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$55+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Feb 16 — Feb 231
Sun 2/16
Sun 2/23
1 adult, Economy
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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 February 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$148
(Mytrip)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

September

Average price

$247

Good round-trip deal

$198 or less

Good one-way deal

$109 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. 15% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 11, 2025.

This Mytrip deal was found by Cheapflights users on 2/11. 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.
Mon 3/107:42 pmORD - BOS
3 stops24h 26mSpirit Airlines
Mon 3/178:35 pmBOS - ORD
2 stops22h 51mSpirit Airlines
Deal found 2/11$148
This CheapOair deal was found by Cheapflights users on 2/11. 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.
Wed 2/267:25 amORD - BOS
1 stop24h 46mFrontier
Sun 3/26:00 amBOS - ORD
1 stop28h 27mFrontier
Deal found 2/11$150
This Mytrip deal was found by Cheapflights users on 2/10. 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.
Thu 3/278:10 amORD - BOS
1 stop24h 31mMultiple Airlines
Thu 4/311:14 amBOS - ORD
1 stop13h 45mMultiple Airlines
Deal found 2/10$152
This JetBlue deal was found by Cheapflights users on 2/10. 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 2/2712:50 pmORD - BOS
Nonstop2h 23mJetBlue
Mon 3/33:00 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 2/10$156
This United Airlines deal was found by Cheapflights users on 2/10. 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 2/279:15 amORD - BOS
Nonstop2h 23mUnited Airlines
Mon 3/106:20 pmBOS - ORD
Nonstop3h 05mUnited Airlines
Deal found 2/10$157
This Delta deal was found by Cheapflights users on 2/11. 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 3/106:55 pmORD - BOS
Nonstop2h 22mDelta
Mon 3/178:15 pmBOS - ORD
Nonstop3h 00mDelta
Deal found 2/11$177
This American Airlines deal was found by Cheapflights users on 2/11. 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 3/118:55 amORD - ALB
Nonstop2h 06mAmerican Airlines
Tue 3/1812:29 pmALB - ORD
Nonstop2h 33mAmerican Airlines
Deal found 2/11$177
This American Airlines deal was found by Cheapflights users on 2/11. 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.
Fri 3/146:40 pmORD - BOS
Nonstop2h 23mAmerican Airlines
Sun 3/165:15 amBOS - ORD
Nonstop2h 59mAmerican Airlines
Deal found 2/11$185
This United Airlines deal was found by Cheapflights users on 2/11. 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 3/124:05 pmORD - ALB
1 stop6h 39mUnited Airlines
Thu 3/1311:55 amALB - ORD
Nonstop2h 55mUnited Airlines
Deal found 2/11$187
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/187:15 amORD - ALB
1 stop4h 53mDelta
Wed 3/191:50 pmALB - ORD
1 stop7h 48mDelta
Deal found 2/10$197
This Southwest deal was found by Cheapflights users on 2/10. 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.
Sat 2/224:45 pmORD - BOS
1 stop5h 25mSouthwest
Sun 2/235:25 amBOS - ORD
1 stop10h 00mSouthwest
Deal found 2/10$211
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Thu 3/274:27 pmORD - ORH
1 stop20h 13mAmerican Airlines
Thu 4/32:10 pmORH - ORD
1 stop19h 38mAmerican Airlines
Deal found 2/10$214

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 February 11, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/10

7:42 pm-9:08 pm

3 stops24h 26m

Boston Logan Intl

Mon 3/17

8:35 pm-6:26 pm

2 stops22h 51m

$148

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/26

7:25 am-9:11 am

1 stop24h 46m

Boston Logan Intl

Sun 3/2

6:00 am-9:27 am

1 stop28h 27m

$150

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/27

8:10 am-9:41 am

1 stop24h 31m

Boston Logan Intl

Thu 4/3

11:14 am-11:59 pm

1 stop13h 45m

$152

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/27

12:50 pm-4:13 pm

Nonstop2h 23m

Boston Logan Intl

Mon 3/3

3:00 pm-5:00 pm

Nonstop3h 00m

$156

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/27

9:15 am-12:38 pm

Nonstop2h 23m

Boston Logan Intl

Mon 3/10

6:20 pm-8:25 pm

Nonstop3h 05m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/10

10:55 am-2:12 pm

Nonstop2h 17m

Boston Logan Intl

Thu 3/13

7:25 am-9:34 am

Nonstop3h 09m

$177

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Tue 3/11

8:55 am-12:01 pm

Nonstop2h 06m

Albany Intl

Tue 3/18

12:29 pm-2:02 pm

Nonstop2h 33m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/14

6:40 pm-10:03 pm

Nonstop2h 23m

Boston Logan Intl

Sun 3/16

5:15 am-7:14 am

Nonstop2h 59m

$185

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Thu 4/3

7:30 am-10:36 am

Nonstop2h 06m

Albany Intl

Tue 4/8

7:30 pm-11:29 pm

1 stop4h 59m

$187

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

Tue 3/18

7:15 am-1:08 pm

1 stop4h 53m

Albany Intl

Wed 3/19

1:50 pm-8:38 pm

1 stop7h 48m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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.

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 February 11, 2025.

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 February 11, 2025.

The most flights from ORD to USMA are scheduled on a Tuesday (48 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 February 11, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Delta 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
4,482 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Southwest
8.1
Very good
4,482 reviews
Southwest
8.1
Very good
4,482 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Alaska Airlines
8.0
Very good
9,691 reviews
Southwest
8.1
Very good
4,482 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Delta
8.0
Very good
8,336 reviews
Southwest
8.1
Very good
4,482 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

Qatar Airways
7.5
Good
3,673 reviews
Southwest
8.1
Very good
4,482 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

JetBlue
7.4
Good
3,111 reviews
Southwest
8.1
Very good
4,482 reviews

Boarding

8.2

Comfort

8.1

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Steven,Feb 2025

BZN - DEN

Bozeman Airport knows how to deal with snow. I saw many airlines leave with only small delays due to the foot of snow. Our plane was 4 hours delayed. I missed my connection in Denver with a 3.5 hour layover. Because of that, the best you Southwest could do was make me wait more hours, them send me to Chicago Midway, where I had to wait overnight, for 7 more hours until a flight to RSW was available. Nobody at Southwest told me that Midway shuts down after 8pm. Everything was closed. I had no idea. You just dumped me there. I am a 65 year old man and you dumped me in Midway without even a couch to lie on. I was awake 21 hours because of this. No, it was not an act of God. Other airlines were moving passengers out. It was incompetence Shame on you.

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 Frontier, which is currently one of the cheapest options available, starting at $55. JetBlue flights start at $79 while deals on Spirit Airlines start at $79 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 WestJet (100%), Air France (100%) or LATAM Airlines (100%) 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 $539. The most popular route, (Chicago O'Hare Intl - Boston Logan Intl), can usually be booked for $82.

  • 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.

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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 February 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$110FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$85Average$464FlexibilityNo cancel feeOn-time62%
DeltaCheapest$89Average$256FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$138Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$448FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$214Average$280FlexibilityNo cancel feeOn-time63%
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