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O'Hare Intl

$68+ Cheap flights from Massachusetts to O'Hare Intl (ORD)

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Massachusetts to O'Hare Intl

Keep the following information in mind while searching for Massachusetts to O'Hare Intl flight deals. Data was last updated August 14, 2025.

Round-trip from

$135
(Cheapflightsfares)

One-way from

$68
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$223

Good round-trip deal

$239 or less

Good one-way deal

$141 or less
From Massachusetts to Chicago O'Hare Intl
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One-way flight from Massachusetts to Chicago O'Hare Intl
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Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Massachusetts to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Massachusetts to Chicago O'Hare Intl.
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Find flight deals from Massachusetts to O'Hare Intl

Cheapest flights from Massachusetts to O'Hare Intl
Explore the most affordable flight options available from Massachusetts to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/63:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Wed 9/1011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/14$135
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:34 amBOS - ORD
1 stop12h 48mSpirit Airlines
Tue 9/28:12 pmORD - BOS
1 stop14h 06mSpirit Airlines
Deal found 8/12$136
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/184:05 pmBOS - ORD
Nonstop2h 54mDelta
Wed 9/246:59 pmORD - BOS
Nonstop2h 41mDelta
Deal found 8/14$137
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/42:55 pmBOS - ORD
Nonstop2h 57mDelta
Sun 9/77:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 8/14$138
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/37:12 pmBOS - ORD
1 stop5h 03mUnited Airlines
Fri 9/59:37 pmORD - BOS
Nonstop2h 32mUnited Airlines
Deal found 8/12$139
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/410:53 amBOS - ORD
1 stop14h 17mMultiple Airlines
Tue 9/911:57 amORD - BOS
1 stop11h 00mMultiple Airlines
Deal found 8/14$142
This United Airlines deal was found by Cheapflights users on 8/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:27 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Fri 9/269:20 pmORD - BOS
Nonstop2h 30mUnited Airlines
Deal found 8/14$143
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Sat 8/232:53 pmBOS - ORD
1 stop8h 29mSpirit Airlines
Tue 9/28:12 pmORD - BOS
1 stop14h 06mSpirit Airlines
Deal found 8/12$146
This Delta deal was found by Cheapflights users on 8/12. 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.
Fri 9/197:30 pmBOS - ORD
Nonstop2h 45mDelta
Wed 9/247:25 amORD - BOS
Nonstop2h 30mDelta
Deal found 8/12$147
This JetBlue deal was found by Cheapflights users on 8/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/87:00 amBOS - ORD
Nonstop2h 57mJetBlue
Sun 12/711:30 amORD - BOS
Nonstop2h 16mJetBlue
Deal found 8/13$148
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/206:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Tue 9/2311:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/12$149
This American Airlines deal was found by Cheapflights users on 8/12. 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 9/265:00 amBOS - ORD
Nonstop2h 51mAmerican Airlines
Fri 10/38:25 pmORD - BOS
Nonstop2h 28mAmerican Airlines
Deal found 8/12$150

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to O'Hare Intl 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 August 14, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago O'Hare Intl Airport that are best for you.

Fly from

Massachusetts

Fly to

O'Hare Intl

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/20

7:25 am-9:15 am

Nonstop2h 50m

Chicago O'Hare Intl

Sat 9/20

2:00 pm-5:39 pm

Nonstop2h 39m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/28

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Sat 9/6

9:51 am-1:20 pm

Nonstop2h 29m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/18

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 9/20

6:05 am-9:32 am

Nonstop2h 27m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 11/3

8:30 pm-10:30 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 11/10

9:25 pm-12:45 am

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/13

5:05 pm-7:05 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 9/16

2:05 pm-5:44 pm

Nonstop2h 39m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 11/10

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 11/13

11:20 am-2:44 pm

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 9/17

7:30 pm-9:15 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 9/22

7:25 am-10:55 am

Nonstop2h 30m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/19

7:30 pm-9:15 pm

Nonstop2h 45m

Chicago O'Hare Intl

Mon 9/22

7:25 am-10:55 am

Nonstop2h 30m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/20

5:05 pm-7:05 pm

Nonstop3h 00m

Chicago O'Hare Intl

Wed 9/24

6:59 pm-10:40 pm

Nonstop2h 41m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/8

4:10 pm-6:07 pm

Nonstop2h 57m

Chicago O'Hare Intl

Tue 11/11

2:10 pm-5:44 pm

Nonstop2h 34m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 O'Hare Intl Airport

What is the cheapest month to book a flight from Massachusetts to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $245). Flying from Massachusetts to Chicago O'Hare Intl Airport 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 ORD?

Find hourly flight availability from Massachusetts to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Massachusetts to Chicago O'Hare Intl Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Massachusetts to Chicago O'Hare Intl Airport

Explore weekly flight availability from Massachusetts to O'Hare Intl. 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 August 14, 2025.

The most flights from USMA to ORD are scheduled on a Thursday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Massachusetts to Chicago O'Hare Intl Airport one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $68. United Airlines flights start at $69 while deals on Southwest start at $79 one-way.

  • What are the most popular routes from Massachusetts to Chicago O'Hare Intl Airport?

    The most popular route from Massachusetts to Chicago O'Hare Intl Airport is Boston Logan Intl - Chicago O'Hare Intl. You may also consider Hartford Bradley Intl - Chicago O'Hare Intl or Albany Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Massachusetts to Chicago O'Hare Intl Airport?

    Before booking your flight to Chicago O'Hare Intl Airport from Massachusetts, check out the most reliable airlines to get you to your destination on time: TAP AIR PORTUGAL (92%), Icelandair (91%), Royal Jordanian( 90%).

  • What are the cheapest flights from Massachusetts to Chicago O'Hare Intl Airport?

    Looking at all options, your cheapest flight can be booked for $68. While the most popular route (Boston Logan Intl - Chicago O'Hare Intl) can be booked for $99 on average our data indicates $810 when flying from Massachusetts to Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Massachusetts to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Massachusetts to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to O'Hare Intl.

  • Can I find deals for business class flights from Massachusetts to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Massachusetts to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $245). Flying from Massachusetts to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Beloit
Hoffman Estates
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Merrillville
Naperville
Waukegan
Elk Grove Village
Downers Grove
Tinley Park
Evanston

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Alternative routes for Massachusetts to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Baltimore to Midway flights
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Ontario to O'Hare Intl flights
LaGuardia to Midway flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to Midway flights
Austin to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Hobby to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Atlanta to Midway flights
Love Field to O'Hare Intl flights
San Jose to O'Hare Intl flights
Burbank to O'Hare Intl flights
Orlando to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Love Field to Midway flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
San Diego to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
Seattle to Midway flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Reagan-National to Midway flights
Orlando to Midway flights
Cleveland to O'Hare Intl flights
Los Angeles to Midway flights
Oakland to O'Hare Intl flights
Boston to Midway flights

Top 7 airlines flying from Massachusetts to O'Hare Intl

Discover the top 7 airlines that operate flights from Massachusetts to O'Hare Intl. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$151FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$76Average$203FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$243FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$112FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$254FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$137Average$283FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$156Average$203FlexibilityNo cancel feeOn-time63%

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