$70+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 22 — Apr 291
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 March 23, 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 March 23, 2026.
This Frontier deal was found by Cheapflights users on 3/20. 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 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Wed 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sat 5/3011:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/20![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/21![American Airlines logo]()
$153
This SmartFares deal was found by Cheapflights users on 3/20. 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 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This SmartFares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/18![JetBlue logo]()
$155
This American Airlines deal was found by Cheapflights users on 3/23. 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 5/28:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Mon 5/47:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/23![American Airlines logo]()
$156
This United Airlines deal was found by Cheapflights users on 3/20. 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.
Fri 5/18:00 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/20![United Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/21![American Airlines logo]()
$158
This Priceline deal was found by Cheapflights users on 3/20. 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.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Fri 5/16:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 3/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Fri 5/112:42 pm
BOS
- ORD
1 stop10h 57m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 3/20. 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.
Thu 4/94:31 pm
ORD
- BOS
1 stop7h 55m
Frontier
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Deal found 3/20![Frontier logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Fri 5/228:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Tue 6/25:26 pm
BOS
- ORD
Nonstop3h 09m
JetBlue
Deal found 3/20![JetBlue logo]()
$162
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 March 23, 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 March 23, 2026.
This United Airlines deal was found by Cheapflights users on 3/20. 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 4/136:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Wed 4/156:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/20![United Airlines logo]()
$157
This Delta deal was found by Cheapflights users on 3/22. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 6/38:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 3/22![Delta logo]()
$157
This JetBlue deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 5/69:41 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sat 5/97:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/18![JetBlue logo]()
$177
This Southwest deal was found by Cheapflights users on 3/22. 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.
Thu 5/282:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Tue 6/27:35 am
BOS
- ORD
2 stops9h 30m
Southwest
Deal found 3/22![Southwest logo]()
$187
This American Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/26:40 am
ORD
- ORH
1 stop5h 39m
American Airlines
Mon 4/61:44 pm
ORH
- ORD
1 stop18h 55m
American Airlines
Deal found 3/18![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 3/19. 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 8/207:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Tue 8/2511:00 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/19![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/21. 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 6/49:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/21![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/67:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Thu 4/97:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/18![Delta logo]()
$167
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 8/86:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Fri 8/146:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/18![United Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 3/20. 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 7/96:00 am
ORD
- MVY
1 stop4h 20m
Delta
Tue 7/1412:15 pm
MVY
- ORD
1 stop6h 33m
Delta
Deal found 3/20![Delta logo]()
$176
This United Airlines deal was found by Cheapflights users on 3/22. 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 5/297:40 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Fri 6/126:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/22![United Airlines logo]()
$189
This Delta deal was found by Cheapflights users on 3/19. 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 5/277:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Fri 5/298:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 3/19![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 3/22. 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 5/306:55 am
ORD
- ORH
2 stops8h 58m
American Airlines
Mon 6/15:18 pm
ORH
- ORD
1 stop14h 52m
American Airlines
Deal found 3/22![American Airlines logo]()
$252
This United Airlines deal was found by Cheapflights users on 3/22. 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 4/29:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Fri 4/39:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/22![United Airlines logo]()
$205
This JetBlue deal was found by Cheapflights users on 3/22. 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 6/309:33 am
ORD
- ACK
1 stop4h 50m
JetBlue
Wed 7/112:02 pm
ACK
- ORD
1 stop6h 00m
JetBlue
Deal found 3/22![JetBlue logo]()
$284
This KAYAK deal was found by Cheapflights users on 3/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/119:33 am
ORD
- EWB
2 stops7h 22m
Multiple Airlines
Wed 6/177:00 am
EWB
- ORD
2 stops11h 02m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 3/21. 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 4/298:52 am
ORD
- ORH
2 stops6h 51m
Delta
Tue 5/55:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/21![Delta logo]()
$202
This United Airlines deal was found by Cheapflights users on 3/22. 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 7/246:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Wed 7/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/22![United Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 3/22. 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.
Fri 5/292:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Tue 6/27:05 am
BDL
- ORD
1 stop10h 00m
Southwest
Deal found 3/22![Southwest logo]()
$343
This American Airlines deal was found by Cheapflights users on 3/19. 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 6/276:00 am
ORD
- HYA
1 stop7h 24m
American Airlines
Sat 7/43:02 pm
HYA
- ORD
1 stop5h 35m
American Airlines
Deal found 3/19![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 3/21. 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 4/309:35 am
ORD
- ORH
1 stop6h 08m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 55m
Delta
Deal found 3/21![Delta logo]()
$233
This KAYAK deal was found by Cheapflights users on 3/22. 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 7/229:33 am
ORD
- HYA
1 stop4h 44m
JetBlue
Wed 7/294:20 pm
HYA
- ORD
1 stop5h 24m
JetBlue
Deal found 3/22![JetBlue logo]()
$366
This Delta deal was found by Cheapflights users on 3/19. 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.
Fri 9/117:00 am
ORD
- ORH
1 stop6h 39m
Delta
Fri 9/183:18 pm
ORH
- ORD
1 stop6h 27m
Delta
Deal found 3/19![Delta logo]()
$240
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Sat 7/48:00 am
ORD
- HYA
1 stop5h 24m
American Airlines
Sat 7/113:54 pm
HYA
- ORD
Nonstop3h 34m
American Airlines
Deal found 3/21![American Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 3/22. 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.
Fri 4/172:40 pm
ORD
- ALB
2 stops7h 35m
Southwest
Mon 4/205:50 am
ALB
- ORD
2 stops8h 00m
Southwest
Deal found 3/22![Southwest logo]()
$399
This KAYAK deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 6/209:33 am
ORD
- ACK
1 stop4h 50m
JetBlue
Sat 6/274:20 pm
ACK
- ORD
1 stop5h 24m
JetBlue
Deal found 3/18![JetBlue logo]()
$377
This Delta deal was found by Cheapflights users on 3/19. 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.
Fri 9/117:00 am
ORD
- ORH
1 stop6h 39m
Delta
Wed 9/163:18 pm
ORH
- ORD
1 stop6h 27m
Delta
Deal found 3/19![Delta logo]()
$240
This American Airlines deal was found by Cheapflights users on 3/22. 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 6/2011:40 am
ORD
- HYA
Nonstop2h 42m
American Airlines
Sat 6/272:05 pm
HYA
- ORD
1 stop5h 48m
American Airlines
Deal found 3/22![American Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 3/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
Mon 5/45:50 am
BDL
- ORD
2 stops8h 00m
Southwest
Deal found 3/19![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 3/19. 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 9/97:00 am
ORD
- ORH
1 stop6h 39m
Delta
Thu 9/173:18 pm
ORH
- ORD
1 stop5h 04m
Delta
Deal found 3/19![Delta logo]()
$257
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated March 23, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated March 23, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/28:55 am
ORD
- BOS
Nonstop2h 32m
JetBlue
Mon 4/66:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/18![JetBlue logo]()
$162
This SmartFares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” 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 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Mon 4/136:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/18![JetBlue logo]()
$155
This Frontier deal was found by Cheapflights users on 3/20. 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.
Thu 4/94:31 pm
ORD
- BOS
1 stop7h 55m
Frontier
Mon 4/1312:45 pm
BOS
- ORD
1 stop6h 45m
Frontier
Deal found 3/20![Frontier logo]()
$161
This SmartFares deal was found by Cheapflights users on 3/20. 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 4/108:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/20![JetBlue logo]()
$154
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sat 4/116:48 pm
BOS
- ORD
Nonstop3h 12m
American Airlines
Deal found 3/21![American Airlines logo]()
$153
This American Airlines deal was found by Cheapflights users on 3/21. 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.
Sat 4/111:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/21![American Airlines logo]()
$158
This Expedia deal was found by Cheapflights users on 3/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
Tue 4/146:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$164
This Frontier deal was found by Cheapflights users on 3/20. 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 4/134:34 pm
ORD
- BOS
1 stop7h 52m
Frontier
Wed 4/156:00 am
BOS
- ORD
1 stop12h 00m
Frontier
Deal found 3/20![Frontier logo]()
$140
This Priceline deal was found by Cheapflights users on 3/20. 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.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Fri 5/16:52 am
BOS
- ORD
Nonstop2h 59m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 3/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Fri 5/112:42 pm
BOS
- ORD
1 stop10h 57m
Frontier
Deal found 3/20![Frontier logo]()
$160
This Delta deal was found by Cheapflights users on 3/21. 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 4/2910:45 am
ORD
- ORH
1 stop4h 58m
Delta
Tue 5/55:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/21![Delta logo]()
$192
This United Airlines deal was found by Cheapflights users on 3/20. 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.
Thu 4/307:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Mon 5/48:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
Deal found 3/20![United Airlines 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 March 23, 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 March 23, 2026.
This Frontier deal was found by Cheapflights users on 3/20. 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.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/20![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- BDL
1 stop5h 49m
Frontier
Deal found 3/21![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/20. 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.
Wed 5/61:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/20![Frontier logo]()
$76
This Super.com deal was found by Cheapflights users on 3/20. 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.
Tue 8/48:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/20![JetBlue logo]()
$78
This Delta deal was found by Cheapflights users on 3/19. 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 4/166:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/19![Delta logo]()
$79
This Super.com deal was found by Cheapflights users on 3/20. 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.
Sat 4/49:06 am
ORD
- BOS
1 stop8h 03m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$80
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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.
Tue 4/712:45 pm
ORD
- BOS
1 stop7h 48m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$81
This Cheapflightsfares deal was found by Cheapflights users on 3/22. 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.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Spirit Airlines
Deal found 3/22![Spirit Airlines logo]()
$84
This Super.com deal was found by Cheapflights users on 3/20. 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 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/20![JetBlue logo]()
$87
This Super.com deal was found by Cheapflights users on 3/20. 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.
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/20![JetBlue logo]()
$88
This Delta deal was found by Cheapflights users on 3/19. 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 5/279:36 am
ORD
- MVY
1 stop4h 46m
Delta
Deal found 3/19![Delta logo]()
$88
This United Airlines deal was found by Cheapflights users on 3/20. 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 4/66:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 3/20![United Airlines logo]()
$89
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 March 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $70 (Frontier) |
Popular in | April |
Cheapest in | January |
Average price | $225 |
Good round-trip deal | $179 or less |
Good one-way deal | $128 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 March 23, 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
Mon 4/13
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Wed 4/15
6:00 am-7:59 am
Nonstop2h 59m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/30
7:00 am-10:35 am
Nonstop2h 35m
Boston Logan Intl
Wed 6/3
8:40 pm-10:35 pm
Nonstop2h 55m
$157
Quickest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Tue 8/25
11:00 am-12:52 pm
Nonstop2h 52m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 6/4
9:26 pm-12:59 am
Nonstop2h 33m
Boston Logan Intl
Sun 6/7
6:00 am-7:58 am
Nonstop2h 58m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 4/6
7:35 pm-11:02 pm
Nonstop2h 27m
Boston Logan Intl
Thu 4/9
7:15 am-9:25 am
Nonstop3h 10m
$167
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Thu 7/9
6:00 am-11:20 am
1 stop4h 20m
West Tisbury Martha's Vineyard
Tue 7/14
12:15 pm-5:48 pm
1 stop6h 33m
$176
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/6
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
Sat 5/9
7:35 pm-9:36 pm
Nonstop3h 01m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/28
2:40 pm-11:55 pm
2 stops8h 15m
Boston Logan Intl
Tue 6/2
7:35 am-4:05 pm
2 stops9h 30m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/8
6:00 am-11:16 am
1 stop4h 16m
Boston Logan Intl
Fri 8/14
6:00 am-7:58 am
Nonstop2h 58m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/27
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Fri 5/29
8:40 pm-10:35 pm
Nonstop2h 55m
$187
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-BDL
ORD-MVY
ORD-HYA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Massachusetts
ORD-USMA
ORD-BOS
ORD-ORH
ORD-BDL
ORD-MVY
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $91). Flying from Chicago O'Hare Intl Airport to Massachusetts in January is currently the most expensive (average of $117). 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 March 23, 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 50% 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 March 23, 2026.
The most flights from ORD to USMA are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).
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 March 23, 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
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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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on March 23, 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 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 March 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$248 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |