago vary, from religious-based institutions to general education schools. Some of the most well-known are Latin School, Francis W. Parker School and DePaul College Prep.

These schools are well known for offering quality education with high academic standards. There are also many charter schools in Chicago that focus on personalized teaching and different approaches to learning.

No matter what type of private school you’re looking for, Chicago has options for everyone.

Chicago Colleges and Universities

Chicago has many well-known universities and colleges that give students access to a wide range of academic resources and opportunities. Each school offers different undergraduate, graduate, professional degree programs and Ph.D. options.

Notable universities and colleges in Chicago include the University of Chicago, DePaul University, Illinois Institute of Technology, Northwestern University and Loyola University Chicago.

The city also has smaller schools like the City Colleges of Chicago, which provide associate degrees, certificates and transfer programs.

#10. Chicago’s Culinary Scene

Chicago is famous for its food and is known for classics like the Chicago-style hot dog which is served without ketchup. The city also has 24 Michelin-starred restaurants, with nine of them in the West Loop and Fulton Market areas.

Notable Michelin-star restaurants include:

  • Goosefoot: Chef-owners Chris and Nina Nugent run this well-known BYO spot in Lincoln Square, which earned one Michelin star; for a more affordable choice, their nearby Goosefoot Food and Wine market offers a five-course tasting menu with French and Italian influences;
  • Oriole: Found in Chicago’s West Loop, Oriole is led by Executive Chef Noah Sandoval and Pastry Chef Genie Kwon; with wine director Alisha Elenz, the restaurant offers a tasting-menu-only experience that blends warm hospitality with creative culinary exploration;
  • EL Ideas: Guests visiting this Michelin-starred spot in Douglas Park can enjoy creative tasting menus which now include the well-loved french fries and ice cream dish; for takeout, Foss’ Boxcar BBQ still offers tasty chicken and ribs.

To explore Chicago’s food scene, you can check out Eater’s Guide for the best places to eat. Craft beer fans can visit the city’s 20 top taprooms. All year long, Chicago shows its love for food with different events and festivals.

The huge Taste of Chicago is the world’s largest food festival, while Craft Beer Week happens in May and the Lincoln Park Wine Fest takes place in October.

#11. Parks & Recreation in Chicago

Chicago has lots of well-known parks that give residents space to relax and enjoy the outdoors.

Millennium Park

Opened in 2004 and located in the heart of the city, Millennium Park offers acres of green space, gardens, art displays and an outdoor concert stage. It also hosts activities like ice skating, farmers’ markets and more for everyone to enjoy.

Wicker Park

At the heart of Wicker Park is the Wicker Park Field House, built in the 1930s, which offers fitness facilities, recreation programs and meeting space. The park also features some of Chicago’s most famous murals, like the Milky Way Mural and the Meguro Mural.

Lincoln Park

Lincoln Park includes sports fields, tennis courts, jogging paths, playgrounds, picnic spots, lake access, an outdoor theater and the Lincoln Park Zoo. It also has many art displays, monuments and gardens.

#12. Activities and Things to Do in Chicago

Whether you’re interested in outdoor fun, entertainment or cultural experiences, there’s no shortage of things to do in Chicago.

Theater & Events

Well-known live shows in the city include the Second City improv troupe and the Steppenwolf Theatre Company. Other major attractions are Broadway-style shows at the Goodman Theatre and performances at the Lyric Opera of Chicago.

Art Galleries

The Art Institute of Chicago is one of the city’s oldest and most respected galleries, showcasing art from around the world across many centuries. The city also has many smaller independent galleries that feature different styles, including street art, sculpture, fashion and photography.

Music Festivals

Chicago is home to lively festivals that celebrate culture, diversity and history. The Chicago Cultural Center Art Festival offers events year-round. Bigger summer festivals include the Chicago Blues Festival with both traditional and modern performers, and Lollapalooza, a multi-day international music event. The city also hosts the World Music Festival and the Chicago Jazz Festival.

Museums & Attractions

The Shedd Aquarium has long been a favorite spot, showcasing aquatic life from around the world. Other well-known museums include the Field Museum, Adler Planetarium, Museum of Science and Industry, and the Chicago History Museum.

Shopping Destinations

The Magnificent Mile on North Michigan Avenue is one of the city’s most popular shopping spots, filled with many stores and restaurants. State Street is another major shopping area, home to the historic Marshall Field department store. Other favorites include Water Tower Place, Navy Pier and the Shops at North Bridge.

#13. Chicago Sports Teams

Whether you’re at the arena or watching from a local sports bar, cheering for Chicago’s teams with friends or family is always a fun and exciting experience.

  • The Chicago Cubs are one of the oldest and most historic franchises in Major League Baseball.
  • The Chicago White Sox are seen as the tough team with die-hard fans and one of the best ballparks; football fans keep the spirit of former head coach Mike Ditka alive as they cheer for the Chicago Bears at Soldier Field — especially against rivals like the Green Bay Packers.
  • Hockey fans have high expectations for the Chicago Blackhawks, who have won three Stanley Cups in recent years with their loud and passionate supporters.
  • Chicagoans treasure the memories of the dominant ’90s Bulls and know that the Michael Jordan, Scottie Pippen and Dennis Rodman era is a sign of more great moments to come.

A Chicago-Moving Checklist

A clear moving checklist can help you stay organized and handle all the tasks needed to make your move easier. Here are some tips for moving to Chicago:

  • Update your voter registration.
  • Go to the Illinois Secretary of State/DMV website to register your car and update your driver’s license.
  • In Illinois, if your vehicle is four years old or more, it must pass an emissions test every two years.
  • Forward your mail with the United States Postal Service (USPS). Keep in mind this doesn’t automatically update your address everywhere, so use this checklist to make sure you change it where needed.

Pros and Cons of Moving to Chicago

If you’re wondering, “Should I move to Chicago?” here’s a quick look at the pros and cons.

Pros

  • Great Lob Opportunities: With its strong economy and wide range of jobs, Chicago is a great place for newcomers to build their careers.
  • Cultural Diversity: The city offers rich cultural experiences, from world-class museums and art galleries to countless festivals.
  • Unique Cuisine: From Italian beef sandwiches to Garrett’s popcorn and more — you’ll never go hungry in Chicago.
  • Great Music Scene: Chicago is home to famous jazz and blues venues and regularly hosts well-known performers;
  • Beautiful Architecture: A walk along Michigan Avenue will leave you impressed by the city’s stunning buildings.

Cons

  • Cost of Living: Chicago is one of the pricier cities in the U.S., with some of the highest rent costs in the nation.
  • Cold Winters: Temperatures in the Windy City can get very cold and snowfall can be heavy.
  • Traffic Congestion: With crowded streets and highways, drivers should expect delays when moving around the city.
  • Unpredictable Weather: Chicago’s weather can change quickly, so it’s best to be ready for anything.

Get Ready to Relocate to Chicago

From reliable public transportation to amazing attractions, Chicago has plenty to offer its residents. Moving to a new city like Chicago can feel overwhelming at times, but being prepared makes the process much easier.

With the right preparation and mindset, you can get the best out of your new life in the Windy City and enjoy all the amazing experiences it offers.

Wondering how to move to Chicago? If you need help with packing and moving, reach out to us. STI Moving & Storage provides full moving services to make the process easier for you.