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$64+ Cheap flights from O'Hare Intl (ORD) to Massachusetts

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.
ORD — BOS
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Massachusetts

Cheapest flights from O'Hare Intl to Massachusetts
Explore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This JetBlue deal was found by Cheapflights users on 12/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 1/67:45 amBOS - ORD
Nonstop3h 11mJetBlue
Deal found 12/25$137
This JetBlue deal was found by Cheapflights users on 12/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Thu 1/14:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/25$157
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 12/316:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Sat 1/36:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Deal found 12/26$158
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 12/301:55 pmORD - BOS
Nonstop2h 22mUnited Airlines
Thu 1/17:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/26$161
This American Airlines deal was found by Cheapflights users on 12/25. 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.
Sun 12/288:20 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Thu 1/16:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 12/25$172
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 12/307:45 amORD - BOS
Nonstop2h 23mUnited Airlines
Wed 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/26$187
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:17 pmORD - BOS
1 stop3h 59mAmerican Airlines
Wed 2/186:41 pmBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 12/26$192
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 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Fri 1/24:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/27$194
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Wed 1/73:35 pmBOS - ORD
Nonstop3h 08mJetBlue
Deal found 12/26$196
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 12/309:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Sat 1/36:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/27$197
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:41 pmORD - BOS
Nonstop2h 29mJetBlue
Mon 1/54:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/26$202
This American Airlines deal was found by Cheapflights users on 12/25. 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.
Tue 12/305:35 pmORD - ORH
1 stop17h 19mAmerican Airlines
Sun 1/41:45 pmORH - ORD
1 stop21h 18mAmerican Airlines
Deal found 12/25$224

Find flight deals from O'Hare Intl to Massachusetts

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(American Airlines)

One-way from

$64
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$269

Good round-trip deal

$185 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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From Chicago O'Hare Intl to Massachusetts
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One-way flight from Chicago O'Hare Intl to Massachusetts
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Highest demand for flights based on searches. 1% potential increase in price ($3 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 December 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Massachusetts.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Massachusetts.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Massachusetts 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 Chicago O'Hare Intl Airport to Massachusetts that are best for you.

Fly from

O'Hare Intl

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/5

8:21 pm-11:56 pm

Nonstop2h 35m

Boston Logan Intl

Sun 6/7

6:00 am-7:55 am

Nonstop2h 55m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/23

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Fri 1/30

11:30 am-1:39 pm

Nonstop3h 09m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 2/6

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Sun 2/8

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/29

7:00 am-10:30 am

Nonstop2h 30m

Boston Logan Intl

Sat 5/2

5:10 pm-7:17 pm

Nonstop3h 07m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/7

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Wed 1/14

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/24

6:40 pm-10:09 pm

Nonstop2h 29m

Boston Logan Intl

Wed 2/25

7:15 am-9:28 am

Nonstop3h 13m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/10

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Tue 2/10

1:40 pm-7:31 pm

1 stop6h 51m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/28

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

Mon 3/2

7:45 pm-9:48 pm

Nonstop3h 03m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/6

10:00 am-1:23 pm

Nonstop2h 23m

Boston Logan Intl

Sun 3/8

7:00 am-9:09 am

Nonstop3h 09m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/17

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

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

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $89). Flying from Chicago O'Hare Intl Airport to Massachusetts in February is currently the most expensive (average of $137). 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 ORD to MA?

Find hourly flight availability from O'Hare Intl to Massachusetts. 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.

It’s optimal to fly from Chicago O'Hare Intl Airport to Massachusetts in the evening. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Massachusetts. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Massachusetts flight should consider departing on Tuesday 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 Chicago O'Hare Intl Airport to Massachusetts

Explore weekly flight availability from O'Hare Intl to Massachusetts. 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 ORD to USMA are scheduled on a Friday (56 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (27 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated December 28, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Delta, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,019 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,113 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,073 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,901 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,211 reviews
Delta
7.9
Good
8,019 reviews

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Boarding

8.1

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Massachusetts. 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 Chicago O'Hare Intl Airport to Massachusetts?

    JetBlue, Delta, and American Airlines can get you from Chicago O'Hare Intl Airport to Massachusetts in just under 2h 35m. Your travel time can differ by up to 3h 36m. Chicago O'Hare Intl Airport and Massachusetts are separated by a distance of 864 mi. This flight may include one or multiple stops.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $55. JetBlue flights start at $58 while deals on United Airlines start at $64 one-way.

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

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

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

    Consider Etihad Airways (79%), Envoy Air (78%) or Avianca (73%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Massachusetts.

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

    The cheapest flight price from Chicago O'Hare Intl Airport to Massachusetts is $63. On average you can expect to pay $721. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $115.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $89). Flying from Chicago O'Hare Intl Airport to Massachusetts in February is currently the most expensive (average of $137). 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.

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Alternative routes for O'Hare Intl to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from O'Hare Intl to Massachusetts

Discover the top 7 airlines that operate flights from O'Hare Intl to Massachusetts. 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$75Average$317FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$104Average$259FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$107Average$122FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$446FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$439FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$144Average$206FlexibilityNo cancel feeOn-time63%

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