HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$70+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jan 4 — Jan 111
Sat 1/4
Sat 1/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from O'Hare Intl to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Massachusetts (USMA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 30, 2024.

Round-trip from

$132
(Frontier)

One-way from

$79
(Delta)
From Chicago O'Hare Intl to Massachusetts
Search Deals
One-way flight from Chicago O'Hare Intl to Massachusetts
Search Deals

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 December 30, 2024.

This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Tue 12/311:47 pmORD - BOS
1 stop19h 33mFrontier
Tue 1/76:00 amBOS - ORD
1 stop8h 34mFrontier
Deal found 12/28$217
This American Airlines deal was found by Cheapflights users on 12/29. 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.
Tue 12/318:05 amORD - BOS
Nonstop2h 21mAmerican Airlines
Sun 2/28:45 amBOS - ORD
Nonstop3h 00mAmerican Airlines
Deal found 12/29$277
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Mon 12/308:14 pmORD - BOS
1 stop12h 44mMultiple Airlines
Tue 1/76:00 amBOS - ORD
1 stop8h 34mMultiple Airlines
Deal found 12/28$300
This JetBlue deal was found by Cheapflights users on 12/30. 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.
Mon 12/306:55 pmORD - BOS
Nonstop2h 26mJetBlue
Mon 1/66:00 amBOS - ORD
Nonstop3h 07mJetBlue
Deal found 12/30$322
This Delta deal was found by Cheapflights users on 12/28. 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 12/3010:00 amORD - BOS
1 stop6h 25mDelta
Mon 1/63:30 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 12/28$332
This Mytrip deal was found by Cheapflights users on 12/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/311:24 pmORD - BOS
1 stop6h 56mSpirit Airlines
Sun 1/56:21 pmBOS - ORD
2 stops16h 46mSpirit Airlines
Deal found 12/29$338
This Southwest deal was found by Cheapflights users on 12/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3111:25 amORD - BOS
2 stops10h 00mSouthwest
Sun 1/53:05 pmBOS - ORD
1 stop7h 25mSouthwest
Deal found 12/28$361
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/317:15 amORD - ALB
Nonstop2h 16mUnited Airlines
Tue 2/186:09 amALB - ORD
Nonstop2h 48mUnited Airlines
Deal found 12/30$553
This American Airlines deal was found by Cheapflights users on 12/30. 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 12/318:25 amORD - ALB
Nonstop2h 09mAmerican Airlines
Tue 2/182:43 pmALB - ORD
1 stop5h 40mAmerican Airlines
Deal found 12/30$563
This United Airlines deal was found by Cheapflights users on 12/28. 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.
Sat 12/289:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Sun 1/56:02 amBOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 12/28$607
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/305:30 pmORD - ALB
1 stop4h 50mDelta
Sat 1/45:45 amALB - ORD
1 stop4h 24mDelta
Deal found 12/29$713
This Mytrip deal was found by Cheapflights users on 12/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/296:05 amORD - BDL
1 stop7h 56mMultiple Airlines
Tue 12/317:00 amBDL - ORD
3 stops25h 47mMultiple Airlines
Deal found 12/28$776

Find flights from O'Hare Intl to Massachusetts within your budget

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 30, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 2/17

4:58 pm-12:44 am

1 stop6h 46m

Boston Logan Intl

Fri 2/21

5:10 am-4:51 pm

1 stop12h 41m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/18

12:25 pm-10:00 pm

1 stop8h 35m

Boston Logan Intl

Wed 1/22

6:00 am-12:45 pm

1 stop7h 45m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/7

6:15 am-5:40 pm

1 stop10h 25m

Boston Logan Intl

Sat 5/10

9:25 am-10:21 pm

1 stop13h 56m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/23

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

Mon 1/27

6:10 am-8:14 am

Nonstop3h 04m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/23

12:30 pm-3:49 pm

Nonstop2h 19m

Boston Logan Intl

Sun 1/26

6:00 am-8:08 am

Nonstop3h 08m

$159

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/16

4:15 pm-7:38 pm

Nonstop2h 23m

Boston Logan Intl

Sun 1/19

9:30 am-11:28 am

Nonstop2h 58m

$167

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 2/12

4:22 pm-1:43 pm

1 stop20h 21m

Worcester

Wed 2/19

2:15 pm-10:46 am

1 stop21h 31m

$209

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/10

2:35 pm-6:10 pm

Nonstop2h 35m

Boston Logan Intl

Sun 1/12

7:15 am-9:25 am

Nonstop3h 10m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 2/6

7:30 am-2:55 pm

1 stop6h 25m

Worcester

Sun 2/9

4:00 pm-10:36 pm

1 stop7h 36m

$232

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Sat 1/25

6:15 pm-9:19 pm

Nonstop2h 04m

Albany Intl

Tue 1/28

4:30 pm-6:22 pm

Nonstop2h 52m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from O'Hare Intl to Massachusetts

Get recent, data-driven insights about flights from O'Hare Intl to Massachusetts including ideal travel times, pricing trends, and more.

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 $218). Flying from Chicago O'Hare Intl Airport to Massachusetts in July is currently the most expensive (average of $311). 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 30, 2024.

When flying from Chicago O'Hare Intl Airport to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 30, 2024.

The most flights from ORD to USMA are scheduled on a Sunday (57 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (23 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 30, 2024.
Peruse reviews from past customers who have flown with Frontier, United Airlines and Southwest from Chicago to Massachusetts to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,715 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,715 reviews
Southwest
8.1
Very good
4,715 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,594 reviews
Southwest
8.1
Very good
4,715 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,540 reviews
Southwest
8.1
Very good
4,715 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Qatar Airways
7.5
Good
3,762 reviews
Southwest
8.1
Very good
4,715 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,231 reviews
Southwest
8.1
Very good
4,715 reviews

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

  • 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 Delta, which is currently one of the cheapest options available, starting at $79. Frontier flights start at $82 while deals on Spirit Airlines start at $85 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 (94%), Royal Jordanian (91%) or Etihad Airways (90%) 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 $78. On average you can expect to pay $664. 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $218). Flying from Chicago O'Hare Intl Airport to Massachusetts in July is currently the most expensive (average of $311). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Seattle flights
Midway to Las Vegas flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Denver flights
O'Hare Intl to Newark flights
O'Hare Intl to Tampa flights
O'Hare Intl to San Francisco flights
Midway to Orlando flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Boston flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Honolulu flights
Midway to Miami flights
Midway to Newark flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to San Diego flights
O'Hare Intl to Hobby flights
Midway to LaGuardia flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Santa Ana flights
Midway to Los Angeles flights
Midway to Tampa flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Austin flights
Midway to Atlanta flights
Midway to Hobby flights
O'Hare Intl to Ontario flights
O'Hare Intl to Burbank flights
Midway to Fort Lauderdale flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Nashville flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Key West flights
O'Hare Intl to Portland flights
O'Hare Intl to Kahului flights

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 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$110FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$86Average$556FlexibilityNo cancel feeOn-time62%
DeltaCheapest$89Average$237FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$139Average$439FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$151Average$435FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$214Average$274FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.