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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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$125
(Kiwi.com)

One-way from

$64
(United Airlines)

Popular in

March

Cheapest in

January

Average price

$199

Good round-trip deal

$203 or less

Good one-way deal

$106 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. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/72:15 pmBOS - ORD
1 stop8h 18mSpirit Airlines
mié. 10/86:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/14$126
This Southwest deal was found by Cheapflights users on 9/15. 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.
jue. 10/25:35 amBOS - MDW
1 stop5h 40mSouthwest
lun. 10/66:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/15$127
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/307:00 amBOS - ORD
Nonstop2h 56mJetBlue
mar. 10/710:08 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 9/14$127
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/153:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
sáb. 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$129
This Priceline deal was found by Cheapflights users on 9/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/48:38 amBOS - ORD
1 stop9h 07mMultiple Airlines
mar. 10/76:00 amORD - BOS
1 stop6h 20mMultiple Airlines
Deal found 9/14$131
This JetBlue deal was found by Cheapflights users on 9/15. 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.
vie. 9/264:40 pmBOS - ORD
Nonstop3h 15mJetBlue
vie. 10/37:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 9/15$132
This Southwest deal was found by Cheapflights users on 9/14. 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.
jue. 10/305:15 amBOS - MDW
Nonstop2h 40mSouthwest
dom. 11/29:10 amMDW - BOS
1 stop8h 00mSouthwest
Deal found 9/14$133
This United Airlines deal was found by Cheapflights users on 9/15. 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.
sáb. 10/186:00 amBOS - ORD
Nonstop2h 56mUnited Airlines
dom. 10/196:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 9/15$133
This JetBlue deal was found by Cheapflights users on 9/15. 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.
mié. 10/157:09 amBOS - ORD
Nonstop3h 13mJetBlue
mié. 10/157:13 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 9/15$135
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/83:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
sáb. 10/1111:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$136
This Southwest deal was found by Cheapflights users on 9/13. 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.
sáb. 9/205:50 amBOS - MDW
Nonstop2h 35mSouthwest
dom. 9/215:55 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/13$137
This United Airlines deal was found by Cheapflights users on 9/15. 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.
jue. 9/258:00 amBOS - ORD
Nonstop2h 55mUnited Airlines
sáb. 9/277:30 amORD - BOS
Nonstop2h 32mUnited Airlines
Deal found 9/15$137

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 septiembre 15, 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

jue. 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

lun. 10/6

6:05 am-9:20 am

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 11/20

10:40 am-12:40 pm

Nonstop3h 00m

Chicago O'Hare Intl

mié. 11/26

9:25 pm-12:45 am

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 12/6

4:05 pm-6:02 pm

Nonstop2h 57m

Chicago O'Hare Intl

lun. 12/8

3:45 pm-7:12 pm

Nonstop2h 27m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 9/25

3:17 pm-5:07 pm

Nonstop2h 50m

Chicago O'Hare Intl

dom. 9/28

7:30 am-11:02 am

Nonstop2h 32m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 10/22

9:10 am-2:25 pm

1 stop6h 15m

Chicago Midway

mié. 10/29

10:10 am-7:20 pm

2 stops8h 10m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 11/14

12:05 pm-8:10 pm

1 stop9h 05m

Chicago Midway

lun. 11/17

6:40 am-4:35 pm

1 stop8h 55m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 10/30

6:55 am-4:25 pm

2 stops10h 30m

Chicago O'Hare Intl

sáb. 11/1

1:30 pm-6:50 pm

1 stop4h 20m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dom. 10/26

5:00 am-12:45 pm

1 stop8h 45m

Chicago O'Hare Intl

mar. 10/28

1:50 pm-9:10 pm

1 stop6h 20m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 11/20

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

mié. 11/26

4:05 pm-7:20 pm

Nonstop2h 15m

$143

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

vie. 12/5

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

dom. 12/7

9:35 am-12:50 pm

Nonstop2h 15m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 septiembre 15, 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 septiembre 15, 2025.

The most flights from USMA to CHI are scheduled on a Sunday (86 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (49 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 57m. Southwest provides one of the quickest options available for as low as $137. 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 Southwest, which is currently one of the cheapest options available, starting at $69. JetBlue flights start at $69 while deals on United Airlines 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: Icelandair (89%), TAP AIR PORTUGAL (89%), 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 $755, our data indicates the cheapest price to be $65. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $117.

  • 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$50Average$215FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$197FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$97Average$230FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$107FlexibilityNo cancel feeOn-time62%
DeltaCheapest$107Average$298FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$120Average$235FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$255FlexibilityNo cancel feeOn-time71%

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