There are 9 ways to get from Illinois 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  •  4 h 17 min

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

$95 - $387

Cheapest option

Fly Chicago O'Hare to Boston  •  4 h 34 min

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

$84 - $270

7 alternative options

Fly Chicago Midway to Manchester  •  4 h 27 min

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

$302 - $654

Fly Chicago Midway to Hartford, bus  •  5 h 41 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 Midway to Providence, bus  •  7 h 10 min

  1. Fly from Chicago Midway (MDW) to Providence (PVD) MDW - PVD
  2. Take the bus from SRTA Fall River Terminal to SRTA New Bedford Terminal

$116 - $366

Bus D&J Bus  •  20 h 37 min

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

$117 - $127

Train  •  22 h 48 min

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

$132 - $392

Bus Greyhound USA  •  23 h 13 min

  1. Take the bus from Chicago, Il to New York, Ny 1604
  2. Take the bus from New York, Ny to Boston, Ma 2504 / ...

$105 - $271

Drive  •  16 h 30 min

  1. Drive from Chicago to Boston 996.7 miles

$95 - $150

Questions & Answers

The cheapest way to get from Illinois to Massachusetts is to drive which costs $95 - $150 and takes 16 h 30 min.

More details

The quickest way to get from Illinois to Massachusetts is to fly which costs $95 - $390 and takes 4 h 17 min.

More details

The distance between Illinois and Massachusetts is 922 miles. The road distance is 996.7 miles.

Get driving directions

It takes approximately 4 h 17 min to get from Illinois to Massachusetts, including transfers.

More details

No, there is no direct bus from Illinois to Massachusetts. However, there are services departing from 929 W Cermak and arriving at Boston, MA via Chicago, IL and New York. The journey, including transfers, takes approximately 20 h 37 min.

More details

What companies run services between Illinois, 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 Cermak & Clark, Chicago, IL, and New York in around 20 h 37 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 Manchester
Ave. Duration
2 h 5 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Manchester via Baltimore
Ave. Duration
4 h 25 min
When
Every day
Estimated price
$120 - $900
Flights from Chicago Midway to Hartford
Ave. Duration
1 h 58 min
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
4 h 11 min
When
Every day
Estimated price
$190 - $900
Flights from Chicago Midway to Providence
Ave. Duration
2 h 9 min
When
Every day
Estimated price
$140 - $700
Flights from Chicago Midway to Providence via Baltimore
Ave. Duration
4 h 8 min
When
Every day
Estimated price
$140 - $700
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 17 min
When
Every day
Estimated price
$120 - $490
United Airlines
Website
united.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 19 min
When
Every day
Estimated price
$130 - $650
Delta
Website
delta.com
Flights from Chicago Midway to Boston via Detroit
Ave. Duration
4 h 6 min
When
Every day
Estimated price
$140 - $850
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 8 min
When
Every day
Estimated price
$200 - $750
Flights from Chicago Midway to Providence via Detroit
Ave. Duration
4 h 13 min
When
Every day
Estimated price
$140 - $650
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
Porter Airlines
Website
flyporter.com
Flights from Chicago Midway to Boston via Toronto Island
Ave. Duration
4 h 10 min
When
Sunday
Estimated price
$220 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Chicago O'Hare to Boston
Ave. Duration
2 h 27 min
When
Every day
Estimated price
$110 - $450
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 Amtrak to Boston South Station Amtrak
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
4 h 20 min
Frequency
Every 30 minutes
Estimated price
$25 - $65
Website
greyhound.com
Economy
$25 - $40
Flexible
$45 - $65
Southeastern RTA
Phone
+1 508-999-5211
Email
info@srtabus.com
Website
srtabus.com
Bus from SRTA Fall River Terminal to SRTA New Bedford Terminal
Ave. Duration
1 h
Frequency
Every 20 minutes
Estimated price
$2
Schedules at
srtabus.com
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from Fall River, MA to New Bedford, MA
Ave. Duration
25 min
Frequency
Twice daily
Estimated price
$11 - $15
Schedules at
peterpanbus.com
Book at
webstore.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
Schedules at
peterpanbus.com
Book at
webstore.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

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