$105+ Cheap flights from O'Hare Intl (ORD) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 30 — Nov 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from O'Hare Intl to Massachusetts
Cheapest
Best
Last-minute
One-way
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 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:36 am -
1 stop5h 22m
Tue 10/274:10 pm -
1 stop5h 33m
Deal found 9/27![Delta logo]()
$204
This JetBlue deal was found by Cheapflights users on 9/28. 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.
Wed 10/1412:38 pm -
1 stop7h 11m
Sat 10/174:11 pm -
1 stop6h 59m
Deal found 9/28![JetBlue logo]()
$217
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:36 am -
1 stop5h 22m
Tue 10/274:10 pm -
1 stop7h 07m
Deal found 9/27![Delta logo]()
$217
This Super.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:04 pm -
Nonstop2h 55m
Wed 10/146:55 am -
Nonstop2h 52m
Deal found 9/25![JetBlue logo]()
$218
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/139:24 pm -
Nonstop2h 30m
Tue 10/205:45 am -
1 stop4h 53m
Deal found 9/29![United Airlines logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 pm -
Nonstop2h 55m
Mon 10/196:55 am -
Nonstop2h 52m
Deal found 9/29![JetBlue logo]()
$220
This Delta deal was found by Cheapflights users on 9/29. 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.
Tue 10/207:10 pm -
Nonstop2h 43m
Sat 10/247:50 am -
Nonstop2h 58m
Deal found 9/29![Delta logo]()
$222
This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline 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 9/29![Multiple Airlines logo]()
$223
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 pm -
Nonstop2h 55m
Tue 10/206:55 am -
1 stop5h 29m
Deal found 9/27![JetBlue logo]()
$224
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/228:04 pm -
Nonstop2h 55m
Sat 10/246:55 am -
1 stop5h 29m
Deal found 9/26![JetBlue logo]()
$225
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:10 am -
1 stop7h 19m
Mon 10/196:55 am -
Nonstop2h 52m
Deal found 9/26![JetBlue logo]()
$226
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:10 am -
1 stop7h 19m
Sat 10/246:55 am -
1 stop5h 29m
Deal found 9/27![JetBlue logo]()
$227
Best flights from O'Hare Intl to MassachusettsDiscover carefully curated flight deals from O'Hare Intl to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 30, 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 30, 2026.
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:00 am -
1 stop4h 35m
Wed 10/1410:36 am -
Nonstop2h 53m
Deal found 9/26![United Airlines logo]()
$219
This JetBlue deal was found by Cheapflights users on 9/28. 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Sat 10/246:55 am -
1 stop5h 29m
Deal found 9/28![JetBlue logo]()
$235
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:00 am -
2 stops6h 58m
Fri 10/234:15 pm -
1 stop5h 28m
Deal found 9/27![Delta logo]()
$252
This American Airlines deal was found by Cheapflights users on 9/29. 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 12/48:22 am -
1 stop9h 16m
Mon 12/77:04 pm -
1 stop15h 01m
Deal found 9/29![American Airlines logo]()
$280
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 am -
Nonstop2h 23m
Sat 10/245:45 am -
1 stop4h 52m
Deal found 9/25![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 10/157:00 am -
1 stop6h 58m
Sun 10/184:15 pm -
1 stop7h 02m
Deal found 9/29![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:10 am -
Nonstop2h 23m
Thu 10/225:45 am -
1 stop4h 53m
Deal found 9/26![United Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 9/29. 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.
Sat 11/75:30 pm -
1 stop5h 50m
Wed 11/117:30 am -
Nonstop3h 05m
Deal found 9/29![Delta logo]()
$262
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:38 am -
Nonstop2h 28m
Mon 10/196:55 am -
Nonstop2h 52m
Deal found 9/29![JetBlue logo]()
$297
This KAYAK deal was found by Cheapflights users on 9/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:04 pm -
1 stop13h 28m
Mon 10/264:20 pm -
1 stop20h 40m
Deal found 9/27![Multiple Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/205:07 pm -
1 stop4h 38m
Sun 10/256:00 am -
Nonstop3h 00m
Deal found 9/29![United Airlines logo]()
$272
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:39 am -
Nonstop2h 28m
Tue 10/136:55 am -
1 stop5h 29m
Deal found 9/29![JetBlue logo]()
$301
This Delta deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 11/208:45 am -
1 stop5h 34m
Mon 11/234:00 pm -
1 stop5h 45m
Deal found 9/26![Delta logo]()
$280
This Delta deal was found by Cheapflights users on 9/29. 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 10/117:00 am -
2 stops6h 58m
Wed 10/144:15 pm -
1 stop7h 02m
Deal found 9/29![Delta logo]()
$283
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:10 am -
Nonstop2h 23m
Mon 10/199:23 am -
Nonstop2h 52m
Deal found 9/26![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1411:00 am -
Nonstop2h 25m
Sun 11/155:30 am -
1 stop6h 09m
Deal found 9/27![Delta logo]()
$285
This Delta deal was found by Cheapflights users on 9/29. 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.
Fri 11/137:00 am -
1 stop7h 19m
Tue 12/14:08 pm -
2 stops8h 48m
Deal found 9/29![Delta logo]()
$290
This Delta deal was found by Cheapflights users on 9/29. 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 10/710:24 am -
Nonstop2h 30m
Wed 10/147:30 am -
Nonstop2h 54m
Deal found 9/29![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 9/27. 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 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 9/27![Delta logo]()
$305
This KAYAK deal was found by Cheapflights users on 9/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 pm -
1 stop11h 24m
Tue 10/276:45 am -
1 stop13h 44m
Deal found 9/27![Multiple Airlines logo]()
$646
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/711:19 am -
1 stop3h 56m
Sat 11/148:00 am -
1 stop7h 52m
Deal found 9/25![Delta logo]()
$315
This KAYAK deal was found by Cheapflights users on 9/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:04 pm -
1 stop13h 28m
Tue 10/276:45 am -
1 stop13h 44m
Deal found 9/27![Multiple Airlines logo]()
$659
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/137:00 am -
1 stop7h 19m
Sun 11/154:03 pm -
1 stop5h 42m
Deal found 9/25![Delta logo]()
$327
This KAYAK deal was found by Cheapflights users on 9/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:04 pm -
1 stop11h 24m
Sat 10/248:49 am -
1 stop11h 25m
Deal found 9/27![Multiple Airlines logo]()
$672
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 -
2 stops8h 44m
Deal found 9/25![Delta logo]()
$327
This KAYAK deal was found by Cheapflights users on 9/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 pm -
1 stop11h 24m
Sun 10/2511:28 am -
1 stop25h 32m
Deal found 9/27![Multiple Airlines logo]()
$715
This KAYAK deal was found by Cheapflights users on 9/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 pm -
1 stop18h 05m
Mon 10/196:45 am -
1 stop27h 02m
Deal found 9/27![Multiple Airlines logo]()
$715
This United deal was found by Cheapflights users on 9/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/48:12 pm -
1 stop14h 53m
Sun 11/84:30 pm -
1 stop18h 04m
Deal found 9/29![Multiple Airlines logo]()
$789
This Expedia deal was found by Cheapflights users on 9/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:38 am -
1 stop6h 11m
Sun 10/1811:00 am -
1 stop9h 14m
Deal found 9/29![JetBlue logo]()
$1,130
This KAYAK deal was found by Cheapflights users on 9/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 pm -
1 stop13h 28m
Sun 10/184:20 pm -
1 stop17h 27m
Deal found 9/29![Multiple Airlines logo]()
$808
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated September 30, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:04 pm -
Nonstop2h 55m
Wed 10/146:55 am -
Nonstop2h 52m
Deal found 9/25![JetBlue logo]()
$218
This JetBlue deal was found by Cheapflights users on 9/28. 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.
Sat 10/1012:38 pm -
1 stop7h 11m
Tue 10/136:55 am -
Nonstop2h 52m
Deal found 9/28![JetBlue logo]()
$223
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Tue 10/139:24 pm -
Nonstop2h 30m
Tue 10/205:45 am -
1 stop4h 53m
Deal found 9/29![United Airlines logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 pm -
Nonstop2h 55m
Sat 10/176:55 am -
Nonstop2h 52m
Deal found 9/29![JetBlue logo]()
$220
This JetBlue deal was found by Cheapflights users on 9/28. 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.
Wed 10/1412:38 pm -
1 stop7h 11m
Sat 10/174:11 pm -
1 stop6h 59m
Deal found 9/28![JetBlue logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:04 pm -
Nonstop2h 55m
Tue 10/206:55 am -
1 stop5h 29m
Deal found 9/27![JetBlue logo]()
$224
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:10 am -
1 stop7h 19m
Mon 10/196:55 am -
Nonstop2h 52m
Deal found 9/26![JetBlue logo]()
$226
This JetBlue deal was found by Cheapflights users on 9/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:10 am -
1 stop7h 19m
Sat 10/246:55 am -
1 stop5h 29m
Deal found 9/27![JetBlue logo]()
$227
This Delta deal was found by Cheapflights users on 9/29. 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.
Tue 10/207:10 pm -
Nonstop2h 43m
Sat 10/247:50 am -
Nonstop2h 58m
Deal found 9/29![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:36 am -
1 stop5h 22m
Tue 10/274:10 pm -
1 stop5h 33m
Deal found 9/27![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/228:36 am -
1 stop5h 22m
Tue 10/274:10 pm -
1 stop7h 07m
Deal found 9/27![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” 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 10/228:04 pm -
Nonstop2h 55m
Sat 10/246:55 am -
1 stop5h 29m
Deal found 9/26![JetBlue logo]()
$225
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 30, 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 30, 2026.
This Delta deal was found by Cheapflights users on 9/28. 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 10/278:36 am -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Delta logo]()
$105
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:04 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![JetBlue logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/68:00 am -
1 stop24h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$113
This Super.com deal was found by Cheapflights users on 9/27. 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![JetBlue logo]()
$114
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/285:55 am -
1 stop5h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![United Airlines logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:00 pm -
Nonstop2h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![JetBlue logo]()
$116
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/248:29 am -
Nonstop2h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![American Airlines logo]()
$117
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:38 am -
Nonstop2h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![JetBlue logo]()
$118
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
1 stop6h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Delta logo]()
$118
This JetBlue deal was found by Cheapflights users on 9/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:24 pm -
Nonstop2h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![JetBlue logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1010:37 pm -
1 stop11h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Frontier logo]()
$122
This American Airlines deal was found by Cheapflights users on 9/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:29 am -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$123
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 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Delta) |
One-way from | $105 (Delta) |
Popular in | September |
Cheapest in | January |
Average price | $290 |
Good round-trip deal | $275 or less |
Good one-way deal | $162 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 30, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Tue 10/27
8:36 am-3:27 pm
1 stop5h 51m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/27
8:24 pm-12:08 am
Nonstop2h 44m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$112
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 10/13
5:07 pm-10:45 pm
1 stop4h 38m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$115
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Sat 10/17
8:29 am-4:49 pm
1 stop7h 20m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
Quickest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/22
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 10/26
8:24 pm-12:08 am
Nonstop2h 44m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Thu 11/5
10:05 am-3:27 pm
1 stop4h 22m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
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
$118
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/29
6:59 am-1:31 pm
1 stop5h 32m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/10
6:06 pm-11:59 pm
1 stop4h 53m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
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-PVC
ORD-MVY
ORD-ACK
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-PVC
ORD-MVY
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 $333). 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 30, 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 47% 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 30, 2026.
The most flights from ORD to USMA are scheduled on a Monday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 $221 and $386 in October.The cheapest round-trip price found within the last 5 days was $217 on JetBlue (Oct 14-Oct 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 September 26, 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 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 30, 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.
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Crew
8.5
Overall
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for O'Hare Intl to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Massachusetts by cabin class
Find flights from O'Hare Intl to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on September 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$355 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$315 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$135 | Average$308 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$141 | Average$424 | FlexibilityNo cancel fee | On-time71% |