$90+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Sep 19 — Sep 261
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 August 20, 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 20, 2026.
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop14h 10m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/15![Frontier logo]()
$176
This Super.com deal was found by Cheapflights users on 8/18. 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 -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/18![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 8/19. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Tue 10/2712:35 pm -
1 stop8h 09m
Deal found 8/19![Frontier logo]()
$186
This Trip.com deal was found by Cheapflights users on 8/17. 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 9/163:50 pm -
1 stop17h 32m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/17![Frontier logo]()
$187
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/15![Frontier logo]()
$195
This Frontier deal was found by Cheapflights users on 8/19. 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 -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/19![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 8/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/610:04 am -
1 stop14h 04m
Deal found 8/16![Frontier logo]()
$197
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/911:59 am -
Nonstop2h 05m
Tue 9/158:10 am -
Nonstop2h 34m
Deal found 8/17![United Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/109:00 pm -
Nonstop2h 18m
Mon 9/146:36 pm -
Nonstop2h 54m
Deal found 8/18![American Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 8/19. 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 12/18:45 am -
1 stop5h 07m
Fri 12/43:35 pm -
1 stop7h 48m
Deal found 8/19![Delta logo]()
$260
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/305:00 am -
1 stop10h 49m
Wed 10/75:16 pm -
1 stop6h 14m
Deal found 8/16![American Airlines logo]()
$261
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 20, 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 20, 2026.
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/26:24 pm -
Nonstop2h 35m
Mon 9/76:01 am -
Nonstop2h 59m
Deal found 8/17![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/19. 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 9/33:19 pm -
Nonstop2h 40m
Sun 9/67:30 am -
Nonstop2h 56m
Deal found 8/19![Delta logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/18. 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 10/209:38 am -
Nonstop2h 28m
Mon 10/265:00 pm -
Nonstop3h 12m
Deal found 8/18![JetBlue logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/176:29 am -
1 stop9h 20m
Mon 9/215:16 pm -
2 stops15h 42m
Deal found 8/15![American Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 8/19. 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 10/17:35 am -
Nonstop2h 33m
Sun 10/47:30 am -
Nonstop2h 54m
Deal found 8/19![Delta logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/17. 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 -
Nonstop2h 45m
Sun 10/186:55 am -
Nonstop2h 51m
Deal found 8/17![JetBlue logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/197:30 am -
Nonstop2h 31m
Sun 9/206:00 am -
Nonstop2h 59m
Deal found 8/17![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/19. 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 9/910:29 am -
Nonstop2h 36m
Thu 9/108:50 pm -
Nonstop2h 42m
Deal found 8/19![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/18. 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 10/206:10 am -
Nonstop2h 23m
Sat 10/249:23 am -
Nonstop2h 51m
Deal found 8/18![United Airlines logo]()
$255
This Expedia deal was found by Cheapflights users on 8/15. 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 9/147:00 am -
2 stops14h 55m
Mon 9/2111:02 am -
1 stop8h 59m
Deal found 8/15![Multiple Airlines logo]()
$575
This JetBlue deal was found by Cheapflights users on 8/17. 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 9/193:00 pm -
1 stop7h 39m
Thu 10/224:00 pm -
1 stop6h 56m
Deal found 8/17![JetBlue logo]()
$265
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/511:15 am -
Nonstop2h 42m
Sun 9/612:42 pm -
1 stop8h 04m
Deal found 8/20![American Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:30 pm -
Nonstop2h 39m
Wed 10/77:40 pm -
Nonstop2h 51m
Deal found 8/16![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/18. 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 9/177:15 am -
Nonstop2h 09m
Mon 9/214:53 pm -
Nonstop2h 37m
Deal found 8/18![United Airlines logo]()
$257
This JetBlue deal was found by Cheapflights users on 8/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am -
1 stop7h 47m
Sun 10/254:45 pm -
1 stop7h 59m
Deal found 8/15![JetBlue logo]()
$290
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:15 am -
Nonstop2h 09m
Mon 9/214:53 pm -
Nonstop2h 37m
Deal found 8/16![United Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 8/19. 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 10/2710:24 am -
Nonstop2h 30m
Fri 10/307:30 am -
Nonstop2h 54m
Deal found 8/19![Delta logo]()
$275
This JetBlue deal was found by Cheapflights users on 8/17. 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 -
1 stop7h 47m
Sun 10/254:45 pm -
1 stop7h 59m
Deal found 8/17![JetBlue logo]()
$290
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/510:25 am -
Nonstop2h 42m
Tue 9/812:37 pm -
Nonstop2h 52m
Deal found 8/19![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 8/18. 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 9/165:30 am -
2 stops9h 07m
Wed 9/234:20 pm -
2 stops8h 39m
Deal found 8/18![Delta logo]()
$275
This JetBlue deal was found by Cheapflights users on 8/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am -
1 stop8h 24m
Mon 9/145:00 pm -
1 stop7h 08m
Deal found 8/15![JetBlue logo]()
$290
This Delta deal was found by Cheapflights users on 8/19. 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 10/146:30 am -
2 stops7h 28m
Tue 10/204:15 pm -
2 stops8h 42m
Deal found 8/19![Delta logo]()
$275
This American Airlines deal was found by Cheapflights users on 8/20. 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 8/286:45 am -
1 stop6h 45m
Wed 9/25:25 pm -
1 stop5h 46m
Deal found 8/20![American Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 8/17. 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 10/225:29 pm -
1 stop4h 58m
Mon 10/267:06 pm -
1 stop5h 51m
Deal found 8/17![Delta logo]()
$277
This JetBlue deal was found by Cheapflights users on 8/19. 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 9/243:00 pm -
1 stop7h 14m
Fri 10/27:00 am -
1 stop7h 45m
Deal found 8/19![JetBlue logo]()
$309
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2411:06 am -
Nonstop2h 23m
Tue 10/279:37 am -
Nonstop2h 52m
Deal found 8/16![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 8/19. 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 10/216:30 am -
2 stops7h 28m
Thu 10/294:10 pm -
1 stop7h 07m
Deal found 8/19![Delta logo]()
$285
This KAYAK deal was found by Cheapflights users on 8/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/243:25 pm -
1 stop7h 06m
Thu 8/2711:00 am -
Nonstop2h 41m
Deal found 8/15![American Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2811:00 am -
Nonstop2h 18m
Sat 10/315:02 pm -
Nonstop2h 48m
Deal found 8/16![United Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/19. 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 10/167:30 am -
Nonstop2h 09m
Sun 10/186:20 am -
Nonstop2h 33m
Deal found 8/19![United Airlines logo]()
$319
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated August 20, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:59 pm -
1 stop14h 10m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/15![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/19. 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 -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/19![Frontier logo]()
$196
This Frontier deal was found by Cheapflights users on 8/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/610:04 am -
1 stop14h 04m
Deal found 8/16![Frontier logo]()
$197
This Super.com deal was found by Cheapflights users on 8/18. 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 -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/18![Frontier logo]()
$183
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/911:59 am -
Nonstop2h 05m
Tue 9/158:10 am -
Nonstop2h 34m
Deal found 8/17![United Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 8/18. 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 9/109:00 pm -
Nonstop2h 18m
Mon 9/146:36 pm -
Nonstop2h 54m
Deal found 8/18![American Airlines logo]()
$258
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm -
1 stop18h 08m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/15![Frontier logo]()
$195
This Trip.com deal was found by Cheapflights users on 8/17. 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 9/163:50 pm -
1 stop17h 32m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/17![Frontier logo]()
$187
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/168:45 am -
1 stop7h 04m
Wed 9/235:16 pm -
1 stop21h 53m
Deal found 8/17![American Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/237:11 am -
1 stop26h 14m
Mon 9/288:18 pm -
2 stops27h 41m
Deal found 8/17![Multiple Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 8/16. 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 9/305:00 am -
1 stop10h 49m
Wed 10/75:16 pm -
1 stop6h 14m
Deal found 8/16![American Airlines logo]()
$261
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 20, 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 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 am -
1 stop26h 16m
Deal found 8/16![Multiple Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Sat 9/197:11 am -
1 stop26h 14m
Deal found 8/17![Multiple Airlines logo]()
$93
This Frontier deal was found by Cheapflights users on 8/18. 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 -
1 stop12h 25m
Deal found 8/18![Frontier logo]()
$94
This Trip.com deal was found by Cheapflights users on 8/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/43:50 pm -
1 stop18h 01m
Deal found 8/15![Frontier logo]()
$97
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/19![Frontier logo]()
$99
This Super.com deal was found by Cheapflights users on 8/19. 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 9/57:44 pm -
1 stop12h 25m
Deal found 8/19![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:11 am -
1 stop25h 18m
Deal found 8/16![Multiple Airlines logo]()
$106
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/17![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/148:04 am -
1 stop25h 51m
Deal found 8/18![Multiple Airlines logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sat 9/1912:56 pm -
2 stops21h 02m
Deal found 8/18![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/218:04 am -
1 stop26h 01m
Deal found 8/19![Multiple Airlines logo]()
$108
This CheapOair deal was found by Cheapflights users on 8/18. 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 10/304:44 pm -
1 stop16h 25m
Deal found 8/18![Frontier logo]()
$109
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 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $176 (Frontier) |
One-way from | $90 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $264 |
Good round-trip deal | $245 or less |
Good one-way deal | $157 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 7,457,451 searches. Data last updated August 20, 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 Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 9/2
6:24 pm-9:59 pm
Nonstop2h 35m
Boston Logan Intl
Mon 9/7
6:01 am-8:00 am
Nonstop2h 59m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 9/3
3:19 pm-6:59 pm
Nonstop2h 40m
Boston Logan Intl
Sun 9/6
7:30 am-9:26 am
Nonstop2h 56m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/20
9:38 am-1:06 pm
Nonstop2h 28m
Boston Logan Intl
Mon 10/26
5:00 pm-7:12 pm
Nonstop3h 12m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/1
7:35 am-11:08 am
Nonstop2h 33m
Boston Logan Intl
Sun 10/4
7:30 am-9:24 am
Nonstop2h 54m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 9/15
8:24 pm-12:09 am
Nonstop2h 45m
Boston Logan Intl
Sun 10/18
6:55 am-8:46 am
Nonstop2h 51m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 9/19
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Sun 9/20
6:00 am-7:59 am
Nonstop2h 59m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 9/9
10:29 am-2:05 pm
Nonstop2h 36m
Boston Logan Intl
Thu 9/10
8:50 pm-10:32 pm
Nonstop2h 42m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/20
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Sat 10/24
9:23 am-11:14 am
Nonstop2h 51m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 9/30
7:30 pm-11:09 pm
Nonstop2h 39m
Boston Logan Intl
Wed 10/7
7:40 pm-9:31 pm
Nonstop2h 51m
$255
ChicagoAlbany
ORD Chicago O'Hare Intl - ALB Albany Intl
ORDALB
Chicago O'Hare Intl
Thu 9/17
7:15 am-10:24 am
Nonstop2h 09m
Albany Intl
Mon 9/21
4:53 pm-6:30 pm
Nonstop2h 37m
$257
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-ALB
ORD-ORH
ORD-ACK
ORD-HYA
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-ALB
ORD-ORH
ORD-ACK
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 20, 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 20, 2026.
The most flights from ORD to USMA are scheduled on a Tuesday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 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 $188 and $340 in September.The cheapest round-trip price found within the last 5 days was $176 on Frontier (Sep 2-Sep 5).
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 20, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Delta,United Airlines, andAmerican Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Boarding
8.1
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Related info for your journey
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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on August 20, 2026.
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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 7,457,451 searches. Data last updated August 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$76 | Average$349 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$313 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$129 | Average$287 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$420 | FlexibilityNo cancel fee | On-time71% |