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$66+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/177:00 am
ORD
-
BOS
1 stop9h 15m
Multiple Airlines
Fri 2/276:00 am
BOS
-
ORD
1 stop29h 51m
Multiple Airlines
Deal found 1/27$131
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:02 pm
ORD
-
BOS
1 stop6h 11m
Multiple Airlines
Sat 2/287:00 am
BOS
-
ORD
Nonstop3h 10m
Multiple Airlines
Deal found 1/28$132
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:23 pm
ORD
-
BOS
1 stop20h 22m
Multiple Airlines
Tue 3/36:00 am
BOS
-
ORD
1 stop11h 52m
Multiple Airlines
Deal found 1/27$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 1/317:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Mon 2/23:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Deal found 1/28$134
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:05 am
ORD
-
BOS
Nonstop2h 24m
United Airlines
Sat 2/214:25 pm
BOS
-
ORD
Nonstop3h 05m
United Airlines
Deal found 1/28$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.
Sun 2/157:05 am
ORD
-
BOS
Nonstop2h 32m
Delta
Tue 3/33:50 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 1/27$136
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.
Sun 2/157:05 am
ORD
-
BOS
Nonstop2h 32m
Delta
Wed 2/257:45 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 1/27$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 2/256:40 pm
ORD
-
BOS
Nonstop2h 29m
Delta
Sat 2/289:05 am
BOS
-
ORD
1 stop8h 49m
Delta
Deal found 1/28$138
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/307:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Sun 2/16:10 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 1/27$139
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:02 pm
ORD
-
BOS
1 stop6h 11m
Multiple Airlines
Tue 3/105:27 am
BOS
-
ORD
1 stop14h 44m
Multiple Airlines
Deal found 1/27$140
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.
Mon 2/96:59 pm
ORD
-
BOS
Nonstop2h 32m
Delta
Wed 2/114:10 pm
BOS
-
ORD
Nonstop3h 09m
Delta
Deal found 1/28$141
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:51 am
ORD
-
BOS
2 stops10h 53m
Multiple Airlines
Wed 3/1111:51 am
BOS
-
ORD
1 stop7h 06m
Multiple Airlines
Deal found 1/27$142

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(Kiwi.com)

One-way from

$66
(Kiwi.com)

Popular in

April

Cheapest in

January

Average price

$207

Good round-trip deal

$165 or less

Good one-way deal

$90 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago O'Hare Intl to Massachusetts
Search Deals
One-way flight from Chicago O'Hare Intl to Massachusetts
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 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 Chicago O'Hare Intl to Massachusetts.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Massachusetts.
Search Deals

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 January 29, 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

Wed 4/29

9:41 am-1:09 pm

Nonstop2h 28m

Boston Logan Intl

Sat 5/2

7:35 pm-9:36 pm

Nonstop3h 01m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/28

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

Tue 3/3

3:50 pm-5:53 pm

Nonstop3h 03m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/3

6:15 am-9:39 am

Nonstop2h 24m

Boston Logan Intl

Sat 6/6

6:00 am-7:58 am

Nonstop2h 58m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/27

7:00 am-10:28 am

Nonstop2h 28m

Boston Logan Intl

Sat 5/30

7:00 am-8:58 am

Nonstop2h 58m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/21

9:41 am-1:09 pm

Nonstop2h 28m

Boston Logan Intl

Wed 5/13

6:52 am-8:51 am

Nonstop2h 59m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/25

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Wed 3/4

7:07 am-12:04 pm

1 stop5h 57m

$151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/22

8:31 am-2:16 pm

1 stop4h 45m

Boston Logan Intl

Tue 4/28

7:35 pm-9:36 pm

Nonstop3h 01m

$151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/28

1:02 pm-7:08 pm

1 stop5h 06m

Boston Logan Intl

Mon 3/2

6:28 pm-8:30 pm

Nonstop3h 02m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/17

6:40 pm-10:09 pm

Nonstop2h 29m

Boston Logan Intl

Fri 2/27

7:15 am-9:28 am

Nonstop3h 13m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/4

8:21 pm-11:56 pm

Nonstop2h 35m

Boston Logan Intl

Sun 6/7

6:00 am-7:55 am

Nonstop2h 55m

$157

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 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 $117). 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 January 29, 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 January 29, 2026.

The most flights from ORD to USMA are scheduled on a Wednesday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 January 29, 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
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

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
8,128 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

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
9,215 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

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
11,205 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

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
2,892 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

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
8,393 reviews
Delta
7.9
Good
8,128 reviews

Overall

7.9

Entertainment

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Comfort

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 United Airlines can get you from Chicago O'Hare Intl Airport to Massachusetts in just under 2h 24m. Your travel time will be generally consistent. Chicago O'Hare Intl Airport and Massachusetts are separated by a distance of 864 mi. All flights are typically nonstop.

  • 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%), WestJet (85%) or Air France (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 $67. On average you can expect to pay $611. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $128.

  • 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 $117). 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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Midway to Orlando flights
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Midway to Los Angeles flights
O'Hare Intl to Salt Lake City flights
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O'Hare Intl to Dulles Intl flights
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Midway to John F Kennedy Intl flights
Midway to Tampa flights
Midway to Hobby flights
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Midway to Newark flights
Midway to Fort Myers flights
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Midway to Denver flights

Top 6 airlines flying from O'Hare Intl to Massachusetts

Discover the top 6 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$61Average$309FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$158FlexibilityNo cancel feeOn-time65%
DeltaCheapest$94Average$255FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$117Average$442FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$437FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$144Average$206FlexibilityNo cancel feeOn-time63%

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