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How to Travel from

Chicago to Massachusetts

by Rideshare, Route or Car

Chicago
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Massachusetts
Transport search to Massachusetts
Chicago
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Massachusetts
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Eight ways to Travel from Chicago to Massachusetts

Select an Option Below to Start Your Journey
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Transport providers

Airlines

JetBlue Airways

Website:
jetblue.com/
Plane from Chicago O'Hare International Airport to General
Ave. Duration:
2h 22m
Frequency:
Every day
Estimated price:
$56.05–$573.24

American Airlines

Website:
aa.com/
Plane from Chicago O'Hare International Airport to General
Ave. Duration:
2h 21m
Frequency:
Every day
Estimated price:
$82.80–$458.59
Plane from Chicago O'Hare International Airport to Theodore
Ave. Duration:
2h 19m
Frequency:
Every day
Estimated price:
$121.02–$522.28
Plane from Chicago O'Hare International Airport to Bradley
Ave. Duration:
2h 12m
Frequency:
Every day
Estimated price:
$140.12–$624.19

Delta

Website:
delta.com/
Plane from Chicago O'Hare International Airport to General
Ave. Duration:
2h 22m
Frequency:
Every day
Estimated price:
$127.39–$318.46
Plane from Chicago O'Hare International Airport to Theodore
Ave. Duration:
4h 52m
Frequency:
Every day
Estimated price:
$114.65–$292.99
Plane from Chicago O'Hare International Airport to Bradley
Ave. Duration:
4h 31m
Frequency:
Every day
Estimated price:
$127.39–$343.94

United Airlines

Website:
united.com/
Plane from Chicago O'Hare International Airport to General
Ave. Duration:
2h 21m
Frequency:
Every day
Estimated price:
$89.17–$573.24
Plane from Chicago O'Hare International Airport to Theodore
Ave. Duration:
2h 31m
Frequency:
Monday
Estimated price:
$152.86–$522.28
Plane from Chicago O'Hare International Airport to Bradley
Ave. Duration:
2h 12m
Frequency:
Every day
Estimated price:
$178.34–$624.19

Southwest Airlines

Website:
southwest.com/
Plane from Midway International Airport to General
Ave. Duration:
2h 10m
Frequency:
Every day
Estimated price:
$127.39–$343.94
Plane from Midway International Airport to Theodore
Ave. Duration:
2h 5m
Frequency:
Every day
Estimated price:
$140.12–$420.37
Plane from Chicago O'Hare International Airport to Theodore
Ave. Duration:
4h 12m
Frequency:
Tuesday and Wednesday
Estimated price:
$127.39–$394.90
Plane from Midway International Airport to Manchester
Ave. Duration:
2h 2m
Frequency:
Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
Estimated price:
$178.34–$560.50
Plane from Midway International Airport to Bradley
Ave. Duration:
2h 1m
Frequency:
Every day
Estimated price:
$152.86–$496.81
Plane from Chicago O'Hare International Airport to Bradley
Ave. Duration:
4h 55m
Frequency:
Tuesday and Wednesday
Estimated price:
$152.86–$471.33

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Chicago Union Station to Boston
Ave. Duration:
22h 2m
Frequency:
Once daily
Estimated price:
$101.91–$343.94
Train from Windsor Locks to Springfield
Ave. Duration:
25 min
Frequency:
Every 4 hours
Estimated price:
$4.97–$70.06

MBTA

Phone:
+1-617-222-3200
Website:
mbta.com
Train from Providence to South
Ave. Duration:
1h 15m
Frequency:
Hourly
Estimated price:
$6.24–$16.56

Amtrak Northeast Regional

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Providence to South
Ave. Duration:
48 min
Frequency:
Every 3 hours
Estimated price:
$17.83–$242.03
Train from Windsor Locks to Springfield
Ave. Duration:
27 min
Frequency:
Twice daily
Estimated price:
$14.01–$229.29

Amtrak Acela

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Providence to South
Ave. Duration:
47 min
Frequency:
Every 4 hours
Estimated price:
$24.20–$394.90

Bus operators

Greyhound USA

Phone:
+1 214-849-8100
Website:
greyhound.com/
Bus from Boston Manchester Airport to Boston
Ave. Duration:
1h 5m
Frequency:
Once daily
Estimated price:
$4.08–$76.43

Flixbus USA

Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Chicago Bus Station to New
Ave. Duration:
20h 20m
Frequency:
Once daily
Estimated price:
$82.80–$267.51
Bus from New York Midtown to Boston
Ave. Duration:
4h 30m
Frequency:
Hourly
Estimated price:
$21.66–$82.80

Questions and Answers

What is the cheapest way to get from Chicago to Massachusetts?

The cheapest way to get from Chicago to Massachusetts is to fly which costs $45.65 - $271.74 and takes 4h 26m.

What is the fastest way to get from Chicago to Massachusetts?

The fastest way to get from Chicago to Massachusetts is to fly which takes 4h 3m and costs $76.09 - $652.17 .

Is there a direct bus between Chicago and Massachusetts?

No, there is no direct bus from Chicago station to Massachusetts. However, there are services departing from Chicago Bus Station and arriving at Boston via New York Midtown. The journey, including transfers, takes approximately 25h 36m.

Is there a direct train between Chicago and Massachusetts?

Yes, there is a direct train departing from Chicago Union Station station and arriving at Boston. Services depart once daily, and operate every day. The journey takes approximately 22h 2m.

How far is it from Chicago to Massachusetts?

The distance between Chicago and Massachusetts is 1431 km. The road distance is 1595 km.

How do I travel from Chicago to Massachusetts without a car?

The best way to get from Chicago to Massachusetts without a car is to train which takes 22h 2m and costs $86.96 - $293.48 .

How long does it take to get from Chicago to Massachusetts?

It takes approximately 4h 26m to get from Chicago to Massachusetts, including transfers.

Where do I catch the Chicago to Massachusetts bus from?

Chicago to Massachusetts bus services, operated by Flixbus USA, depart from Chicago Bus Station.

Where do I catch the Chicago to Massachusetts train from?

Chicago to Massachusetts train services, operated by Amtrak, depart from Chicago Union Station.

Train, bus or fly from Chicago to Massachusetts?

The best way to get from Chicago to Massachusetts is to fly which takes 4h 26m and costs $45.65 - $271.74 . Alternatively, you can train, which costs $86.96 - $293.48 and takes 22h 2m, you could also bus, which costs $92.39 - $293.48 and takes 25h 36m.

Where does the Chicago to Massachusetts bus arrive?

Chicago to Massachusetts bus services, operated by Flixbus USA, arrive at New York Midtown station.

What is the time difference between Chicago and Massachusetts?

Massachusetts is 1h ahead of Chicago. It is currently 06:12 in Chicago and 07:12 in Massachusetts.

Where does the Chicago to Massachusetts train arrive?

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

Can I drive from Chicago to Massachusetts?

Yes, the driving distance between Chicago to Massachusetts is 1595 km. It takes approximately 16h 33m to drive from Chicago to Massachusetts.

How do I get a train ticket from Chicago to Massachusetts?

Book your Chicago to Massachusetts train tickets online with Omio.

How do I get a bus ticket from Chicago to Massachusetts?

Book your Chicago to Massachusetts bus tickets online with Omio and FlixBus.

Where can I stay near Massachusetts?

There are 23+ hotels available in Massachusetts. Prices start at $70.74 per night.
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