$105+ Cheap flights from O'Hare Intl (ORD) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 17 — Oct 241
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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/2610:05 am -
1 stop4h 22m
Tue 10/274:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/266:30 am -
2 stops7h 57m
Thu 10/294:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$214
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 10/268:36 am -
1 stop5h 51m
Tue 11/34:10 pm -
1 stop5h 33m
Deal found 9/17![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/266:30 am -
2 stops7h 57m
Wed 10/284:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/179:38 am -
Nonstop2h 28m
Wed 10/2112:57 pm -
1 stop6h 34m
Deal found 9/17![Multiple Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/17. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Mon 10/2611:47 am -
1 stop30h 16m
Deal found 9/17![Frontier logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sun 10/116:10 am -
Nonstop2h 23m
Tue 10/135:45 am -
1 stop4h 53m
Deal found 9/17![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/197:25 am -
Nonstop2h 35m
Thu 10/227:40 pm -
Nonstop2h 51m
Deal found 9/16![Delta logo]()
$223
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:38 pm -
1 stop7h 11m
Sat 10/245:12 pm -
Nonstop3h 02m
Deal found 9/16![JetBlue logo]()
$224
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop5h 21m
Mon 10/267:40 pm -
Nonstop2h 51m
Deal found 9/14![Delta logo]()
$225
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:59 am -
1 stop5h 25m
Tue 10/136:55 am -
1 stop5h 29m
Deal found 9/16![JetBlue logo]()
$226
This CheapOair deal was found by Cheapflights users on 9/15. 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 10/238:11 pm -
1 stop13h 51m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 9/15![Multiple Airlines logo]()
$227
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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/2710:05 am -
1 stop4h 22m
Thu 10/294:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$204
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:06 pm -
1 stop4h 53m
Tue 10/207:40 pm -
1 stop4h 52m
Deal found 9/14![United Airlines logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:38 pm -
1 stop7h 11m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 9/14![JetBlue logo]()
$295
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/277:00 am -
2 stops7h 27m
Wed 10/284:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/275:27 am -
2 stops9h 00m
Fri 10/304:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This KAYAK deal was found by Cheapflights users on 9/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:30 pm -
1 stop22h 39m
Thu 11/267:30 am -
1 stop27h 29m
Deal found 9/17![Multiple Airlines logo]()
$532
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop6h 58m
Mon 10/194:15 pm -
1 stop7h 02m
Deal found 9/14![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/2012:55 pm -
1 stop5h 11m
Thu 10/226:00 am -
Nonstop2h 59m
Deal found 9/17![United Airlines logo]()
$279
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:55 pm -
1 stop8h 03m
Wed 10/216:25 am -
1 stop5h 59m
Deal found 9/13![JetBlue logo]()
$295
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/69:24 pm -
Nonstop2h 30m
Wed 10/146:00 am -
2 stops9h 42m
Deal found 9/17![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 9/15. 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 11/75:30 pm -
1 stop5h 50m
Mon 11/94:57 pm -
1 stop4h 20m
Deal found 9/15![Delta logo]()
$235
This JetBlue deal was found by Cheapflights users on 9/15. 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.
Wed 11/2511:00 am -
Nonstop2h 24m
Mon 11/307:55 am -
Nonstop3h 04m
Deal found 9/15![JetBlue logo]()
$297
This Delta deal was found by Cheapflights users on 9/17. 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.
Fri 10/308:36 am -
1 stop5h 51m
Tue 11/34:10 pm -
1 stop7h 07m
Deal found 9/17![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 10/166:15 pm -
Nonstop2h 22m
Wed 10/2112:38 pm -
Nonstop2h 45m
Deal found 9/17![United Airlines logo]()
$293
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1512:38 pm -
1 stop6h 56m
Sun 10/186:55 am -
Nonstop2h 52m
Deal found 9/13![JetBlue logo]()
$315
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 10/268:36 am -
1 stop5h 51m
Fri 10/304:10 pm -
1 stop7h 07m
Deal found 9/17![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/16. 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 2/242:15 pm -
Nonstop1h 55m
Sun 2/2810:00 am -
Nonstop2h 30m
Deal found 9/16![United Airlines logo]()
$318
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/293:00 pm -
1 stop7h 14m
Sat 10/36:25 am -
1 stop4h 33m
Deal found 9/14![JetBlue logo]()
$335
This Delta deal was found by Cheapflights users on 9/16. 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 10/75:29 pm -
1 stop5h 30m
Thu 10/156:00 am -
1 stop8h 08m
Deal found 9/16![Delta logo]()
$261
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:06 am -
Nonstop2h 23m
Mon 10/265:02 pm -
Nonstop2h 48m
Deal found 9/15![United Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/167:10 pm -
Nonstop2h 43m
Mon 10/194:25 pm -
Nonstop2h 55m
Deal found 9/16![Delta logo]()
$263
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:30 am -
Nonstop2h 19m
Mon 10/195:03 pm -
Nonstop2h 45m
Deal found 9/14![United Airlines logo]()
$327
This KAYAK deal was found by Cheapflights users on 9/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2511:00 am -
1 stop5h 09m
Thu 11/267:30 am -
1 stop27h 29m
Deal found 9/17![Multiple Airlines logo]()
$532
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:10 pm -
Nonstop2h 12m
Mon 10/126:20 am -
Nonstop2h 33m
Deal found 9/14![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 9/16. 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.
Sat 11/146:49 am -
1 stop5h 53m
Sun 11/155:40 pm -
1 stop7h 14m
Deal found 9/16![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 9/17. 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.
Sun 10/117:30 am -
1 stop6h 28m
Wed 10/144:15 pm -
1 stop7h 02m
Deal found 9/17![Delta logo]()
$278
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Thu 10/2911:05 am -
1 stop6h 37m
Mon 11/25:02 pm -
Nonstop2h 48m
Deal found 9/17![United Airlines logo]()
$337
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:30 pm -
1 stop22h 39m
Sun 11/291:30 pm -
1 stop21h 29m
Deal found 9/14![Multiple Airlines logo]()
$620
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:30 am -
1 stop5h 07m
Fri 10/24:20 pm -
1 stop6h 58m
Deal found 9/14![Delta logo]()
$280
This United Airlines deal was found by Cheapflights users on 9/17. 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 11/710:57 am -
Nonstop2h 18m
Sun 11/86:00 am -
Nonstop2h 51m
Deal found 9/17![United Airlines logo]()
$356
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated September 17, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:59 am -
1 stop5h 25m
Tue 10/136:55 am -
1 stop5h 29m
Deal found 9/16![JetBlue logo]()
$226
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sun 10/116:10 am -
Nonstop2h 23m
Tue 10/135:45 am -
1 stop4h 53m
Deal found 9/17![United Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 9/17. 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 10/179:38 am -
Nonstop2h 28m
Wed 10/2112:57 pm -
1 stop6h 34m
Deal found 9/17![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/197:25 am -
Nonstop2h 35m
Thu 10/227:40 pm -
Nonstop2h 51m
Deal found 9/16![Delta logo]()
$223
This JetBlue deal was found by Cheapflights users on 9/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:38 pm -
1 stop7h 11m
Sat 10/245:12 pm -
Nonstop3h 02m
Deal found 9/16![JetBlue logo]()
$224
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop5h 21m
Mon 10/267:40 pm -
Nonstop2h 51m
Deal found 9/14![Delta logo]()
$225
This CheapOair deal was found by Cheapflights users on 9/17. 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.
Fri 10/238:11 pm -
1 stop13h 51m
Mon 10/2611:47 am -
1 stop30h 16m
Deal found 9/17![Frontier logo]()
$221
This CheapOair deal was found by Cheapflights users on 9/15. 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 10/238:11 pm -
1 stop13h 51m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 9/15![Multiple Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/2610:05 am -
1 stop4h 22m
Tue 10/274:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/266:30 am -
2 stops7h 57m
Fri 10/304:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$214
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/266:30 am -
2 stops7h 57m
Wed 10/284:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:59 am -
Nonstop2h 19m
Mon 11/26:36 pm -
Nonstop3h 04m
Deal found 9/15![United Airlines logo]()
$228
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 September 17, 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 September 17, 2026.
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/278:36 am -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$107
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 10/267:00 am -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$118
This Delta deal was found by Cheapflights users on 9/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/59:30 am -
1 stop5h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$118
This KAYAK deal was found by Cheapflights users on 9/14. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:00 pm -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$119
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/207:30 am -
Nonstop2h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$119
This Expedia deal was found by Cheapflights users on 9/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$120
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:50 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$121
This KAYAK deal was found by Cheapflights users on 9/16. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/53:05 pm -
Nonstop2h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$124
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:24 pm -
Nonstop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$125
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 12/215:00 am -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$126
This Frontier deal was found by Cheapflights users on 9/15. 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.
Fri 10/98:11 pm -
1 stop13h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$127
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 September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Delta) |
One-way from | $105 (Delta) |
Popular in | August |
Cheapest in | January |
Average price | $271 |
Good round-trip deal | $258 or less |
Good one-way deal | $158 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 September 17, 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
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Tue 10/27
8:36 am-3:27 pm
1 stop5h 51m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/31
8:05 am-2:54 pm
1 stop5h 49m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoAlbany
ORD Chicago O'Hare Intl - ALB Albany Intl
ORDALB
Chicago O'Hare Intl
Tue 11/17
6:00 am-1:25 pm
1 stop6h 25m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/24
6:24 pm-9:59 pm
Nonstop2h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Thu 10/8
7:00 am-2:58 pm
1 stop6h 58m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Fri 10/16
7:00 am-2:58 pm
1 stop6h 58m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoAlbany
ORD Chicago O'Hare Intl - ALB Albany Intl
ORDALB
Chicago O'Hare Intl
Thu 10/22
7:30 am-10:39 am
Nonstop2h 09m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoAlbany
ORD Chicago O'Hare Intl - ALB Albany Intl
ORDALB
Chicago O'Hare Intl
Thu 12/17
6:00 am-1:22 pm
1 stop6h 22m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$147
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 9/28
7:00 am-2:27 pm
1 stop6h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/6
10:59 am-5:24 pm
1 stop5h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
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-ORH
ORD-BDL
ORD-BOS
ORD-PVC
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-ORH
ORD-BDL
ORD-BOS
ORD-PVC
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 $206). Flying from Chicago O'Hare Intl Airport to Massachusetts in August is currently the most expensive (average of $309). 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 September 17, 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.
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 September 17, 2026.
The most flights from ORD to USMA are scheduled on a Wednesday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 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 $228 and $369 in October.The cheapest round-trip price found within the last 5 days was $220 on Multiple Airlines (Oct 17-Oct 21).
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 60 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 September 17, 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
Overall
7.8
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Crew
8.5
Overall
7.8
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Crew
8.5
Overall
7.8
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Crew
8.5
Overall
7.8
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Boarding
8.1
Crew
8.5
Overall
7.8
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 September 17, 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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$371 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$316 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$297 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$139 | Average$422 | FlexibilityNo cancel fee | On-time71% |