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

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How to find the cheapest flight from
Chicago (CHI) to Massachusetts

How far in advance should I book a flight from Chicago to Massachusetts?

To save up to 23% on this flight, we recommend booking at least 26 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to Massachusetts from $270 1-2 weeks out and tickets from $316 for flights departing within the next 72 hours.

Cheap flights from Chicago to Massachusetts in July, August 2020

The best prices found for CHI to Massachusetts flights for July, August
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 4 Aug
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Chicago to Massachusetts 2020 flight deals

Cheap flights to Massachusetts from Chicago found for this year
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 4 Aug
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Non-stop flights to Massachusetts from Chicago

Save time with Chicago to Massachusetts direct flight deals
14 Jul - 28 Jul
$32pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
14 Jul - 15 Jul
$34pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
28 Jul - 29 Jul
$35pp
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Massachusetts

Late deals on round-trip flights to Massachusetts from Chicago, departing today and this week
27 Jun - 11 Jul
$95pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
25 Jun - 11 Jul
$96pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
27 Jun - 12 Jul
$104pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
BOS
Boston Logan Intl
BOS
Boston Logan Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl

One-way flights to Massachusetts from Chicago

The cheapest one-way flights from Chicago to Massachusetts
2:45 pm - 6:17 pm
British Airways
Nonstop
2h 32m
ORD - BOS
British Airways
$51
Ovago
2:16 pm - 5:33 pm
JetBlue
Nonstop
2h 17m
ORD - BOS
JetBlue
1:10 pm - 4:36 pm
Major Airline
Nonstop
2h 26m
ORD - BOS
Major Airline
$64
StudentUniverse

Related info for your journey

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

Flight FAQs

From Chicago to Massachusetts

Are flight prices decreasing from Chicago to Massachusetts 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 Chicago and Massachusetts 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 Chicago to Massachusetts for under $100 on Cheapflights?

Yes, there are multiple flights from Chicago to Massachusetts for under $100. The cheapest flight booked recently is on Spirit Airlines for just $32, but on average you can expect to pay $45.

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

Cheapflights has at least 20 direct flights from Chicago to Massachusetts under $100. A good price for a nonstop flight from Chicago to Massachusetts is less than $47.

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

There are currently 20+ open flights from Chicago to Massachusetts within the next 7 days for less than $100.

What days are nonstop flights available from Chicago to Massachusetts?

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

How popular is this flight route?

Within the past month, 207 users have taken a look at flights from Chicago to Massachusetts.

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

The most popular airlines flying from Chicago to Massachusetts are Endeavor Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

What are the most popular routes from Chicago to Massachusetts?

While some choose either Chicago O'Hare Intl - West Tisbury Martha's Vineyard or Chicago O'Hare Intl - Nantucket Memorial, Chicago O'Hare Intl - Boston Logan Intl is the most popular route from Chicago to Massachusetts.

What are the cheapest Flights from Chicago to Massachusetts?

Looking for the cheapest flight from Chicago to Massachusetts? While on average our users pay $174, our data indicates the cheapest price to be $77. The most popular route (Chicago O'Hare Intl - Boston Logan Intl), is priced around $32.

What are the most reliable airlines from Chicago to Massachusetts?

Before booking your flight to Massachusetts from Chicago, check out the most reliable airlines to get you to your destination on time: Japan Airlines (100%), Icelandair (100%), Emirates( 100%).

Arrival points for flights from Chicago to Massachusetts

Destination information for Massachusetts

Things to know before you go. Useful info for your trip from Chicago to Massachusetts
Flight duration
2h 36m

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

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