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$64+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Nov 19 — Nov 261
Mi 11/19
Mi 11/26
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 Oktober 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$119
(Southwest)

One-way from

$64
(Southwest)

Popular in

April

Cheapest in

September

Average price

$247

Good round-trip deal

$210 or less

Good one-way deal

$136 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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 ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in October 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 Oktober 20, 2025.

This Southwest deal was found by Cheapflights users on 10/19. 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.
Mo 12/85:30 amBOS - MDW
Nonstop2h 45mSouthwest
So 1/255:50 amMDW - BOS
1 stop4h 30mSouthwest
Deal found 10/19$119
This Southwest deal was found by Cheapflights users on 10/19. 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.
Sa 11/14:45 pmBOS - MDW
Nonstop2h 45mSouthwest
Di 11/412:55 pmMDW - BOS
1 stop5h 25mSouthwest
Deal found 10/19$127
This United Airlines deal was found by Cheapflights users on 10/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/96:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Mo 12/229:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/18$127
This Southwest deal was found by Cheapflights users on 10/19. 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.
Di 12/95:30 amBOS - MDW
Nonstop2h 45mSouthwest
Sa 12/131:15 pmMDW - BOS
1 stop5h 20mSouthwest
Deal found 10/19$129
This Southwest deal was found by Cheapflights users on 10/18. 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.
Sa 11/85:55 amBOS - MDW
2 stops11h 35mSouthwest
Mi 11/121:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 10/18$132
This United Airlines deal was found by Cheapflights users on 10/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 11/67:45 amBOS - ORD
Nonstop3h 00mUnited Airlines
Sa 11/81:55 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 10/18$133
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Do 11/67:45 amBOS - ORD
Nonstop3h 00mUnited Airlines
So 11/96:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Deal found 10/19$134
This JetBlue deal was found by Cheapflights users on 10/17. 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.
Mo 11/108:30 amBOS - ORD
Nonstop3h 05mJetBlue
Do 11/136:55 pmORD - BOS
Nonstop2h 32mJetBlue
Deal found 10/17$135
This lastminute.com deal was found by Cheapflights users on 10/18. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 12/28:30 amBOS - ORD
Nonstop3h 05mJetBlue
Di 12/911:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 10/18$136
This Southwest deal was found by Cheapflights users on 10/19. 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.
Do 11/133:25 pmBOS - MDW
1 stop6h 15mSouthwest
Sa 11/155:50 amMDW - BOS
1 stop7h 55mSouthwest
Deal found 10/19$137
This Delta deal was found by Cheapflights users on 10/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 11/84:10 pmBOS - ORD
Nonstop2h 57mDelta
Fr 11/147:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 10/17$137
This United Airlines deal was found by Cheapflights users on 10/17. 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.
So 11/236:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Mi 12/39:19 amORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 10/17$138

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 Oktober 20, 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

Di 12/9

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Sa 12/13

9:50 am-1:10 pm

Nonstop2h 20m

$119

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Do 11/13

5:55 pm-11:00 pm

1 stop6h 05m

Chicago Midway

Sa 11/15

12:50 pm-4:05 pm

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Do 10/30

6:50 pm-8:40 pm

Nonstop2h 50m

Chicago Midway

Do 11/6

6:45 am-6:10 pm

1 stop10h 25m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sa 11/8

5:55 am-4:45 pm

1 stop11h 50m

Chicago Midway

Fr 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sa 11/8

4:10 pm-6:07 pm

Nonstop2h 57m

Chicago O'Hare Intl

So 11/9

7:10 am-10:36 am

Nonstop2h 26m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sa 10/25

5:05 am-12:20 pm

2 stops8h 15m

Chicago Midway

Mo 10/27

2:15 pm-9:00 pm

1 stop5h 45m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sa 11/8

5:55 am-4:30 pm

2 stops11h 35m

Chicago Midway

Mi 11/12

11:25 am-5:20 pm

1 stop4h 55m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sa 11/1

5:05 am-12:20 pm

2 stops8h 15m

Chicago Midway

Do 11/6

5:15 pm-10:55 pm

1 stop4h 40m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Di 11/18

12:45 pm-2:45 pm

Nonstop3h 00m

Chicago O'Hare Intl

Do 11/20

7:10 am-10:35 am

Nonstop2h 25m

$145

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Di 11/18

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago O'Hare Intl

Fr 11/28

9:20 am-12:44 pm

Nonstop2h 24m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

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, November is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $87). Flying from Massachusetts to Chicago in December is currently the most expensive (average of $125). 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 Oktober 20, 2025.

When flying from Massachusetts to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 69% versus a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 Oktober 20, 2025.

The most flights from USMA to CHI are scheduled on a Sunday (82 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (41 on average).

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 45m. Southwest provides one of the quickest options available for as low as $119. The distance from Massachusetts to Chicago is about 857 mi. All flights are typically nonstop.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $64. Southwest flights start at $69 while deals on Delta start at $69 one-way.

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

    While some choose either Hartford Bradley Intl - Chicago O'Hare Intl or Boston Logan Intl - Chicago Midway, 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: TAP AIR PORTUGAL (88%), Icelandair (88%), Avianca (85%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $712, our data indicates the cheapest price to be $60. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $116.

  • 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, November is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $87). Flying from Massachusetts to Chicago in December is currently the most expensive (average of $125). 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
Porter
Benton Harbor
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 Oktober 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$71Average$250FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$80Average$195FlexibilityNo cancel feeOn-time62%
FrontierCheapest$100Average$112FlexibilityNo cancel feeOn-time62%
DeltaCheapest$115Average$289FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$238FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$134Average$279FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$137Average$257FlexibilityNo cancel feeOn-time71%

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