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O'Hare Intl

$60+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Orbitz deal was found by Cheapflights users on 1/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:27 am
BOS
-
ORD
1 stop14h 44m
Multiple Airlines
Wed 3/410:00 am
ORD
-
BOS
Nonstop2h 20m
Multiple Airlines
Deal found 1/26$132
This Super.com deal was found by Cheapflights users on 1/29. 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.
Thu 2/53:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Mon 2/97:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Deal found 1/29$133
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 1/313:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Wed 2/47:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Deal found 1/28$134
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 1/304:16 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Sun 2/17:30 am
ORD
-
BOS
Nonstop2h 22m
United Airlines
Deal found 1/27$135
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:15 am
BOS
-
ORD
Nonstop3h 13m
Delta
Sat 2/287:05 am
ORD
-
BOS
Nonstop2h 32m
Delta
Deal found 1/27$136
This American Airlines deal was found by Cheapflights users on 1/29. 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 2/277:16 pm
BOS
-
ORD
Nonstop3h 14m
American Airlines
Mon 3/28:45 pm
ORD
-
BOS
Nonstop2h 14m
American Airlines
Deal found 1/29$137
This Delta deal was found by Cheapflights users on 1/28. 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.
Wed 2/257:45 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Mon 3/25:37 pm
ORD
-
BOS
1 stop4h 49m
Delta
Deal found 1/28$138
This Delta deal was found by Cheapflights users on 1/28. 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 2/284:58 pm
BOS
-
ORD
1 stop4h 46m
Delta
Tue 3/37:10 am
ORD
-
BOS
1 stop5h 09m
Delta
Deal found 1/28$139
This lastminute.com deal was found by Cheapflights users on 1/27. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:38 pm
BOS
-
ORD
1 stop6h 21m
JetBlue
Wed 2/2510:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Deal found 1/27$140
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BOS
-
ORD
1 stop17h 39m
Frontier
Mon 3/24:42 pm
ORD
-
BOS
1 stop7h 31m
Frontier
Deal found 1/26$141
This Delta deal was found by Cheapflights users on 1/28. 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 2/261:00 pm
BOS
-
ORD
1 stop6h 25m
Delta
Tue 3/32:25 pm
ORD
-
BOS
Nonstop2h 26m
Delta
Deal found 1/28$142
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 2/185:50 pm
BOS
-
ORD
1 stop16h 49m
Spirit Airlines
Tue 2/247:23 pm
ORD
-
BOS
1 stop20h 22m
Spirit Airlines
Deal found 1/28$143

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Orbitz)

One-way from

$60
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$206

Good round-trip deal

$209 or less

Good one-way deal

$120 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 O'Hare Intl
Search Deals
One-way flight from Massachusetts to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($25 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 January 2026
Search Deals
Price to beat on a round-trip flight from Massachusetts to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Massachusetts to Chicago O'Hare Intl.
Search Deals

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 January 29, 2026.
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

Wed 6/3

6:35 pm-8:35 pm

Nonstop3h 00m

Chicago O'Hare Intl

Thu 6/4

9:26 pm-12:59 am

Nonstop2h 33m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/8

7:10 am-9:10 am

Nonstop3h 00m

Chicago O'Hare Intl

Wed 4/15

6:00 am-9:15 am

Nonstop2h 15m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/3

7:00 am-8:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Sat 6/6

7:00 am-10:28 am

Nonstop2h 28m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/30

7:00 am-8:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Sat 6/6

7:00 am-10:28 am

Nonstop2h 28m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/14

6:52 am-8:51 am

Nonstop2h 59m

Chicago O'Hare Intl

Wed 4/22

6:00 am-9:15 am

Nonstop2h 15m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/7

4:25 pm-6:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Fri 4/10

7:35 pm-11:02 pm

Nonstop2h 27m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/2

8:55 am-11:00 am

Nonstop3h 05m

Chicago O'Hare Intl

Sat 5/9

7:00 am-10:28 am

Nonstop2h 28m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/31

4:25 pm-6:31 pm

Nonstop3h 06m

Chicago O'Hare Intl

Wed 4/8

10:40 am-2:04 pm

Nonstop2h 24m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/2

6:45 pm-11:56 pm

1 stop6h 11m

Chicago O'Hare Intl

Wed 3/4

2:12 pm-10:51 pm

1 stop7h 39m

$139

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/28

4:58 pm-8:44 pm

1 stop4h 46m

Chicago O'Hare Intl

Tue 3/3

7:10 am-1:19 pm

1 stop5h 09m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, April is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $89). Flying from Massachusetts to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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 January 29, 2026.

It’s typically best to fly out from Massachusetts to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 66% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Massachusetts to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to O'Hare Intl. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Massachusetts to Chicago O'Hare Intl Airport flight should consider departing on Monday 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 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 January 29, 2026.

The most flights from USMA to ORD are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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.

  • How long is the flight from Massachusetts to Chicago O'Hare Intl Airport?

    A quick flight from Massachusetts to Chicago O'Hare Intl Airport can take about 2h 58m. United Airlines provides one of the quickest options available for as low as $135. The distance between Massachusetts and Chicago O'Hare Intl Airport is about 864 mi. All flights are typically nonstop.

  • 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 Frontier, which is currently one of the cheapest options available, starting at $47. JetBlue flights start at $58 while deals on Delta start at $58 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: ANA (88%), Envoy Air (84%), Emirates( 82%).

  • 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 $119 on average, our data indicates $856 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, April is the cheapest month in which you can book a flight from Massachusetts to Chicago O'Hare Intl Airport (average of $89). Flying from Massachusetts to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $134). 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
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

Browse thousands of different options on Cheapflights for your next trip

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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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John F Kennedy Intl to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Austin to O'Hare Intl flights
Dulles Intl to Midway flights
Los Angeles to Midway flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Charlotte to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
LaGuardia to Midway flights
Reagan-National to Midway flights
Atlanta to Midway flights
Raleigh to O'Hare Intl flights
Baltimore to Midway flights
Cleveland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Diego to O'Hare Intl flights
Philadelphia to Midway flights
Orlando to O'Hare Intl flights
Denver to Midway flights
Tampa to O'Hare Intl flights
Hartford to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Sky Harbor Intl to Midway flights
Love Field to O'Hare Intl flights
San Francisco to Midway flights
Sacramento to O'Hare Intl flights
Hobby to O'Hare Intl flights
Minneapolis to Midway flights
San Antonio to O'Hare Intl flights
Kansas City to O'Hare Intl flights
Miami to O'Hare Intl flights
Detroit to O'Hare Intl flights

Top 6 airlines flying from Massachusetts to O'Hare Intl

Discover the top 6 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$45Average$145FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$68Average$178FlexibilityNo cancel feeOn-time62%
DeltaCheapest$80Average$245FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$264FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$128Average$256FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$156Average$164FlexibilityNo cancel feeOn-time63%

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