There are 11 ways to get from Chicago to Massachusetts by plane, bus, train or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Chicago Midway to Boston  •  3 h 59 min

  1. Fly from Chicago Midway (MDW) to Boston (BOS) MDW - BOS

$95 - $387

Cheapest option

Fly Chicago O'Hare to Boston  •  4 h 14 min

  1. Fly from Chicago O'Hare (ORD) to Boston (BOS) ORD - BOS

$80 - $268

9 alternative options

Fly Chicago Midway to Manchester  •  4 h 9 min

  1. Fly from Chicago Midway (MDW) to Manchester (MHT) MDW - MHT

$302 - $654

Fly Chicago Midway to Hartford, bus  •  5 h 23 min

  1. Fly from Chicago Midway (MDW) to Hartford (BDL) MDW - BDL
  2. Take the bus from Hartford, Ct to Springfield, Ma

$182 - $438

Fly Chicago O'Hare to Hartford, bus  •  5 h 42 min

  1. Fly from Chicago O'Hare (ORD) to Hartford (BDL) ORD - BDL
  2. Take the bus from Hartford, Ct to Springfield, Ma

$172 - $379

Bus to Milwaukee, fly to Boston  •  6 h

  1. Take the bus from Chicago, IL - O'Hare International Airport to Milwaukee, WI - Airport
  2. Fly from Milwaukee (MKE) to Boston (BOS) MKE - BOS

$155 - $353

Fly Chicago Midway to Providence, bus  •  6 h

  1. Fly from Chicago Midway (MDW) to Providence (PVD) MDW - PVD
  2. Take the bus from Providence, RI to New Bedford

$116 - $353

Bus D&J Bus  •  19 h 30 min

  1. Take the bus from Chicago, IL to New York Djb149 / ...
  2. Take the bus from New York to Boston, MA New York

$115 - $125

Train  •  21 h 31 min

  1. Take the train from Chicago Union Station to Boston South Station Lake Shore Limited

$130 - $390

Bus Greyhound USA  •  21 h 59 min

  1. Take the bus from Chicago, Il to New York, Ny 1604
  2. Take the bus from New York City, NY - Port Authority Bus Terminal to Boston, MA - South Station Ny / ...

$101 - $262

Drive  •  16 h 31 min

  1. Drive from Chicago to Boston 996.8 miles

$95 - $150

Questions & Answers

No, there is no direct bus from Chicago to Massachusetts. However, there are services departing from Chicago, IL and arriving at Boston, MA via New York. The journey, including transfers, takes approximately 19 h 30 min.

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Yes, there is a direct train departing from Chicago Union Station station and arriving at Boston South Station station. Services depart once daily, and operate every day. The journey takes approximately 21 h 31 min.

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The distance between Chicago and Massachusetts is 803 miles. The road distance is 996.8 miles.

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The best way to get from Chicago to Massachusetts without a car is to bus which takes 19 h 30 min and costs .

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It takes approximately 3 h 59 min to get from Chicago to Massachusetts, including transfers.

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Chicago to Massachusetts bus services, operated by Greyhound USA, depart from Chicago, Il station.

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Chicago to Massachusetts train services, operated by Amtrak, arrive at Chicago Union Station.

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The best way to get from Chicago to Massachusetts is to fly which takes 3 h 59 min and costs . Alternatively, you can bus, which costs and takes 19 h 30 min, you could also train, which costs and takes 21 h 31 min.

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The quickest flight from Chicago Midway Airport to Boston Airport is the direct flight which takes 2 h 10 min.

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Chicago to Massachusetts bus services, operated by Peter Pan Bus Lines, arrive at Boston, MA - South Station.

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Map of how to get from Chicago to Massachusetts.
Launch map view
  • Distance: 803.5 miles
  • Duration: 3 h 59 min

What companies run services between Chicago, IL, USA and Massachusetts, USA?

Southwest Airlines, Delta and Porter Airlines fly from Chicago to Boston hourly. Alternatively, you can take a bus from Chicago to Boston via New York in around 19 h 30 min.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Boston
Ave. Duration
2 h 14 min
When
Every day
Estimated price
$130 - $550
Flights from Chicago Midway to Boston via Baltimore
Ave. Duration
4 h 5 min
When
Monday to Friday
Estimated price
$130 - $550
Flights from Chicago Midway to Manchester
Ave. Duration
2 h 2 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Manchester via Baltimore
Ave. Duration
4 h 22 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Hartford
Ave. Duration
1 h 57 min
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$190 - $900
Flights from Milwaukee to Boston
Ave. Duration
2 h 15 min
When
Every day
Estimated price
$170 - $550
Flights from Chicago Midway to Providence
Ave. Duration
2 h 6 min
When
Every day
Estimated price
$140 - $700
Flights from Chicago Midway to Providence via Baltimore
Ave. Duration
4 h 16 min
When
Every day
Estimated price
$140 - $700
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 18 min
When
Every day
Estimated price
$120 - $490
Flights from Chicago O'Hare to Hartford
Ave. Duration
2 h 3 min
When
Every day
Estimated price
$320 - $700
Flights from Chicago O'Hare to Hartford via Philadelphia
Ave. Duration
3 h 56 min
When
Every day
Estimated price
$320 - $700
Flights from Milwaukee to Boston via Chicago O'Hare
Ave. Duration
4 h 20 min
When
Every day
Estimated price
$200 - $600
Flights from Milwaukee to Boston via Philadelphia
Ave. Duration
4 h 22 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$200 - $600
Delta
Website
delta.com
Flights from Chicago Midway to Boston via Detroit
Ave. Duration
3 h 55 min
When
Every day
Estimated price
$140 - $850
Flights from Chicago O'Hare to Boston via Detroit
Ave. Duration
3 h 56 min
When
Saturday
Estimated price
$100 - $550
Flights from Chicago Midway to Manchester via Detroit
Ave. Duration
4 h 13 min
When
Every day
Estimated price
$180 - $850
Flights from Chicago Midway to Hartford via Detroit
Ave. Duration
4 h 1 min
When
Every day
Estimated price
$200 - $750
Flights from Chicago O'Hare to Hartford via Detroit
Ave. Duration
4 h 2 min
When
Every day
Estimated price
$340 - $750
Flights from Milwaukee to Boston
Ave. Duration
2 h 11 min
When
Every day
Estimated price
$130 - $480
Flights from Milwaukee to Boston via Detroit
Ave. Duration
4 h
When
Every day
Estimated price
$130 - $480
Flights from Milwaukee to Boston via New York La Guardia
Ave. Duration
4 h 24 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$130 - $480
Flights from Chicago Midway to Providence via Detroit
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$140 - $650
United Airlines
Website
united.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 21 min
When
Every day
Estimated price
$130 - $650
Flights from Chicago O'Hare to Hartford
Ave. Duration
2 h 9 min
When
Every day
Estimated price
$320 - $750
Flights from Chicago O'Hare to Hartford via Washington Dulles
Ave. Duration
4 h 8 min
When
Every day
Estimated price
$320 - $750
Flights from Milwaukee to Boston via Chicago O'Hare
Ave. Duration
4 h 20 min
When
Every day
Estimated price
$140 - $700
Flights from Milwaukee to Boston via Newark
Ave. Duration
4 h 24 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$140 - $700
JetBlue Airways
Website
jetblue.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 22 min
When
Every day
Estimated price
$140 - $600
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Chicago Union Station to Boston South Station
Ave. Duration
21 h 31 min
Frequency
Once daily
Estimated price
$130 - $390
Website
amtrak.com
Coach Seat
$130 - $200
Flexi Coach Seat
$240 - $340
Business Coach Seat
$280 - $390
Room
$500 - $750
Bus operators
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Hartford, Ct to Springfield, Ma
Ave. Duration
35 min
Frequency
Every 20 minutes
Estimated price
$9 - $20
Website
greyhound.com
Economy
$9 - $13
Flexible
$16 - $20
Bus from Chicago, Il to New York, Ny
Ave. Duration
17 h 40 min
Frequency
Hourly
Estimated price
$80 - $200
Website
greyhound.com
Economy
$80 - $130
Flexible
$150 - $200
Bus from New York, Ny to Boston, Ma
Ave. Duration
7 h 39 min
Frequency
Every 10 minutes
Estimated price
$26 - $65
Website
greyhound.com
Economy
$26 - $40
Flexible
$45 - $65
Coach USA
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from Providence, RI to New Bedford
Ave. Duration
45 min
Frequency
Every 4 hours
Estimated price
$12 - $17
Website
peterpanbus.com
Bus from New York City, NY - Port Authority Bus Terminal to Boston, MA - South Station
Ave. Duration
4 h 15 min
Frequency
Hourly
Estimated price
$21 - $40
Website
peterpanbus.com
D&J Bus
Bus from Chicago, IL to New York
Ave. Duration
14 h
Frequency
Once daily
Estimated price
$90
Schedules at
gotobus.com
Book at
gotobus.com
Wanda Coach
Phone
6466307186
Email
help@wandacoach.com
Website
wandacoach.com
Bus from Chicago to New York, NY
Ave. Duration
13 h
Frequency
3 times a week
Estimated price
$100
Schedules at
wandacoach.com
Lucky Star Bus
Phone
(888) 881-0887 / (617) 269-5468
Email
info@luckystarbus.com
Website
luckystarbus.com
Bus from New York to Boston, MA
Ave. Duration
4 h 30 min
Frequency
Every 2 hours
Estimated price
$25
Schedules at
luckystarbus.com

Want to know more about travelling around United States

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More Questions & Answers

Massachusetts is 1 h ahead of Chicago. It is currently 7:10 PM in Chicago and 8:10 PM in Massachusetts.

Chicago to Massachusetts train services, operated by Amtrak, arrive at Boston South Station.

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Yes, the driving distance between Chicago to Massachusetts is 997 miles. It takes approximately 16 h 31 min to drive from Chicago to Massachusetts.

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Delta and Southwest Airlines offer flights from Chicago Midway Airport to Boston Airport.

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Book your Chicago to Massachusetts train tickets online with Rome2rio.

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There are 16+ hotels available in Massachusetts. Prices start at $102 USD per night.

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The best way to get from Chicago to Chicago Midway Airport is to subway which takes 23 min and costs .

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