HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$76+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
May 26 — Jun 21
Tue 5/26
Tue 6/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 26, 2026.

This JetBlue deal was found by Cheapflights users on 4/22. 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.
Sat 5/3011:00 am
BOS
-
ORD
Nonstop3h 01m
JetBlue
Mon 6/18:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 4/22$154
This Southwest deal was found by Cheapflights users on 4/22. 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 6/105:35 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Sat 6/135:25 am
MDW
-
BOS
Nonstop2h 15m
Southwest
Deal found 4/22$156
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Wed 6/107:19 am
BOS
-
ORD
Nonstop2h 58m
United Airlines
Sat 6/137:40 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Deal found 4/21$156
This Delta deal was found by Cheapflights users on 4/23. 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.
Sat 5/305:51 am
BOS
-
MDW
1 stop8h 28m
Delta
Tue 6/25:15 pm
MDW
-
BOS
1 stop7h 13m
Delta
Deal found 4/23$157
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:30 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Sun 5/247:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 4/21$157
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:51 am
BOS
-
MDW
1 stop8h 28m
Delta
Mon 6/16:36 pm
MDW
-
BOS
1 stop3h 53m
Delta
Deal found 4/21$158
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/305:40 am
BOS
-
ORD
1 stop5h 49m
Delta
Mon 6/16:06 pm
ORD
-
BOS
1 stop6h 22m
Delta
Deal found 4/21$158
This Delta deal was found by Cheapflights users on 4/23. 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.
Thu 5/285:40 am
BOS
-
MDW
1 stop4h 03m
Delta
Mon 6/16:36 pm
MDW
-
BOS
1 stop3h 53m
Delta
Deal found 4/23$159
This Priceline deal was found by Cheapflights users on 4/22. 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.
Sat 5/166:47 pm
BOS
-
ORD
Nonstop3h 06m
Multiple Airlines
Tue 5/191:59 pm
ORD
-
BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/22$159
This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
BOS
-
MDW
1 stop6h 09m
Frontier
Tue 5/1912:24 pm
MDW
-
BOS
1 stop12h 00m
Frontier
Deal found 4/21$160
This Priceline deal was found by Cheapflights users on 4/26. 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.
Wed 5/1312:01 pm
BOS
-
ORD
1 stop8h 50m
Frontier
Wed 5/201:59 pm
ORD
-
BOS
1 stop10h 25m
Frontier
Deal found 4/26$160
This Southwest deal was found by Cheapflights users on 4/22. 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 5/91:50 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Tue 5/123:15 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Deal found 4/22$161

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 April 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(American Airlines)

One-way from

$76
(Frontier)

Popular in

April

Cheapest in

September

Average price

$260

Good round-trip deal

$232 or less

Good one-way deal

$133 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 ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 26, 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

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 7/16

7:19 am-9:17 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 7/20

9:35 pm-1:08 am

Nonstop2h 33m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/12

4:35 pm-6:35 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 5/19

12:45 pm-4:16 pm

Nonstop2h 31m

$177

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/9

5:45 am-9:36 am

1 stop4h 51m

Chicago O'Hare Intl

Thu 6/11

9:26 pm-12:59 am

Nonstop2h 33m

$182

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 5/23

1:50 pm-3:30 pm

Nonstop2h 40m

Chicago Midway

Sat 5/30

5:25 pm-11:40 pm

1 stop5h 15m

$192

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/13

5:45 am-9:33 am

1 stop4h 48m

Chicago O'Hare Intl

Sun 8/16

6:00 am-9:23 am

Nonstop2h 23m

$201

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/24

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Sun 7/26

6:15 am-9:39 am

Nonstop2h 24m

$205

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 8/8

5:23 pm-10:04 pm

1 stop5h 41m

Chicago O'Hare Intl

Wed 8/12

6:34 am-4:58 pm

1 stop9h 24m

$207
Quickest round-trip

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 6/9

5:35 am-7:10 am

Nonstop2h 35m

Chicago Midway

Thu 6/11

7:35 pm-10:50 pm

Nonstop2h 15m

$207

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/21

6:00 am-7:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Tue 5/26

7:45 pm-11:21 pm

Nonstop2h 36m

$207

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 5/30

7:15 am-9:05 am

Nonstop2h 50m

Chicago Midway

Mon 6/1

5:40 pm-11:10 pm

1 stop4h 30m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
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

How far ahead should I book a flight from Massachusetts to Chicago?

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 $166). Flying from Massachusetts to Chicago in April is currently the most expensive (average of $296). 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 April 26, 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 45% 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 April 18, 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 April 26, 2026.

The most flights from USMA to CHI are scheduled on a Sunday (67 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (27 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 40m. Southwest provides one of the quickest options available for as low as $161. 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 Southwest, which is currently one of the cheapest options available, starting at $58. JetBlue flights start at $58 while deals on American Airlines 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 (81%), Envoy Air (80%), United Airlines (77%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $621, our data indicates the cheapest price to be $83. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $134.

  • 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 $166). Flying from Massachusetts to Chicago in April is currently the most expensive (average of $296). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Newark to Midway flights
Denver to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Boston to O'Hare Intl flights
Los Angeles to Midway flights
Ontario to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Hobby to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Dulles Intl to Midway flights
Santa Ana to O'Hare Intl flights
Orlando to O'Hare Intl flights
Raleigh to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Atlanta to Midway flights
Miami to O'Hare Intl flights
Philadelphia to Midway flights
LaGuardia to Midway flights
Tampa to O'Hare Intl flights
Austin to O'Hare Intl flights
Minneapolis to Midway flights
Baltimore to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Reagan-National to Midway flights
San Diego to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Hartford to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
Newark to St. Louis flights
Love Field to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Orlando to Midway flights
San Jose to O'Hare Intl flights
Boston to Midway flights

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 April 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$32Average$187FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$67Average$176FlexibilityNo cancel feeOn-time62%
DeltaCheapest$87Average$321FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$118Average$263FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$125Average$217FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$130Average$258FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.