Offering world-class cultural attractions, exciting career opportunities, and affordable living, moving from Boston to Chicago has become a super popular relocation opportunity in recent years. Chi-town is also home to excellent schools, including the University of Illinois and the University of Chicago, as well as dynamic & diverse neighborhoods and myriad points of interest.

Cheaper than most major cities while packing in a ton of amenities and prospects, the Windy City will carry you along in a favorable direction! But before you book moving services, give yourself the advantage of knowing exactly what to expect when you move to Chicago from Boston including who are the best moving companies that can offer high-quality interstate services.

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What to Know About Moving from Boston to Chicago

Abundant job opportunities, iconic architecture, tasty eats, cheaper living expenses… moving to Chicago from Boston has a long list of benefits! Relocating from New England to the Midwest can be a significant change, so make sure to prepare.


When moving to a new city and state, it’s always smart to know about taxation. Chicago and Boston are among the greatest cities in America, and when we look at taxes in the biggest metropolises, we find that Chicago is quite a bit more expensive when it comes to sales tax. More specifically, the Windy City has a total sales tax of 10.25% compared to 6.25% in Beantown. When it comes to total top income tax rate (both states have graduated tax rates), it’s slightly lower in Chicago (4.95% versus 5.1%).

Want to be a homeowner? Be prepared to pay more in property taxes in Chicago. The average county tax rate is currently 2.117%, or $10,585 per year (based on an assessed home value of $500,000). That’s a chunk of change, particularly compared to 0.804% in Boston, or $4,020 annually for the same home value. But before you have second thoughts, check out the ‘House and Cost of Living’ section. We think you’ll be more than pleasantly surprised by Chicago’s housing prices.

Economy and Job Growth

Offering one of the strongest economies in America – it’s got the third-largest city economy based on GDP – as well as much lower living costs than many other major cities, Chicago has a lot to offer.

With ten Fortune 500 companies within the city (as well as 26 others within proximity), business opportunities abound! As for key industries, four immediately come to mind: manufacturing, transportation, information technology, and health services & technology.

As of the beginning of 2020, the unemployment rate in Chicago was 4.4%. This rate was higher than the US average of 3.9% and Boston’s rate of just 3.1%. Future job growth in the Windy City is projected to be 25.7%, while Boston looks to enjoy a healthy 42.5% over the next ten years.

Housing and Cost of Living

Most people make a beeline to this section, and for a good reason. With rising housing costs in places like Boston, it’s hard to find a major city that offers as much as Chicago does with such a small price tag. When it comes to the cost of living in Chicago, you’ll keep more money in your pocket! The index is 106.9. It’s higher than the US average index of 100, but compared to Boston’s index of 162.4, it’s a bargain!

Okay, so now for the big reveal. Housing is a top reason why folks relocate from Boston to Chicago. The median list price in Chi-town is $329,000 (with a median rent price of $1,761). Boston, for comparison, commands a whopping median list price of $769,000 (with a median rent price of $2,950). Wow. Just, wow. In Chicago, you might have the opportunity to become a homeowner!

Things to Do

Chicago has no shortage of fun things to do. One thing’s for sure; you shouldn’t have to worry about getting bored here! Yes, Boston offers a great selection of sports, arts, entertainment, and more. But if you’re an outdoor enthusiast, foodie, music lover, or sports fan, then the City of Chicago is a fantastic place to have fun & explore.

Love sports? There are five major franchises here, including the Chicago Bulls and Chicago Cubs. Into the outdoors? Endless exploration of Lake Michigan and kayaking adventures on the Chicago River spoil nature lovers. Are you a culture buff? The Windy City is also home to many acclaimed museums, including Field Museum, Chicago History Museum, and the Museum of Contemporary Art. Bigtime foodie? From classic deep-dish pizza to French-Filipino fusion, there’s something to get your taste buds going! Visit Centre Street Kitchen for innovative and locally-sourced dishes. Looking for a crazy combo of influences? Proxi mixes American, Middle-Eastern, Indian, Thai, and Japanese into a final form that will leave you fully satisfied.

Educational Opportunities

Chicago Public Schools (CPS), home to nearly 360,000 students and 650 schools, is made up of a collection of traditional, contract, and charter schools. The average student-teacher ratio is 16:1. Be sure to research each school in which you’re interested. We recommend the phenomenal resource that is

Home to a wide selection of colleges, universities, junior colleges, and trade schools, Chicago offers a long list of post-secondary options. Notable institutions of higher learning include the University of Chicago (#6 in the nation), Loyola University Chicago (#104 in the nation), and Illinois Institute of Technology (#117 in the nation). If you’re interested in attending some of the best schools in the country, Chicago certainly does not disappoint!

Crime Rates

Are you concerned about safety? We’ve all heard the stories coming out of Chicago. Yes, it has higher crime rates than Boston – Chicago has a violent crime rate and property crime rate of 49.9 and 46.3, respectively, while Boston has rates of 37.3 and 35.8 – but that doesn’t mean crime plagues the entire city.

According to HomeSnacks, the safest neighborhoods in Chicago include Edison Park, Forest Glen, Norwood Park, Mount Greenwood, and O’Hare. Despite what we see on the news, there is plenty of family-friendly, safe mini-communities ideal for raising kids and enjoying peace of mind.


Sure, Boston has its iconic food – baked beans, cream pies, clam chowder, seafood – but Chicago is legendary for its cuisine. Of course, one of the first items that comes to mind is Chicago-style pizza, particularly deep-dish pizza. You can enjoy some of the best pizza at Burt’s Place, Bartoli’s Pizzeria, and The Art of Pizza. Another major mainstay is Chi-town’s Italian beef sandwich. Without a doubt, Al’s Italian Beef is one of the best spots for mouthwatering roasted sirloin and thick rolls.

Revered by hip hop’s elite, including the likes of Kanye West and Common, Harold’s Chicken Shack is a must-stop for fried chicken lovers. Love donuts? Hit up Do-Rite Donuts, especially for their signature buttermilk old-fashioned donut. And we couldn’t end our recommendations without mentioning Chicago-style hotdogs. For the quintessential dog, it doesn’t get any tastier than at Portillo’s!

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Best Boston to Chicago Movers


Boston, MA

Exceptional! based on 3200+ data points.
Since 2001, Stairhopper Movers has operated as a Boston-based local moving company that performs local and long-distance residential and commercial moves. As a full-service moving... Continue Reading

Somerville, MA

Superb! based on 1200+ data points.
Born and bred in Boston, Gentle Giant has been the go-to moving and storage company for residents and business owners of Beantown for over forty... Continue Reading

Newton, MA

Superb! based on 650+ data points.
This full-service moving company has been helping people move in the Boston area for over five years. Flash Moving and Storage performs residential and commercial... Continue Reading

Best Neighborhoods in Chicago

The neighborhoods are some of the top places to call home in the Windy City.

Albany Park

One of the most diverse neighborhoods not only in Chicago but the US, Albany Park is home to more than 52,000 residents. Despite its size, it’s a friendly & safe community boasting a colorful tapestry of multiculturism – from Middle Eastern to Korean and Yugoslavian residents. Over the years, Albany Park has rightfully earned the title as one of the most loved CHI neighborhoods. Learn more here.

Hyde Park

Straddled between two of Chicago’s most iconic institutions – the University of Chicago is to the west and the Museum of Science & Industry is to the east – Hyde Park is another culturally rich neighborhood. Home of President Barack Obama, the community, is rich in cultural significance and history. Discover more about Hyde Park here.

River West

Once a part of River North, River West is now its own thriving neighborhood. Ideal for those looking for a break from the noise of downtown, yet still close enough to all the action, this mini-community has many phenomenal restaurants, which is a big draw for residents and folks from all over Chicago. Get more information on this relatively newer neighborhood here.

Wicker Park

Are you looking for fantastic nightlife, cuisine, and overall entertainment? Wicker Park certainly checks all the boxes! If you’re into music specifically, this is the neighborhood for you. Home to some of the best live venues in the city, here, you’ll find a large concentration of millennials and Gen-Xers. Offering a mix of affordable rent and more expensive homes, Wicker Park has a nice variety. Find out more here.

Lincoln Park

Home to Lincoln Park Zoo, fantastic restaurants, and an assortment of trendy shops & top retailers, Lincoln Park is one of the most popular neighborhoods in Chi-town. Residents represent a diverse demographic, from ambitious professionals to college students, and the community offers relaxing outdoor areas and much more. Lincoln Park is also a heaven for those that enjoy retail therapy. Learn more here.

South Loop

Home to the city’s museum campus – that includes the Adler Planetarium, the Field Museum, and the Shedd Aquarium – South Loop is also home to Grant Park, which comprises nearly 320 acres of recreation areas and rejuvenating green space. These amenities alone are a huge draw for the neighborhood’s happy residents. Take a look at South Loop in more detail here.

Logan Square

If tree-lined streets and elegant Chicago homes are more your jam, look no further than Logan Square. As one of Chicago’s most desirable neighborhoods, it offers a great blend of family-friendly atmosphere and lively nightlife. Indeed, this trendy community has a bit of something for everyone. Dive into greater detail on Logan Square here.

Roscoe Village

Known as the Village with a City, Roscoe Village offers a decidedly small-town, laidback vibe on Chicago’s north side. You’ll find a nice assortment of housing from apartments to single-family homes, perfect for raising a family. There are also several intimate shops and restaurants. Close-knit and cozy, Roscoe Village is a beautiful place to grow up and live. Discover more on this charming neighborhood here.

Cost of Moving from Boston to Chicago

On average, it costs about $2,500-$4,000 to move from Boston to Chicago. Though this might sound expensive, consider that you are hauling your stuff about 984 miles across the country. The total cost of your move will depend on several variables, including your origin and destination zip codes, the time of year you’re moving, the size of your household, and which services you require. The best way to get an accurate estimate is by scheduling an in-home or virtual (no contact) walkthrough with a licensed and insured interstate mover. Get free moving quotes from the best Boston to Chicago movers now!

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Devin Barroga

Ever been bitten by the wanderlust bug? It's a powerful force, one which has captivated Devin for his entire life.... Read More