$107+ Cheap flights from O'Hare Intl (ORD) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 2 — Oct 91
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 September 2, 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 2, 2026.
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Wed 9/237:00 am -
Nonstop2h 48m
Deal found 8/27![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:38 am -
Nonstop2h 28m
Fri 10/212:54 pm -
1 stop6h 29m
Deal found 8/27![Multiple Airlines logo]()
$206
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Mon 9/2112:54 pm -
1 stop6h 29m
Deal found 8/28![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/98:11 pm -
1 stop13h 51m
Mon 10/126:55 am -
Nonstop2h 52m
Deal found 9/1![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/228:04 pm -
Nonstop2h 55m
Mon 10/269:59 am -
Nonstop3h 00m
Deal found 8/27![JetBlue logo]()
$215
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/299:00 am -
Nonstop2h 39m
Tue 9/295:45 pm -
Nonstop3h 20m
Deal found 9/1![American Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/110:30 am -
Nonstop2h 35m
Mon 10/58:50 pm -
Nonstop2h 42m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/18:24 pm -
Nonstop2h 45m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/1![JetBlue logo]()
$218
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Tue 10/2711:12 am -
1 stop8h 33m
Deal found 9/1![Frontier logo]()
$221
This CheapOair deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/1![Frontier logo]()
$222
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm -
Nonstop2h 45m
Mon 10/56:50 am -
Nonstop2h 52m
Deal found 9/1![JetBlue logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/98:00 pm -
Nonstop2h 58m
Thu 10/155:12 pm -
Nonstop3h 02m
Deal found 9/1![JetBlue logo]()
$224
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 2, 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 2, 2026.
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/157:25 am -
Nonstop2h 35m
Tue 10/204:25 pm -
Nonstop2h 55m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 11/108:15 pm -
Nonstop2h 44m
Wed 11/185:05 pm -
Nonstop3h 12m
Deal found 9/1![JetBlue logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/277:30 am -
Nonstop2h 31m
Wed 9/309:23 am -
Nonstop2h 52m
Deal found 8/28![United Airlines logo]()
$275
This KAYAK deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/257:29 pm -
Nonstop2h 27m
Sun 9/277:01 am -
Nonstop2h 53m
Deal found 9/1![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:35 pm -
Nonstop2h 45m
Tue 9/297:30 am -
Nonstop2h 54m
Deal found 9/1![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:30 am -
1 stop5h 07m
Wed 10/74:15 pm -
1 stop7h 02m
Deal found 8/31![Delta logo]()
$232
This JetBlue deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:15 pm -
Nonstop2h 30m
Tue 11/1711:15 am -
Nonstop3h 05m
Deal found 8/28![JetBlue logo]()
$275
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:24 pm -
Nonstop2h 30m
Sun 9/276:00 am -
Nonstop2h 59m
Deal found 8/29![United Airlines logo]()
$275
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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
Tue 12/14:08 pm -
1 stop7h 05m
Deal found 8/29![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/226:10 pm -
Nonstop2h 12m
Sun 10/256:00 am -
Nonstop2h 43m
Deal found 9/1![United Airlines logo]()
$308
This FlightHub deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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.
Sat 9/51:49 pm -
1 stop24h 06m
Tue 9/812:50 pm -
1 stop7h 35m
Deal found 9/1![Multiple Airlines logo]()
$691
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/68:36 am -
1 stop5h 22m
Tue 10/134:15 pm -
1 stop5h 28m
Deal found 8/30![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/17:30 am -
Nonstop2h 19m
Sat 10/315:02 pm -
Nonstop2h 48m
Deal found 9/1![United Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:30 am -
2 stops9h 07m
Wed 9/234:20 pm -
1 stop6h 58m
Deal found 8/29![Delta logo]()
$270
This KAYAK deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Sun 10/117:52 pm -
Nonstop2h 21m
Wed 10/147:23 pm -
Nonstop2h 52m
Deal found 8/28![American Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 12/66:10 pm -
Nonstop2h 18m
Sat 12/127:45 pm -
1 stop4h 30m
Deal found 9/1![United Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/63:05 pm -
Nonstop2h 39m
Sun 10/117:30 am -
Nonstop2h 54m
Deal found 8/28![Delta logo]()
$275
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:53 am -
1 stop4h 39m
Tue 9/812:42 pm -
1 stop8h 04m
Deal found 8/29![American Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/47:35 am -
Nonstop2h 33m
Sat 10/107:40 pm -
Nonstop2h 51m
Deal found 8/29![Delta logo]()
$275
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:45 am -
Nonstop2h 09m
Mon 9/286:03 am -
1 stop4h 35m
Deal found 8/31![United Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 12/2411:53 am -
Nonstop2h 13m
Sun 1/36:00 am -
Nonstop2h 52m
Deal found 8/29![United Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 10/87:25 am -
Nonstop2h 35m
Sun 10/117:30 am -
Nonstop2h 54m
Deal found 8/30![Delta logo]()
$295
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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 9/65:30 am -
2 stops10h 30m
Wed 9/164:20 pm -
1 stop5h 11m
Deal found 8/30![Delta logo]()
$301
This FlightHub deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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.
Wed 9/309:38 am -
1 stop24h 44m
Mon 10/53:30 pm -
1 stop18h 19m
Deal found 8/31![JetBlue logo]()
$603
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/46:45 am -
1 stop7h 26m
Sun 9/611:17 am -
1 stop5h 48m
Deal found 8/29![American Airlines logo]()
$575
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/237:30 am -
Nonstop2h 19m
Sun 10/256:00 am -
1 stop4h 45m
Deal found 9/1![United Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:05 am -
2 stops7h 32m
Wed 9/164:20 pm -
1 stop5h 11m
Deal found 8/30![Delta logo]()
$301
This United deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” 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.
Thu 10/156:10 am -
1 stop10h 53m
Mon 10/194:20 pm -
1 stop17h 40m
Deal found 8/30![Multiple Airlines logo]()
$742
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 10/316:12 pm -
1 stop4h 47m
Mon 11/26:00 am -
Nonstop2h 51m
Deal found 8/31![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” 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 9/225:40 pm -
1 stop4h 37m
Tue 9/299:10 am -
1 stop4h 49m
Deal found 8/31![Delta logo]()
$315
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated September 2, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Wed 9/237:00 am -
Nonstop2h 48m
Deal found 8/27![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:50 pm -
1 stop18h 08m
Mon 9/2112:54 pm -
1 stop6h 29m
Deal found 8/28![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/253:50 pm -
1 stop18h 01m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 9/1![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:38 am -
Nonstop2h 28m
Fri 10/212:54 pm -
1 stop6h 29m
Deal found 8/27![Multiple Airlines logo]()
$206
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/299:00 am -
Nonstop2h 39m
Tue 9/295:45 pm -
Nonstop3h 20m
Deal found 9/1![American Airlines logo]()
$216
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/110:30 am -
Nonstop2h 35m
Mon 10/58:50 pm -
Nonstop2h 42m
Deal found 9/1![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/18:24 pm -
Nonstop2h 45m
Mon 10/55:00 pm -
Nonstop3h 03m
Deal found 9/1![JetBlue logo]()
$218
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm -
Nonstop2h 45m
Tue 10/66:55 am -
Nonstop2h 54m
Deal found 9/1![JetBlue logo]()
$223
This CheapOair deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/98:11 pm -
1 stop13h 51m
Mon 10/126:55 am -
Nonstop2h 52m
Deal found 9/1![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/98:00 pm -
Nonstop2h 58m
Thu 10/155:12 pm -
Nonstop3h 02m
Deal found 9/1![JetBlue logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 10/228:04 pm -
Nonstop2h 55m
Mon 10/269:59 am -
Nonstop3h 00m
Deal found 8/27![JetBlue logo]()
$215
This Frontier deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Tue 10/2711:12 am -
1 stop8h 33m
Deal found 9/1![Frontier logo]()
$221
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 2, 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 2, 2026.
This Super.com deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop6h 27m
Deal found 8/27![JetBlue logo]()
$107
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 9/298:19 pm -
Nonstop2h 35m
Deal found 9/1![American Airlines logo]()
$108
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/287:30 pm -
Nonstop2h 39m
Deal found 8/28![Delta logo]()
$109
This Jetabroad deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2112:38 pm -
1 stop7h 11m
Deal found 8/28![JetBlue logo]()
$111
This Super.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:24 pm -
Nonstop2h 45m
Deal found 9/1![JetBlue logo]()
$114
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/28![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:50 pm -
1 stop17h 32m
Deal found 8/28![Frontier logo]()
$116
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/27:30 pm -
Nonstop2h 39m
Deal found 9/1![Delta logo]()
$118
This Trip.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/233:50 pm -
1 stop17h 32m
Deal found 8/28![Frontier logo]()
$119
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:00 pm -
Nonstop2h 18m
Deal found 9/1![American Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” 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 10/77:00 am -
1 stop6h 58m
Deal found 9/1![Delta logo]()
$119
This Trip.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:15 am -
1 stop22h 36m
Deal found 8/28![Frontier logo]()
$120
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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $211 (CheapOair) |
One-way from | $107 (Super.com) |
Popular in | August |
Cheapest in | January |
Average price | $258 |
Good round-trip deal | $255 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 2, 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 10/15
7:25 am-11:00 am
Nonstop2h 35m
Boston Logan Intl
Tue 10/20
4:25 pm-6:20 pm
Nonstop2h 55m
$217
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 11/10
8:15 pm-11:59 pm
Nonstop2h 44m
Boston Logan Intl
Wed 11/18
5:05 pm-7:17 pm
Nonstop3h 12m
$217
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 9/26
4:35 pm-8:20 pm
Nonstop2h 45m
Boston Logan Intl
Tue 9/29
7:30 am-9:24 am
Nonstop2h 54m
$217
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Wed 9/30
9:30 am-3:37 pm
1 stop5h 07m
Worcester
Wed 10/7
4:15 pm-10:17 pm
1 stop7h 02m
$232
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
Tue 12/1
4:08 pm-10:13 pm
1 stop7h 05m
$260
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Tue 10/6
8:36 am-2:58 pm
1 stop5h 22m
Worcester
Tue 10/13
4:15 pm-8:43 pm
1 stop5h 28m
$260
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Wed 9/16
5:30 am-3:37 pm
2 stops9h 07m
Worcester
Wed 9/23
4:20 pm-10:18 pm
1 stop6h 58m
$270
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 9/27
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Wed 9/30
9:23 am-11:15 am
Nonstop2h 52m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 11/9
2:15 pm-5:45 pm
Nonstop2h 30m
Boston Logan Intl
Tue 11/17
11:15 am-1:20 pm
Nonstop3h 05m
$275
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/25
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Sun 9/27
6:00 am-7:59 am
Nonstop2h 59m
$275
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-ALB
ORD-BDL
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-ALB
ORD-BDL
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $205). Flying from Chicago O'Hare Intl Airport to Massachusetts in August is currently the most expensive (average of $298). 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 2, 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 51% 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 2, 2026.
The most flights from ORD to USMA are scheduled on a Monday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
Airfare is typical for this route at the moment.
Chicago O'Hare Intl Airport to Massachusetts flights typically cost between $200 and $330 in September.The cheapest round-trip price found within the last 5 days was $211 on Frontier (Sep 19-Sep 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 2, 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.
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
Food
7.2
Overall
7.8
Comfort
7.8
Boarding
8.1
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentNanette,Sep 2023
TPA - BOS
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 September 2, 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$350 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$336 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$291 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$421 | FlexibilityNo cancel fee | On-time71% |