$89+ Cheap flights from O'Hare Intl (ORD) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Jun 26 — Jul 31
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 May 27, 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 May 27, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/26![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Wed 6/108:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/25![United Airlines logo]()
$187
This Flysmarter deal was found by Cheapflights users on 5/22. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sat 6/1311:05 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Deal found 5/26![JetBlue logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/86:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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.
Fri 6/1910:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Fri 6/195:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/23![JetBlue logo]()
$195
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/97:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Fri 6/128:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/26![United Airlines logo]()
$196
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
Wed 7/88:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 5/26![Delta logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
Mon 7/135:10 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/26![JetBlue logo]()
$200
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
Sun 7/57:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 5/26![Delta logo]()
$201
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:54 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Sun 7/55:10 am
BOS
- ORD
Nonstop2h 54m
American Airlines
Deal found 5/24![American Airlines logo]()
$202
This Delta deal was found by Cheapflights users on 5/22. 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.
Tue 9/17:00 am
ORD
- ORH
1 stop6h 39m
Delta
Mon 9/73:18 pm
ORH
- ORD
1 stop5h 04m
Delta
Deal found 5/22![Delta logo]()
$220
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 May 27, 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 May 27, 2026.
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/184:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Tue 7/288:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 5/26![Delta logo]()
$197
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Sat 8/19:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 8/96:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/22![United Airlines logo]()
$201
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 8/76:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Sun 8/96:14 am
BOS
- ORD
Nonstop3h 06m
American Airlines
Deal found 5/26![American Airlines logo]()
$205
This JetBlue deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/135:27 pm
ORD
- BDL
1 stop5h 32m
JetBlue
Thu 7/165:07 pm
BDL
- ORD
1 stop7h 37m
JetBlue
Deal found 5/26![JetBlue logo]()
$384
This Delta deal was found by Cheapflights users on 5/23. 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 6/207:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Mon 6/228:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 5/23![Delta logo]()
$205
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Mon 6/299:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Thu 7/210:35 am
BOS
- ORD
Nonstop2h 53m
United Airlines
Deal found 5/22![United Airlines logo]()
$205
This Sun Country Air deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:09 pm
ORD
- BDL
1 stop13h 48m
Sun Country Air
Thu 6/2511:26 am
BDL
- ORD
1 stop9h 18m
Sun Country Air
Deal found 5/26![Sun Country Air logo]()
$445
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Tue 6/238:15 am
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/25![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/1510:30 am
ORD
- ORH
1 stop5h 30m
Delta
Wed 7/225:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 5/26![Delta logo]()
$220
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/109:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/145:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/26![United Airlines logo]()
$211
This American Airlines deal was found by Cheapflights users on 5/23. 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 8/276:34 am
ORD
- ORH
1 stop9h 24m
American Airlines
Thu 9/35:23 pm
ORH
- ORD
1 stop16h 46m
American Airlines
Deal found 5/23![American Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 5/24. 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.
Fri 7/310:35 am
ORD
- ORH
1 stop5h 28m
Delta
Mon 7/65:43 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 5/24![Delta logo]()
$220
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 8/96:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 5/22![United Airlines logo]()
$215
This American Airlines deal was found by Cheapflights users on 5/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:52 am
ORD
- HYA
1 stop6h 45m
American Airlines
Sat 6/276:07 pm
HYA
- ORD
1 stop6h 23m
American Airlines
Deal found 5/25![American Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
Tue 7/215:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 5/26![Delta logo]()
$220
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/1510:30 am
ORD
- ORH
1 stop5h 30m
Delta
Tue 7/215:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 5/26![Delta logo]()
$220
This American Airlines deal was found by Cheapflights users on 5/23. 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.
Wed 8/266:00 am
ORD
- ORH
2 stops9h 58m
American Airlines
Thu 9/35:23 pm
ORH
- ORD
1 stop16h 46m
American Airlines
Deal found 5/23![American Airlines logo]()
$271
This United Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/49:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 6/105:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/22![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 5/25. 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.
Mon 6/17:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Mon 6/88:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 5/25![Delta logo]()
$227
This Priceline deal was found by Cheapflights users on 5/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:56 am
ORD
- PVC
1 stop8h 12m
Multiple Airlines
Fri 7/2411:28 am
PVC
- ORD
1 stop8h 47m
Multiple Airlines
Deal found 5/22![Multiple Airlines logo]()
$733
This United Airlines deal was found by Cheapflights users on 5/23. 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.
Sun 6/286:05 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Wed 7/15:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 5/23![United Airlines logo]()
$236
This JetBlue deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/136:00 am
ORD
- ACK
1 stop8h 34m
JetBlue
Sat 6/2012:18 pm
ACK
- ORD
1 stop4h 58m
JetBlue
Deal found 5/23![JetBlue logo]()
$392
This Delta deal was found by Cheapflights users on 5/25. 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.
Tue 6/235:30 am
ORD
- ORH
2 stops10h 33m
Delta
Fri 7/35:43 pm
ORH
- ORD
1 stop6h 05m
Delta
Deal found 5/25![Delta logo]()
$230
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:00 am
ORD
- HYA
1 stop6h 15m
American Airlines
Tue 7/216:22 pm
HYA
- ORD
1 stop6h 08m
American Airlines
Deal found 5/24![American Airlines logo]()
$312
This JetBlue deal was found by Cheapflights users on 5/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:40 am
ORD
- HYA
1 stop4h 33m
JetBlue
Wed 7/224:53 pm
HYA
- ORD
1 stop6h 05m
JetBlue
Deal found 5/25![JetBlue logo]()
$413
This Delta deal was found by Cheapflights users on 5/22. 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.
Tue 9/17:10 am
ORD
- ORH
2 stops6h 29m
Delta
Wed 9/93:18 pm
ORH
- ORD
2 stops9h 39m
Delta
Deal found 5/22![Delta logo]()
$235
This JetBlue deal was found by Cheapflights users on 5/22. 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 9/19:39 am
ORD
- HYA
1 stop4h 32m
JetBlue
Tue 9/84:23 pm
HYA
- ORD
1 stop6h 32m
JetBlue
Deal found 5/22![JetBlue logo]()
$413
This Delta deal was found by Cheapflights users on 5/25. 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 6/247:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Sun 6/287:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 5/25![Delta logo]()
$237
This JetBlue deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
Tue 7/215:26 pm
MVY
- ORD
1 stop5h 32m
JetBlue
Deal found 5/26![JetBlue logo]()
$416
This Delta deal was found by Cheapflights users on 5/25. 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.
Tue 6/2310:35 am
ORD
- ORH
1 stop5h 28m
Delta
Mon 6/295:43 pm
ORH
- ORD
1 stop6h 05m
Delta
Deal found 5/25![Delta logo]()
$246
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated May 27, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated May 27, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 5/22. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 9/305:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 5/22![JetBlue logo]()
$204
This Flysmarter deal was found by Cheapflights users on 5/22. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$189
This Cheapflightsfares deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/86:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/22![JetBlue logo]()
$192
This American Airlines deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:04 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Sun 6/77:00 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Deal found 5/22![American Airlines logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Wed 6/106:00 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 5/26![JetBlue logo]()
$182
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/93:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Wed 6/108:20 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 5/25![United Airlines logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sat 6/1311:05 am
BOS
- ORD
Nonstop2h 55m
JetBlue
Deal found 5/26![JetBlue logo]()
$191
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/93:15 pm
ORD
- BOS
Nonstop2h 38m
Delta
Fri 6/128:45 pm
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 5/26![Delta logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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.
Fri 6/1910:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Fri 6/195:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/23![JetBlue logo]()
$195
This Delta deal was found by Cheapflights users on 5/25. 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.
Tue 6/2310:35 am
ORD
- ORH
1 stop5h 28m
Delta
Tue 6/305:43 pm
ORH
- ORD
1 stop6h 05m
Delta
Deal found 5/25![Delta logo]()
$220
This United Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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
Tue 6/306:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 5/26![United Airlines logo]()
$201
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/268:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Fri 7/245:10 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 5/26![JetBlue logo]()
$200
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 May 27, 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 May 27, 2026.
This Super.com deal was found by Cheapflights users on 5/25. 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.
Wed 6/108:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 5/25![JetBlue logo]()
$89
This Super.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/98:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/26![JetBlue logo]()
$90
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/97:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/26![Delta logo]()
$94
This Super.com deal was found by Cheapflights users on 5/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/61:55 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 5/22![JetBlue logo]()
$95
This Super.com deal was found by Cheapflights users on 5/25. 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.
Tue 6/1610:56 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 5/25![JetBlue logo]()
$98
This Delta deal was found by Cheapflights users on 5/25. 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.
Sat 8/2210:28 am
ORD
- BOS
Nonstop2h 31m
Delta
Deal found 5/25![Delta logo]()
$99
This Super.com deal was found by Cheapflights users on 5/25. 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.
Fri 6/268:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/25![JetBlue logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 6/128:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 5/26![JetBlue logo]()
$102
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/137:45 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 5/25![United Airlines logo]()
$103
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:00 am
ORD
- BOS
1 stop5h 16m
United Airlines
Deal found 5/25![United Airlines logo]()
$104
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” 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 7/17:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 5/26![Delta logo]()
$109
This Delta deal was found by Cheapflights users on 5/23. 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 8/119:30 am
ORD
- ORH
1 stop6h 30m
Delta
Deal found 5/23![Delta logo]()
$119
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 May 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $182 (Cheapflightsfares) |
One-way from | $89 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $239 |
Good round-trip deal | $215 or less |
Good one-way deal | $122 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 May 27, 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
Sat 7/18
4:30 pm-8:11 pm
Nonstop2h 41m
Boston Logan Intl
Tue 7/28
8:45 pm-10:39 pm
Nonstop2h 54m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 8/1
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Sun 8/9
6:43 pm-8:40 pm
Nonstop2h 57m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/7
6:00 am-9:32 am
Nonstop2h 32m
Boston Logan Intl
Sun 8/9
6:14 am-8:20 am
Nonstop3h 06m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 6/20
7:10 am-10:46 am
Nonstop2h 36m
Boston Logan Intl
Mon 6/22
8:45 pm-10:42 pm
Nonstop2h 57m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 6/29
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Thu 7/2
10:35 am-12:28 pm
Nonstop2h 53m
$205
Quickest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 6/17
6:05 am-9:29 am
Nonstop2h 24m
Boston Logan Intl
Tue 6/23
8:15 am-10:12 am
Nonstop2h 57m
$205
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 7/10
9:41 pm-1:14 am
Nonstop2h 33m
Boston Logan Intl
Tue 7/14
5:45 am-9:36 am
1 stop4h 51m
$211
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 8/7
6:00 am-11:16 am
1 stop4h 16m
Boston Logan Intl
Sun 8/9
6:43 pm-8:40 pm
Nonstop2h 57m
$215
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Wed 7/15
10:30 am-5:00 pm
1 stop5h 30m
Worcester
Wed 7/22
5:40 pm-10:36 pm
1 stop5h 56m
$220
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Fri 7/3
10:35 am-5:03 pm
1 stop5h 28m
Worcester
Mon 7/6
5:43 pm-10:34 pm
1 stop5h 51m
$220
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from O'Hare Intl with our price prediction graph.
ORD-BOS
ORD-ORH
ORD-BDL
ORD-HYA
ORD-PVC
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Massachusetts
ORD-USMA
ORD-BOS
ORD-ORH
ORD-BDL
ORD-HYA
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 $425). 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 May 27, 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 55% 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 May 27, 2026.
The most flights from ORD to USMA are scheduled on a Tuesday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 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 May 27, 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.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on May 27, 2026.
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O'Hare Intl to Massachusetts flights
Consider these flights traveling from O'Hare Intl to Massachusetts.
Top 6 airlines flying from O'Hare Intl to Massachusetts
Discover the top 6 airlines that operate flights from O'Hare Intl to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$68 | Average$373 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$86 | Average$307 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$262 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$136 | Average$359 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |