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$60+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$120
(United Airlines)

One-way from

$60
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$244

Good round-trip deal

$169 or less

Good one-way deal

$102 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. 5% potential increase in price ($14 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 October 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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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 October 22, 2025.

This United Airlines deal was found by Cheapflights users on 10/21. 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.
Mon 12/229:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Thu 12/256:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/21$120
This American Airlines deal was found by Cheapflights users on 10/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:25 pmORD - BOS
Nonstop2h 29mAmerican Airlines
Sat 11/17:00 amBOS - ORD
Nonstop3h 13mAmerican Airlines
Deal found 10/22$122
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/101:45 pmORD - BOS
1 stop7h 30mSouthwest
Sun 12/145:00 amBOS - ORD
1 stop8h 15mSouthwest
Deal found 10/21$123
This JetBlue deal was found by Cheapflights users on 10/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:55 pmORD - BOS
Nonstop2h 32mJetBlue
Sat 11/157:10 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/21$125
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:10 amORD - BOS
Nonstop2h 25mAmerican Airlines
Thu 1/16:51 pmBOS - ORD
Nonstop3h 13mAmerican Airlines
Deal found 10/21$126
This Delta deal was found by Cheapflights users on 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:10 amORD - BOS
Nonstop2h 26mDelta
Mon 12/84:46 pmBOS - ORD
1 stop4h 49mDelta
Deal found 10/22$127
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amORD - BOS
Nonstop2h 24mAmerican Airlines
Sat 12/67:00 amBOS - ORD
Nonstop3h 32mAmerican Airlines
Deal found 10/21$128
This Delta deal was found by Cheapflights users on 10/21. 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.
Fri 12/55:59 pmORD - BOS
1 stop6h 28mDelta
Fri 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Deal found 10/21$131
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/85:45 pmORD - BOS
1 stop14h 15mFrontier
Mon 11/109:55 amBOS - ORD
1 stop26h 19mFrontier
Deal found 10/20$133
This United Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 10/309:20 amORD - BOS
Nonstop2h 24mUnited Airlines
Thu 11/67:45 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/19$134
This JetBlue deal was found by Cheapflights users on 10/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/128:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/21$135
This Delta deal was found by Cheapflights users on 10/20. 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 12/115:30 amORD - BDL
1 stop6h 47mDelta
Sun 12/146:09 amBDL - ORD
1 stop6h 31mDelta
Deal found 10/20$177

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 October 22, 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

Mon 12/22

9:12 pm-12:45 am

Nonstop2h 33m

Boston Logan Intl

Thu 12/25

6:01 am-8:05 am

Nonstop3h 04m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/10

1:45 pm-10:15 pm

1 stop7h 30m

Boston Logan Intl

Sun 12/14

5:00 am-12:15 pm

1 stop8h 15m

$123

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 12/8

10:45 am-4:03 pm

1 stop4h 18m

Boston Logan Intl

Thu 12/11

12:50 pm-2:47 pm

Nonstop2h 57m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/29

1:30 pm-10:33 pm

1 stop8h 03m

Boston Logan Intl

Wed 2/4

8:10 pm-10:15 pm

Nonstop3h 05m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/23

10:35 am-4:00 pm

1 stop4h 25m

Boston Logan Intl

Sun 1/25

7:00 am-9:10 am

Nonstop3h 10m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/26

9:17 am-12:46 pm

Nonstop2h 29m

Boston Logan Intl

Sun 3/1

5:30 am-9:38 am

1 stop5h 08m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

10:36 am-4:11 pm

1 stop4h 35m

Boston Logan Intl

Sat 12/13

5:29 am-10:00 am

1 stop5h 31m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/30

10:35 am-4:00 pm

1 stop4h 25m

Boston Logan Intl

Mon 2/2

1:00 pm-7:25 pm

1 stop7h 25m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/27

10:35 am-2:03 pm

Nonstop2h 28m

Boston Logan Intl

Tue 12/2

7:52 pm-9:47 pm

Nonstop2h 55m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

Thu 11/13

5:30 am-9:46 am

1 stop5h 16m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $71). Flying from Chicago O'Hare Intl Airport to Massachusetts in February is currently the most expensive (average of $138). 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 October 22, 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 54% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Massachusetts flight should consider departing on Monday evenings when fares are most often at their lowest. Tuesday afternoons 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 October 22, 2025.

The most flights from ORD to USMA are scheduled on a Monday (66 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (13 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 October 22, 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
7,981 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,981 reviews
Delta
7.9
Good
7,981 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,990 reviews
Delta
7.9
Good
7,981 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,028 reviews
Delta
7.9
Good
7,981 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
JetBlue
7.2
Good
2,908 reviews
Delta
7.9
Good
7,981 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Spirit Airlines
6.3
Okay
8,098 reviews
Delta
7.9
Good
7,981 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Entertainment

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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?

    United Airlines, Southwest, and Delta can get you from Chicago O'Hare Intl Airport to Massachusetts in just under 2h 33m. Your travel time can differ by up to 4h 57m. 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 United Airlines, which is currently one of the cheapest options available, starting at $64. Delta flights start at $69 while deals on Southwest start at $115 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 (83%), TAP AIR PORTUGAL (83%) or Envoy Air (80%) 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 $58. On average you can expect to pay $639. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $91.

  • 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, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $71). Flying from Chicago O'Hare Intl Airport to Massachusetts in February is currently the most expensive (average of $138). 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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$56Average$143FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$322FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$261FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$117FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$443FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$121Average$452FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$144Average$206FlexibilityNo cancel feeOn-time63%

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