$68+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jul 5 — Jul 121
1 adult, Economy
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Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
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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
Keep the following information in mind while searching for O'Hare Intl to Massachusetts flight deals. Data was last updated June 30, 2025.
Round-trip from | $132 (Priceline) |
|---|---|
One-way from | $68 (FlightHub) |
Popular in | April |
Cheapest in | August |
Average price | $223 |
Good round-trip deal | $174 or less |
Good one-way deal | $105 or less |
Find flight deals from O'Hare Intl to Massachusetts
Cheapest flights from O'Hare Intl to MassachusettsExplore 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 June 30, 2025.
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 June 30, 2025.
This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/911:45 amORD - BOS
1 stop11h 10mMultiple Airlines
Sat 9/138:38 amBOS - ORD
1 stop9h 11mMultiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$132
This CheapOair deal was found by Cheapflights users on 6/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/126:16 pmORD - BOS
1 stop12h 27mFrontier
Mon 9/158:47 amBOS - ORD
1 stop9h 15mFrontier
Deal found 6/28![Frontier logo]()
$134
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Tue 8/128:40 amORD - BOS
Nonstop2h 24mJetBlue
Wed 8/136:00 amBOS - ORD
Nonstop2h 55mJetBlue
Deal found 6/30![JetBlue logo]()
$137
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Thu 7/108:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
Sun 7/135:00 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 6/29![American Airlines logo]()
$139
This Mytrip deal was found by Cheapflights users on 6/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/125:05 amORD - BOS
1 stop13h 29mSpirit Airlines
Tue 8/196:05 amBOS - ORD
1 stop14h 02mSpirit Airlines
Deal found 6/27![Spirit Airlines logo]()
$140
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/1511:05 amORD - BOS
Nonstop2h 37mUnited Airlines
Tue 7/157:04 pmBOS - ORD
1 stop5h 37mUnited Airlines
Deal found 6/30![United Airlines logo]()
$143
This Delta deal was found by Cheapflights users on 6/27. 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.
Mon 8/117:00 amORD - BOS
Nonstop2h 29mDelta
Wed 8/277:55 pmBOS - ORD
Nonstop2h 59mDelta
Deal found 6/27![Delta logo]()
$155
This Southwest deal was found by Cheapflights users on 6/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/152:55 pmORD - BOS
1 stop6h 40mSouthwest
Wed 8/207:05 amBOS - ORD
1 stop8h 05mSouthwest
Deal found 6/30![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 6/28. 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.
Tue 8/127:15 amORD - ORH
1 stop6h 41mDelta
Tue 8/193:55 pmORH - ORD
1 stop7h 25mDelta
Deal found 6/28![Delta logo]()
$212
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Thu 8/146:15 amORD - ACK
1 stop8h 08mJetBlue
Thu 8/214:18 pmACK - ORD
1 stop7h 10mJetBlue
Deal found 6/30![JetBlue logo]()
$214
This Booking.com deal was found by Cheapflights users on 6/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1410:12 amORD - BDL
1 stop5h 47mMultiple Airlines
Thu 8/2111:05 amBDL - ORD
1 stop8h 36mMultiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/281:45 pmORD - BDL
Nonstop2h 09mAmerican Airlines
Sun 8/317:10 amBDL - ORD
Nonstop2h 40mAmerican Airlines
Deal found 6/28![American Airlines logo]()
$219
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 June 30, 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
Tue 9/9
11:45 am-11:55 pm
1 stop11h 10m
Boston Logan Intl
Sat 9/13
8:38 am-4:49 pm
1 stop9h 11m
$132
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 9/12
6:16 pm-7:43 am
1 stop12h 27m
Boston Logan Intl
Mon 9/15
8:47 am-5:02 pm
1 stop9h 15m
$134
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/12
8:40 am-12:04 pm
Nonstop2h 24m
Boston Logan Intl
Wed 8/13
6:00 am-7:55 am
Nonstop2h 55m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 7/10
8:30 pm-12:14 am
Nonstop2h 44m
Boston Logan Intl
Sun 7/13
5:00 am-6:58 am
Nonstop2h 58m
$139
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/12
5:05 am-7:34 pm
1 stop13h 29m
Boston Logan Intl
Tue 8/19
6:05 am-7:07 pm
1 stop14h 02m
$140
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/22
8:05 pm-11:32 pm
Nonstop2h 27m
Boston Logan Intl
Tue 7/29
7:04 pm-11:41 pm
1 stop5h 37m
$143
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/11
7:00 am-10:29 am
Nonstop2h 29m
Boston Logan Intl
Wed 8/27
7:55 pm-9:54 pm
Nonstop2h 59m
$155
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/15
2:55 pm-10:35 pm
1 stop6h 40m
Boston Logan Intl
Wed 8/20
7:05 am-2:10 pm
1 stop8h 05m
$157
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Tue 8/12
7:15 am-2:56 pm
1 stop6h 41m
Worcester
Tue 8/19
3:55 pm-10:20 pm
1 stop7h 25m
$212
ChicagoNantucket
ORD - ACK
ORDACK
Chicago O'Hare Intl
Thu 8/14
6:15 am-3:23 pm
1 stop8h 08m
Nantucket Memorial
Thu 8/21
4:18 pm-10:28 pm
1 stop7h 10m
$214
Showing 1-10 of 60 results
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, 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 June is currently the most expensive (average of $306). 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 June 30, 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 June 30, 2025.
The most flights from ORD to USMA are scheduled on a Monday (75 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (36 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 June 30, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.6
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.2
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.2
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.2
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.2
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.2
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
Entertainment
7.6
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.2
Food
7.0
Reviews
1 / 20
8.0
ExcellentJohn,May 2025
PVD - BNA
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.
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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.
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 June 30, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$36 | Average$95 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$78 | Average$410 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$90 | Average$257 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$100 | Average$115 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$125 | Average$414 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$130 | Average$454 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$264 | FlexibilityNo cancel fee | On-time63% |