$65+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
אפר' 1 — אפר' 81
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 מרץ 2, 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 מרץ 2, 2026.
This Delta deal was found by Cheapflights users on 2/26. 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.
ו' 5/87:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
ה' 8/207:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 2/26![Delta logo]()
$126
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ג' 3/312:10 pm
ORD
- BOS
Nonstop2h 28m
Delta
ג' 4/77:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/1![Delta logo]()
$127
This Delta deal was found by Cheapflights users on 2/26. 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.
ה' 4/306:50 am
ORD
- BOS
Nonstop2h 21m
Delta
א' 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 2/26![Delta logo]()
$128
This Expedia deal was found by Cheapflights users on 2/27. 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.
ש' 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
ד' 4/156:45 am
BOS
- ORD
1 stop7h 15m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$129
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ד' 5/63:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
ו' 5/86:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/2![United Airlines logo]()
$130
This Delta deal was found by Cheapflights users on 2/26. 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.
ג' 3/177:00 am
ORD
- BOS
Nonstop2h 25m
Delta
ה' 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/26![Delta logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 2/27. 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.
ו' 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
ב' 6/86:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/27![JetBlue logo]()
$132
This American Airlines deal was found by Cheapflights users on 2/26. 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.
ה' 4/910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
א' 4/128:03 am
BOS
- ORD
Nonstop3h 09m
American Airlines
Deal found 2/26![American Airlines logo]()
$133
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ד' 5/62:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
ש' 5/96:00 am
BOS
- ORD
2 stops10h 30m
Southwest
Deal found 3/1![Southwest logo]()
$134
This Orbitz deal was found by Cheapflights users on 2/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 4/88:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
ג' 4/146:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$135
This United Airlines deal was found by Cheapflights users on 2/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 3/117:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
ב' 3/234:30 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/27![United Airlines logo]()
$136
This JetBlue deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ד' 6/38:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
ב' 6/86:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/2![JetBlue logo]()
$137
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 מרץ 2, 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 מרץ 2, 2026.
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ד' 4/11:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
ד' 4/87:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/2![United Airlines logo]()
$127
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ש' 5/28:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
ד' 5/67:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/1![JetBlue logo]()
$147
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ב' 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
ה' 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/2![Delta logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ו' 5/18:00 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
א' 5/35:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Deal found 3/1![United Airlines logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ג' 4/77:38 pm
ORD
- BDL
Nonstop2h 19m
American Airlines
ש' 4/117:29 pm
BDL
- ORD
Nonstop2h 51m
American Airlines
Deal found 3/2![American Airlines logo]()
$314
This JetBlue deal was found by Cheapflights users on 2/26. 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.
ד' 3/2512:20 pm
ORD
- BOS
1 stop8h 05m
JetBlue
ב' 3/303:20 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 2/26![JetBlue logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ג' 4/74:21 pm
ORD
- BDL
1 stop17h 40m
Frontier
ש' 4/1111:00 am
BDL
- ORD
2 stops14h 38m
Frontier
Deal found 3/2![Frontier logo]()
$366
This Delta deal was found by Cheapflights users on 2/27. 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.
ש' 5/309:36 am
ORD
- MVY
1 stop4h 46m
Delta
ה' 6/412:04 pm
MVY
- ORD
1 stop7h 03m
Delta
Deal found 2/27![Delta logo]()
$196
This Sun Country Air deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
א' 6/218:09 pm
ORD
- BDL
1 stop13h 38m
Sun Country Air
ו' 7/311:52 am
BDL
- ORD
1 stop6h 27m
Sun Country Air
Deal found 3/2![Sun Country Air logo]()
$397
This Southwest deal was found by Cheapflights users on 2/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 4/302:40 pm
ORD
- BDL
2 stops7h 30m
Southwest
ב' 5/45:50 am
BDL
- ORD
2 stops8h 00m
Southwest
Deal found 2/27![Southwest logo]()
$401
This Delta deal was found by Cheapflights users on 2/25. 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.
ד' 5/137:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
א' 5/175:40 am
BOS
- ORD
1 stop5h 47m
Delta
Deal found 2/25![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/25. 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.
ג' 3/317:00 am
ORD
- BOS
1 stop6h 26m
United Airlines
ג' 3/317:30 pm
BOS
- ORD
1 stop5h 13m
United Airlines
Deal found 2/25![United Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 2/27. 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.
א' 5/317:00 am
ORD
- MVY
2 stops7h 22m
Delta
ה' 6/412:04 pm
MVY
- ORD
2 stops7h 01m
Delta
Deal found 2/27![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/28. 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.
ו' 5/299:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
ש' 6/66:00 am
BOS
- ORD
2 stops9h 41m
United Airlines
Deal found 2/28![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/27. 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.
ש' 3/287:00 am
ORD
- BOS
Nonstop2h 25m
Delta
ה' 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/27![Delta logo]()
$217
This Expedia deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ב' 3/1611:00 am
ORD
- HYA
1 stop5h 20m
Multiple Airlines
ו' 3/2012:07 pm
HYA
- ORD
2 stops11h 49m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$586
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ד' 3/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
ש' 3/145:35 pm
BOS
- ORD
Nonstop3h 08m
Delta
Deal found 3/2![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 2/27. 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.
ש' 3/287:00 am
ORD
- BOS
Nonstop2h 25m
Delta
ד' 4/17:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/27![Delta logo]()
$222
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ו' 5/156:05 am
ORD
- ORH
2 stops7h 09m
American Airlines
ב' 5/182:39 pm
ORH
- ORD
2 stops17h 08m
American Airlines
Deal found 3/2![American Airlines logo]()
$405
This United Airlines deal was found by Cheapflights users on 2/26. 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.
ו' 5/159:38 pm
ORD
- ALB
Nonstop2h 10m
United Airlines
א' 5/176:00 am
ALB
- ORD
Nonstop2h 34m
United Airlines
Deal found 2/26![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 2/26. 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.
ו' 8/147:00 am
ORD
- ORH
1 stop6h 39m
Delta
ג' 8/183:18 pm
ORH
- ORD
1 stop5h 04m
Delta
Deal found 2/26![Delta logo]()
$242
This United Airlines deal was found by Cheapflights users on 2/26. 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.
ה' 4/212:08 pm
ORD
- ALB
Nonstop2h 04m
United Airlines
א' 4/54:50 pm
ALB
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/26![United Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 2/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ב' 4/134:20 pm
ORD
- ALB
1 stop6h 39m
United Airlines
ב' 4/204:50 pm
ALB
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/27![United Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ו' 5/157:05 am
ORD
- ORH
1 stop7h 28m
Delta
ב' 5/184:15 pm
ORH
- ORD
1 stop7h 21m
Delta
Deal found 3/2![Delta logo]()
$262
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ו' 4/1012:08 pm
ORD
- ALB
Nonstop2h 04m
United Airlines
ב' 4/137:33 pm
ALB
- ORD
1 stop5h 10m
United Airlines
Deal found 3/1![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/28. 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.
ו' 7/317:00 am
ORD
- ORH
1 stop6h 39m
Delta
א' 8/23:18 pm
ORH
- ORD
1 stop5h 04m
Delta
Deal found 2/28![Delta logo]()
$282
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ה' 3/1211:00 am
ORD
- MVY
1 stop6h 50m
JetBlue
ב' 3/1610:10 am
MVY
- ORD
1 stop8h 14m
JetBlue
Deal found 3/1![JetBlue logo]()
$560
This United Airlines deal was found by Cheapflights users on 2/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 4/96:05 pm
ORD
- ALB
Nonstop2h 14m
United Airlines
א' 4/126:00 am
ALB
- ORD
1 stop4h 38m
United Airlines
Deal found 2/27![United Airlines logo]()
$324
This Mytrip deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 3/187:17 am
ORD
- MVY
2 stops27h 58m
Multiple Airlines
א' 3/221:28 pm
MVY
- ORD
2 stops22h 49m
Multiple Airlines
Deal found 3/2![Multiple Airlines logo]()
$652
This Delta deal was found by Cheapflights users on 2/26. 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.
ש' 8/1512:15 pm
ORD
- ORH
1 stop25h 24m
Delta
ב' 8/173:18 pm
ORH
- ORD
1 stop5h 04m
Delta
Deal found 2/26![Delta logo]()
$284
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated מרץ 2, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated מרץ 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 2/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 3/117:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
ב' 3/234:30 pm
BOS
- ORD
Nonstop3h 05m
United Airlines
Deal found 2/27![United Airlines logo]()
$136
This American Airlines deal was found by Cheapflights users on 2/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ב' 3/168:55 pm
ORD
- ORH
1 stop15h 24m
American Airlines
ו' 3/201:44 pm
ORH
- ORD
1 stop21h 28m
American Airlines
Deal found 2/28![American Airlines logo]()
$160
This Delta deal was found by Cheapflights users on 2/26. 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.
ג' 3/177:00 am
ORD
- BOS
Nonstop2h 25m
Delta
ה' 4/27:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/26![Delta logo]()
$131
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ג' 3/312:10 pm
ORD
- BOS
Nonstop2h 28m
Delta
ג' 4/77:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/1![Delta logo]()
$127
This Jetabroad deal was found by Cheapflights users on 2/27. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 4/28:55 am
ORD
- BOS
Nonstop2h 32m
JetBlue
א' 4/56:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/27![JetBlue logo]()
$134
This Orbitz deal was found by Cheapflights users on 2/26. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 4/88:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
ג' 4/146:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Deal found 2/26![Multiple Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 2/26. 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.
ה' 4/97:05 am
ORD
- BOS
Nonstop2h 34m
American Airlines
ב' 4/137:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/26![American Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 2/26. 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.
ה' 4/910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
א' 4/128:03 am
BOS
- ORD
Nonstop3h 09m
American Airlines
Deal found 2/26![American Airlines logo]()
$133
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ו' 4/102:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
ב' 4/138:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Deal found 3/2![Southwest logo]()
$137
This Expedia deal was found by Cheapflights users on 2/27. 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.
ש' 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
ד' 4/156:45 am
BOS
- ORD
1 stop7h 15m
Multiple Airlines
Deal found 2/27![Multiple Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 2/27. 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.
ה' 4/236:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
א' 4/267:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/27![JetBlue logo]()
$132
This Delta deal was found by Cheapflights users on 2/26. 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.
ה' 4/306:50 am
ORD
- BOS
Nonstop2h 21m
Delta
א' 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 2/26![Delta logo]()
$128
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 מרץ 2, 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 מרץ 2, 2026.
This Trip.com deal was found by Cheapflights users on 2/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ב' 5/45:50 am
ORD
- BDL
1 stop7h 59m
Frontier
Deal found 2/26![Frontier logo]()
$65
This Super.com deal was found by Cheapflights users on 2/28. 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.
ה' 4/166:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 2/28![JetBlue logo]()
$68
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ד' 4/17:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 3/2![Delta logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 2/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 4/15:05 am
ORD
- BOS
1 stop9h 23m
Spirit Airlines
Deal found 2/28![Spirit Airlines logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 2/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 4/296:08 pm
ORD
- BDL
1 stop19h 41m
Frontier
Deal found 2/26![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ה' 5/144:28 pm
ORD
- BDL
1 stop18h 47m
Frontier
Deal found 2/27![Frontier logo]()
$71
This Super.com deal was found by Cheapflights users on 2/26. 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.
ד' 3/1110:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/26![JetBlue logo]()
$72
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ו' 3/69:15 pm
ORD
- BOS
Nonstop2h 20m
United Airlines
Deal found 3/2![United Airlines logo]()
$73
This Southwest deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
ש' 4/42:40 pm
ORD
- BOS
1 stop8h 15m
Southwest
Deal found 3/2![Southwest logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 2/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ד' 3/255:05 am
ORD
- BOS
1 stop9h 23m
Spirit Airlines
Deal found 2/27![Spirit Airlines logo]()
$75
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ש' 5/161:55 pm
ORD
- BOS
1 stop7h 10m
Southwest
Deal found 3/1![Southwest logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
ה' 4/304:28 pm
ORD
- BDL
1 stop22h 53m
Frontier
Deal found 3/1![Frontier logo]()
$76
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 מרץ 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Delta) |
One-way from | $65 (Trip.com) |
Popular in | April |
Cheapest in | January |
Average price | $227 |
Good round-trip deal | $173 or less |
Good one-way deal | $101 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 מרץ 2, 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
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ד' 4/1
1:55 pm-5:26 pm
Nonstop2h 31m
Boston Logan Intl
ד' 4/8
7:15 am-9:14 am
Nonstop2h 59m
$127
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ש' 5/2
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
ד' 5/6
7:35 pm-9:36 pm
Nonstop3h 01m
$147
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ו' 5/1
8:00 pm-11:35 pm
Nonstop2h 35m
Boston Logan Intl
א' 5/3
5:45 am-9:37 am
1 stop4h 52m
$152
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ד' 3/25
12:20 pm-9:25 pm
1 stop8h 05m
Boston Logan Intl
ב' 3/30
3:20 pm-5:24 pm
Nonstop3h 04m
$172
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ב' 3/30
7:35 pm-11:02 pm
Nonstop2h 27m
Boston Logan Intl
ה' 4/2
7:15 am-9:25 am
Nonstop3h 10m
$187
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
ש' 5/30
9:36 am-3:22 pm
1 stop4h 46m
West Tisbury Martha's Vineyard
ה' 6/4
12:04 pm-6:07 pm
1 stop7h 03m
$196
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ד' 5/13
7:15 pm-10:49 pm
Nonstop2h 34m
Boston Logan Intl
א' 5/17
5:40 am-10:27 am
1 stop5h 47m
$207
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
א' 5/31
7:00 am-3:22 pm
2 stops7h 22m
West Tisbury Martha's Vineyard
ה' 6/4
12:04 pm-6:05 pm
2 stops7h 01m
$207
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ש' 3/28
7:00 am-10:25 am
Nonstop2h 25m
Boston Logan Intl
ה' 4/2
7:15 am-9:25 am
Nonstop3h 10m
$217
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
ד' 3/11
7:00 am-10:25 am
Nonstop2h 25m
Boston Logan Intl
ש' 3/14
5:35 pm-7:43 pm
Nonstop3h 08m
$217
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-ACK
ORD-MVY
ORD-ALB
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-ACK
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 מרץ 2, 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 51% 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 מרץ 2, 2026.
The most flights from ORD to USMA are scheduled on a Monday (55 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (38 on average).
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 מרץ 2, 2026.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Massachusetts, such as Delta, United Airlines, and JetBlue. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Comfort
7.9
Entertainment
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Entertainment
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Entertainment
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Entertainment
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Entertainment
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Comfort
7.9
Entertainment
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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 מרץ 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
O'Hare Intl to Massachusetts flights
Consider these flights traveling from O'Hare Intl to Massachusetts.
Top 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 מרץ 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$249 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$426 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |