$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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jul 10 — Jul 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from O'Hare Intl to Massachusetts
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to MassachusettsExplore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 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 10, 2026.
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/219:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Wed 7/225:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/7![JetBlue logo]()
$158
This Priceline deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/76:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Tue 7/1412:02 pm
ACK
- ORD
1 stop6h 32m
JetBlue
Deal found 6/8![JetBlue logo]()
$158
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/179:39 am
ORD
- ACK
1 stop4h 44m
JetBlue
Tue 8/2512:02 pm
ACK
- ORD
1 stop6h 18m
JetBlue
Deal found 6/5![JetBlue logo]()
$166
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/216:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 7/224:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/9![JetBlue logo]()
$167
This Priceline deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/149:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Sat 7/185:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/9![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/156:00 am
ORD
- ACK
1 stop8h 23m
JetBlue
Wed 8/1912:02 pm
ACK
- ORD
1 stop6h 18m
JetBlue
Deal found 6/5![JetBlue logo]()
$174
This Priceline deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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.
Sun 8/166:00 am
ORD
- HYA
1 stop8h 11m
JetBlue
Wed 8/194:23 pm
HYA
- ORD
1 stop6h 32m
JetBlue
Deal found 6/5![JetBlue logo]()
$175
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/99:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Thu 7/98:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/8![United Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/297:30 am
ORD
- BOS
Nonstop2h 29m
Delta
Sat 9/121:10 pm
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 6/8![Delta logo]()
$182
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/279:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Mon 8/315:05 pm
MVY
- ORD
1 stop5h 50m
JetBlue
Deal found 6/8![JetBlue logo]()
$182
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 8/156:00 am
ORD
- ACK
1 stop8h 23m
JetBlue
Fri 8/214:20 pm
ACK
- ORD
1 stop6h 35m
JetBlue
Deal found 6/5![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/227:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sun 7/267:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/9![Delta logo]()
$183
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 10, 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 10, 2026.
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/159:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Sat 7/185:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/5![JetBlue logo]()
$158
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/227:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sun 7/267:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/9![Delta logo]()
$183
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/309:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 8/26:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/6![United Airlines logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:00 am
ORD
- HYA
1 stop7h 32m
American Airlines
Sat 8/2212:42 pm
HYA
- ORD
1 stop8h 04m
American Airlines
Deal found 6/5![American Airlines logo]()
$263
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/259:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Wed 8/265:05 pm
MVY
- ORD
1 stop5h 50m
JetBlue
Deal found 6/9![JetBlue logo]()
$158
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/216:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 7/224:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/9![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 7/44:00 pm
ORD
- BOS
Nonstop2h 45m
Delta
Sat 7/117:59 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 6/6![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/9![United Airlines logo]()
$197
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/186:00 am
ORD
- ACK
1 stop8h 19m
JetBlue
Sat 7/2512:03 pm
ACK
- ORD
1 stop5h 13m
JetBlue
Deal found 6/7![JetBlue logo]()
$174
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 9/59:40 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Sat 9/1210:38 am
BOS
- ORD
Nonstop2h 51m
United Airlines
Deal found 6/5![United Airlines logo]()
$206
This KAYAK deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 8/276:00 am
ORD
- EWB
2 stops11h 38m
Multiple Airlines
Mon 8/316:45 am
EWB
- ORD
2 stops16h 10m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/47:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Sat 8/87:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/9![Delta logo]()
$209
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/279:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Mon 8/315:05 pm
MVY
- ORD
1 stop5h 50m
JetBlue
Deal found 6/8![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/110:35 am
ORD
- ORH
1 stop5h 28m
Delta
Tue 7/75:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 6/7![Delta logo]()
$218
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/199:39 am
ORD
- BOS
1 stop6h 36m
JetBlue
Wed 8/268:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/8![JetBlue logo]()
$183
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/246:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Fri 6/267:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/7![United Airlines logo]()
$224
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/156:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Sat 7/184:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/5![JetBlue logo]()
$183
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 6/232:07 pm
ORD
- BOS
1 stop4h 53m
Delta
Sat 7/45:05 pm
BOS
- ORD
Nonstop3h 12m
Delta
Deal found 6/7![Delta logo]()
$233
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sat 8/86:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/7![United Airlines logo]()
$238
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/209:39 am
ORD
- BOS
1 stop6h 36m
JetBlue
Wed 8/2612:42 pm
BOS
- ORD
1 stop5h 38m
JetBlue
Deal found 6/8![JetBlue logo]()
$185
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/297:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sat 8/87:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/5![Delta logo]()
$242
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/179:42 am
ORD
- HYA
1 stop6h 57m
American Airlines
Mon 7/206:22 pm
HYA
- ORD
1 stop6h 08m
American Airlines
Deal found 6/9![American Airlines logo]()
$388
This Priceline deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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.
Sat 8/86:00 am
ORD
- HYA
1 stop8h 11m
JetBlue
Sat 8/294:53 pm
HYA
- ORD
1 stop6h 02m
JetBlue
Deal found 6/8![JetBlue logo]()
$211
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/29:35 am
ORD
- ORH
1 stop6h 28m
Delta
Tue 7/75:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 6/7![Delta logo]()
$267
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/236:59 am
ORD
- MVY
1 stop5h 29m
American Airlines
Sat 6/271:13 pm
MVY
- ORD
Nonstop3h 06m
American Airlines
Deal found 6/5![American Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/149:30 am
ORD
- ORH
1 stop6h 30m
Delta
Wed 7/225:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 6/7![Delta logo]()
$267
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/306:15 pm
ORD
- ALB
Nonstop2h 12m
United Airlines
Wed 7/18:15 am
ALB
- ORD
Nonstop2h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$327
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Wed 9/25:05 pm
MVY
- ORD
1 stop5h 50m
JetBlue
Deal found 6/7![JetBlue logo]()
$237
This KAYAK deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/46:00 am
ORD
- EWB
2 stops8h 45m
Multiple Airlines
Tue 7/77:00 am
EWB
- ORD
2 stops11h 34m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/410:29 am
ORD
- ALB
Nonstop2h 21m
United Airlines
Wed 7/86:00 am
ALB
- ORD
1 stop6h 53m
United Airlines
Deal found 6/8![United Airlines logo]()
$337
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated June 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/277:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Wed 7/17:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 6/9![United Airlines logo]()
$182
This Super.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 6/306:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Fri 7/34:40 pm
BOS
- ORD
1 stop5h 50m
JetBlue
Deal found 6/5![JetBlue logo]()
$184
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/36:00 am
ORD
- BOS
1 stop7h 51m
JetBlue
Sat 7/44:43 pm
BOS
- ORD
1 stop5h 47m
JetBlue
Deal found 6/8![JetBlue logo]()
$185
This Priceline deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/76:00 am
ORD
- ACK
1 stop8h 24m
JetBlue
Tue 7/1412:02 pm
ACK
- ORD
1 stop6h 32m
JetBlue
Deal found 6/8![JetBlue logo]()
$158
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/99:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Thu 7/98:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/8![United Airlines logo]()
$181
This Priceline deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/149:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Sat 7/185:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/9![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 7/156:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Sat 7/184:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/5![JetBlue logo]()
$183
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/186:00 am
ORD
- ACK
1 stop8h 19m
JetBlue
Sat 7/2512:03 pm
ACK
- ORD
1 stop5h 13m
JetBlue
Deal found 6/7![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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 7/219:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Wed 7/225:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 6/7![JetBlue logo]()
$158
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/216:00 am
ORD
- HYA
1 stop8h 13m
JetBlue
Wed 7/224:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 6/9![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/227:25 pm
ORD
- BOS
Nonstop2h 35m
Delta
Sun 7/267:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/9![Delta logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/2210:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/9![JetBlue logo]()
$186
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 10, 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 10, 2026.
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Deal found 6/5![JetBlue logo]()
$79
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/46:00 am
ORD
- ACK
1 stop6h 25m
JetBlue
Deal found 6/8![JetBlue logo]()
$79
This JetBlue deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/49:40 am
ORD
- HYA
1 stop4h 33m
JetBlue
Deal found 6/10![JetBlue logo]()
$85
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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
- ACK
1 stop8h 24m
JetBlue
Deal found 6/7![JetBlue logo]()
$85
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/46:00 am
ORD
- HYA
1 stop7h 42m
JetBlue
Deal found 6/8![JetBlue logo]()
$90
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” 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 23m
JetBlue
Deal found 6/5![JetBlue logo]()
$93
This Super.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/2710:05 am
ORD
- BOS
1 stop6h 17m
JetBlue
Deal found 6/9![JetBlue logo]()
$95
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/39:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Deal found 6/8![JetBlue logo]()
$95
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/237:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 6/9![Delta logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/216:00 am
ORD
- BOS
1 stop7h 41m
JetBlue
Deal found 6/9![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” 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 8/128:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 6/6![JetBlue logo]()
$98
This JetBlue deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” 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.
Sun 8/96:00 am
ORD
- HYA
1 stop8h 11m
JetBlue
Deal found 6/7![JetBlue logo]()
$98
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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $158 (JetBlue) |
One-way from | $79 (JetBlue) |
Popular in | April |
Cheapest in | January |
Average price | $255 |
Good round-trip deal | $220 or less |
Good one-way deal | $126 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 10, 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
Wed 7/15
9:40 am-4:10 pm
1 stop5h 30m
West Tisbury Martha's Vineyard
Sat 7/18
5:26 pm-9:58 pm
1 stop5h 32m
$158
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Tue 8/25
9:39 am-4:09 pm
1 stop5h 30m
West Tisbury Martha's Vineyard
Wed 8/26
5:05 pm-9:55 pm
1 stop5h 50m
$158
ChicagoHyannis
ORD - HYA
ORDHYA
Chicago O'Hare Intl
Tue 7/21
6:00 am-3:13 pm
1 stop8h 13m
Hyannis Barnstable
Wed 7/22
4:53 pm-9:58 pm
1 stop6h 05m
$167
ChicagoNantucket
ORD - ACK
ORDACK
Chicago O'Hare Intl
Sat 7/18
6:00 am-3:19 pm
1 stop8h 19m
Nantucket Memorial
Sat 7/25
12:03 pm-4:16 pm
1 stop5h 13m
$174
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Thu 8/27
9:39 am-4:09 pm
1 stop5h 30m
West Tisbury Martha's Vineyard
Mon 8/31
5:05 pm-9:55 pm
1 stop5h 50m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 7/22
7:25 pm-11:00 pm
Nonstop2h 35m
Boston Logan Intl
Sun 7/26
7:30 am-9:26 am
Nonstop2h 56m
$183
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 8/19
9:39 am-5:15 pm
1 stop6h 36m
Boston Logan Intl
Wed 8/26
8:10 am-10:06 am
Nonstop2h 56m
$183
ChicagoHyannis
ORD - HYA
ORDHYA
Chicago O'Hare Intl
Wed 7/15
6:00 am-3:13 pm
1 stop8h 13m
Hyannis Barnstable
Sat 7/18
4:53 pm-9:58 pm
1 stop6h 05m
$183
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
9:39 am-5:15 pm
1 stop6h 36m
Boston Logan Intl
Wed 8/26
12:42 pm-5:20 pm
1 stop5h 38m
$185
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 7/30
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Sun 8/2
6:00 am-7:58 am
Nonstop2h 58m
$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-MVY
ORD-BOS
ORD-HYA
ORD-ACK
ORD-EWB
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-BOS
ORD-HYA
ORD-ACK
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $65). Flying from Chicago O'Hare Intl Airport to Massachusetts in February is currently the most expensive (average of $419). 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 10, 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 10, 2026.
The most flights from ORD to USMA are scheduled on a Monday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 10, 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
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for O'Hare Intl to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Massachusetts by cabin class
Find flights from O'Hare Intl to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on June 10, 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 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$362 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$85 | Average$308 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$126 | Average$266 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$349 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |