$111+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 14 — Nov 211
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
1. Tell us where you want to go
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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 October 15, 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 October 15, 2026.
This Priceline deal was found by Cheapflights users on 10/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:15 pm -
Nonstop2h 44m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/10![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:00 pm -
Nonstop2h 49m
Sat 11/1411:27 am -
1 stop8h 03m
Deal found 10/12![Multiple Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 10/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:00 pm -
Nonstop2h 48m
Wed 11/412:39 pm -
1 stop6h 51m
Deal found 10/14![Multiple Airlines logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Fri 11/68:15 pm -
Nonstop2h 44m
Sat 11/149:59 am -
Nonstop3h 01m
Deal found 10/10![JetBlue logo]()
$227
This Kissandfly.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:00 am -
Nonstop2h 25m
Thu 12/311:34 am -
1 stop11h 06m
Deal found 10/12![Frontier logo]()
$228
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:05 am -
Nonstop2h 27m
Sat 11/147:45 am -
Nonstop3h 10m
Deal found 10/13![Delta logo]()
$229
This Priceline deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
Nonstop2h 49m
Mon 11/912:39 pm -
1 stop7h 06m
Deal found 10/12![Multiple Airlines logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:50 pm -
1 stop10h 51m
Sun 11/2211:06 am -
1 stop14h 37m
Deal found 10/13![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/11. 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 12/1110:37 pm -
1 stop11h 02m
Mon 12/1411:08 am -
1 stop23h 40m
Deal found 10/11![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 10/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:46 pm -
Nonstop2h 28m
Sun 12/611:34 am -
1 stop11h 08m
Deal found 10/14![Multiple Airlines logo]()
$235
This Frontier deal was found by Cheapflights users on 10/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:37 pm -
1 stop10h 56m
Sat 12/511:08 am -
1 stop14h 53m
Deal found 10/11![Frontier logo]()
$236
This Delta deal was found by Cheapflights users on 10/11. 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.
Fri 12/47:00 am -
1 stop7h 07m
Mon 12/74:08 pm -
1 stop7h 05m
Deal found 10/11![Delta 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 October 15, 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 October 15, 2026.
This KAYAK deal was found by Cheapflights users on 10/13. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/910:35 am -
Nonstop2h 24m
Tue 11/107:30 am -
Nonstop3h 05m
Deal found 10/13![Delta logo]()
$236
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:59 pm -
1 stop4h 39m
Mon 12/77:04 pm -
1 stop20h 16m
Deal found 10/14![American Airlines logo]()
$244
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/252:09 pm -
Nonstop2h 27m
Sun 12/275:45 am -
Nonstop3h 06m
Deal found 10/11![United Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 10/15. 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 11/173:05 pm -
Nonstop2h 24m
Mon 11/237:30 am -
Nonstop3h 05m
Deal found 10/15![Delta logo]()
$244
This Delta deal was found by Cheapflights users on 10/11. 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.
Fri 12/47:00 am -
1 stop7h 07m
Mon 12/74:08 pm -
1 stop7h 05m
Deal found 10/11![Delta logo]()
$244
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/278:29 am -
1 stop7h 20m
Sat 10/315:16 pm -
1 stop6h 14m
Deal found 10/12![American Airlines logo]()
$280
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 11/57:00 am -
1 stop7h 23m
Mon 11/98:40 pm -
Nonstop2h 56m
Deal found 10/11![Delta logo]()
$267
This KAYAK deal was found by Cheapflights users on 10/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:24 pm -
1 stop13h 08m
Thu 10/296:45 am -
1 stop6h 15m
Deal found 10/10![Multiple Airlines logo]()
$702
This Delta deal was found by Cheapflights users on 10/14. 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 10/297:00 am -
2 stops7h 27m
Mon 11/24:10 pm -
2 stops8h 47m
Deal found 10/14![Delta logo]()
$273
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:02 am -
2 stops10h 05m
Sun 11/85:36 pm -
1 stop21h 44m
Deal found 10/12![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 10/14. 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.
Wed 10/2811:19 am -
1 stop3h 56m
Tue 11/1012:05 pm -
Nonstop3h 00m
Deal found 10/14![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/227:05 am -
Nonstop2h 27m
Fri 11/277:30 am -
Nonstop3h 08m
Deal found 10/12![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 10/10. 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 10/265:27 am -
2 stops9h 00m
Wed 10/284:10 pm -
1 stop7h 07m
Deal found 10/10![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:05 pm -
Nonstop2h 24m
Sun 11/155:30 am -
1 stop6h 09m
Deal found 10/12![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/163:05 pm -
Nonstop2h 31m
Fri 1/111:05 am -
Nonstop3h 10m
Deal found 10/13![Delta logo]()
$299
This KAYAK deal was found by Cheapflights users on 10/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:24 pm -
1 stop11h 04m
Wed 10/286:45 am -
1 stop13h 44m
Deal found 10/10![Multiple Airlines logo]()
$702
This Delta deal was found by Cheapflights users on 10/13. 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 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
Mon 11/234:00 pm -
1 stop5h 45m
Deal found 10/13![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 10/10. 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 11/207:00 am -
1 stop7h 19m
Sun 11/224:03 pm -
1 stop7h 15m
Deal found 10/10![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 10/10. 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 11/87:25 am -
Nonstop2h 35m
Fri 11/134:35 pm -
Nonstop3h 09m
Deal found 10/10![Delta logo]()
$314
This FlightHub deal was found by Cheapflights users on 10/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:00 pm -
1 stop19h 15m
Mon 11/29:20 am -
1 stop10h 57m
Deal found 10/10![Multiple Airlines logo]()
$861
This Delta deal was found by Cheapflights users on 10/11. 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.
Fri 12/258:05 am -
Nonstop2h 33m
Tue 1/512:55 pm -
1 stop4h 42m
Deal found 10/11![Delta logo]()
$315
This KAYAK deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:25 am -
Nonstop2h 35m
Thu 10/297:30 am -
Nonstop2h 54m
Deal found 10/12![Delta logo]()
$319
This United deal was found by Cheapflights users on 10/13. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/206:00 am -
2 stops8h 35m
Sun 12/274:30 pm -
1 stop16h 21m
Deal found 10/13![Multiple Airlines logo]()
$923
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:36 am -
1 stop5h 51m
Sun 11/84:10 pm -
1 stop7h 07m
Deal found 10/12![Delta logo]()
$327
This Priceline deal was found by Cheapflights users on 10/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:00 pm -
1 stop4h 50m
Sat 10/317:00 am -
1 stop6h 00m
Deal found 10/11![Multiple Airlines logo]()
$952
This Priceline deal was found by Cheapflights users on 10/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:00 pm -
1 stop5h 45m
Sat 10/313:24 pm -
1 stop5h 05m
Deal found 10/11![Multiple Airlines logo]()
$952
This Priceline deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:00 pm -
1 stop4h 50m
Sun 11/17:00 am -
1 stop6h 00m
Deal found 10/13![Multiple Airlines logo]()
$998
This Expedia deal was found by Cheapflights users on 10/14. 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.
Thu 12/107:00 am -
2 stops11h 45m
Sun 12/1311:40 am -
1 stop6h 02m
Deal found 10/14![Multiple Airlines logo]()
$1,051
This FlightHub deal was found by Cheapflights users on 10/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:30 pm -
1 stop14h 45m
Mon 11/304:23 pm -
1 stop25h 19m
Deal found 10/11![Multiple Airlines logo]()
$1,063
This Mytrip deal was found by Cheapflights users on 10/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:14 pm -
3 stops24h 21m
Thu 10/2910:26 am -
3 stops30h 11m
Deal found 10/10![Multiple Airlines logo]()
$1,098
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated October 15, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated October 15, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:29 am -
1 stop9h 20m
Mon 11/25:36 pm -
1 stop19h 43m
Deal found 10/14![American Airlines logo]()
$258
This Delta deal was found by Cheapflights users on 10/14. 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 10/297:00 am -
2 stops7h 27m
Mon 11/24:10 pm -
2 stops8h 47m
Deal found 10/14![Delta logo]()
$273
This CheapOair deal was found by Cheapflights users on 10/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:00 pm -
Nonstop2h 48m
Wed 11/412:39 pm -
1 stop6h 51m
Deal found 10/14![Multiple Airlines logo]()
$223
This KAYAK deal was found by Cheapflights users on 10/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:40 pm -
Nonstop2h 41m
Wed 11/47:10 pm -
Nonstop2h 56m
Deal found 10/11![Delta logo]()
$236
This CheapOair deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates ” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/41:00 pm -
Nonstop2h 48m
Mon 11/912:39 pm -
1 stop7h 06m
Deal found 10/12![Multiple Airlines logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Fri 11/61:00 pm -
Nonstop2h 49m
Mon 11/99:59 am -
Nonstop3h 01m
Deal found 10/10![JetBlue logo]()
$227
This Priceline deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
Nonstop2h 49m
Mon 11/912:39 pm -
1 stop7h 06m
Deal found 10/12![Multiple Airlines logo]()
$232
This Priceline deal was found by Cheapflights users on 10/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:15 pm -
Nonstop2h 44m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/10![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:15 pm -
Nonstop2h 44m
Mon 11/1612:39 pm -
1 stop7h 06m
Deal found 10/12![Multiple Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/137:05 am -
Nonstop2h 27m
Sat 11/147:45 am -
Nonstop3h 10m
Deal found 10/13![Delta logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:50 pm -
1 stop10h 51m
Sun 11/2211:06 am -
1 stop14h 37m
Deal found 10/13![Frontier logo]()
$233
This Kissandfly.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:00 am -
Nonstop2h 25m
Thu 12/311:34 am -
1 stop11h 06m
Deal found 10/12![Frontier 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 October 15, 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 October 15, 2026.
This United Airlines deal was found by Cheapflights users on 10/14. 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.
Tue 11/35:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![United Airlines logo]()
$111
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:00 am -
1 stop7h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$111
This KAYAK deal was found by Cheapflights users on 10/14. 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 11/187:05 am -
Nonstop2h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$115
This KAYAK deal was found by Cheapflights users on 10/14. 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.
Mon 11/163:05 pm -
Nonstop2h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$118
This Cheapflightsfares deal was found by Cheapflights users on 10/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1110:37 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Sun 12/610:37 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:37 pm -
1 stop10h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$123
This CheapOair deal was found by Cheapflights users on 10/15. 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.
Tue 11/245:40 am -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Fri 11/61:00 pm -
Nonstop2h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![JetBlue logo]()
$127
This American Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:00 pm -
Nonstop2h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![American Airlines logo]()
$128
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:45 pm -
Nonstop2h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/138:25 am -
1 stop24h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Multiple Airlines logo]()
$130
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 October 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (Priceline) |
One-way from | $111 (United Airlines) |
Popular in | September |
Cheapest in | January |
Average price | $293 |
Good round-trip deal | $294 or less |
Good one-way deal | $171 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 October 15, 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
Wed 11/18
7:00 am-3:19 pm
1 stop7h 19m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$111
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Wed 11/11
5:30 am-3:19 pm
2 stops8h 49m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$116
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Fri 11/13
7:00 am-3:19 pm
1 stop7h 19m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Thu 11/12
7:00 am-3:19 pm
1 stop7h 19m
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
Tue 10/27
8:36 am-3:27 pm
1 stop5h 51m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 11/20
7:45 pm-11:08 pm
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Sun 10/25
6:29 am-4:49 pm
1 stop9h 20m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
Quickest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 1/5
2:55 pm-6:17 pm
Nonstop2h 22m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 1/14
2:55 pm-6:17 pm
Nonstop2h 22m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$157
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 11/8
10:30 am-1:59 pm
Nonstop2h 29m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$158
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from O'Hare Intl with our price prediction graph.
ORD-BOS
ORD-ORH
ORD-MVY
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-ORH
ORD-MVY
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 $206). Flying from Chicago O'Hare Intl Airport to Massachusetts in September is currently the most expensive (average of $334). 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 October 15, 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 46% 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 October 15, 2026.
The most flights from ORD to USMA are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 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 $244 and $411 in November.The cheapest round-trip price found within the last 5 days was $219 on Multiple Airlines (Nov 12-Nov 17).
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 October 10, 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 October 15, 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.
Overall
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Overall
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
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 October 15, 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 October 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$357 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$317 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$313 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$142 | Average$425 | FlexibilityNo cancel fee | On-time71% |