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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
feb. 7 — feb. 141
sáb. 2/7
sáb. 2/14
1 adult, Economy
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Cheap 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 enero 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$128
(Expedia)

One-way from

$64
(United Airlines)

Popular in

April

Cheapest in

January

Average price

$207

Good round-trip deal

$173 or less

Good one-way deal

$96 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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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. 6% potential increase in price ($15 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 January 2026
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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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Find 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 enero 8, 2026.

This Expedia deal was found by Cheapflights users on 1/6. 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.
mar. 2/32:53 pmORD - BOS
1 stop9h 10mFrontier
mar. 2/106:00 amBOS - ORD
1 stop12h 12mFrontier
Deal found 1/6$128
This Delta deal was found by Cheapflights users on 1/7. 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.
sáb. 2/710:29 amORD - BOS
1 stop4h 24mDelta
lun. 2/96:35 pmBOS - ORD
1 stop6h 21mDelta
Deal found 1/7$129
This Southwest deal was found by Cheapflights users on 1/7. 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.
mié. 4/222:40 pmORD - BOS
1 stop6h 50mSouthwest
lun. 4/275:30 amBOS - ORD
2 stops11h 35mSouthwest
Deal found 1/7$130
This Delta deal was found by Cheapflights users on 1/8. 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.
jue. 1/2910:45 amORD - BOS
1 stop4h 38mDelta
lun. 2/28:25 pmBOS - ORD
Nonstop3h 04mDelta
Deal found 1/8$131
This JetBlue deal was found by Cheapflights users on 1/8. 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.
sáb. 5/26:00 amORD - BOS
Nonstop2h 15mJetBlue
lun. 5/46:52 amBOS - ORD
Nonstop2h 59mJetBlue
Deal found 1/8$132
This Delta deal was found by Cheapflights users on 1/7. 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.
jue. 1/2210:29 amORD - BOS
1 stop7h 01mDelta
sáb. 2/77:30 amBOS - ORD
Nonstop3h 11mDelta
Deal found 1/7$133
This Priceline deal was found by Cheapflights users on 1/7. 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.
mié. 3/410:00 amORD - BOS
Nonstop2h 20mMultiple Airlines
sáb. 3/712:35 pmBOS - ORD
1 stop11h 04mMultiple Airlines
Deal found 1/7$134
This Delta deal was found by Cheapflights users on 1/6. 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.
jue. 2/199:35 amORD - BOS
1 stop4h 44mDelta
mar. 3/312:50 pmBOS - ORD
1 stop4h 51mDelta
Deal found 1/6$135
This Frontier deal was found by Cheapflights users on 1/7. 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.
jue. 1/292:42 pmORD - BOS
1 stop9h 31mFrontier
mar. 2/106:00 amBOS - ORD
1 stop12h 12mFrontier
Deal found 1/7$136
This United Airlines deal was found by Cheapflights users on 1/7. 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.
vie. 2/67:30 amORD - BOS
Nonstop2h 22mUnited Airlines
dom. 2/86:00 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 1/7$137
This JetBlue deal was found by Cheapflights users on 1/6. 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.
jue. 6/48:21 pmORD - BOS
Nonstop2h 35mJetBlue
dom. 6/76:00 amBOS - ORD
Nonstop2h 55mJetBlue
Deal found 1/6$138
This American Airlines deal was found by Cheapflights users on 1/7. 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.
mié. 1/147:00 amORD - BOS
Nonstop2h 23mAmerican Airlines
mié. 1/142:43 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Deal found 1/7$139

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 enero 8, 2026.
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

jue. 1/29

9:35 am-3:22 pm

1 stop4h 47m

Boston Logan Intl

lun. 2/2

8:25 pm-10:29 pm

Nonstop3h 04m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 2/19

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

lun. 3/2

7:00 am-9:10 am

Nonstop3h 10m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 1/30

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

lun. 2/9

5:26 pm-11:56 pm

1 stop7h 30m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 2/24

10:45 am-4:20 pm

1 stop4h 35m

Boston Logan Intl

lun. 3/2

5:00 pm-10:05 pm

1 stop6h 05m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 2/12

5:15 pm-12:10 am

1 stop5h 55m

Boston Logan Intl

lun. 2/16

9:45 pm-12:15 pm

2 stops15h 30m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 1/24

7:00 am-1:22 pm

1 stop5h 22m

Boston Logan Intl

sáb. 1/31

7:30 am-9:41 am

Nonstop3h 11m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 4/19

6:00 am-9:15 am

Nonstop2h 15m

Boston Logan Intl

lun. 4/20

7:35 pm-9:36 pm

Nonstop3h 01m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 2/19

9:35 am-3:19 pm

1 stop4h 44m

Boston Logan Intl

sáb. 2/28

4:58 pm-8:44 pm

1 stop4h 46m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 2/26

6:00 am-12:20 pm

1 stop5h 20m

Boston Logan Intl

lun. 3/2

5:00 pm-10:05 pm

1 stop6h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 1/23

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

dom. 1/25

7:30 am-9:41 am

Nonstop3h 11m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $91). Flying from Chicago O'Hare Intl Airport to Massachusetts in February 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 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 enero 8, 2026.

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 52% 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 enero 8, 2026.

The most flights from ORD to USMA are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 on average).

How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?

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 enero 8, 2026.
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
8,025 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Food

7.2

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
8,025 reviews
Delta
7.9
Good
8,025 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Food

7.2

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
9,139 reviews
Delta
7.9
Good
8,025 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Food

7.2

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
11,095 reviews
Delta
7.9
Good
8,025 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Food

7.2

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
2,896 reviews
Delta
7.9
Good
8,025 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Food

7.2

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
8,287 reviews
Delta
7.9
Good
8,025 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Food

7.2

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?

    Delta, JetBlue, and American Airlines can get you from Chicago O'Hare Intl Airport to Massachusetts in just under 2h 20m. Your travel time can differ by up to 12h 51m. 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 Envoy Air (86%), Avianca (76%) or United Airlines (76%) 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 $758. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $105.

  • 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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $91). Flying from Chicago O'Hare Intl Airport to Massachusetts in February 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.

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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 enero 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$73Average$316FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$104Average$258FlexibilityNo 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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