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$68+ Cheap flights from Massachusetts to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
1 adult, Economy
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Cheap flight deals from Massachusetts to Chicago

Keep the following information in mind while searching for Massachusetts to Chicago flight deals. Data was last updated August 21, 2025.

Round-trip from

$132
(Southwest)

One-way from

$68
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$223

Good round-trip deal

$194 or less

Good one-way deal

$146 or less
From Massachusetts to Chicago (CHI)
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One-way flight from Massachusetts to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Massachusetts to Chicago (CHI).
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Price to beat on a one-way flight from Massachusetts to Chicago (CHI).
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Find flight deals from Massachusetts to Chicago

Cheapest flights from Massachusetts to Chicago
Explore the most affordable flight options available from Massachusetts to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2025.

This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/185:35 amBOS - MDW
1 stop4h 25mSouthwest
Mon 9/227:15 amMDW - BOS
1 stop8h 10mSouthwest
Deal found 8/18$132
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:35 amBOS - ORD
1 stop8h 10mSouthwest
Sat 10/181:30 pmORD - BOS
1 stop4h 20mSouthwest
Deal found 8/21$132
This Cheapflightsfares deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1612:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Sat 9/2011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/20$135
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1812:15 pmBOS - MDW
Nonstop2h 35mSouthwest
Sun 9/218:35 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 8/20$137
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:35 pmBOS - ORD
Nonstop3h 15mJetBlue
Thu 11/2712:28 pmORD - BOS
Nonstop2h 26mJetBlue
Deal found 8/21$137
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/225:35 amBOS - MDW
2 stops8h 35mSouthwest
Wed 9/246:25 amMDW - BOS
1 stop8h 00mSouthwest
Deal found 8/18$138
This CheapOair deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:05 amBOS - ORD
1 stop14h 02mSpirit Airlines
Wed 9/1011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/20$138
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:00 amBOS - ORD
Nonstop2h 56mJetBlue
Mon 10/66:50 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 8/21$142
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Sun 12/77:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/20$143
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/57:00 amBOS - ORD
Nonstop2h 56mJetBlue
Tue 9/99:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 8/21$143
This Mytrip deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Wed 9/175:05 amORD - BOS
1 stop17h 52mSpirit Airlines
Deal found 8/20$145
This United Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:00 pmBOS - ORD
1 stop5h 10mUnited Airlines
Sun 9/76:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 8/21$147

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 21, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.

Fly from

Massachusetts

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/18

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Mon 9/22

7:15 am-4:25 pm

1 stop8h 10m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 9/7

7:00 am-10:30 am

Nonstop2h 30m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/7

7:50 am-2:25 pm

1 stop7h 35m

Chicago Midway

Sun 10/12

6:05 am-9:20 am

Nonstop2h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/1

7:20 am-9:16 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/3

6:00 pm-9:38 pm

Nonstop2h 38m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 9/22

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Wed 9/24

6:25 am-3:25 pm

1 stop8h 00m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/17

5:35 am-12:45 pm

1 stop8h 10m

Chicago O'Hare Intl

Sat 10/18

1:30 pm-6:50 pm

1 stop4h 20m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/9

7:00 am-8:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 10/12

9:42 am-1:10 pm

Nonstop2h 28m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/28

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 8/31

5:36 pm-9:12 pm

Nonstop2h 36m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Wed 10/29

6:05 am-9:20 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/3

9:35 pm-11:15 pm

Nonstop2h 40m

Chicago Midway

Mon 10/6

9:20 pm-12:40 am

Nonstop2h 20m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Chicago

What is the cheapest month to book a flight from Massachusetts to Chicago?

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $245). Flying from Massachusetts to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to CHI?

Find hourly flight availability from Massachusetts to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2025.

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.

Weekly flight availability from Massachusetts to Chicago

Explore weekly flight availability from Massachusetts to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 21, 2025.

The most flights from USMA to CHI are scheduled on a Thursday (81 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

How much does it cost to fly round-trip from Massachusetts to Chicago?

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Massachusetts to Chicago?

    A quick flight from Massachusetts to Chicago can take about 2h 55m. Southwest provides one of the quickest options available for as low as $132. The distance from Massachusetts to Chicago is about 864 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 $68. Southwest flights start at $69 while deals on American Airlines start at $75 one-way.

  • What are the most popular routes from Massachusetts to Chicago?

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

  • 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 (91%), TAP AIR PORTUGAL (90%), Avianca (89%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $694, our data indicates the cheapest price to be $68. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $107.

  • Can I find deals for flights from Massachusetts to Chicago that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Chicago.

  • Can I find deals for business class flights from Massachusetts to Chicago?

    Yes. Cheapflights offers flight deals from Massachusetts to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $245). Flying from Massachusetts to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Massachusetts to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Massachusetts to Chicago

Discover the top 7 airlines that operate flights from Massachusetts to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$32Average$173FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$77Average$204FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$97Average$235FlexibilityNo cancel feeOn-time69%
DeltaCheapest$99Average$295FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$107FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$120Average$228FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$254FlexibilityNo cancel feeOn-time71%

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