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

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Cheap flights from Massachusetts to Chicago in February 2020

The best prices found for Massachusetts to ORD flights for February
29 Feb - 5 Mar
$95pp
BOS
Boston Logan Intl
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
BOS
Boston Logan Intl
25 Feb - 27 Feb
$105pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
26 Feb - 27 Feb
$110pp
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl

Massachusetts to Chicago 2020 flight deals

Cheap flights to Chicago from Massachusetts found for this year
29 Apr - 5 May
$76pp
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
7 May - 12 May
$85pp
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
6 May - 10 May
$86pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl

Non-stop flights to Chicago from Massachusetts

Save time with Massachusetts to Chicago direct flight deals
29 Apr - 5 May
$76pp
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
7 May - 12 May
$85pp
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
6 May - 10 May
$86pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
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
19 Feb - 20 Feb
$105pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
18 Feb - 19 Feb
$106pp
BOS
Boston Logan Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl
23 Feb - 27 Feb
$110pp
BOS
Boston Logan Intl
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
BOS
Boston Logan Intl

One-way flights to Chicago from Massachusetts

The cheapest one-way flights from Massachusetts to Chicago
4:40 am - 6:43 am
Delta
Nonstop
3h 03m
BOS - ORD
Delta
$139
Delta
2:20 pm - 4:21 pm
United Airlines
Nonstop
3h 01m
BOS - ORD
United Airlines
$150
United
2:43 am - 5:00 am
Major Airline
Nonstop
3h 17m
BOS - ORD
Major Airline
$157
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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 February in Chicago
39.2 °F
Avg rainfall for February in Chicago
1.0 ″

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 163 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 $162 for a flight from Massachusetts to Chicago. The cheapest flight overall is $32 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $76.

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: SkyWest Airlines(100%), ANA(90%), Royal Jordanian(89%.)