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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 37 days early can save you up to 10% on average compared to booking a flight this week. If booking 37 days before your flight isn’t an option for you, users have found flights from Massachusetts to Chicago for as little as $177 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 $177 for flights departing within the next 3 days.

Cheap flights from Massachusetts to Chicago in August, September 2020

The best prices found for Massachusetts to CHI flights for August, September
7 Aug - 21 Aug
$31pp
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
1 Aug - 5 Aug
$32pp
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
23 Jul - 26 Jul
$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

Massachusetts to Chicago 2020 flight deals

Cheap flights to Chicago from Massachusetts found for this year
7 Aug - 21 Aug
$31pp
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
1 Aug - 3 Aug
$32pp
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
23 Jul - 26 Jul
$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
7 Aug - 21 Aug
$31pp
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
1 Aug - 5 Aug
$32pp
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
23 Jul - 26 Jul
$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
25 Jul - 28 Jul
$32pp
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
23 Jul - 26 Jul
$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
24 Jul - 28 Jul
$34pp
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

One-way flights to Chicago from Massachusetts

The cheapest one-way flights from Massachusetts to Chicago
3:12 am - 5:01 am
Major Airline
Nonstop
2h 49m
BOS - ORD
Major Airline
$23
StudentUniverse
10:45 am - 3:11 pm
Delta
1 Stop
5h 26m
BOS - MDW
Delta
$45
Delta
4:29 am - 6:19 am
JetBlue
Nonstop
2h 50m
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.

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 $31, but on average you can expect to pay $42.

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 $45.

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: Sunday, Thursday, Friday.

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 West Tisbury Martha's Vineyard - 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 $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 $32.

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%), Japan Airlines(100%), Royal Jordanian(100%.)

How long is the flight from Massachusetts to Chicago?

Departing from Massachusetts to Chicago will take you 2h 33m. Most flights are nonstop.

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

Currently priced at $31, 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 Major Airline for as low as $45.

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 $16 on Spirit Airlines. Other airlines that offer cheap prices include Major Airline from $23 and JetBlue from $25 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 36m
Average temperature for August in Chicago
82.4 °F
Avg rainfall for August in Chicago
3.9 ″

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)
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