$84+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 9 — Aug 161
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to MassachusettsExplore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 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 July 10, 2026.
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Wed 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Mon 8/177:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/9![United Airlines logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 7/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/8![JetBlue logo]()
$169
This United Airlines deal was found by Cheapflights users on 7/8. 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 7/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 7/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/8![United Airlines logo]()
$170
This JetBlue deal was found by Cheapflights users on 7/8. 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 8/151:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/8![JetBlue logo]()
$171
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Sat 8/156:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Tue 8/186:00 pm
BOS
- ORD
1 stop5h 15m
United Airlines
Deal found 7/6![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 7/6. 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 9/54:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Wed 9/98:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/6![Delta logo]()
$173
This Super.com deal was found by Cheapflights users on 7/8. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:38 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sun 9/206:55 am
BOS
- ORD
Nonstop2h 51m
JetBlue
Deal found 7/8![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/19:35 am
ORD
- BOS
1 stop7h 17m
JetBlue
Sat 9/511:00 am
BOS
- ORD
Nonstop2h 54m
JetBlue
Deal found 7/6![JetBlue logo]()
$175
This United Airlines deal was found by Cheapflights users on 7/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Wed 8/57:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/10![United Airlines logo]()
$176
This American Airlines deal was found by Cheapflights users on 7/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:50 am
ORD
- BOS
Nonstop2h 39m
American Airlines
Sun 9/208:33 am
BOS
- ORD
Nonstop3h 02m
American Airlines
Deal found 7/8![American Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/9. 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 7/257:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 8/38:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/9![United Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Fri 7/249:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/289:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Deal found 7/6![United Airlines logo]()
$179
Best flights from O'Hare Intl to MassachusettsDiscover carefully curated flight deals from O'Hare Intl to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 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 July 10, 2026.
This Delta deal was found by Cheapflights users on 7/9. 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 9/237:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Mon 9/288:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/9![Delta logo]()
$169
This JetBlue deal was found by Cheapflights users on 7/8. 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 8/151:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Tue 8/182:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 7/8![JetBlue logo]()
$171
This American Airlines deal was found by Cheapflights users on 7/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:00 am
ORD
- ORH
1 stop10h 51m
American Airlines
Sun 8/25:16 pm
ORH
- ORD
1 stop8h 13m
American Airlines
Deal found 7/8![American Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Mon 9/286:24 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Thu 10/15:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/6![United Airlines logo]()
$225
This JetBlue deal was found by Cheapflights users on 7/6. 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 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 7/6![JetBlue logo]()
$175
This Delta deal was found by Cheapflights users on 7/8. 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.
Tue 8/1110:30 am
ORD
- ORH
1 stop5h 30m
Delta
Wed 8/195:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/8![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 7/5. 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 8/116:45 am
ORD
- ORH
1 stop9h 13m
American Airlines
Wed 8/195:23 pm
ORH
- ORD
1 stop16h 42m
American Airlines
Deal found 7/5![American Airlines logo]()
$192
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Wed 9/95:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/6![JetBlue logo]()
$181
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:20 pm
ORD
- BOS
Nonstop2h 56m
JetBlue
Fri 9/115:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/6![JetBlue logo]()
$182
This Delta deal was found by Cheapflights users on 7/8. 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.
Wed 8/59:30 am
ORD
- ORH
1 stop6h 30m
Delta
Tue 8/115:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/8![Delta logo]()
$208
This United Airlines deal was found by Cheapflights users on 7/5. 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.
Sun 7/196:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Wed 7/225:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 7/5![United Airlines logo]()
$234
This JetBlue deal was found by Cheapflights users on 7/7. 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.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/7![JetBlue logo]()
$183
This KAYAK deal was found by Cheapflights users on 7/6. 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 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 8/3112:23 pm
EWB
- ORD
2 stops10h 35m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$508
This United Airlines deal was found by Cheapflights users on 7/8. 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 10/86:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Tue 10/137:01 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/8![United Airlines logo]()
$239
This Delta deal was found by Cheapflights users on 7/5. 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.
Tue 8/48:48 am
ORD
- ORH
2 stops7h 12m
Delta
Wed 8/55:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/5![Delta logo]()
$218
This Priceline deal was found by Cheapflights users on 7/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Wed 8/265:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 7/10![JetBlue logo]()
$190
This American Airlines deal was found by Cheapflights users on 7/5. 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.
Sun 8/26:37 am
ORD
- ORH
1 stop9h 14m
American Airlines
Wed 8/55:23 pm
ORH
- ORD
1 stop7h 21m
American Airlines
Deal found 7/5![American Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 7/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:30 am
ORD
- MVY
2 stops8h 38m
Delta
Wed 8/261:18 pm
MVY
- ORD
2 stops8h 37m
Delta
Deal found 7/10![Delta logo]()
$228
This JetBlue deal was found by Cheapflights users on 7/9. 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.
Sat 8/299:40 am
ORD
- ACK
1 stop4h 44m
JetBlue
Wed 9/212:02 pm
ACK
- ORD
1 stop6h 33m
JetBlue
Deal found 7/9![JetBlue logo]()
$190
This American Airlines deal was found by Cheapflights users on 7/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:00 am
ORD
- ORH
1 stop10h 58m
American Airlines
Sun 8/95:23 pm
ORH
- ORD
2 stops13h 51m
American Airlines
Deal found 7/10![American Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 7/5. 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 8/1511:59 am
ORD
- ACK
Nonstop2h 50m
United Airlines
Wed 8/194:15 pm
ACK
- ORD
1 stop5h 45m
United Airlines
Deal found 7/5![United Airlines logo]()
$288
This JetBlue deal was found by Cheapflights users on 7/9. 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.
Fri 7/315:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Wed 8/54:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/9![JetBlue logo]()
$201
This Delta deal was found by Cheapflights users on 7/7. 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 10/77:30 am
ORD
- BOS
Nonstop2h 36m
Delta
Mon 10/127:40 pm
BOS
- ORD
Nonstop2h 48m
Delta
Deal found 7/7![Delta logo]()
$245
This JetBlue deal was found by Cheapflights users on 7/9. 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.
Thu 8/69:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Wed 8/124:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/9![JetBlue logo]()
$201
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Fri 8/1411:06 am
ORD
- BDL
Nonstop2h 23m
United Airlines
Mon 8/177:55 pm
BDL
- ORD
1 stop4h 45m
United Airlines
Deal found 7/8![United Airlines logo]()
$303
This United Airlines deal was found by Cheapflights users on 7/9. 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 8/611:03 am
ORD
- BDL
Nonstop2h 21m
United Airlines
Thu 8/136:00 am
BDL
- ORD
Nonstop2h 46m
United Airlines
Deal found 7/9![United Airlines logo]()
$307
This JetBlue deal was found by Cheapflights users on 7/7. 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 8/219:40 am
ORD
- MVY
1 stop5h 30m
JetBlue
Fri 8/285:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 7/7![JetBlue logo]()
$218
This Delta deal was found by Cheapflights users on 7/6. 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.
Thu 8/276:40 am
ORD
- ORH
2 stops9h 20m
Delta
Mon 8/315:40 pm
ORH
- ORD
1 stop5h 44m
Delta
Deal found 7/6![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 7/7. 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.
Tue 9/13:00 pm
ORD
- BDL
Nonstop2h 20m
United Airlines
Wed 9/23:01 pm
BDL
- ORD
1 stop4h 36m
United Airlines
Deal found 7/7![United Airlines logo]()
$317
This JetBlue deal was found by Cheapflights users on 7/9. 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.
Sat 8/299:40 am
ORD
- MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
- ORD
1 stop5h 53m
JetBlue
Deal found 7/9![JetBlue logo]()
$218
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated July 10, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated July 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Fri 7/249:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/289:50 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Deal found 7/6![United Airlines logo]()
$179
This United Airlines deal was found by Cheapflights users on 7/8. 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 7/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 7/296:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/8![United Airlines logo]()
$170
This United Airlines deal was found by Cheapflights users on 7/9. 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 7/257:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 8/38:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/9![United Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 7/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Wed 8/57:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/10![United Airlines logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 7/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:25 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/1212:44 pm
BOS
- ORD
1 stop5h 51m
JetBlue
Deal found 7/7![JetBlue logo]()
$173
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Sun 8/96:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Thu 8/135:45 am
BOS
- ORD
1 stop4h 53m
United Airlines
Deal found 7/9![United Airlines logo]()
$180
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Wed 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Mon 8/177:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 7/9![United Airlines logo]()
$168
This JetBlue deal was found by Cheapflights users on 7/8. 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 8/155:27 pm
ORD
- BOS
1 stop5h 32m
JetBlue
Thu 8/205:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 7/8![JetBlue logo]()
$171
This United Airlines deal was found by Cheapflights users on 7/6. 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.
Sat 8/156:15 am
ORD
- BOS
Nonstop2h 21m
United Airlines
Tue 8/186:00 pm
BOS
- ORD
1 stop5h 15m
United Airlines
Deal found 7/6![United Airlines logo]()
$172
This SmartFares deal was found by Cheapflights users on 7/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/265:21 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 7/7![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 7/8. 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 8/199:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Tue 8/255:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 7/8![JetBlue logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 7/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/235:01 am
BOS
- ORD
1 stop4h 51m
JetBlue
Deal found 7/8![JetBlue logo]()
$169
One-way flights from O'Hare Intl to MassachusettsSearch for one-way flight options from O'Hare Intl to Massachusetts. Find affordable one-way fares based on user searches. Data last updated July 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 July 10, 2026.
This American Airlines deal was found by Cheapflights users on 7/9. 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.
Sat 9/512:29 pm
ORD
- MVY
Nonstop2h 44m
American Airlines
Deal found 7/9![American Airlines logo]()
$84
This Super.com deal was found by Cheapflights users on 7/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/10![JetBlue logo]()
$91
This Super.com deal was found by Cheapflights users on 7/9. 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.
Wed 8/59:37 am
ORD
- BOS
1 stop6h 40m
JetBlue
Deal found 7/9![JetBlue logo]()
$92
This Super.com deal was found by Cheapflights users on 7/9. 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 8/226:00 am
ORD
- BOS
1 stop7h 24m
JetBlue
Deal found 7/9![JetBlue logo]()
$93
This Delta deal was found by Cheapflights users on 7/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
ORD
- MVY
1 stop5h 38m
Delta
Deal found 7/10![Delta logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 7/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/8![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 7/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/251:09 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$95
This JetBlue deal was found by Cheapflights users on 7/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:35 am
ORD
- MVY
1 stop5h 35m
JetBlue
Deal found 7/6![JetBlue logo]()
$95
This JetBlue deal was found by Cheapflights users on 7/8. 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 9/59:41 am
ORD
- ACK
1 stop4h 43m
JetBlue
Deal found 7/8![JetBlue logo]()
$95
This United Airlines deal was found by Cheapflights users on 7/8. 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 7/257:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 7/8![United Airlines logo]()
$96
This Super.com deal was found by Cheapflights users on 7/5. 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 9/158:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/5![JetBlue logo]()
$97
This United Airlines deal was found by Cheapflights users on 7/9. 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.
Tue 8/411:07 am
ORD
- BOS
1 stop5h 17m
United Airlines
Deal found 7/9![United Airlines 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 July 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $168 (United Airlines) |
One-way from | $84 (American Airlines) |
Popular in | April |
Cheapest in | January |
Average price | $243 |
Good round-trip deal | $215 or less |
Good one-way deal | $132 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 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
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/23
7:30 pm-11:09 pm
Nonstop2h 39m
Boston Logan Intl
Mon 9/28
8:50 pm-10:32 pm
Nonstop2h 42m
$169
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/15
1:55 pm-5:31 pm
Nonstop2h 36m
Boston Logan Intl
Tue 8/18
2:45 pm-9:58 pm
1 stop8h 13m
$171
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/25
6:00 am-2:43 pm
1 stop7h 43m
Boston Logan Intl
Wed 8/26
8:15 am-10:11 am
Nonstop2h 56m
$175
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 9/6
10:56 am-2:23 pm
Nonstop2h 27m
Boston Logan Intl
Wed 9/9
5:00 pm-7:22 pm
Nonstop3h 22m
$181
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/2
8:20 pm-12:16 am
Nonstop2h 56m
Boston Logan Intl
Fri 9/11
5:00 pm-7:22 pm
Nonstop3h 22m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/20
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Sun 8/23
5:01 am-8:52 am
1 stop4h 51m
$183
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Wed 8/19
9:35 am-4:10 pm
1 stop5h 35m
West Tisbury Martha's Vineyard
Wed 8/26
5:26 pm-9:58 pm
1 stop5h 32m
$190
ChicagoNantucket
ORD - ACK
ORDACK
Chicago O'Hare Intl
Sat 8/29
9:40 am-3:24 pm
1 stop4h 44m
Nantucket Memorial
Wed 9/2
12:02 pm-5:35 pm
1 stop6h 33m
$190
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Thu 7/30
5:00 am-4:51 pm
1 stop10h 51m
Worcester
Sun 8/2
5:16 pm-12:29 am
1 stop8h 13m
$192
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Tue 8/11
10:30 am-5:00 pm
1 stop5h 30m
Worcester
Wed 8/19
5:40 pm-10:24 pm
1 stop5h 44m
$192
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-MVY
ORD-ORH
ORD-EWB
ORD-ACK
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-MVY
ORD-ORH
ORD-EWB
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 July 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 50% on the cost of your flight, compared to a flight in the morning.
Weekly flight availability from Chicago O'Hare Intl Airport to Massachusetts
Explore weekly flight availability from O'Hare Intl to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 10, 2026.
The most flights from ORD to USMA are scheduled on a Friday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
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 afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated July 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
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Food
7.0
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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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on July 10, 2026.
Popular flight searches
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O'Hare Intl to Massachusetts flights
Consider these flights traveling from O'Hare Intl to Massachusetts.
Top 5 airlines flying from O'Hare Intl to Massachusetts
Discover the top 5 airlines that operate flights from O'Hare Intl to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$285 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$81 | Average$309 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$206 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$127 | Average$274 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$447 | FlexibilityNo cancel fee | On-time71% |