$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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jul 25 — Aug 11
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
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Cheapest flights from O'Hare Intl to MassachusettsExplore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 25, 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 June 25, 2026.
This Priceline deal was found by Cheapflights users on 6/21. 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.
Tue 7/219:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Tue 7/285:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/21![JetBlue logo]()
$158
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Mon 8/319:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Wed 9/25:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 6/23![JetBlue logo]()
$166
This JetBlue deal was found by Cheapflights users on 6/22. 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.
Mon 8/316:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Tue 9/112:02 pm
ACK
- ORD
1 stop6h 33m
JetBlue
Deal found 6/22![JetBlue logo]()
$166
This JetBlue deal was found by Cheapflights users on 6/22. 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 7/146:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 7/154:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/22![JetBlue logo]()
$167
This Jetabroad deal was found by Cheapflights users on 6/22. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Sat 8/154:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 6/22![JetBlue logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 6/23. 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 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
Fri 8/218:41 am
BOS
- ORD
1 stop8h 36m
JetBlue
Deal found 6/23![JetBlue logo]()
$177
This Delta deal was found by Cheapflights users on 6/23. 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.
Sat 9/57:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Fri 9/117:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$178
This Delta deal was found by Cheapflights users on 6/23. 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.
Fri 7/107:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Wed 7/158:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$179
This JetBlue deal was found by Cheapflights users on 6/22. 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 8/256:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Wed 8/268:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/22![JetBlue logo]()
$180
This Delta deal was found by Cheapflights users on 6/23. 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.
Sun 9/67:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Sat 9/126:00 pm
BOS
- ORD
Nonstop2h 59m
Delta
Deal found 6/23![Delta logo]()
$181
This Delta deal was found by Cheapflights users on 6/24. 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 8/2910:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Fri 9/48:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/24![Delta logo]()
$182
This Priceline deal was found by Cheapflights users on 6/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:40 am
ORD
- ACK
1 stop4h 44m
JetBlue
Mon 8/314:21 pm
ACK
- ORD
1 stop6h 37m
JetBlue
Deal found 6/24![JetBlue logo]()
$182
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 June 25, 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 June 25, 2026.
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Mon 8/319:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Wed 9/25:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 6/23![JetBlue logo]()
$166
This Delta deal was found by Cheapflights users on 6/20. 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 7/810:28 am
ORD
- BOS
Nonstop2h 31m
Delta
Sun 7/127:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/20![Delta logo]()
$178
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Thu 8/206:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Sun 8/235:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 6/23![United Airlines logo]()
$182
This JetBlue deal was found by Cheapflights users on 6/22. 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 7/146:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 7/154:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/22![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 6/22. 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.
Thu 7/97:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sat 7/117:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/22![Delta logo]()
$200
This KAYAK deal was found by Cheapflights users on 6/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:00 pm
ORD
- ALB
Nonstop2h 14m
American Airlines
Thu 7/91:18 pm
ALB
- ORD
Nonstop2h 47m
American Airlines
Deal found 6/23![American Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 6/22. 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.
Tue 7/76:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Thu 7/95:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 6/22![United Airlines logo]()
$210
This JetBlue deal was found by Cheapflights users on 6/22. 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.
Fri 11/61:00 pm
ORD
- BOS
1 stop5h 51m
JetBlue
Mon 11/97:05 am
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 6/22![JetBlue logo]()
$201
This Delta deal was found by Cheapflights users on 6/23. 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 7/143:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Mon 7/207:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$203
This Expedia deal was found by Cheapflights users on 6/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:41 am
ORD
- HYA
1 stop4h 52m
Multiple Airlines
Tue 7/286:00 am
HYA
- ORD
2 stops14h 15m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 6/21. 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 8/47:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Thu 8/67:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/21![Delta logo]()
$203
This JetBlue deal was found by Cheapflights users on 6/20. 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.
Tue 7/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Fri 7/108:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/20![JetBlue logo]()
$210
This JetBlue deal was found by Cheapflights users on 6/20. 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.
Tue 7/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Sun 7/128:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/20![JetBlue logo]()
$210
This Delta deal was found by Cheapflights users on 6/21. 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 7/136:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Fri 7/178:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/21![Delta logo]()
$211
This JetBlue deal was found by Cheapflights users on 6/24. 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.
Thu 7/98:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sat 7/115:01 am
BOS
- ORD
1 stop4h 50m
JetBlue
Deal found 6/24![JetBlue logo]()
$210
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Sat 8/2211:06 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Mon 8/247:55 pm
BDL
- ORD
1 stop4h 45m
United Airlines
Deal found 6/23![United Airlines logo]()
$318
This Delta deal was found by Cheapflights users on 6/21. 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 9/187:05 am
ORD
- ORH
2 stops7h 32m
Delta
Mon 9/214:20 pm
ORH
- ORD
1 stop6h 58m
Delta
Deal found 6/21![Delta logo]()
$240
This JetBlue deal was found by Cheapflights users on 6/20. 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.
Thu 7/95:27 pm
ORD
- BOS
1 stop5h 37m
JetBlue
Sun 7/128:07 am
BOS
- ORD
Nonstop2h 58m
JetBlue
Deal found 6/20![JetBlue logo]()
$219
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Sat 10/1011:59 am
ORD
- ALB
Nonstop2h 05m
United Airlines
Sun 10/116:03 am
ALB
- ORD
1 stop4h 35m
United Airlines
Deal found 6/23![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 6/23. 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.
Thu 8/136:45 am
ORD
- MVY
1 stop6h 45m
American Airlines
Tue 8/1810:41 am
MVY
- ORD
2 stops11h 49m
American Airlines
Deal found 6/23![American Airlines logo]()
$415
This JetBlue deal was found by Cheapflights users on 6/20. 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.
Tue 7/149:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Sat 7/185:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/20![JetBlue logo]()
$237
This Delta deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:30 am
ORD
- ORH
1 stop5h 30m
Delta
Sun 8/25:40 pm
ORH
- ORD
1 stop14h 49m
Delta
Deal found 6/25![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 6/21. 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 10/87:30 am
ORD
- ALB
Nonstop2h 09m
United Airlines
Mon 10/129:55 am
ALB
- ORD
Nonstop2h 34m
United Airlines
Deal found 6/21![United Airlines logo]()
$334
This JetBlue deal was found by Cheapflights users on 6/22. 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 8/229:40 am
ORD
- HYA
1 stop4h 33m
JetBlue
Sat 8/294:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/22![JetBlue logo]()
$246
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Sat 8/227:15 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Sun 8/236:00 am
BDL
- ORD
Nonstop2h 46m
United Airlines
Deal found 6/23![United Airlines logo]()
$347
This Expedia deal was found by Cheapflights users on 6/24. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:00 am
ORD
- HYA
1 stop8h 13m
Multiple Airlines
Sun 7/2610:55 am
HYA
- ORD
2 stops9h 20m
Multiple Airlines
Deal found 6/24![Multiple Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 6/21. 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 8/195:30 am
ORD
- ACK
2 stops9h 27m
Delta
Tue 8/253:24 pm
ACK
- ORD
1 stop7h 28m
Delta
Deal found 6/21![Delta logo]()
$288
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Fri 8/146:45 am
ORD
- MVY
1 stop6h 45m
American Airlines
Mon 8/173:00 pm
MVY
- ORD
1 stop5h 46m
American Airlines
Deal found 6/20![American Airlines logo]()
$488
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Mon 8/179:42 am
ORD
- MVY
1 stop5h 28m
JetBlue
Tue 8/185:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/23![JetBlue logo]()
$253
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Sat 9/122:25 pm
ORD
- BDL
Nonstop2h 20m
United Airlines
Sun 9/209:40 am
BDL
- ORD
Nonstop2h 46m
United Airlines
Deal found 6/23![United Airlines logo]()
$347
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated June 25, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated June 25, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 7/76:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 7/145:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/21![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 6/23. 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.
Wed 7/87:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Thu 7/167:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$178
This Delta deal was found by Cheapflights users on 6/23. 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.
Fri 7/107:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Wed 7/158:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/23![Delta logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/108:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 7/154:31 pm
BOS
- ORD
1 stop6h 27m
JetBlue
Deal found 6/24![JetBlue logo]()
$181
This JetBlue deal was found by Cheapflights users on 6/22. 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 7/146:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 7/154:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/22![JetBlue logo]()
$167
This JetBlue deal was found by Cheapflights users on 6/22. 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 7/149:40 am
ORD
- BOS
1 stop6h 37m
JetBlue
Sat 7/184:43 pm
BOS
- ORD
1 stop6h 15m
JetBlue
Deal found 6/22![JetBlue logo]()
$185
This Jetabroad deal was found by Cheapflights users on 6/22. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/169:40 am
ORD
- BOS
1 stop6h 27m
JetBlue
Wed 7/225:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/22![JetBlue logo]()
$176
This United Airlines deal was found by Cheapflights users on 6/23. 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.
Fri 7/179:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 7/225:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 6/23![United Airlines logo]()
$180
This Priceline deal was found by Cheapflights users on 6/21. 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.
Tue 7/219:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Tue 7/285:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/21![JetBlue logo]()
$158
This Delta deal was found by Cheapflights users on 6/23. 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 7/216:59 am
ORD
- BOS
Nonstop2h 31m
Delta
Fri 7/247:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/23![Delta logo]()
$183
This United Airlines deal was found by Cheapflights users on 6/24. 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.
Mon 7/276:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Tue 7/287:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 6/24![United Airlines logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 6/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Mon 8/35:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 6/24![JetBlue logo]()
$177
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 June 25, 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 June 25, 2026.
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Tue 8/189:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Deal found 6/23![JetBlue logo]()
$79
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Tue 9/89:39 am
ORD
- ACK
1 stop4h 44m
JetBlue
Deal found 6/23![JetBlue logo]()
$79
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Wed 8/199:35 am
ORD
- HYA
1 stop4h 38m
JetBlue
Deal found 6/23![JetBlue logo]()
$85
This CheapOair deal was found by Cheapflights users on 6/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/24![JetBlue logo]()
$85
This Expedia deal was found by Cheapflights users on 6/22. 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.
Thu 8/209:35 am
ORD
- ACK
1 stop4h 49m
JetBlue
Deal found 6/22![JetBlue logo]()
$87
This JetBlue deal was found by Cheapflights users on 6/23. 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.
Wed 7/226:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Deal found 6/23![JetBlue logo]()
$90
This JetBlue deal was found by Cheapflights users on 6/24. 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.
Thu 8/209:35 am
ORD
- HYA
1 stop4h 38m
JetBlue
Deal found 6/24![JetBlue logo]()
$93
This JetBlue deal was found by Cheapflights users on 6/23. 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 7/245:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Deal found 6/23![JetBlue logo]()
$93
This JetBlue deal was found by Cheapflights users on 6/21. 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.
Thu 8/66:00 am
ORD
- ACK
1 stop8h 23m
JetBlue
Deal found 6/21![JetBlue logo]()
$93
This Super.com deal was found by Cheapflights users on 6/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 6/25![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 6/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/810:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 6/23![JetBlue logo]()
$95
This JetBlue deal was found by Cheapflights users on 6/24. 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.
Sat 8/229:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Deal found 6/24![JetBlue logo]()
$95
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 June 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $158 (Priceline) |
One-way from | $79 (JetBlue) |
Popular in | April |
Cheapest in | January |
Average price | $260 |
Good round-trip deal | $217 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 June 25, 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
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Mon 8/31
9:35 am-4:10 pm
1 stop5h 35m
West Tisbury Martha's Vineyard
Wed 9/2
5:05 pm-9:58 pm
1 stop5h 53m
$166
ChicagoHyannis
ORD - HYA
ORDHYA
Chicago O'Hare Intl
Tue 7/14
6:00 am-3:13 pm
1 stop8h 13m
Hyannis Barnstable
Wed 7/15
4:53 pm-9:58 pm
1 stop6h 05m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/8
10:28 am-1:59 pm
Nonstop2h 31m
Boston Logan Intl
Sun 7/12
7:30 am-9:26 am
Nonstop2h 56m
$178
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
6:15 am-9:36 am
Nonstop2h 21m
Boston Logan Intl
Sun 8/23
5:45 am-9:38 am
1 stop4h 53m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 7/9
7:25 pm-11:00 pm
Nonstop2h 35m
Boston Logan Intl
Sat 7/11
7:59 pm-9:59 pm
Nonstop3h 00m
$200
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 11/6
1:00 pm-7:51 pm
1 stop5h 51m
Boston Logan Intl
Mon 11/9
7:05 am-11:56 am
1 stop5h 51m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/14
3:19 pm-6:59 pm
Nonstop2h 40m
Boston Logan Intl
Mon 7/20
7:30 am-9:26 am
Nonstop2h 56m
$203
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/4
7:30 pm-11:00 pm
Nonstop2h 30m
Boston Logan Intl
Thu 8/6
7:30 am-9:26 am
Nonstop2h 56m
$203
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/7
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Thu 7/9
5:45 am-9:36 am
1 stop4h 51m
$210
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/7
6:00 am-2:43 pm
1 stop7h 43m
Boston Logan Intl
Fri 7/10
8:10 am-10:06 am
Nonstop2h 56m
$210
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-MVY
ORD-ACK
ORD-HYA
ORD-BOS
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-MVY
ORD-ACK
ORD-HYA
ORD-BOS
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 February is currently the most expensive (average of $413). 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 June 25, 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 54% 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 June 25, 2026.
The most flights from ORD to USMA are scheduled on a Thursday (81 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
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 June 25, 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
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
7.9
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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Complete your trip
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 June 25, 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 June 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$285 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$82 | Average$308 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$127 | Average$270 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$468 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$156 | Average$206 | FlexibilityNo cancel fee | On-time63% |