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

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

All the information you need to plan the best null to CHI flight in 2021: compare Massachusetts to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
When is the cheapest time to fly from Massachusetts to Chicago (MA - CHI)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.

What is the cheapest month to fly from Massachusetts to Chicago?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to Chicago. Flights to Chicago from Massachusetts in August are about $146 on average during August, but can be found for as low as $34.

Cheap flights from Massachusetts to Chicago in October, November 2021

The best prices found for Massachusetts to CHI flights for October, November
19 Oct - 21 Oct
$77pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
27 Oct - 1 Nov
$78pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
26 Oct - 30 Oct
$79pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

Massachusetts to Chicago 2021 flight deals

Cheap flights to Chicago from Massachusetts found for this year
19 Oct - 21 Oct
$77pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
27 Oct - 1 Nov
$78pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
26 Oct - 30 Oct
$79pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

Non-stop flights to Chicago from Massachusetts

Save time with Massachusetts to Chicago direct flight deals
11 Nov - 15 Nov
$97pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
4 Nov - 6 Nov
$118pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
12 Nov - 15 Nov
$119pp
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

Last minute flights from Massachusetts to Chicago

Late deals on round-trip flights to Chicago from Massachusetts, departing today and this week
19 Oct - 21 Oct
$77pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
20 Oct - 23 Oct
$82pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl
20 Oct - 25 Oct
$87pp
BOS
Boston Logan Intl
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
BOS
Boston Logan Intl

One-way flights to Chicago from Massachusetts

The cheapest one-way flights from Massachusetts to Chicago
6:13 am - 2:56 pm
Frontier
1 Stop
9h 43m
BOS - ORD
Frontier
$52
Kiwi.com
12:00 am - 1:59 am
Major Airline
Nonstop
2h 59m
BOS - ORD
Major Airline
$61
StudentUniverse
2:56 pm - 7:41 pm
Delta
1 Stop
5h 45m
BOS - MDW
Delta
$68
iWofly

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Massachusetts</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Massachusetts to Chicago

Which airlines flying from Massachusetts to Chicago have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Massachusetts to Chicago that may be offering flexible cancellation policies are United Airlines, American Airlines, and JetBlue. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

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 $78, but on average you can expect to pay $92.

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

Cheapflights has at least 20 direct flights from Massachusetts to Chicago under $100. A good price for a nonstop flight from Massachusetts to Chicago is less than $143.

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

There are currently 20+ 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?

Nonstop flights are available for this route on the following days: Friday, Saturday.

How many flights depart from Massachusetts to Chicago on average per day?

On average, you can expect to see 11 flights from Massachusetts to Chicago a day.
Morning (6am - Noon) - 27% of flight departures
Evening (6pm - Midnight) - 73% of flight departures

How long is the flight from Massachusetts to Chicago?

A quick flight from Massachusetts to Chicago can take about 2h 59m. Spirit Airlines provides one of the quickest options available for as low as $78. The distance from Massachusetts to Chicago is about 869 mi. This flight may include one or multiple stops.

What are the cheapest airlines to fly from Massachusetts to Chicago one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $36. Frontier flights start at $52 while deals on Major Airline start at $61 one-way.

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

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

What are the cheapest flights from Massachusetts to Chicago?

Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $341, our data indicates the cheapest price to be $52. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $78.

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: Cathay Pacific (100%), Royal Jordanian (98%), ANA (97%).

What are the most popular routes from Massachusetts to Chicago?

While some choose either Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Massachusetts to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Massachusetts?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Massachusetts need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Massachusetts must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Massachusetts are not required to quarantine after entering Chicago.

Do I need a test to fly back to Massachusetts from Chicago?

Returning to Massachusetts from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Massachusetts.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Massachusetts.

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Massachusetts to Chicago

Select to see more specific information for flights to Chicago from all departure points in Massachusetts.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Massachusetts to Chicago.
Flight duration from Massachusetts to Chicago
2h 35m
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing

Bedford Hanscom Field (BED)
Boston Harbor SPB (BNH)
Boston (BOS)
Beverly (BVY)
New Bedford Regional (EWB)
Hyannis Barnstable (HYA)

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 6 airlines flying from Massachusetts to Chicago

The chart below displays the airlines Cheapflights users traveling from Massachusetts to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Spirit Airlines
$56 $168 No cancel fee 65%
Delta
$62 $253 No cancel fee N/A
JetBlue
$71 $250 No cancel fee 62%
American Airlines
$77 $247 No cancel fee 71%
United Airlines
$80 $237 No cancel fee 69%
Southwest
$185 $387 No cancel fee 63%
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