Menu

Cheap flights from Massachusetts (MA) to Chicago (CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

Massachusetts to Chicago 2020 flight deals

Cheap flights to Chicago from Massachusetts found for this year
6 May - 15 May
$151pp
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
8 Jan - 12 Jan
$157pp
BOS
Boston Logan Intl
Delta
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
Non-Stop
BOS
Boston Logan Intl
9 Jan - 13 Jan
$157pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl

Last minute flights from Massachusetts to Chicago

Late deals on round-trip flights to Chicago from Massachusetts, departing today and this week
15 Dec - 17 Dec
$181pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
 
1 STOP
BOS
Boston Logan Intl
14 Dec - 18 Dec
$183pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
14 Dec - 16 Dec
$234pp
BOS
Boston Logan Intl
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
BOS
Boston Logan Intl

Departure points for flights from Massachusetts to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Massachusetts to Chicago
Flight duration
2h 40m
Average temperature for December in Chicago
37.4 °F
Avg rainfall for December in Chicago
1.2 ″

Airports servicing

Boston (BOS)
Beverly (BVY)
New Bedford (EWB)
Hyannis (HYA)
West Tisbury Martha's Vineyard (MVY)

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)

Related info for your journey

Useful info, stats and facts about Massachusetts to Chicago flights.

Flight FAQs

From Massachusetts to Chicago

What days are nonstop flights available from Massachusetts to Chicago?

You can find nonstop flights on the following days: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

This flight path from Massachusetts to Chicago was viewed by 169 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What are the most popular airlines that fly from Massachusetts to Chicago?

Consider Major Airline, JetBlue or Delta when booking your flight. These represent the most popular airlines when flying from Massachusetts to Chicago.

What are the most popular routes from Massachusetts to Chicago?

Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Worcester - Chicago O'Hare Intl when deciding on the best route from Massachusetts to Chicago.

What are the cheapest Flights from Massachusetts to Chicago?

On average you can expect to pay $197 for a flight from Massachusetts to Chicago. The cheapest flight overall is $76 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $149.

What are the most reliable airlines from Massachusetts to Chicago?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Massachusetts to Chicago on time: KLM(100%), Japan Airlines(93%), Delta(92%.)