$94+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 23 — Aug 301
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to MassachusettsExplore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 24, 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 July 24, 2026.
This SmartFares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Fri 8/284:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$185
This SmartFares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Sun 9/136:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/20![JetBlue logo]()
$191
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/20![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This SmartFares deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Mon 9/145:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$195
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/221:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Sat 10/245:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/21![JetBlue logo]()
$197
This Flysmarter deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1110:59 am
ORD
- BOS
1 stop8h 50m
JetBlue
Sun 9/135:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Deal found 7/23![JetBlue logo]()
$199
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Priceline deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/206:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Sat 8/224:22 pm
ACK
- ORD
1 stop6h 36m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/2510:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Mon 9/285:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$203
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/129:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sat 9/124:00 pm
BOS
- ORD
1 stop7h 06m
JetBlue
Deal found 7/21![JetBlue logo]()
$204
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/296:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 9/24:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/21![JetBlue logo]()
$209
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 July 24, 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 July 24, 2026.
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/296:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 9/24:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/20![JetBlue logo]()
$209
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/57:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Thu 8/66:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/19![United Airlines logo]()
$225
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/162:40 pm
ORD
- BOS
1 stop8h 00m
Southwest
Sun 8/235:20 am
BOS
- ORD
1 stop10h 05m
Southwest
Deal found 7/22![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/57:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Mon 9/77:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 7/24![Delta logo]()
$245
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/55:00 am
ORD
- HYA
1 stop6h 12m
American Airlines
Sun 9/65:59 pm
HYA
- ORD
1 stop6h 38m
American Airlines
Deal found 7/23![American Airlines logo]()
$309
This JetBlue deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/23![JetBlue logo]()
$220
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/39:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Thu 8/66:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/20![United Airlines logo]()
$225
This Expedia deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/179:42 am
ORD
- MVY
1 stop5h 28m
Multiple Airlines
Fri 8/211:35 pm
MVY
- ORD
2 stops9h 23m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$469
This JetBlue deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/128:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Sun 9/137:00 am
BOS
- ORD
Nonstop2h 48m
JetBlue
Deal found 7/23![JetBlue logo]()
$226
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/79:24 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Fri 10/166:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/23![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/2810:30 am
ORD
- ORH
1 stop5h 30m
Delta
Wed 8/55:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$266
This JetBlue deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/226:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Wed 8/263:33 pm
ACK
- ORD
1 stop4h 54m
JetBlue
Deal found 7/19![JetBlue logo]()
$237
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Fri 8/147:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/24![United Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/296:35 am
ORD
- ORH
2 stops9h 25m
Delta
Tue 8/115:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$276
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/148:19 am
ORD
- MVY
1 stop5h 11m
American Airlines
Wed 8/195:25 pm
MVY
- ORD
1 stop7h 12m
American Airlines
Deal found 7/19![American Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/186:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Sat 8/224:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 7/21![JetBlue logo]()
$247
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/307:05 am
ORD
- ORH
2 stops8h 55m
Delta
Wed 8/55:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/79:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sat 8/87:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/22![United Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/285:30 am
ORD
- ORH
2 stops10h 30m
Delta
Tue 8/115:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/20![Delta logo]()
$276
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/45:00 am
ORD
- HYA
1 stop6h 12m
American Airlines
Tue 9/812:42 pm
HYA
- ORD
1 stop8h 04m
American Airlines
Deal found 7/23![American Airlines logo]()
$339
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/109:42 am
ORD
- HYA
1 stop4h 31m
JetBlue
Tue 8/114:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/20![JetBlue logo]()
$265
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/410:30 am
ORD
- ORH
1 stop5h 30m
Delta
Mon 8/105:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/22![Delta logo]()
$276
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/49:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sat 8/87:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/23![United Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/2911:15 am
ORD
- HYA
Nonstop2h 42m
American Airlines
Thu 9/35:59 pm
HYA
- ORD
1 stop6h 38m
American Airlines
Deal found 7/19![American Airlines logo]()
$373
This KAYAK deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/2610:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Thu 8/278:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/22![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:20 pm
ORD
- BDL
1 stop6h 37m
United Airlines
Wed 12/166:15 am
BDL
- ORD
Nonstop2h 35m
United Airlines
Deal found 7/23![United Airlines logo]()
$287
This JetBlue deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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.
Fri 8/282:35 pm
ORD
- BDL
1 stop8h 23m
JetBlue
Sun 8/305:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Deal found 7/23![JetBlue logo]()
$289
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 7/302:07 pm
ORD
- BOS
1 stop4h 53m
Delta
Tue 8/47:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 7/21![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/208:45 am
ORD
- BDL
1 stop4h 20m
United Airlines
Thu 8/274:50 pm
BDL
- ORD
Nonstop2h 45m
United Airlines
Deal found 7/21![United Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 10/2211:19 am
ORD
- ALB
2 stops11h 37m
Delta
Mon 10/2612:21 pm
ALB
- ORD
1 stop5h 36m
Delta
Deal found 7/23![Delta logo]()
$282
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated July 24, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated July 24, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Fri 8/284:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$185
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/149:42 am
ORD
- BOS
1 stop6h 49m
JetBlue
Mon 8/175:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/20![JetBlue logo]()
$192
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/148:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Wed 8/194:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/19![JetBlue logo]()
$203
This Priceline deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/206:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Sat 8/224:22 pm
ACK
- ORD
1 stop6h 36m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/206:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/19![JetBlue logo]()
$209
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/226:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Wed 8/263:33 pm
ACK
- ORD
1 stop4h 54m
JetBlue
Deal found 7/21![JetBlue logo]()
$209
This Super.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/266:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 8/305:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/21![JetBlue logo]()
$193
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/285:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 8/315:20 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 7/20![JetBlue logo]()
$206
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/20![JetBlue logo]()
$200
This Cheapflightsfares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Sat 9/125:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/20![JetBlue logo]()
$207
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/296:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 9/24:20 pm
HYA
- ORD
1 stop6h 38m
JetBlue
Deal found 7/21![JetBlue logo]()
$209
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 July 24, 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 July 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/268:05 am
ORD
- ALB
1 stop25h 20m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/129:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/20![JetBlue logo]()
$97
This Jetabroad deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Mon 8/108:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/24![JetBlue logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/198:05 am
ORD
- ALB
1 stop27h 20m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$99
This Flysmarter deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/20![JetBlue logo]()
$100
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/199:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Deal found 7/20![JetBlue logo]()
$100
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/135:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Deal found 7/22![JetBlue logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/269:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 7/20![JetBlue logo]()
$102
This Super.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/296:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/22![JetBlue logo]()
$103
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/266:45 pm
ORD
- BOS
Nonstop2h 42m
American Airlines
Deal found 7/22![American Airlines logo]()
$104
This JetBlue deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/26:00 am
ORD
- BOS
1 stop7h 49m
JetBlue
Deal found 7/21![JetBlue logo]()
$105
This JetBlue deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/189:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Deal found 7/22![JetBlue logo]()
$105
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 July 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $185 (SmartFares) |
One-way from | $94 (Kiwi.com) |
Popular in | April |
Cheapest in | January |
Average price | $259 |
Good round-trip deal | $210 or less |
Good one-way deal | $133 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 2,558,603 searches. Data last updated July 24, 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
ChicagoHyannis
ORD - HYA
ORDHYA
Chicago O'Hare Intl
Sat 8/29
6:00 am-3:13 pm
1 stop8h 13m
Hyannis Barnstable
Wed 9/2
4:20 pm-9:58 pm
1 stop6h 38m
$209
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Sat 8/29
9:40 am-4:12 pm
1 stop5h 32m
West Tisbury Martha's Vineyard
Tue 9/1
5:05 pm-9:58 pm
1 stop5h 53m
$220
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/5
7:45 pm-11:21 pm
Nonstop2h 36m
Boston Logan Intl
Thu 8/6
6:00 am-7:58 am
Nonstop2h 58m
$225
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 8/3
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Thu 8/6
6:00 am-7:58 am
Nonstop2h 58m
$225
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/12
8:24 pm-12:09 am
Nonstop2h 45m
Boston Logan Intl
Sun 9/13
7:00 am-8:48 am
Nonstop2h 48m
$226
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 10/7
9:24 pm-12:54 am
Nonstop2h 30m
Boston Logan Intl
Fri 10/16
6:00 am-7:59 am
Nonstop2h 59m
$227
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 8/16
2:40 pm-11:40 pm
1 stop8h 00m
Boston Logan Intl
Sun 8/23
5:20 am-2:25 pm
1 stop10h 05m
$235
ChicagoNantucket
ORD - ACK
ORDACK
Chicago O'Hare Intl
Sat 8/22
6:00 am-3:24 pm
1 stop8h 24m
Nantucket Memorial
Wed 8/26
3:33 pm-7:27 pm
1 stop4h 54m
$237
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/5
7:30 am-10:59 am
Nonstop2h 29m
Boston Logan Intl
Mon 9/7
7:30 am-9:26 am
Nonstop2h 56m
$245
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/12
12:16 pm-5:52 pm
1 stop4h 36m
Boston Logan Intl
Fri 8/14
7:05 am-9:04 am
Nonstop2h 59m
$246
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-ALB
ORD-BOS
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-ALB
ORD-BOS
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 $205). Flying from Chicago O'Hare Intl Airport to Massachusetts in June is currently the most expensive (average of $290). 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 July 24, 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 49% 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 July 24, 2026.
The most flights from ORD to USMA are scheduled on a Thursday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Massachusetts flights typically cost between $189 and $337 in August.The cheapest round-trip price found within the last 5 days was $185 on JetBlue (Aug 14-Aug 28).
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 64 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 July 24, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Southwest,Delta, andUnited Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Overall
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - 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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Alternative routes for O'Hare Intl to Massachusetts
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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on July 24, 2026.
Popular flight searches
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O'Hare Intl to Massachusetts flights
Consider these flights traveling from O'Hare Intl to Massachusetts.
Top 5 airlines flying from O'Hare Intl to Massachusetts
Discover the top 5 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 2,558,603 searches. Data last updated July 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$69 | Average$346 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$276 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$156 | Average$252 | FlexibilityNo cancel fee | On-time63% |