$69+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 15 — Apr 221
Round-trip
1 adult, Economy
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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 March 16, 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 March 16, 2026.
This SmartFares deal was found by Cheapflights users on 3/16. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/16![JetBlue logo]()
$137
This Flysmarter deal was found by Cheapflights users on 3/13. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:55 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/13![JetBlue logo]()
$144
This SmartFares deal was found by Cheapflights users on 3/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Wed 4/227:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$147
This Priceline deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Multiple Airlines
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 3/13. 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 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/13![JetBlue logo]()
$150
This American Airlines deal was found by Cheapflights users on 3/16. 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 4/810:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Wed 4/84:34 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 3/16![American Airlines logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/15. 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 6/38:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Fri 6/55:26 pm
BOS
- ORD
Nonstop3h 09m
JetBlue
Deal found 3/15![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/16. 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 7/35:00 am
ORD
- ORH
1 stop10h 51m
American Airlines
Tue 7/75:16 pm
ORH
- ORD
1 stop16h 53m
American Airlines
Deal found 3/16![American Airlines logo]()
$192
This American Airlines deal was found by Cheapflights users on 3/13. 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 3/176:40 am
ORD
- ORH
1 stop5h 39m
American Airlines
Thu 3/191:44 pm
ORH
- ORD
1 stop20h 05m
American Airlines
Deal found 3/13![American Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 3/12. 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 5/510:45 am
ORD
- ORH
1 stop4h 58m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/12![Delta logo]()
$212
This American Airlines deal was found by Cheapflights users on 3/14. 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 3/178:45 pm
ORD
- ORH
2 stops15h 34m
American Airlines
Fri 3/201:44 pm
ORH
- ORD
2 stops11h 32m
American Airlines
Deal found 3/14![American Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 4/268:50 pm
ORD
- ORH
1 stop16h 24m
American Airlines
Sun 5/32:39 pm
ORH
- ORD
1 stop19h 15m
American Airlines
Deal found 3/15![American Airlines logo]()
$223
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 March 16, 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 March 16, 2026.
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/219:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/12![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 3/11. 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.
Sat 5/97:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Fri 8/214:10 pm
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 3/11![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 3/14. 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.
Thu 4/92:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Mon 4/138:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Deal found 3/14![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Tue 8/189:30 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sat 8/2212:34 pm
BOS
- ORD
1 stop4h 58m
United Airlines
Deal found 3/11![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 3/15. 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 4/287:15 pm
ORD
- ORH
1 stop17h 59m
American Airlines
Thu 4/302:39 pm
ORH
- ORD
1 stop19h 15m
American Airlines
Deal found 3/15![American Airlines logo]()
$192
This CheapOair deal was found by Cheapflights users on 3/15. 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 5/295:30 pm
ORD
- BDL
1 stop24h 35m
Multiple Airlines
Sun 5/316:25 am
BDL
- ORD
1 stop17h 31m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 3/15. 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 5/122:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Tue 5/196:20 am
BOS
- ORD
2 stops10h 45m
Southwest
Deal found 3/15![Southwest logo]()
$182
This United Airlines deal was found by Cheapflights users on 3/11. 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 9/97:46 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Mon 9/148:22 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 3/11![United Airlines logo]()
$185
This JetBlue deal was found by Cheapflights users on 3/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/68:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
Sat 5/97:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/11![JetBlue logo]()
$187
This American Airlines deal was found by Cheapflights users on 3/14. 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 3/276:48 pm
ORD
- ORH
1 stop17h 31m
American Airlines
Mon 3/301:44 pm
ORH
- ORD
1 stop21h 16m
American Airlines
Deal found 3/14![American Airlines logo]()
$200
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/218:31 am
ORD
- BOS
1 stop4h 47m
JetBlue
Sat 4/257:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$187
This Delta deal was found by Cheapflights users on 3/15. 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 9/57:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Tue 9/811:00 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/15![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 3/12. 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 6/95:00 am
ORD
- BOS
1 stop5h 16m
United Airlines
Tue 6/97:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Deal found 3/12![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 3/12. 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 5/57:00 am
ORD
- ORH
2 stops8h 43m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/12![Delta logo]()
$222
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 4/268:50 pm
ORD
- ORH
1 stop16h 24m
American Airlines
Sun 5/32:39 pm
ORH
- ORD
1 stop19h 15m
American Airlines
Deal found 3/15![American Airlines logo]()
$223
This JetBlue deal was found by Cheapflights users on 3/12. 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 5/228:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/245:20 am
BOS
- ORD
1 stop5h 33m
JetBlue
Deal found 3/12![JetBlue logo]()
$205
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:15 am
ORD
- ORH
2 stops10h 28m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/12![Delta logo]()
$222
This JetBlue deal was found by Cheapflights users on 3/12. 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 3/2611:00 am
ORD
- BOS
Nonstop2h 24m
JetBlue
Fri 3/273:20 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$211
This Delta deal was found by Cheapflights users on 3/12. 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 5/57:00 am
ORD
- ORH
2 stops8h 43m
Delta
Fri 5/84:15 pm
ORH
- ORD
2 stops8h 44m
Delta
Deal found 3/12![Delta logo]()
$227
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 4/196:40 am
ORD
- ORH
1 stop6h 34m
American Airlines
Wed 4/222:39 pm
ORH
- ORD
1 stop7h 56m
American Airlines
Deal found 3/15![American Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:15 am
ORD
- ORH
2 stops10h 28m
Delta
Fri 5/84:15 pm
ORH
- ORD
2 stops8h 44m
Delta
Deal found 3/12![Delta logo]()
$227
This Expedia deal was found by Cheapflights users on 3/15. 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.
Mon 4/138:58 am
ORD
- BDL
2 stops14h 01m
Multiple Airlines
Mon 4/203:50 pm
BDL
- ORD
1 stop7h 49m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 3/14. 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 5/15:00 am
ORD
- ORH
1 stop8h 14m
American Airlines
Sun 5/32:39 pm
ORH
- ORD
1 stop18h 00m
American Airlines
Deal found 3/14![American Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 3/11. 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.
Fri 4/106:05 pm
ORD
- ALB
Nonstop2h 14m
United Airlines
Mon 4/136:00 am
ALB
- ORD
1 stop4h 38m
United Airlines
Deal found 3/11![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 3/12. 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 7/286:00 am
ORD
- MVY
1 stop4h 20m
Delta
Tue 8/44:59 pm
MVY
- ORD
1 stop6h 44m
Delta
Deal found 3/12![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 3/11. 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 4/811:00 am
ORD
- BDL
Nonstop2h 15m
United Airlines
Wed 4/156:00 am
BDL
- ORD
Nonstop2h 49m
United Airlines
Deal found 3/11![United Airlines logo]()
$317
This Southwest deal was found by Cheapflights users on 3/14. 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 5/82:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Sat 5/95:50 am
BDL
- ORD
2 stops10h 40m
Southwest
Deal found 3/14![Southwest logo]()
$414
This United Airlines deal was found by Cheapflights users on 3/11. 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 4/158:45 am
ORD
- ALB
1 stop4h 23m
United Airlines
Sun 4/197:33 pm
ALB
- ORD
1 stop5h 10m
United Airlines
Deal found 3/11![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 3/15. 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 7/48:00 am
ORD
- HYA
1 stop5h 24m
American Airlines
Sat 7/113:54 pm
HYA
- ORD
Nonstop3h 34m
American Airlines
Deal found 3/15![American Airlines logo]()
$340
This Southwest deal was found by Cheapflights users on 3/14. 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 5/91:55 pm
ORD
- BDL
2 stops8h 00m
Southwest
Sun 5/1012:30 pm
BDL
- ORD
1 stop6h 55m
Southwest
Deal found 3/14![Southwest logo]()
$429
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated March 16, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated March 16, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/13. 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 3/176:40 am
ORD
- ORH
1 stop5h 39m
American Airlines
Thu 3/191:44 pm
ORH
- ORD
1 stop20h 05m
American Airlines
Deal found 3/13![American Airlines logo]()
$200
This JetBlue deal was found by Cheapflights users on 3/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/28:55 am
ORD
- BOS
Nonstop2h 32m
JetBlue
Mon 4/66:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/11![JetBlue logo]()
$158
This Priceline deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Multiple Airlines
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 3/13. 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 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/13![JetBlue logo]()
$150
This American Airlines deal was found by Cheapflights users on 3/13. 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 4/88:05 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Wed 4/83:16 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/13![American Airlines logo]()
$151
This SmartFares deal was found by Cheapflights users on 3/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/13![JetBlue logo]()
$138
This American Airlines deal was found by Cheapflights users on 3/15. 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 4/910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/15![American Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 3/15. 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 4/98:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Mon 4/137:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/15![American Airlines logo]()
$156
This SmartFares deal was found by Cheapflights users on 3/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Wed 4/227:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$147
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/206:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Sat 4/257:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/15. 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 4/287:15 pm
ORD
- ORH
1 stop17h 59m
American Airlines
Thu 4/302:39 pm
ORH
- ORD
1 stop19h 15m
American Airlines
Deal found 3/15![American Airlines logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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.
Thu 4/306:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Sun 5/36:52 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 3/12![JetBlue logo]()
$152
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 March 16, 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 March 16, 2026.
This Super.com deal was found by Cheapflights users on 3/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/85:05 am
ORD
- BOS
1 stop9h 23m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$69
This Trip.com deal was found by Cheapflights users on 3/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/15:15 am
ORD
- BOS
1 stop19h 11m
Frontier
Deal found 3/11![Frontier logo]()
$74
This Super.com deal was found by Cheapflights users on 3/12. 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.
Mon 4/206:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/12![JetBlue logo]()
$77
This Super.com deal was found by Cheapflights users on 3/13. 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 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/13![JetBlue logo]()
$78
This United Airlines deal was found by Cheapflights users on 3/12. 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 4/56:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 3/12![United Airlines logo]()
$79
This JetBlue deal was found by Cheapflights users on 3/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/11![JetBlue logo]()
$80
This Jettzy deal was found by Cheapflights users on 3/13. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/13![JetBlue logo]()
$82
This Super.com deal was found by Cheapflights users on 3/12. 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 4/176:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/12![JetBlue logo]()
$87
This Frontier deal was found by Cheapflights users on 3/13. 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.
Mon 4/135:15 am
ORD
- BDL
1 stop5h 49m
Frontier
Deal found 3/13![Frontier logo]()
$90
This Priceline deal was found by Cheapflights users on 3/14. 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.
Fri 5/15:50 am
ORD
- BDL
1 stop9h 31m
Frontier
Deal found 3/14![Frontier logo]()
$96
This Delta deal was found by Cheapflights users on 3/11. 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.
Wed 4/89:35 am
ORD
- ORH
1 stop5h 15m
Delta
Deal found 3/11![Delta logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BDL
1 stop19h 41m
Frontier
Deal found 3/14![Frontier logo]()
$99
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 March 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $138 (SmartFares) |
One-way from | $69 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $225 |
Good round-trip deal | $172 or less |
Good one-way deal | $123 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 March 16, 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
Tue 4/21
9:41 am-1:07 pm
Nonstop2h 26m
Boston Logan Intl
Thu 4/30
7:02 am-8:59 am
Nonstop2h 57m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/9
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Fri 8/21
4:10 pm-6:07 pm
Nonstop2h 57m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/9
2:40 pm-11:15 pm
1 stop7h 35m
Boston Logan Intl
Mon 4/13
8:25 am-12:50 pm
1 stop5h 25m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/18
9:30 pm-1:05 am
Nonstop2h 35m
Boston Logan Intl
Sat 8/22
12:34 pm-4:32 pm
1 stop4h 58m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/12
2:40 pm-10:30 pm
1 stop6h 50m
Boston Logan Intl
Tue 5/19
6:20 am-4:05 pm
2 stops10h 45m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/9
7:46 pm-11:20 pm
Nonstop2h 34m
Boston Logan Intl
Mon 9/14
8:22 pm-10:19 pm
Nonstop2h 57m
$185
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/6
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
Sat 5/9
7:35 pm-9:36 pm
Nonstop3h 01m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/21
8:31 am-2:18 pm
1 stop4h 47m
Boston Logan Intl
Sat 4/25
7:35 pm-9:39 pm
Nonstop3h 04m
$187
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Tue 4/28
7:15 pm-2:14 pm
1 stop17h 59m
Worcester
Thu 4/30
2:39 pm-8:54 am
1 stop19h 15m
$192
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Fri 3/27
6:48 pm-1:19 pm
1 stop17h 31m
Worcester
Mon 3/30
1:44 pm-10:00 am
1 stop21h 16m
$200
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-BDL
ORD-ORH
ORD-MVY
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-BDL
ORD-ORH
ORD-MVY
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $91). Flying from Chicago O'Hare Intl Airport to Massachusetts in January is currently the most expensive (average of $117). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to MA?
Find hourly flight availability from O'Hare Intl to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 16, 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 50% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Massachusetts. Price data was last updated on September 7, 2025.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Massachusetts flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago O'Hare Intl Airport to Massachusetts
Explore weekly flight availability from O'Hare Intl to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 16, 2026.
The most flights from ORD to USMA are scheduled on a Friday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 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 March 16, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Southwest,Delta, andUnited Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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
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 March 16, 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 6 airlines flying from O'Hare Intl to Massachusetts
Discover the top 6 airlines that operate flights from O'Hare Intl to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$248 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |