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

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Cheap flights from Massachusetts to Chicago in April 2020

The best prices found for Massachusetts to ORD flights for April
22 Apr - 30 Apr
$27pp
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
24 Apr - 26 Apr
$30pp
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
16 Apr - 2 May
$34pp
BOS
Boston Logan Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
BOS
Boston Logan Intl

Massachusetts to Chicago 2020 flight deals

Cheap flights to Chicago from Massachusetts found for this year
27 May - 8 Jun
$27pp
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 - 12 May
$30pp
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
18 May - 21 May
$33pp
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

Non-stop flights to Chicago from Massachusetts

Save time with Massachusetts to Chicago direct flight deals
22 Apr - 25 Apr
$27pp
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
24 Apr - 26 Apr
$30pp
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
18 May - 21 May
$33pp
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

Last minute flights from Massachusetts to Chicago

Late deals on round-trip flights to Chicago from Massachusetts, departing today and this week
1 Apr - 5 May
$36pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
6 Apr - 5 May
$41pp
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
8 Apr - 30 Apr
$42pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl

One-way flights to Chicago from Massachusetts

The cheapest one-way flights from Massachusetts to Chicago
2:30 am - 4:26 am
Spirit Airlines
Nonstop
2h 56m
BOS - ORD
Spirit Airlines
$27
Spirit
7:00 am - 8:57 am
Major Airline
Nonstop
2h 57m
BOS - ORD
Major Airline
$29
StudentUniverse
11:30 am - 1:27 pm
Delta
Nonstop
2h 57m
BOS - ORD
Delta
$45
Delta

Arrival 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 41m
Average temperature for April in Chicago
62.6 °F
Avg rainfall for April in Chicago
2.3 ″

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

Are flight prices decreasing from Massachusetts to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Massachusetts and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Massachusetts to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Massachusetts to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $27, but on average you can expect to pay $30.

Are there nonstop flights from Massachusetts to Chicago for under $100 on Cheapflights?

Cheapflights has 3 direct flights from Massachusetts to Chicago under $100. A good price for a nonstop flight from Massachusetts to Chicago is less than $30.

Are there last-minute flights available from Massachusetts to Chicago for under $100?

There are currently just 3 open flights from Massachusetts to Chicago within the next 7 days for less than $100.

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 148 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 American Airlines, 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 $96 for a flight from Massachusetts to Chicago. The cheapest flight overall is $17 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $33.

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: Icelandair(100%), SkyWest Airlines(100%), Royal Air Maroc(100%.)