$87+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Sep 3 — Sep 101
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
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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 August 4, 2026.
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 August 4, 2026.
This Frontier deal was found by Cheapflights users on 8/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 8/3![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/31![Frontier logo]()
$168
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/30![Frontier logo]()
$169
This Expedia deal was found by Cheapflights users on 7/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Sun 9/612:45 pm
BOS
- ORD
1 stop8h 19m
Frontier
Deal found 7/29![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Sat 9/1912:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 8/2![Frontier logo]()
$172
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Wed 8/1912:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/29![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Mon 8/319:36 am
BOS
- ORD
1 stop11h 23m
Frontier
Deal found 7/31![Frontier logo]()
$176
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:50 pm
ORD
- BOS
1 stop18h 01m
Frontier
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/31![Frontier logo]()
$177
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Fri 8/2112:45 pm
BOS
- ORD
1 stop8h 14m
Frontier
Deal found 7/31![Frontier logo]()
$182
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Sat 9/58:19 am
ORD
- ORH
1 stop7h 39m
American Airlines
Wed 9/95:16 pm
ORH
- ORD
1 stop7h 40m
American Airlines
Deal found 8/3![American Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 8/1. 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 10/227:00 am
ORD
- ORH
1 stop6h 58m
Delta
Tue 10/274:15 pm
ORH
- ORD
1 stop5h 28m
Delta
Deal found 8/1![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:30 am
ORD
- ORH
1 stop6h 30m
Delta
Tue 8/255:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/30![Delta logo]()
$250
Best flights from O'Hare Intl to MassachusettsDiscover carefully curated flight deals from O'Hare Intl to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
Discover carefully curated flight deals from O'Hare Intl to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 4, 2026.
This Delta deal was found by Cheapflights users on 8/2. 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 9/1610:29 am
ORD
- BOS
Nonstop2h 36m
Delta
Wed 9/2312:15 pm
BOS
- ORD
Nonstop2h 49m
Delta
Deal found 8/2![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/1. 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 9/265:00 am
ORD
- BOS
1 stop5h 24m
United Airlines
Sat 9/266:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 8/1![United Airlines logo]()
$227
This JetBlue deal was found by Cheapflights users on 7/31. 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.
Sat 9/198:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Tue 9/226:19 am
BOS
- ORD
1 stop8h 26m
JetBlue
Deal found 7/31![JetBlue logo]()
$234
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/266:45 am
ORD
- ORH
1 stop9h 13m
American Airlines
Sat 8/295:23 pm
ORH
- ORD
1 stop19h 48m
American Airlines
Deal found 7/31![American Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 8/2. 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.
Sat 9/127:30 am
ORD
- BOS
Nonstop2h 31m
Delta
Mon 9/218:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 8/2![Delta logo]()
$231
This FlightHub deal was found by Cheapflights users on 8/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:40 am
ORD
- HYA
1 stop4h 33m
Multiple Airlines
Wed 9/211:02 am
HYA
- ORD
2 stops7h 33m
Multiple Airlines
Deal found 8/2![Multiple Airlines logo]()
$475
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 10/99:24 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Wed 10/145:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/30![United Airlines logo]()
$241
This KAYAK deal was found by Cheapflights users on 8/3. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/178:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Thu 8/208:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 8/3![JetBlue logo]()
$255
This Delta deal was found by Cheapflights users on 8/1. 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 12/227:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Mon 1/47:30 am
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 8/1![Delta logo]()
$245
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Wed 10/211:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Sun 10/2511:15 am
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 7/30![JetBlue logo]()
$262
This American Airlines deal was found by Cheapflights users on 8/3. 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 8/247:10 am
ORD
- ALB
Nonstop2h 15m
American Airlines
Fri 8/287:00 am
ALB
- ORD
Nonstop2h 48m
American Airlines
Deal found 8/3![American Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:30 am
ORD
- ORH
1 stop6h 30m
Delta
Wed 8/265:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/30![Delta logo]()
$250
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:30 pm
ORD
- BDL
Nonstop2h 23m
United Airlines
Sat 10/39:44 am
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 7/29![United Airlines logo]()
$277
This JetBlue deal was found by Cheapflights users on 7/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Sun 8/308:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 7/29![JetBlue logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/1. 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 8/292:30 pm
ORD
- ALB
Nonstop2h 13m
United Airlines
Sat 9/57:35 pm
ALB
- ORD
1 stop5h 05m
United Airlines
Deal found 8/1![United Airlines logo]()
$278
This Delta deal was found by Cheapflights users on 7/31. 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 9/149:30 am
ORD
- ORH
1 stop5h 07m
Delta
Mon 9/214:20 pm
ORH
- ORD
1 stop6h 58m
Delta
Deal found 7/31![Delta logo]()
$260
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Sat 9/511:40 am
ORD
- ORH
1 stop4h 18m
American Airlines
Wed 9/95:16 pm
ORH
- ORD
2 stops15h 42m
American Airlines
Deal found 8/3![American Airlines logo]()
$330
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Fri 10/162:35 pm
ORD
- BDL
1 stop8h 20m
JetBlue
Sun 10/186:25 am
BDL
- ORD
1 stop6h 22m
JetBlue
Deal found 7/30![JetBlue logo]()
$289
This Delta deal was found by Cheapflights users on 7/31. 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 12/87:00 am
ORD
- ORH
2 stops6h 52m
Delta
Tue 12/153:35 pm
ORH
- ORD
1 stop7h 48m
Delta
Deal found 7/31![Delta logo]()
$270
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Sun 9/68:45 am
ORD
- BDL
1 stop4h 20m
United Airlines
Thu 9/104:50 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 8/1![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:30 am
ORD
- ORH
1 stop5h 30m
Delta
Fri 9/45:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/30![Delta logo]()
$270
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 9/45:00 am
ORD
- HYA
1 stop6h 12m
American Airlines
Sun 9/65:59 pm
HYA
- ORD
1 stop5h 12m
American Airlines
Deal found 7/30![American Airlines logo]()
$369
This JetBlue deal was found by Cheapflights users on 8/1. 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.
Fri 10/167:00 am
ORD
- ORH
1 stop7h 47m
JetBlue
Sun 10/254:45 pm
ORH
- ORD
1 stop7h 59m
JetBlue
Deal found 8/1![JetBlue logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/87:30 am
ORD
- BDL
Nonstop2h 19m
United Airlines
Sun 10/1112:38 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 7/29![United Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 8/1. 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 8/246:40 am
ORD
- ORH
2 stops9h 20m
Delta
Wed 8/265:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 8/1![Delta logo]()
$270
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 10/157:30 am
ORD
- BDL
Nonstop2h 19m
United Airlines
Sun 10/186:00 am
BDL
- ORD
1 stop4h 38m
United Airlines
Deal found 7/30![United Airlines logo]()
$310
This Justfly.com deal was found by Cheapflights users on 7/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:40 am
ORD
- HYA
1 stop4h 33m
JetBlue
Wed 9/24:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/30![JetBlue logo]()
$313
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/228:00 am
ORD
- MVY
1 stop7h 55m
American Airlines
Tue 8/252:11 pm
MVY
- ORD
1 stop9h 00m
American Airlines
Deal found 7/30![American Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/2511:06 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Mon 8/314:50 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 7/31![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 8/283:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Sun 8/306:50 am
BOS
- ORD
1 stop6h 50m
Delta
Deal found 7/29![Delta logo]()
$291
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated August 4, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Wed 8/1912:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/29![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Fri 8/2112:45 pm
BOS
- ORD
1 stop8h 14m
Frontier
Deal found 7/31![Frontier logo]()
$182
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:30 am
ORD
- ORH
1 stop6h 30m
Delta
Tue 8/255:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/30![Delta logo]()
$250
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:30 am
ORD
- ORH
1 stop5h 30m
Delta
Wed 8/265:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/30![Delta logo]()
$255
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Mon 8/319:36 am
BOS
- ORD
1 stop11h 23m
Frontier
Deal found 7/31![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/31![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 8/3. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 8/3![Frontier logo]()
$166
This Expedia deal was found by Cheapflights users on 7/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Sun 9/612:45 pm
BOS
- ORD
1 stop8h 19m
Frontier
Deal found 7/29![Frontier logo]()
$171
This American Airlines deal was found by Cheapflights users on 8/3. 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.
Sat 9/58:19 am
ORD
- ORH
1 stop7h 39m
American Airlines
Wed 9/95:16 pm
ORH
- ORD
1 stop7h 40m
American Airlines
Deal found 8/3![American Airlines logo]()
$241
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:50 pm
ORD
- BOS
1 stop18h 01m
Frontier
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/31![Frontier logo]()
$177
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/30![Frontier logo]()
$169
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Sat 9/1912:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 8/2![Frontier logo]()
$172
One-way flights from O'Hare Intl to MassachusettsSearch for one-way flight options from O'Hare Intl to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
Search for one-way flight options from O'Hare Intl to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Deal found 7/30![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 7/31![Frontier logo]()
$88
This iWofly deal was found by Cheapflights users on 7/31. 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 iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Deal found 7/31![Frontier logo]()
$89
This CheapTickets deal was found by Cheapflights users on 8/2. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm
ORD
- BOS
1 stop18h 01m
Frontier
Deal found 8/2![Frontier logo]()
$90
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:44 pm
ORD
- BOS
1 stop16h 32m
Frontier
Deal found 8/2![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Deal found 7/30![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/119:33 pm
ORD
- BOS
1 stop12h 19m
Frontier
Deal found 7/31![Frontier logo]()
$99
This Trip.com deal was found by Cheapflights users on 8/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:15 am
ORD
- BOS
1 stop22h 36m
Frontier
Deal found 8/1![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 8/3. 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.
Wed 11/182:15 pm
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 8/3![JetBlue logo]()
$102
This JetBlue deal was found by Cheapflights users on 8/3. 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 9/158:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Deal found 8/3![JetBlue logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/31![JetBlue logo]()
$107
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:30 am
ORD
- ORH
1 stop5h 07m
Delta
Deal found 7/30![Delta logo]()
$119
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Frontier) |
One-way from | $87 (Trip.com) |
Popular in | April |
Cheapest in | January |
Average price | $264 |
Good round-trip deal | $221 or less |
Good one-way deal | $143 or less |
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 August 4, 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
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/16
10:29 am-2:05 pm
Nonstop2h 36m
Boston Logan Intl
Wed 9/23
12:15 pm-2:04 pm
Nonstop2h 49m
$217
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/26
5:00 am-11:24 am
1 stop5h 24m
Boston Logan Intl
Sat 9/26
6:43 pm-8:40 pm
Nonstop2h 57m
$227
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/12
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Mon 9/21
8:50 pm-10:32 pm
Nonstop2h 42m
$231
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/19
8:24 pm-12:09 am
Nonstop2h 45m
Boston Logan Intl
Tue 9/22
6:19 am-1:45 pm
1 stop8h 26m
$234
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 10/9
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Wed 10/14
5:45 am-9:38 am
1 stop4h 53m
$241
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 12/22
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Mon 1/4
7:30 am-9:33 am
Nonstop3h 03m
$245
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Thu 8/20
9:30 am-5:00 pm
1 stop6h 30m
Worcester
Wed 8/26
5:40 pm-10:24 pm
1 stop5h 44m
$250
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/17
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Thu 8/20
8:15 am-10:11 am
Nonstop2h 56m
$255
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Mon 9/14
9:30 am-3:37 pm
1 stop5h 07m
Worcester
Mon 9/21
4:20 pm-10:18 pm
1 stop6h 58m
$260
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Wed 8/26
6:45 am-4:58 pm
1 stop9h 13m
Worcester
Sat 8/29
5:23 pm-12:11 pm
1 stop19h 48m
$262
Showing 1-10 of 60 resultsSorted by cheapest first
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.
ORD-BOS
ORD-ORH
ORD-HYA
ORD-BDL
ORD-ALB
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
ORD-USMA
ORD-BOS
ORD-ORH
ORD-HYA
ORD-BDL
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 $205). Flying from Chicago O'Hare Intl Airport to Massachusetts in June is currently the most expensive (average of $290). 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 August 4, 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.
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 August 4, 2026.
The most flights from ORD to USMA are scheduled on a Sunday (78 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Massachusetts flights typically cost between $180 and $338 in September.The cheapest round-trip price found within the last 5 days was $166 on Frontier (Sep 2-Sep 6).
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Massachusetts?
The best time to book flights from Chicago O'Hare Intl Airport to Massachusetts is 64 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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.
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 August 4, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Delta,United Airlines, andJetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Food
7.2
Comfort
7.8
Crew
8.5
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
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
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Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on August 4, 2026.
Popular flight searches
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O'Hare Intl to Massachusetts flights
Consider these flights traveling from O'Hare Intl to Massachusetts.
Top 4 airlines flying from O'Hare Intl to Massachusetts
Discover the top 4 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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$70 | Average$347 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$311 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$282 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$419 | FlexibilityNo cancel fee | On-time71% |