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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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Mar 30 — Apr 61
Mon 3/30
Mon 4/6
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 February 28, 2026.

This Southwest deal was found by Cheapflights users on 2/24. 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.
Sat 5/23:30 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Sat 5/96:05 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 2/24$129
This Priceline deal was found by Cheapflights users on 2/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:35 pm
BOS
-
ORD
Nonstop3h 04m
Multiple Airlines
Thu 4/164:28 pm
ORD
-
BOS
1 stop8h 03m
Multiple Airlines
Deal found 2/26$129
This American Airlines deal was found by Cheapflights users on 2/25. 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.
Sat 4/116:48 pm
BOS
-
ORD
Nonstop3h 12m
American Airlines
Sat 4/188:56 pm
ORD
-
BOS
Nonstop2h 29m
American Airlines
Deal found 2/25$130
This United Airlines deal was found by Cheapflights users on 2/24. 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 4/26:00 am
BOS
-
ORD
Nonstop2h 59m
United Airlines
Sun 4/56:00 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 2/24$131
This Southwest deal was found by Cheapflights users on 2/26. 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.
Fri 3/273:10 pm
BOS
-
MDW
Nonstop2h 45m
Southwest
Fri 4/37:00 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 2/26$132
This United Airlines deal was found by Cheapflights users on 2/24. 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 5/207:30 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Mon 5/259:26 pm
ORD
-
BOS
Nonstop2h 33m
United Airlines
Deal found 2/24$132
This Southwest deal was found by Cheapflights users on 2/25. 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.
Sat 4/117:15 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Mon 4/137:00 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 2/25$133
This American Airlines deal was found by Cheapflights users on 2/25. 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.
Fri 4/107:40 pm
BOS
-
ORD
Nonstop3h 10m
American Airlines
Mon 4/136:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 2/25$133
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Sat 3/286:00 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Sun 4/56:00 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 2/27$134
This Expedia deal was found by Cheapflights users on 2/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:42 pm
BOS
-
ORD
1 stop10h 57m
Multiple Airlines
Mon 5/46:00 am
ORD
-
BOS
Nonstop2h 15m
Multiple Airlines
Deal found 2/25$135
This Delta deal was found by Cheapflights users on 2/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/174:25 pm
BOS
-
ORD
Nonstop3h 06m
Delta
Tue 3/247:00 am
ORD
-
BOS
Nonstop2h 25m
Delta
Deal found 2/26$136
This Southwest deal was found by Cheapflights users on 2/24. 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 3/2311:50 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Tue 3/2412:10 pm
MDW
-
BOS
Nonstop2h 10m
Southwest
Deal found 2/24$137

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 February 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$129
(Southwest)

One-way from

$64
(Southwest)

Popular in

March

Cheapest in

September

Average price

$232

Good round-trip deal

$233 or less

Good one-way deal

$102 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. 7% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 28, 2026.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 3/27

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago Midway

Fri 4/3

7:00 pm-10:15 pm

Nonstop2h 15m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 4/3

6:25 pm-8:25 pm

Nonstop3h 00m

Chicago Midway

Wed 4/15

7:45 am-11:00 am

Nonstop2h 15m

$152

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 3/11

1:44 pm-10:12 am

1 stop21h 28m

Chicago O'Hare Intl

Sat 3/14

8:55 pm-1:19 pm

1 stop15h 24m

$160

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/24

2:00 pm-8:36 pm

1 stop7h 36m

Chicago O'Hare Intl

Mon 4/27

6:50 am-10:11 am

Nonstop2h 21m

$162

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/28

2:39 pm-10:41 am

1 stop21h 02m

Chicago O'Hare Intl

Sat 5/2

6:05 am-2:14 pm

2 stops7h 09m

$164

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/18

9:00 pm-10:55 pm

Nonstop2h 55m

Chicago O'Hare Intl

Wed 4/22

6:00 am-9:26 am

Nonstop2h 26m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 3/4

12:35 pm-2:41 pm

Nonstop3h 06m

Chicago O'Hare Intl

Fri 3/6

2:35 pm-8:15 pm

1 stop4h 40m

$171

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 4/11

3:30 pm-5:15 pm

Nonstop2h 45m

Chicago Midway

Mon 4/13

9:00 am-4:05 pm

1 stop6h 05m

$186

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 4/19

7:10 am-9:15 am

Nonstop3h 05m

Chicago O'Hare Intl

Tue 4/21

7:59 pm-11:27 pm

Nonstop2h 28m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/3

4:25 pm-6:30 pm

Nonstop3h 05m

Chicago O'Hare Intl

Wed 3/4

4:10 pm-9:51 pm

1 stop4h 41m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/24

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, September is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $91). 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 February 28, 2026.

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 60% versus a flight in the morning.

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 February 21, 2026.

Travelers seeking maximum savings on their Massachusetts to Chicago flight should consider departing on Thursday 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 February 28, 2026.

The most flights from USMA to CHI are scheduled on a Friday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 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. Southwest provides one of the quickest options available for as low as $147. The distance from Massachusetts to Chicago is about 857 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 Frontier, which is currently one of the cheapest options available, starting at $47. Southwest flights start at $58 while deals on Delta start at $58 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: ANA (89%), Emirates (87%), LATAM Airlines (84%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $832, our data indicates the cheapest price to be $66. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $97.

  • 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, September is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $91). 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 February 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$66Average$173FlexibilityNo cancel feeOn-time62%
DeltaCheapest$82Average$306FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$85Average$162FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$117Average$226FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$117Average$262FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$127Average$258FlexibilityNo cancel feeOn-time71%

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