Moving from Boston to Chicago is an exciting experience. It’s a chance for a new job, new people, and to start over again. But with that excitement also comes many challenges. 

When moving to a different state, there are many things to consider: getting your finances in order, acclimating to the new environment, and finding the right neighborhood. That’s why we’ve put together this list of tips on making your move as smooth as possible.

Here are 9 tips for moving from Boston to Chicago to help you prepare for your move:

1. Do Your Research Ahead of Time

Before you move, research the area in which you want to live. Make sure you know what the weather is like and how much money you need to live there. Look into how safe the neighborhood you’re moving to and look into the school systems if you have kids.

Check out what kind of jobs are available in your area and see if there’s a healthy job market with opportunities for advancement. You’ll also want to look into how you’ll be getting around in Chicago—including public transportation, rideshare, and vehicle ownership options.

Many websites allow users to submit reviews and ratings for restaurants, shopping centers, and other attractions. Use these sites, as well as word-of-mouth from friends or family members who live in the area to learn more about whether or not Chicago is up your alley.

If possible, try visiting Chicago first before signing a lease or buying a home so that you can get an idea of what it’s like living there.

2. Take Advantage of Cheaper Housing

One of the top reasons to move from Boston to Chicago is that housing is so much more affordable. Apartments and condos are 75 to 100% cheaper. This gives you the opportunity to either decrease your monthly expenses or increase your quality of life (e.g. housing upgrade, etc.)

According to Zillow, the median home price in Boston is roughly 133% larger than the median home price in Chicago. And while rent in Chicago isn’t as low (relatively) as home values, it’s still cheaper— with the average rent being 75% more in Boston.

If you’re on a tight budget, stay outside of fancy new high rises. These can be very expensive and cater mainly to the wealthy people who don’t mind paying premium prices. You’ll still have plenty of choices in other neighborhoods.

3. Choose Your Neighborhood Wisely

When you’re moving from Boston to Chicago, you must choose a neighborhood that suits your needs and lifestyle. Some neighborhoods are great if you want a quiet residential area or need more space for growing kids. In contrast, others offer a mix of urban excitement and suburban comfort.

These are our top picks for the best neighborhoods in Chicago:


Living in Lakeview means you’re close to the beach and a few steps from being able to watch the sunrise over Lake Michigan. It’s got excellent nightlife and tons of young twenty-somethings looking for their next adventure. If you’re single, this is an ideal place for you.

Logan Square

Logan Square is a vibrant neighborhood home to young professionals, families, and retirees. It has a hip, trendy atmosphere with lots of restaurants, bars, and nightlife options in its area—all of which are very walkable, bikeable, and public transit-friendly. 

Logan Square was named one of Forbes’s 15 coolest neighborhoods by the country. Suppose you’re new to Chicago or just visiting. In that case, Logan Square is an excellent place to start exploring if you’re looking for something cool and urban.

Lincoln Park

Lincoln Park is a gorgeous neighborhood on the North Side of Chicago. Lincoln Park is great for families or anyone looking to live near the lake with lots of parks and activities. It’s also more affordable than other comparable neighborhoods, making it a good option if you’re looking to save some money. Plus, it has a low crime rate!

West Loop

If you’re looking to move and want to be in a neighborhood with many cool things to do, West Loop is a good option. West Loop has a population of about 35,000 people and hosts plenty of events throughout the year. 

You can always do something exciting in this neighborhood, whether it’s checking out new restaurants or going on an adventure at one of the many parks in the area.

Wicker Park

Wicker Park’s eclectic mix of historic buildings, vintage shops, and hipster hangouts makes this neighborhood very unique. The most noticeable features in Wicker Park are the beautiful brick buildings that line Milwaukee Avenue, creating a vibrant street scene with various shops and restaurants to explore. 

Wicker Park is a great neighborhood for young professionals. The area is fairly easy to get to, making for a quick commute into the Loop.  


Bucktown is a trendy neighborhood in Chicago. It is home to many art galleries, restaurants, and shopping destinations. 

Located northwest of the Loop and West Town, Bucktown is considered a hip place to live. The main commercial thoroughfares are North, Damen, and Milwaukee Avenues. These three streets have many boutiques, vintage shops, artsy stores, and small studios mixed with taverns, gastropubs, and restaurants.

Gold Coast

If you’re looking for beautiful homes and tree-lined streets, the Gold Coast is a great neighborhood. The Gold Coast is the most affluent neighborhood in Chicago and one of the wealthiest urban areas in North America. 

The Gold Coast is also home to some of the city’s most prestigious mansions and high-rise luxury condominiums. It’s got some of the area’s most expensive restaurants and hotels. It’s easy to get around using public transportation.

Old Town

Old Town is a historic neighborhood on the north side of downtown Chicago, having been settled by the French in the late 18th century. The neighborhood has a lot of history and old Victorian architecture, making it a popular tourist destination.  

Old Town is also home to many small businesses with unique shops and restaurants. It’s also known for its nightlife, with many bars and clubs along Wells Street.

4. Figure Out Your Transportation

Chicago has an excellent public transportation system, which can be a major plus for commuters. Whether you’re trying to get to a meeting across town or going back home after a night out, you can use public transit in Chicago instead of driving yourself.

Chicago’s subway is called the L, which comes from the train cars running on elevated tracks. From downtown (known as the Loop), most L train lines run 24/7 and come every five minutes or so during rush hour.

However, if you’re moving into the city, you’ll likely have more options than just public transit. Your new apartment or home could have parking available or be within walking distance of public transportation options.

Chicago also has bike-share programs, which allow you to rent bikes by the hour or day. Make sure to check out all of these options before deciding on one specific mode of transportation.

5. Prepare for Colder Winters

Chicago gets significantly colder than Boston on average in the winter. It shouldn’t surprise you, but it’s worth mentioning since Chicago winters are notoriously brutal and long. You’ll want to make sure that your car has snow tires, and you’ll also want to think about how you’ll get around town when the weather gets rough.

It’s not uncommon for temperatures to drop below zero with the wind chill in January and February. The weather is also drier in Chicago. While both cities get their fair share of precipitation, Chicago typically has less total snowfall per year.

Also, note that Chicago is nicknamed the “Windy City,” so don’t underestimate how much worse those sub-zero temps can feel because of it.

6. Take Advantage of the Summer

Now that we’ve gotten through the less-than-ideal weather part… Let’s rave about the Chicago summers for a minute!

If you can, line up your move so that you’re moving to Chicago in the summertime. Many people call it the best summer city in the U.S. With Lake Michigan right there, there are dozens of beaches and boating docks to enjoy. There’s also an endless parade of festivals and outdoor events to enjoy.

It’s important to remember that summer in Chicago will be much more enjoyable than any other season when you’re moving from Boston. Get a chance to spend at least one fantastic summer in Chicago before moving here permanently. It will make all the difference in your love for this fantastic city.

Here are just some of the things you can do in the Windy City during the summertime:

  • Get out on the water at Navy Pier and explore the city from a boat.
  • Head to Millennium Park for some free fountains and fun, interactive art installations.
  • Visit one of the sandy lakefront beaches and rent a jet ski, kayak, paddleboard, or fly board.
  • Check out the Art Institute of Chicago. Their outdoor sculpture garden is beautiful—and free!
  • Attend one of the many festivals, concerts, and other fun events such as Lollapalooza and Pride in the Park happening throughout the summer months.

7. Explore the Food Scene

Restaurants are everywhere—from fine dining to hole-in-the-wall joints that serve authentic ethnic cuisines—and they’re all different. Even though Boston has better seafood, Chicago will surprise you with the diversity and breadth of food choices. You can even find great food at street festivals.

Like any big city in America, Chicago has a lot of cheap places to eat that are great for grabbing something on the way home from work or getting something quick for lunch on your break. Chicago is known for its deep-dish pizza and hot dogs, but there are tons more you should know about local cuisine.

Chicago is also known for its incredible restaurants and world-class chefs. You should check out some of the local favorites. But if you’re looking to branch out beyond that, don’t be afraid to try something new!

8. Experience Chicago Nightlife

There’s no better way to bond with your new city than by getting out and meeting people. As you check out some local bars, you’ll find that nightlife is way better in Chicago than in Boston.

If you’re a night owl, you’ll have no trouble finding a place to get a drink late into the night in Chicago. Generally speaking—bars are open later in Chicago than in Boston, so don’t be afraid to try some new spots! Also, if you are over 21 years old, you can buy beer and wine at any pharmacy in Chicago.

There’s more going on in terms of music and nightlife than in Boston, especially for indie music and hip-hop. The people are more diverse, coming from other cities and states to work in education or tech companies—both big industries here—and decided to stay after they fell in love with the city’s culture and people!

9. Be Prepared to Meet People

Generally speaking—Chicago is known as a very friendly city. Many people who have moved from Boston to Chicago have found that they have met new people easier in Chicago.

Chicago is a much more relaxed, welcoming place to make new friends since people in Chicago tend to be down-to-earth. Chicago locals are typically very open about sharing their experiences with potential newcomers like yourself, who are excited about the city. The Midwest is full of people who want to help you.


Moving from Boston to Chicago is a big decision. But it’s also an excellent opportunity to improve your quality of life. The cost of living is also much more affordable in Chicago than in Boston, making it a great city to live in economically. 

It’s filled with lovely and unique neighborhoods that can fit a wide variety of lifestyles. There’s also something more to do in this big, vibrant city–from foods to try, bars to explore, and activities to share with new friends. 

By keeping these tips in mind and researching your new city, you’ll be well equipped to handle this exciting new adventure.

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