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

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

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

Users have found that booking a flight from Massachusetts to Chicago at least 20 days early can save you up to 48% on average compared to booking a flight this week. If booking 20 days before your flight isn’t an option for you, users have found flights from Massachusetts to Chicago for as little as $213 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $293 for flights departing within the next 3 days.

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

August is one of the best times of the year to fly to Chicago from Massachusetts. Prices for August average $182 per person but you can even find prices for as low as $64. The most expensive prices can be found in the month of December. Opting for a August flight can save you 34% on your journey compared to booking in August

Cheap flights from Massachusetts to Chicago in November, December 2020

The best prices found for Massachusetts to CHI flights for November, December
17 Dec - 7 Jan
$44pp
BOS
Boston Logan Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BOS
Boston Logan Intl
17 Dec - 7 Jan
$47pp
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
16 Dec - 18 Dec
$48pp
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 next year
17 Dec - 7 Jan
$44pp
BOS
Boston Logan Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
 
1 STOP
BOS
Boston Logan Intl
17 Dec - 7 Jan
$47pp
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
16 Dec - 18 Dec
$48pp
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
12 Jan - 17 Jan
$89pp
BOS
Boston Logan Intl
JetBlue
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
JetBlue
Non-Stop
BOS
Boston Logan Intl
5 Dec - 5 Dec
$91pp
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
12 Feb - 15 Feb
$93pp
BOS
Boston Logan Intl
Multiple Airlines
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
6 Dec - 8 Dec
$60pp
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
9 Dec - 10 Dec
$64pp
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
6 Dec - 8 Dec
$70pp
BOS
Boston Logan Intl
Multiple Airlines
Non-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
4:39 am - 3:48 pm
Multiple Airlines
1 Stop
12h 09m
BOS - ORD
Multiple Airlines
$34
FlightNetwork
4:52 am - 2:39 pm
Frontier
1 Stop
10h 47m
BOS - ORD
Frontier
$44
Gotogate
3:53 am - 5:50 am
JetBlue
Nonstop
2h 57m
BOS - ORD
JetBlue

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.

What safety measures are being taken by airlines flying from Massachusetts to Chicago to control the spread of COVID-19?

JetBlue, Southwest, and Delta are some of the many airlines that have implemented additional safety measures to control the spread of COVID-19. New policies for travelers booking flights from Massachusetts to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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 Multiple Airlines for just $42, but on average you can expect to pay $56.

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 $113.

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?

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

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 most popular routes from Massachusetts to Chicago?

Most travelers choose Boston Logan Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago Midway or Boston Logan Intl - Chicago Greater Rockford 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 $175 for a flight from Massachusetts to Chicago. The cheapest flight overall is $63 while the most popular route, (Boston Logan Intl - Chicago O'Hare Intl) is currently priced at $44.

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%), EL AL(100%), Royal Air Maroc(100%.)

How long is the flight from Massachusetts to Chicago?

Departing from Massachusetts to Chicago will take you 2h 57m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Massachusetts to Chicago round-trip?

Currently priced at $47, Spirit Airlines will fly you from Massachusetts to Chicago and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Frontier for as low as $68.

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

One-way options have recently been found by users for as low as $22 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $40 and JetBlue from $45 one-way.

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 39m
Average temperature for November in Chicago
51.8 °F
Avg rainfall for November in Chicago
2.4 ″

Airports servicing

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

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 6 airlines 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%
United Airlines
$80 $237 No cancel fee 69%
American Airlines
$77 $247 No cancel fee 71%
JetBlue
$71 $250 No cancel fee 62%
Delta
$62 $253 No cancel fee N/A
Southwest
$185 $387 No cancel fee 63%
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