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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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap 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 December 28, 2025.

This United Airlines deal was found by Cheapflights users on 12/26. 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.
Wed 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Mon 1/59:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/26$137
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Tue 12/3012:20 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Thu 1/16:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/26$149
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Wed 12/316:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/27$157
This American Airlines deal was found by Cheapflights users on 12/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Thu 1/18:20 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 12/27$177
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/27$189
This Super.com deal was found by Cheapflights users on 12/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Fri 1/27:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/27$194
This United Airlines deal was found by Cheapflights users on 12/27. 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.
Wed 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/27$195
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Tue 12/306:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Mon 1/59:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/26$196
This Southwest deal was found by Cheapflights users on 12/27. 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 12/311:35 pmBOS - MDW
Nonstop2h 45mSouthwest
Fri 1/29:40 pmMDW - BOS
1 stop11h 05mSouthwest
Deal found 12/27$203
This Trip.com deal was found by Cheapflights users on 12/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/27$203
This United Airlines deal was found by Cheapflights users on 12/26. 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.
Wed 12/3112:20 pmBOS - ORD
Nonstop3h 03mUnited Airlines
Tue 1/610:35 amORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 12/26$207
This Southwest deal was found by Cheapflights users on 12/26. 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 12/315:35 pmBOS - MDW
1 stop4h 30mSouthwest
Mon 1/56:45 amMDW - BOS
1 stop10h 30mSouthwest
Deal found 12/26$213

Find flight deals from Massachusetts to Chicago

Keep the following information in mind while searching for Massachusetts to Chicago flight deals. Data was last updated December 28, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$127
(Southwest)

One-way from

$64
(Southwest)

Popular in

April

Cheapest in

September

Average price

$257

Good round-trip deal

$261 or less

Good one-way deal

$149 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Massachusetts to Chicago (CHI)
Search Deals
One-way flight from Massachusetts to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Massachusetts to Chicago (CHI).
Search Deals

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 December 28, 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 - ORD

BOSORD

Boston Logan Intl

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/23

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Fri 1/30

10:40 am-2:13 pm

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/23

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/23

8:25 pm-10:29 pm

Nonstop3h 04m

Chicago O'Hare Intl

Wed 1/28

10:40 am-2:13 pm

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/21

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Tue 2/24

10:00 am-1:20 pm

Nonstop2h 20m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/18

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Thu 1/29

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Wed 1/28

2:25 pm-5:54 pm

Nonstop2h 29m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Thu 1/22

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Wed 1/28

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Fri 1/30

7:05 am-10:40 am

Nonstop2h 35m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

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, April is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $89). Flying from Massachusetts to Chicago in January is currently the most expensive (average of $123). 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 December 28, 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 67% 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 27, 2025.

Travelers seeking maximum savings on their Massachusetts to Chicago flight should consider departing on Wednesday at noon 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 December 28, 2025.

The most flights from USMA to CHI are scheduled on a Friday (63 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (34 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 3h 08m. JetBlue provides one of the quickest options available for as low as $127. 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 $46. Frontier flights start at $47 while deals on Southwest start at $58 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: ANA (84%), LATAM Airlines (81%), JetBlue (81%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $687, our data indicates the cheapest price to be $68. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $103.

  • 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, April is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $89). Flying from Massachusetts to Chicago in January is currently the most expensive (average of $123). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 6 airlines flying from Massachusetts to Chicago

Discover the top 6 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$72Average$185FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$162FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$289FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$217FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$124Average$270FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$129Average$256FlexibilityNo cancel feeOn-time71%

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