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How to Travel from

Massachusetts to Chicago

by Rideshare, Route or Car

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

Select an Option Below to Start Your Journey
Cheapest
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Transport providers

Airlines

JetBlue Airways

Website:
jetblue.com/
Plane from General Edward Lawrence Logan International Airport to Chicago
Ave. Duration:
3h 3m
Frequency:
Every day
Estimated price:
$56.20–$574.77
Plane from General Edward Lawrence Logan International Airport to General
Ave. Duration:
2h 40m
Frequency:
Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
Estimated price:
$95.79–$523.68

American Airlines

Website:
aa.com/
Plane from General Edward Lawrence Logan International Airport to Chicago
Ave. Duration:
3h 3m
Frequency:
Every day
Estimated price:
$83.02–$459.82
Plane from Bradley International Airport to Chicago
Ave. Duration:
2h 46m
Frequency:
Every day
Estimated price:
$127.73–$587.54
Plane from General Edward Lawrence Logan International Airport to General
Ave. Duration:
4h 50m
Frequency:
Every day
Estimated price:
$89.41–$562.00

Delta

Website:
delta.com/
Plane from General Edward Lawrence Logan International Airport to Midway
Ave. Duration:
5h 39m
Frequency:
Every day
Estimated price:
$127.73–$332.09
Plane from General Edward Lawrence Logan International Airport to Chicago
Ave. Duration:
3h 3m
Frequency:
Every day
Estimated price:
$102.18–$255.45
Plane from Bradley International Airport to Chicago
Ave. Duration:
4h 35m
Frequency:
Every day
Estimated price:
$127.73–$332.09
Plane from General Edward Lawrence Logan International Airport to General
Ave. Duration:
2h 47m
Frequency:
Every day
Estimated price:
$121.34–$306.54

United Airlines

Website:
united.com/
Plane from General Edward Lawrence Logan International Airport to Chicago
Ave. Duration:
3h 3m
Frequency:
Every day
Estimated price:
$89.41–$574.77
Plane from Bradley International Airport to Chicago
Ave. Duration:
2h 56m
Frequency:
Every day
Estimated price:
$166.04–$587.54
Plane from General Edward Lawrence Logan International Airport to General
Ave. Duration:
5h
Frequency:
Every day
Estimated price:
$166.04–$638.63

Southwest Airlines

Website:
southwest.com/
Plane from General Edward Lawrence Logan International Airport to Midway
Ave. Duration:
2h 48m
Frequency:
Every day
Estimated price:
$127.73–$344.86
Plane from Bradley International Airport to Midway
Ave. Duration:
2h 30m
Frequency:
Every day
Estimated price:
$178.82–$549.22
Plane from Bradley International Airport to Chicago
Ave. Duration:
5h 5m
Frequency:
Monday, Thursday, and Friday
Estimated price:
$140.50–$434.27
Plane from Theodore Francis Green State Airport to Midway
Ave. Duration:
2h 36m
Frequency:
Every day
Estimated price:
$166.04–$498.13
Plane from Manchester Airport to Midway
Ave. Duration:
2h 35m
Frequency:
Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
Estimated price:
$204.36–$625.86
Plane from General Edward Lawrence Logan International Airport to General
Ave. Duration:
4h 40m
Frequency:
Monday to Friday
Estimated price:
$127.73–$408.72

Train operators

Amtrak

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from Boston to Chicago
Ave. Duration:
22h 22m
Frequency:
Once daily
Estimated price:
$102.18–$344.86
Train from Milwaukee to Chicago
Ave. Duration:
1h 29m
Frequency:
Every 4 hours
Estimated price:
$12.77–$89.41

MBTA

Phone:
+1-617-222-3200
Website:
mbta.com
Train from South Station to Providence
Ave. Duration:
1h 10m
Frequency:
Hourly
Estimated price:
$6.26–$16.60

Amtrak Northeast Regional

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from South Station to Providence
Ave. Duration:
39 min
Frequency:
Every 3 hours
Estimated price:
$17.88–$242.68

Amtrak Acela

Phone:
+1 800-872-7245
Website:
amtrak.com/home.html
Train from South Station to Providence
Ave. Duration:
33 min
Frequency:
Every 4 hours
Estimated price:
$24.27–$395.95

Bus operators

Greyhound USA

Phone:
+1 214-849-8100
Website:
greyhound.com/
Bus from Boston to Boston
Ave. Duration:
1h 5m
Frequency:
Once daily
Estimated price:
$3.96–$70.25

Flixbus USA

Phone:
+1 (855) 626-8585
Website:
flixbus.com
Bus from Boston to New
Ave. Duration:
4h 20m
Frequency:
Hourly
Estimated price:
$21.71–$83.02
Bus from New York Midtown to Chicago
Ave. Duration:
20h 25m
Frequency:
Once daily
Estimated price:
$83.02–$255.45

Questions and Answers

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

The cheapest way to get from Massachusetts to Chicago is to fly which costs $45.65 - $271.74 and takes 5h 10m.

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

The fastest way to get from Massachusetts to Chicago is to fly which takes 4h 46m and costs $76.09 - $652.17 .

Is there a direct bus between Massachusetts and Chicago?

No, there is no direct bus from Massachusetts to Chicago station. However, there are services departing from Boston and arriving at Chicago Bus Station via New York Midtown. The journey, including transfers, takes approximately 25h 45m.

Is there a direct train between Massachusetts and Chicago?

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

How far is it from Massachusetts to Chicago?

The distance between Massachusetts and Chicago is 1404 km. The road distance is 1592.7 km.

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

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

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

It takes approximately 4h 46m to get from Massachusetts to Chicago, including transfers.

Where do I catch the Massachusetts to Chicago bus from?

Massachusetts to Chicago bus services, operated by Flixbus USA, depart from Boston station.

Where do I catch the Massachusetts to Chicago train from?

Massachusetts to Chicago train services, operated by Amtrak, depart from Boston station.

Train, bus or fly from Massachusetts to Chicago?

The best way to get from Massachusetts to Chicago is to fly which takes 4h 46m and costs $76.09 - $652.17 . Alternatively, you can train, which costs $86.96 - $293.48 and takes 22h 22m, you could also bus, which costs $86.96 - $293.48 and takes 25h 45m.

Where does the Massachusetts to Chicago bus arrive?

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

What is the time difference between Massachusetts and Chicago?

Chicago is 1h behind Massachusetts. It is currently 11:34 in Massachusetts and 10:34 in Chicago.

Where does the Massachusetts to Chicago train arrive?

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

Can I drive from Massachusetts to Chicago?

Yes, the driving distance between Massachusetts to Chicago is 1593 km. It takes approximately 16h 30m to drive from Massachusetts to Chicago.

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

Book your Massachusetts to Chicago train tickets online with Omio.

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

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

Where can I stay near Chicago?

There are 1249+ hotels available in Chicago. Prices start at $65.98 per night.
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