$109+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Dec 11 — Dec 181
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
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Cheapest flights from O'Hare Intl to MassachusettsExplore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 11, 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 November 11, 2026.
This JetBlue deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/165:46 pm -
Nonstop2h 28m
Tue 12/294:45 pm -
Nonstop3h 13m
Deal found 11/9![JetBlue logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/95:24 pm -
1 stop15h 49m
Sun 12/1311:08 am -
1 stop15h 00m
Deal found 11/10![Frontier logo]()
$231
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 11/275:30 pm -
Nonstop2h 29m
Fri 12/42:40 pm -
Nonstop3h 02m
Deal found 11/9![JetBlue logo]()
$232
This Frontier deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:29 pm -
1 stop11h 29m
Sat 12/511:34 am -
1 stop11h 26m
Deal found 11/9![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/165:35 am -
1 stop26h 55m
Thu 12/314:45 pm -
Nonstop3h 13m
Deal found 11/10![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/165:35 am -
1 stop26h 55m
Sun 12/204:45 pm -
Nonstop3h 13m
Deal found 11/9![Multiple Airlines logo]()
$235
This CheapOair deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/197:55 pm -
Nonstop2h 26m
Sun 12/2010:25 am -
1 stop15h 31m
Deal found 11/9![Multiple Airlines logo]()
$238
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:55 pm -
Nonstop2h 26m
Sat 1/1610:13 am -
1 stop15h 17m
Deal found 11/11![Multiple Airlines logo]()
$239
This CheapOair deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/165:35 am -
1 stop26h 55m
Sat 1/1610:13 am -
1 stop30h 46m
Deal found 11/8![Frontier logo]()
$240
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 -
Nonstop2h 29m
Thu 12/32:40 pm -
Nonstop3h 02m
Deal found 11/9![JetBlue logo]()
$241
This Cheapflightsfares deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:46 pm -
Nonstop2h 28m
Tue 12/82:40 pm -
Nonstop3h 02m
Deal found 11/9![JetBlue logo]()
$243
This JetBlue deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/197:55 pm -
Nonstop2h 26m
Mon 12/214:45 pm -
Nonstop3h 13m
Deal found 11/8![JetBlue logo]()
$244
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 November 11, 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 November 11, 2026.
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/169:10 am -
Nonstop2h 33m
Mon 12/219:10 am -
Nonstop3h 06m
Deal found 11/9![United Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/245:39 pm -
1 stop18h 49m
Mon 12/287:03 pm -
1 stop5h 46m
Deal found 11/7![American Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 11/11. 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.
Tue 12/13:05 pm -
Nonstop2h 31m
Tue 12/1510:10 am -
1 stop7h 56m
Deal found 11/11![Delta logo]()
$307
This KAYAK deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/187:55 pm -
1 stop20h 14m
Thu 12/317:30 am -
1 stop12h 28m
Deal found 11/8![Multiple Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 11/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:30 am -
1 stop11h 08m
Mon 12/77:04 pm -
1 stop15h 01m
Deal found 11/11![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/512:32 pm -
1 stop5h 03m
Sat 12/124:59 pm -
1 stop4h 16m
Deal found 11/6![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/242:09 pm -
Nonstop2h 27m
Sun 12/275:45 am -
Nonstop3h 06m
Deal found 11/6![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 1/2310:33 am -
1 stop5h 02m
Tue 1/264:52 pm -
1 stop4h 40m
Deal found 11/8![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 1/137:10 am -
2 stops7h 39m
Wed 1/204:29 pm -
1 stop5h 45m
Deal found 11/10![Delta logo]()
$320
This American Airlines deal was found by Cheapflights users on 11/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:29 am -
1 stop11h 09m
Mon 1/184:12 pm -
2 stops14h 48m
Deal found 11/11![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/47:45 pm -
Nonstop2h 32m
Sun 12/67:30 am -
Nonstop3h 08m
Deal found 11/9![Delta logo]()
$327
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 11/206:00 am -
1 stop7h 38m
Wed 12/212:20 pm -
1 stop7h 49m
Deal found 11/10![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 2/51:54 pm -
1 stop4h 45m
Sun 2/79:00 am -
1 stop5h 04m
Deal found 11/8![Delta logo]()
$335
This KAYAK deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/187:55 pm -
1 stop20h 14m
Fri 1/17:30 am -
1 stop12h 28m
Deal found 11/8![Multiple Airlines logo]()
$544
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/2512:38 pm -
1 stop5h 12m
Wed 12/22:00 pm -
1 stop7h 45m
Deal found 11/8![Delta logo]()
$335
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 11/207:00 am -
1 stop7h 19m
Sun 11/224:03 pm -
1 stop7h 15m
Deal found 11/9![Delta logo]()
$336
This KAYAK deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/307:55 pm -
1 stop20h 14m
Sun 1/31:30 pm -
1 stop6h 28m
Deal found 11/8![Multiple Airlines logo]()
$607
This Delta deal was found by Cheapflights users on 11/11. 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.
Mon 12/213:56 pm -
1 stop6h 04m
Tue 12/294:50 pm -
1 stop4h 28m
Deal found 11/11![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 11/206:00 am -
1 stop7h 38m
Sun 11/221:00 pm -
1 stop6h 22m
Deal found 11/10![Delta logo]()
$341
This KAYAK deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/297:55 pm -
1 stop20h 14m
Sun 1/31:30 pm -
1 stop6h 28m
Deal found 11/8![Multiple Airlines logo]()
$672
This KAYAK deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/307:55 pm -
1 stop20h 14m
Sat 1/27:30 am -
1 stop12h 28m
Deal found 11/8![Multiple Airlines logo]()
$678
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 11/1610:06 am -
1 stop4h 13m
Wed 11/184:00 pm -
1 stop5h 45m
Deal found 11/10![Delta logo]()
$372
This KAYAK deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/2011:00 am -
1 stop5h 09m
Sun 11/291:30 pm -
1 stop21h 29m
Deal found 11/7![Multiple Airlines logo]()
$739
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 11/157:00 am -
1 stop7h 23m
Mon 11/164:00 pm -
2 stops8h 54m
Deal found 11/9![Delta logo]()
$382
This United deal was found by Cheapflights users on 11/11. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/289:49 pm -
2 stops14h 21m
Sat 1/210:00 am -
1 stop22h 51m
Deal found 11/11![Multiple Airlines logo]()
$783
This United deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/19:49 pm -
1 stop10h 26m
Mon 1/411:40 am -
1 stop7h 56m
Deal found 11/7![Multiple Airlines logo]()
$1,007
This Expedia deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/232:59 pm -
2 stops17h 16m
Fri 11/277:05 am -
1 stop10h 35m
Deal found 11/8![Multiple Airlines logo]()
$1,028
This Expedia deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/77:00 am -
2 stops11h 35m
Mon 12/1410:26 am -
1 stop7h 16m
Deal found 11/9![Multiple Airlines logo]()
$1,071
This Expedia deal was found by Cheapflights users on 11/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:00 am -
1 stop6h 38m
Mon 11/3011:40 am -
1 stop6h 00m
Deal found 11/11![Multiple Airlines logo]()
$1,113
This Mytrip deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/225:26 pm -
2 stops25h 19m
Thu 11/262:15 pm -
3 stops35h 28m
Deal found 11/7![Multiple Airlines logo]()
$1,290
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated November 11, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated November 11, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 -
Nonstop2h 29m
Thu 12/32:40 pm -
Nonstop3h 02m
Deal found 11/9![JetBlue logo]()
$241
This KAYAK deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 11/275:30 pm -
Nonstop2h 29m
Fri 12/42:40 pm -
Nonstop3h 02m
Deal found 11/9![JetBlue logo]()
$232
This Frontier deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:29 pm -
1 stop11h 29m
Sat 12/511:34 am -
1 stop11h 26m
Deal found 11/9![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:46 pm -
Nonstop2h 28m
Tue 12/82:40 pm -
Nonstop3h 02m
Deal found 11/9![JetBlue logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/95:24 pm -
1 stop15h 49m
Sun 12/1311:08 am -
1 stop15h 00m
Deal found 11/10![Frontier logo]()
$231
This JetBlue deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/165:46 pm -
Nonstop2h 28m
Tue 12/294:45 pm -
Nonstop3h 13m
Deal found 11/9![JetBlue logo]()
$228
This CheapOair deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/165:35 am -
1 stop26h 55m
Thu 12/314:45 pm -
Nonstop3h 13m
Deal found 11/10![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/165:35 am -
1 stop26h 55m
Sun 12/204:45 pm -
Nonstop3h 13m
Deal found 11/9![Multiple Airlines logo]()
$235
This CheapOair deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/165:35 am -
1 stop26h 55m
Sat 1/1610:13 am -
1 stop30h 46m
Deal found 11/8![Frontier logo]()
$240
This CheapOair deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/197:55 pm -
Nonstop2h 26m
Sun 12/2010:25 am -
1 stop15h 31m
Deal found 11/9![Multiple Airlines logo]()
$238
This JetBlue deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/197:55 pm -
Nonstop2h 26m
Mon 12/214:45 pm -
Nonstop3h 13m
Deal found 11/8![JetBlue logo]()
$244
This CheapOair deal was found by Cheapflights users on 11/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:55 pm -
Nonstop2h 26m
Sat 1/1610:13 am -
1 stop15h 17m
Deal found 11/11![Multiple Airlines logo]()
$239
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 November 11, 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 November 11, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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.
Tue 12/225:59 pm -
1 stop12h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Frontier logo]()
$109
This CheapOair deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/21:19 pm -
1 stop19h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Frontier logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/227:55 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![JetBlue logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:55 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![JetBlue logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/25:46 pm -
Nonstop2h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![JetBlue logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 11/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/187:55 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![JetBlue logo]()
$122
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/17:45 pm -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$123
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates ” 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 11/226:15 am -
Nonstop2h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$124
This CheapOair deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 11/275:30 pm -
Nonstop2h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![JetBlue logo]()
$128
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/238:45 am -
1 stop5h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$134
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 3/289:35 am -
1 stop5h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/188:45 am -
1 stop5h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Delta logo]()
$189
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 November 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $228 (JetBlue) |
One-way from | $109 (Cheapflightsfares) |
Popular in | November |
Cheapest in | January |
Average price | $323 |
Good round-trip deal | $324 or less |
Good one-way deal | $176 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 November 11, 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
Thu 12/17
6:50 am-10:17 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Mon 11/23
8:45 am-3:19 pm
1 stop5h 34m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 12/18
6:10 pm-11:59 pm
1 stop4h 49m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 11/22
5:00 am-11:07 am
1 stop5h 07m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 1/18
7:00 am-10:36 am
Nonstop2h 36m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 12/17
11:10 am-2:45 pm
Nonstop2h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
Quickest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 2/5
2:25 pm-5:49 pm
Nonstop2h 24m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Sun 3/28
10:35 am-3:47 pm
1 stop4h 12m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 1/26
6:15 pm-11:59 pm
1 stop4h 44m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 12/27
5:55 pm-11:59 pm
1 stop5h 04m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
Showing 1-10 of 49 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from O'Hare Intl with our price prediction graph.
ORD-BOS
ORD-ORH
ORD-ACK
ORD-PVC
ORD-MVY
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Massachusetts
ORD-USMA
ORD-BOS
ORD-ORH
ORD-ACK
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 $207). Flying from Chicago O'Hare Intl Airport to Massachusetts in October is currently the most expensive (average of $345). 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 November 11, 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 45% 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 November 11, 2026.
The most flights from ORD to USMA are scheduled on a Monday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Massachusetts flights typically cost between $245 and $442 in December.The cheapest round-trip price found within the last 5 days was $228 on JetBlue (Dec 16-Dec 29).
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 47 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 November 7, 2026.
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 afternoons 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 November 11, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Delta,United Airlines, andJetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Food
7.2
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on November 11, 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 November 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$100 | Average$305 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$327 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$145 | Average$407 | FlexibilityNo cancel fee | On-time71% |