$70+ Cheap flights from O'Hare Intl (ORD) to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 29 — May 61
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to MassachusettsExplore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.
Explore the most affordable flight options available from O'Hare Intl to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.
This Delta deal was found by Cheapflights users on 3/26. 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 4/226:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Wed 4/294:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 3/26![Delta logo]()
$135
This SmartFares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:49 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/29![JetBlue logo]()
$137
This Priceline deal was found by Cheapflights users on 3/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:21 am
ORD
- BOS
Nonstop2h 28m
Multiple Airlines
Wed 5/612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$138
This Frontier deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Deal found 3/27![Frontier logo]()
$140
This flygcity.se deal was found by Cheapflights users on 3/25. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sat 5/166:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 3/25![JetBlue logo]()
$141
This Expedia deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:41 am
ORD
- BOS
Nonstop2h 26m
Multiple Airlines
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$143
This Super.com deal was found by Cheapflights users on 3/25. 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 5/278:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Thu 5/286:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/25![JetBlue logo]()
$144
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/2111:17 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Thu 4/239:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/26![United Airlines logo]()
$145
This Delta deal was found by Cheapflights users on 3/26. 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 4/215:53 pm
ORD
- BOS
1 stop6h 22m
Delta
Wed 4/227:10 am
BOS
- ORD
Nonstop3h 05m
Delta
Deal found 3/26![Delta logo]()
$146
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/106:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Tue 4/1411:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/26![United Airlines logo]()
$147
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 5/208:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Wed 5/275:05 am
BOS
- ORD
Nonstop2h 57m
American Airlines
Deal found 3/25![American Airlines logo]()
$148
This Priceline deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Thu 4/237:00 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$149
Best flights from O'Hare Intl to MassachusettsDiscover carefully curated flight deals from O'Hare Intl to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 30, 2026.
Discover carefully curated flight deals from O'Hare Intl to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 30, 2026.
This Delta deal was found by Cheapflights users on 3/26. 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 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Wed 4/159:25 am
BOS
- ORD
1 stop4h 20m
Delta
Deal found 3/26![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Fri 4/246:48 pm
BOS
- ORD
Nonstop3h 02m
United Airlines
Deal found 3/24![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Mon 5/48:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Deal found 3/26![Southwest logo]()
$175
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 4/88:50 pm
ORD
- ORH
1 stop16h 24m
American Airlines
Sun 4/122:39 pm
ORH
- ORD
1 stop7h 56m
American Airlines
Deal found 3/25![American Airlines logo]()
$212
This KAYAK deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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.
Fri 6/196:00 am
ORD
- ACK
1 stop8h 23m
JetBlue
Tue 6/234:20 pm
ACK
- ORD
1 stop5h 24m
JetBlue
Deal found 3/28![JetBlue logo]()
$284
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Mon 4/134:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 3/29![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/106:01 pm
ORD
- BOS
1 stop4h 58m
United Airlines
Tue 4/1411:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/26![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 3/25. 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.
Fri 5/297:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Sat 6/65:40 am
BOS
- ORD
1 stop5h 49m
Delta
Deal found 3/25![Delta logo]()
$169
This United Airlines deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/101:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Mon 4/135:25 pm
BOS
- ORD
1 stop5h 08m
United Airlines
Deal found 3/24![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Sat 5/25:25 am
BOS
- ORD
2 stops11h 05m
Southwest
Deal found 3/28![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 3/25. 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.
Thu 4/306:00 am
ORD
- BOS
1 stop4h 25m
Delta
Mon 5/46:00 pm
BOS
- ORD
1 stop5h 15m
Delta
Deal found 3/25![Delta logo]()
$182
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 6/59:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 6/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 3/29![United Airlines logo]()
$199
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2910:45 am
ORD
- ORH
1 stop4h 58m
Delta
Tue 5/55:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/28![Delta logo]()
$192
This American Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 6/137:00 am
ORD
- ACK
1 stop6h 02m
American Airlines
Sat 6/2012:16 pm
ACK
- ORD
Nonstop3h 08m
American Airlines
Deal found 3/29![American Airlines logo]()
$272
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 5/237:40 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 5/256:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/28![United Airlines logo]()
$205
This Priceline deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 5/97:20 am
ORD
- HYA
1 stop9h 00m
Multiple Airlines
Sat 5/1612:07 pm
HYA
- ORD
1 stop9h 46m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$555
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:45 am
ORD
- ORH
1 stop4h 58m
Delta
Wed 4/225:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/27![Delta logo]()
$192
This KAYAK deal was found by Cheapflights users on 3/26. 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 KAYAK 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 23m
JetBlue
Sat 6/2012:02 pm
ACK
- ORD
1 stop4h 59m
JetBlue
Deal found 3/26![JetBlue logo]()
$284
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:35 pm
ORD
- ALB
1 stop8h 15m
Southwest
Mon 5/257:10 am
ALB
- ORD
1 stop9h 55m
Southwest
Deal found 3/26![Southwest logo]()
$305
This KAYAK deal was found by Cheapflights users on 3/26. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:33 am
ORD
- ACK
1 stop4h 50m
JetBlue
Sat 6/274:20 pm
ACK
- ORD
1 stop5h 24m
JetBlue
Deal found 3/26![JetBlue logo]()
$308
This Delta deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” 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 5/227:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Sun 5/247:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 3/29![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:05 pm
ORD
- ALB
2 stops15h 55m
Southwest
Mon 5/187:10 am
ALB
- ORD
1 stop9h 55m
Southwest
Deal found 3/25![Southwest logo]()
$324
This United Airlines deal was found by Cheapflights users on 3/26. 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.
Thu 5/149:38 pm
ORD
- ALB
Nonstop2h 10m
United Airlines
Mon 5/186:00 am
ALB
- ORD
Nonstop2h 34m
United Airlines
Deal found 3/26![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” 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 5/16:00 am
ORD
- ORH
1 stop9h 43m
Delta
Tue 5/55:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/28![Delta logo]()
$249
This American Airlines deal was found by Cheapflights users on 3/25. 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 6/208:00 am
ORD
- ACK
Nonstop2h 46m
American Airlines
Sat 6/273:12 pm
ACK
- ORD
1 stop7h 25m
American Airlines
Deal found 3/25![American Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:52 am
ORD
- ORH
2 stops6h 51m
Delta
Sun 5/35:24 pm
ORH
- ORD
1 stop15h 32m
Delta
Deal found 3/28![Delta logo]()
$259
This United Airlines deal was found by Cheapflights users on 3/26. 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 6/212:15 pm
ORD
- ALB
Nonstop2h 11m
United Airlines
Mon 6/84:43 pm
ALB
- ORD
Nonstop2h 36m
United Airlines
Deal found 3/26![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 3/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:40 pm
ORD
- ALB
2 stops7h 35m
Southwest
Sun 5/106:35 am
ALB
- ORD
1 stop10h 30m
Southwest
Deal found 3/25![Southwest logo]()
$394
This Expedia deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:58 am
ORD
- HYA
1 stop7h 22m
Multiple Airlines
Tue 4/1412:07 pm
HYA
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$555
This Delta deal was found by Cheapflights users on 3/26. 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 6/26:00 am
ORD
- ALB
1 stop6h 33m
Delta
Mon 6/86:00 am
ALB
- ORD
1 stop7h 36m
Delta
Deal found 3/26![Delta logo]()
$265
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated March 30, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated March 30, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 3/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Tue 4/147:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/24![JetBlue logo]()
$144
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 4/88:05 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Wed 4/83:16 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/25![American Airlines logo]()
$153
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/106:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Tue 4/1411:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/26![United Airlines logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/118:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Mon 4/136:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/27![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/25. 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.
Wed 4/158:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Wed 4/224:34 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 3/25![American Airlines logo]()
$148
This Frontier deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Frontier
Deal found 3/27![Frontier logo]()
$140
This Expedia deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:41 am
ORD
- BOS
Nonstop2h 26m
Multiple Airlines
Mon 4/2712:31 pm
BOS
- ORD
1 stop11h 30m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$143
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/2111:17 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Thu 4/239:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/26![United Airlines logo]()
$145
This United Airlines deal was found by Cheapflights users on 3/26. 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 4/216:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Fri 4/247:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/26![United Airlines logo]()
$146
This Priceline deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Thu 4/237:00 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$149
This Delta deal was found by Cheapflights users on 3/26. 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 4/226:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Wed 4/294:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 3/26![Delta logo]()
$135
This SmartFares deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:49 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/29![JetBlue logo]()
$137
One-way flights from O'Hare Intl to MassachusettsSearch for one-way flight options from O'Hare Intl to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
Search for one-way flight options from O'Hare Intl to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 30, 2026.
This Expedia deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Deal found 3/28![Frontier logo]()
$70
This Priceline deal was found by Cheapflights users on 3/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:50 am
ORD
- BDL
1 stop7h 59m
Frontier
Deal found 3/26![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 3/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:08 pm
ORD
- BOS
1 stop6h 23m
Frontier
Deal found 3/26![Frontier logo]()
$71
This Flysmarter deal was found by Cheapflights users on 3/26. 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 Flysmarter 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
Deal found 3/26![JetBlue logo]()
$75
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 3/25![Frontier logo]()
$76
This Jettzy deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:16 pm
ORD
- BOS
1 stop22h 31m
Frontier
Deal found 3/27![Frontier logo]()
$77
This Delta deal was found by Cheapflights users on 3/25. 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.
Thu 4/166:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/25![Delta logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:07 am
ORD
- BDL
1 stop26h 42m
Frontier
Deal found 3/25![Frontier logo]()
$78
This JetBlue deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” 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 31m
JetBlue
Deal found 3/27![JetBlue logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:07 am
ORD
- BDL
1 stop26h 42m
Frontier
Deal found 3/25![Frontier logo]()
$80
This Super.com deal was found by Cheapflights users on 3/26. 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.
Mon 4/139:06 am
ORD
- BOS
1 stop6h 48m
Spirit Airlines
Deal found 3/26![Spirit Airlines logo]()
$81
This Super.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/49:06 am
ORD
- BOS
1 stop8h 03m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$82
Find flight deals from O'Hare Intl to Massachusetts
Keep the following information in mind while searching for O'Hare Intl to Massachusetts flight deals. Data was last updated March 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $135 (Delta) |
One-way from | $70 (Expedia) |
Popular in | April |
Cheapest in | January |
Average price | $225 |
Good round-trip deal | $179 or less |
Good one-way deal | $128 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 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 4/11
7:00 am-10:25 am
Nonstop2h 25m
Boston Logan Intl
Wed 4/15
9:25 am-12:45 pm
1 stop4h 20m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 4/19
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Fri 4/24
6:48 pm-8:50 pm
Nonstop3h 02m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 4/11
7:00 am-10:25 am
Nonstop2h 25m
Boston Logan Intl
Mon 4/13
4:55 pm-6:59 pm
Nonstop3h 04m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 4/10
6:01 pm-11:59 pm
1 stop4h 58m
Boston Logan Intl
Tue 4/14
11:00 am-12:59 pm
Nonstop2h 59m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/29
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Sat 6/6
5:40 am-10:29 am
1 stop5h 49m
$169
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/30
2:40 pm-11:15 pm
1 stop7h 35m
Boston Logan Intl
Mon 5/4
8:25 am-12:50 pm
1 stop5h 25m
$175
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/30
6:00 am-11:25 am
1 stop4h 25m
Boston Logan Intl
Mon 5/4
6:00 pm-10:15 pm
1 stop5h 15m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 4/10
1:55 pm-5:26 pm
Nonstop2h 31m
Boston Logan Intl
Mon 4/13
5:25 pm-9:33 pm
1 stop5h 08m
$187
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Wed 4/29
10:45 am-4:43 pm
1 stop4h 58m
Worcester
Tue 5/5
5:24 pm-10:15 pm
1 stop5h 51m
$192
ChicagoWorcester
ORD - ORH
ORDORH
Chicago O'Hare Intl
Mon 4/20
10:45 am-4:43 pm
1 stop4h 58m
Worcester
Wed 4/22
5:24 pm-10:15 pm
1 stop5h 51m
$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-BDL
ORD-ORH
ORD-MVY
ORD-HYA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Massachusetts
ORD-USMA
ORD-BOS
ORD-BDL
ORD-ORH
ORD-MVY
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Massachusetts (average of $91). Flying from Chicago O'Hare Intl Airport to Massachusetts in January is currently the most expensive (average of $117). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to MA?
Find hourly flight availability from O'Hare Intl to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 30, 2026.
It’s optimal to fly from Chicago O'Hare Intl Airport to Massachusetts in the evening. By choosing this option you can save up to 50% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Massachusetts. Price data was last updated on September 7, 2025.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Massachusetts flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago O'Hare Intl Airport to Massachusetts
Explore weekly flight availability from O'Hare Intl to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 30, 2026.
The most flights from ORD to USMA are scheduled on a Sunday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Massachusetts?
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated March 30, 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.
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Comfort
8.0
Entertainment
7.5
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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Alternative routes for O'Hare Intl to Massachusetts
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Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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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 March 30, 2026.
Popular flight searches
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O'Hare Intl to Massachusetts flights
Consider these flights traveling from O'Hare Intl to Massachusetts.
Top 6 airlines flying from O'Hare Intl to Massachusetts
Discover the top 6 airlines that operate flights from O'Hare Intl to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$366 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$254 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$439 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$247 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |