$79+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
May 24 — May 311
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 April 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 April 24, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Wed 8/128:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/21![JetBlue logo]()
$146
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Deal found 4/20![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 4/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Tue 5/266:36 pm
BOS
- ORD
Nonstop3h 24m
American Airlines
Deal found 4/20![American Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 4/20. 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 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Mon 6/16:00 pm
BOS
- ORD
1 stop5h 36m
Delta
Deal found 4/20![Delta logo]()
$149
This Delta deal was found by Cheapflights users on 4/20. 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.
Fri 5/297:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/18:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/20![Delta logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/22![JetBlue logo]()
$151
This JetBlue deal was found by Cheapflights users on 4/22. 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 8/48:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/128:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/22![JetBlue logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 4/21![JetBlue logo]()
$153
This JetBlue deal was found by Cheapflights users on 4/22. 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.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/22![JetBlue logo]()
$154
This United Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 8/207:33 am
ORD
- BOS
Nonstop2h 34m
United Airlines
Wed 8/2612:30 pm
BOS
- ORD
Nonstop2h 51m
United Airlines
Deal found 4/22![United Airlines logo]()
$155
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Wed 6/36:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sun 6/77:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/20![United Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 4/20. 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 5/267:05 am
ORD
- ORH
1 stop7h 28m
Delta
Wed 6/105:43 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/20![Delta logo]()
$202
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 April 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 April 24, 2026.
This Delta deal was found by Cheapflights users on 4/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:05 am
ORD
- BOS
Nonstop2h 31m
Delta
Wed 7/157:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 4/19![Delta logo]()
$167
This JetBlue deal was found by Cheapflights users on 4/23. 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 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 5/246:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/23![JetBlue logo]()
$173
This United Airlines deal was found by Cheapflights users on 4/23. 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 6/296:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sat 7/46:45 pm
BOS
- ORD
Nonstop2h 56m
United Airlines
Deal found 4/23![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Mon 5/185:00 am
ORD
- ORH
1 stop8h 14m
American Airlines
Mon 5/255:18 pm
ORH
- ORD
1 stop16h 50m
American Airlines
Deal found 4/22![American Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 4/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:35 pm
ORD
- ALB
1 stop8h 15m
Southwest
Wed 5/138:45 am
ALB
- ORD
1 stop8h 20m
Southwest
Deal found 4/20![Southwest logo]()
$291
This Delta deal was found by Cheapflights users on 4/21. 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.
Fri 5/227:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Wed 5/278:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/21![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Sat 5/97:00 am
ORD
- BOS
1 stop4h 51m
United Airlines
Sat 8/228:10 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/20![United Airlines logo]()
$192
This Sun Country Air deal was found by Cheapflights users on 4/23. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:19 pm
ORD
- BDL
1 stop15h 23m
Sun Country Air
Mon 7/1311:04 am
BDL
- ORD
1 stop7h 25m
Sun Country Air
Deal found 4/23![Sun Country Air logo]()
$397
This Delta deal was found by Cheapflights users on 4/21. 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.
Mon 5/187:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Wed 5/209:05 am
BOS
- ORD
1 stop4h 56m
Delta
Deal found 4/21![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/216:40 am
ORD
- ORH
1 stop9h 13m
American Airlines
Thu 5/285:18 pm
ORH
- ORD
2 stops7h 41m
American Airlines
Deal found 4/22![American Airlines logo]()
$222
This United Airlines deal was found by Cheapflights users on 4/23. 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 6/306:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Fri 7/36:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/23![United Airlines logo]()
$217
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 6/27:05 am
ORD
- ORH
1 stop7h 28m
Delta
Tue 6/165:43 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/21![Delta logo]()
$202
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/75:00 am
ORD
- ORH
2 stops8h 14m
American Airlines
Mon 5/112:39 pm
ORH
- ORD
2 stops10h 15m
American Airlines
Deal found 4/22![American Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 5/265:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 4/22![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 4/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/187:00 am
ORD
- ORH
1 stop6h 39m
Delta
Thu 8/203:18 pm
ORH
- ORD
1 stop6h 27m
Delta
Deal found 4/19![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/226:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Fri 5/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/22![United Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 4/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:05 am
ORD
- ORH
1 stop7h 28m
Delta
Sun 5/244:15 pm
ORH
- ORD
1 stop5h 31m
Delta
Deal found 4/19![Delta logo]()
$222
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/49:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Fri 5/88:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
Deal found 4/23![United Airlines logo]()
$227
This JetBlue deal was found by Cheapflights users on 4/19. 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.
Thu 5/213:40 pm
ORD
- BDL
1 stop7h 15m
JetBlue
Sun 5/247:15 am
BDL
- ORD
1 stop8h 15m
JetBlue
Deal found 4/19![JetBlue logo]()
$380
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 5/56:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Fri 5/87:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 4/23![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 4/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Mon 6/15:50 am
BDL
- ORD
2 stops8h 00m
Southwest
Deal found 4/23![Southwest logo]()
$388
This American Airlines deal was found by Cheapflights users on 4/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1111:40 am
ORD
- HYA
Nonstop2h 44m
American Airlines
Sat 7/256:03 pm
HYA
- ORD
1 stop6h 18m
American Airlines
Deal found 4/20![American Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 6/27:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sun 6/147:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 4/21![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Mon 5/117:30 am
ORD
- ALB
Nonstop2h 15m
United Airlines
Sat 5/167:30 pm
ALB
- ORD
1 stop5h 14m
United Airlines
Deal found 4/21![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 4/22. 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.
Wed 7/89:30 am
ORD
- ORH
1 stop6h 30m
Delta
Fri 7/105:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 4/22![Delta logo]()
$237
This American Airlines deal was found by Cheapflights users on 4/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
ORD
- HYA
1 stop5h 03m
American Airlines
Sat 7/113:54 pm
HYA
- ORD
Nonstop3h 34m
American Airlines
Deal found 4/20![American Airlines logo]()
$350
This JetBlue deal was found by Cheapflights users on 4/19. 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 6/206:00 am
ORD
- ACK
1 stop8h 34m
JetBlue
Wed 6/2412:18 pm
ACK
- ORD
1 stop6h 03m
JetBlue
Deal found 4/19![JetBlue logo]()
$429
This Delta deal was found by Cheapflights users on 4/20. 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 8/59:30 am
ORD
- ORH
1 stop6h 30m
Delta
Mon 8/103:18 pm
ORH
- ORD
1 stop6h 27m
Delta
Deal found 4/20![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/23. 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 9/111:10 am
ORD
- ALB
Nonstop2h 13m
United Airlines
Wed 9/21:00 pm
ALB
- ORD
Nonstop2h 32m
United Airlines
Deal found 4/23![United Airlines logo]()
$301
This JetBlue deal was found by Cheapflights users on 4/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/158:20 pm
ORD
- MVY
1 stop12h 48m
JetBlue
Fri 7/1710:58 am
MVY
- ORD
1 stop27h 01m
JetBlue
Deal found 4/24![JetBlue logo]()
$441
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated April 24, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 5/165:35 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 4/21![American Airlines logo]()
$151
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Wed 5/206:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Sun 5/245:05 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/21![United Airlines logo]()
$156
This American Airlines deal was found by Cheapflights users on 4/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Tue 5/266:36 pm
BOS
- ORD
Nonstop3h 24m
American Airlines
Deal found 4/20![American Airlines logo]()
$148
This JetBlue deal was found by Cheapflights users on 4/22. 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.
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/22![JetBlue logo]()
$154
This Delta deal was found by Cheapflights users on 4/20. 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 5/267:05 am
ORD
- ORH
1 stop7h 28m
Delta
Wed 6/105:43 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/20![Delta logo]()
$202
This Delta deal was found by Cheapflights users on 4/20. 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 5/287:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/16:00 pm
BOS
- ORD
1 stop5h 36m
Delta
Deal found 4/20![Delta logo]()
$149
This Jetabroad deal was found by Cheapflights users on 4/21. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/21![JetBlue logo]()
$152
This SmartFares deal was found by Cheapflights users on 4/20. 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.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/20![JetBlue logo]()
$155
This Delta deal was found by Cheapflights users on 4/21. 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 5/286:00 am
ORD
- BOS
1 stop6h 20m
Delta
Tue 6/21:00 pm
BOS
- ORD
1 stop6h 07m
Delta
Deal found 4/21![Delta logo]()
$158
This Delta deal was found by Cheapflights users on 4/20. 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.
Fri 5/297:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/18:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/20![Delta logo]()
$150
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Deal found 4/20![Delta logo]()
$147
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 5/305:19 pm
ORD
- BOS
1 stop5h 10m
Delta
Tue 6/212:05 pm
BOS
- ORD
1 stop8h 15m
Delta
Deal found 4/20![Delta logo]()
$157
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 April 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 April 24, 2026.
This Delta deal was found by Cheapflights users on 4/21. 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.
Wed 9/27:00 am
ORD
- BOS
1 stop5h 24m
Delta
Deal found 4/21![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/20. 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.
Mon 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/20![Delta logo]()
$80
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Sat 5/236:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 4/20![United Airlines logo]()
$81
This SmartFares deal was found by Cheapflights users on 4/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:21 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 4/21![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/21![JetBlue logo]()
$83
This Delta deal was found by Cheapflights users on 4/23. 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.
Tue 6/307:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/23![Delta logo]()
$84
This American Airlines deal was found by Cheapflights users on 4/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:00 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 4/20![American Airlines logo]()
$85
This Jetabroad deal was found by Cheapflights users on 4/20. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 4/20![JetBlue logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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 7/41:55 pm
ORD
- BOS
Nonstop2h 38m
JetBlue
Deal found 4/20![JetBlue logo]()
$88
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Sun 6/76:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/21![United Airlines logo]()
$89
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Deal found 4/20![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 4/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:50 am
ORD
- BDL
1 stop7h 59m
Frontier
Deal found 4/20![Frontier logo]()
$90
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 April 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $146 (Cheapflightsfares) |
One-way from | $79 (Delta) |
Popular in | April |
Cheapest in | January |
Average price | $273 |
Good round-trip deal | $209 or less |
Good one-way deal | $121 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 April 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
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/8
7:05 am-10:36 am
Nonstop2h 31m
Boston Logan Intl
Wed 7/15
7:30 am-9:26 am
Nonstop2h 56m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/23
1:56 pm-5:27 pm
Nonstop2h 31m
Boston Logan Intl
Sun 5/24
6:00 am-8:00 am
Nonstop3h 00m
$173
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 6/29
6:20 pm-9:56 pm
Nonstop2h 36m
Boston Logan Intl
Sat 7/4
6:45 pm-8:41 pm
Nonstop2h 56m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/22
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Wed 5/27
8:40 pm-10:35 pm
Nonstop2h 55m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 5/18
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Wed 5/20
9:05 am-1:01 pm
1 stop4h 56m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/9
7:00 am-12:51 pm
1 stop4h 51m
Boston Logan Intl
Sat 8/22
8:10 am-10:08 am
Nonstop2h 58m
$192
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Tue 6/2
7:05 am-3:33 pm
1 stop7h 28m
Worcester
Tue 6/16
5:43 pm-10:34 pm
1 stop5h 51m
$202
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Mon 5/18
5:00 am-2:14 pm
1 stop8h 14m
Worcester
Mon 5/25
5:18 pm-9:08 am
1 stop16h 50m
$212
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 6/30
6:00 am-11:16 am
1 stop4h 16m
Boston Logan Intl
Fri 7/3
6:00 am-7:58 am
Nonstop2h 58m
$217
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Tue 8/18
7:00 am-2:39 pm
1 stop6h 39m
Worcester
Thu 8/20
3:18 pm-8:45 pm
1 stop6h 27m
$221
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-HYA
ORD-BDL
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-HYA
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 71 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 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 $65). Flying from Chicago O'Hare Intl Airport to Massachusetts in April is currently the most expensive (average of $538). 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 April 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.
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.
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 April 24, 2026.
The most flights from ORD to USMA are scheduled on a Thursday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (32 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
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 April 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.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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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Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on April 24, 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 6 airlines flying from O'Hare Intl to Massachusetts
Discover the top 6 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 April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$368 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$84 | Average$257 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$118 | Average$253 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |