$78+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
May 17 — May 241
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Massachusetts with Cheapflights
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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 April 17, 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 April 17, 2026.
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/16![JetBlue logo]()
$146
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/107:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/16![JetBlue logo]()
$151
This flygcity.se deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Wed 5/278:50 am
ORD
- BOS
Nonstop2h 32m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/12![JetBlue logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Fri 5/15:50 am
ORD
- BOS
1 stop26h 26m
Frontier
Tue 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Deal found 4/12![Frontier logo]()
$153
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:39 pm
ORD
- BOS
Nonstop2h 33m
American Airlines
Thu 4/306:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$155
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Thu 4/304:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Mon 5/412:31 pm
BOS
- ORD
1 stop11h 35m
Frontier
Deal found 4/13![Frontier logo]()
$160
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/18:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Wed 5/66:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/14![JetBlue logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Tue 5/53:55 pm
ORD
- BOS
1 stop16h 17m
Multiple Airlines
Fri 5/87:00 am
BOS
- ORD
1 stop17h 13m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/165:45 pm
ORD
- ORH
1 stop19h 29m
American Airlines
Mon 5/182:39 pm
ORH
- ORD
1 stop21h 59m
American Airlines
Deal found 4/13![American Airlines logo]()
$207
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 April 17, 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 April 17, 2026.
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 9/27:46 pm
ORD
- BOS
Nonstop2h 34m
United Airlines
Tue 9/88:10 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/13![United Airlines logo]()
$167
This JetBlue deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 8/268:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/16![JetBlue logo]()
$167
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/1210:30 am
ORD
- BOS
Nonstop2h 27m
Delta
Sat 5/165:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 4/16![Delta logo]()
$167
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 6/245:00 am
ORD
- ORH
1 stop10h 53m
American Airlines
Mon 6/295:18 pm
ORH
- ORD
1 stop8h 16m
American Airlines
Deal found 4/14![American Airlines logo]()
$207
This Southwest deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sat 5/1611:50 am
ORD
- ALB
1 stop7h 40m
Southwest
Wed 5/208:45 am
ALB
- ORD
1 stop8h 20m
Southwest
Deal found 4/15![Southwest logo]()
$307
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/76:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Thu 5/146:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/12![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 9/13:00 pm
ORD
- BOS
Nonstop2h 35m
Delta
Thu 9/107:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 4/14![Delta logo]()
$186
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/107:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Sat 8/298:22 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 4/16![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/165:45 pm
ORD
- ORH
1 stop19h 29m
American Airlines
Mon 5/182:39 pm
ORH
- ORD
1 stop21h 59m
American Airlines
Deal found 4/13![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/96:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sat 8/227:00 pm
BOS
- ORD
1 stop5h 16m
United Airlines
Deal found 4/16![United Airlines logo]()
$182
This American Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:40 am
ORD
- ORH
1 stop9h 13m
American Airlines
Mon 6/295:18 pm
ORH
- ORD
1 stop8h 16m
American Airlines
Deal found 4/14![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/233:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 5/245:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 4/14![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/217:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Tue 5/267:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 4/16![Delta logo]()
$222
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:15 pm
ORD
- ORH
1 stop17h 59m
American Airlines
Sat 5/22:39 pm
ORH
- ORD
2 stops10h 15m
American Airlines
Deal found 4/12![American Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/307:10 am
ORD
- ORH
2 stops8h 33m
Delta
Mon 5/45:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/15![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/146:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Sat 5/167:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/15![United Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/306:05 am
ORD
- ORH
2 stops7h 09m
American Airlines
Mon 5/42:39 pm
ORH
- ORD
2 stops10h 15m
American Airlines
Deal found 4/15![American Airlines logo]()
$235
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 9/176:00 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Wed 9/236:42 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 4/13![United Airlines logo]()
$205
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/110:45 am
ORD
- ORH
1 stop4h 58m
Delta
Mon 5/45:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/16![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Sat 5/96:00 am
ORD
- ALB
1 stop8h 35m
Southwest
Mon 5/115:50 am
ALB
- ORD
2 stops8h 00m
Southwest
Deal found 4/16![Southwest logo]()
$354
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/296:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Mon 6/17:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/13![United Airlines logo]()
$208
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/19:35 am
ORD
- ORH
1 stop6h 08m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 55m
Delta
Deal found 4/17![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Sat 5/161:55 pm
ORD
- BDL
2 stops8h 00m
Southwest
Tue 5/197:05 am
BDL
- ORD
1 stop10h 00m
Southwest
Deal found 4/12![Southwest logo]()
$368
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 7/46:00 am
ORD
- HYA
1 stop7h 24m
American Airlines
Sat 7/111:55 pm
HYA
- ORD
1 stop6h 00m
American Airlines
Deal found 4/13![American Airlines logo]()
$282
This Priceline deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Mon 4/276:00 am
ORD
- MVY
1 stop5h 15m
Multiple Airlines
Fri 5/11:28 pm
MVY
- ORD
1 stop9h 08m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$828
This JetBlue deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:12 am
ORD
- MVY
1 stop4h 57m
JetBlue
Wed 7/85:05 pm
MVY
- ORD
1 stop5h 22m
JetBlue
Deal found 4/15![JetBlue logo]()
$426
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/15:15 am
ORD
- ORH
2 stops10h 28m
Delta
Tue 5/55:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 4/17![Delta logo]()
$266
This JetBlue deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:39 am
ORD
- MVY
1 stop5h 30m
JetBlue
Wed 7/225:05 pm
MVY
- ORD
1 stop5h 50m
JetBlue
Deal found 4/12![JetBlue logo]()
$426
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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
- BDL
1 stop8h 05m
Southwest
Sun 5/246:10 am
BDL
- ORD
2 stops8h 45m
Southwest
Deal found 4/13![Southwest logo]()
$393
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 7/79:30 am
ORD
- ORH
1 stop6h 30m
Delta
Sun 7/195:40 pm
ORH
- ORD
1 stop5h 56m
Delta
Deal found 4/16![Delta logo]()
$277
Last-minute flights from O'Hare Intl to MassachusettsDiscover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Massachusetts. Data last updated April 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:39 pm
ORD
- BOS
Nonstop2h 33m
American Airlines
Thu 4/306:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$155
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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.
Thu 4/304:28 pm
ORD
- BOS
1 stop8h 03m
Frontier
Mon 5/412:31 pm
BOS
- ORD
1 stop11h 35m
Frontier
Deal found 4/13![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Fri 5/15:50 am
ORD
- BOS
1 stop26h 26m
Frontier
Tue 5/510:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Deal found 4/12![Frontier logo]()
$153
This American Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/18:56 pm
ORD
- BOS
Nonstop2h 29m
American Airlines
Wed 5/66:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 4/12![American Airlines logo]()
$161
This CheapOair deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Multiple Airlines
Sat 5/96:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$164
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Sat 5/97:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Sun 5/107:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/16![JetBlue logo]()
$151
This Priceline deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$159
This Cheapflightsfares deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/126:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/14![JetBlue logo]()
$162
This SmartFares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/16![JetBlue logo]()
$146
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$154
This American Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 5/165:45 pm
ORD
- ORH
1 stop19h 29m
American Airlines
Mon 5/182:39 pm
ORH
- ORD
1 stop21h 59m
American Airlines
Deal found 4/13![American Airlines logo]()
$207
This flygcity.se deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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.
Wed 5/278:50 am
ORD
- BOS
Nonstop2h 32m
JetBlue
Wed 6/36:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/12![JetBlue logo]()
$152
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 April 17, 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 April 17, 2026.
This Expedia deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/14![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$79
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Tue 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/14![JetBlue logo]()
$80
This Super.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” 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 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/12![JetBlue logo]()
$81
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” 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.
Tue 7/218:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/14![JetBlue logo]()
$82
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” 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 6/166:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 4/13![United Airlines logo]()
$84
This American Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 6/246:00 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 4/15![American Airlines logo]()
$85
This Super.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sun 5/248:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/15![JetBlue logo]()
$86
This KAYAK deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 4/14![JetBlue logo]()
$87
This Cheapflightsfares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/86:00 am
ORD
- BOS
Nonstop2h 14m
JetBlue
Deal found 4/16![JetBlue logo]()
$88
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 6/134:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Deal found 4/16![Delta logo]()
$89
This Super.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/305:50 am
ORD
- BDL
1 stop7h 59m
Frontier
Deal found 4/13![Frontier logo]()
$89
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 April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $146 (SmartFares) |
One-way from | $78 (Expedia) |
Popular in | April |
Cheapest in | January |
Average price | $272 |
Good round-trip deal | $198 or less |
Good one-way deal | $119 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 April 17, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/2
7:46 pm-11:20 pm
Nonstop2h 34m
Boston Logan Intl
Tue 9/8
8:10 am-10:08 am
Nonstop2h 58m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/25
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Wed 8/26
8:10 am-10:06 am
Nonstop2h 56m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/12
10:30 am-1:57 pm
Nonstop2h 27m
Boston Logan Intl
Sat 5/16
5:30 pm-7:33 pm
Nonstop3h 03m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/7
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Thu 5/14
6:00 am-8:00 am
Nonstop3h 00m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 5/10
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Sat 8/29
8:22 pm-10:19 pm
Nonstop2h 57m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/9
6:23 pm-9:59 pm
Nonstop2h 36m
Boston Logan Intl
Sat 8/22
7:00 pm-11:16 pm
1 stop5h 16m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/23
3:55 pm-7:30 pm
Nonstop2h 35m
Boston Logan Intl
Sun 5/24
5:45 am-9:36 am
1 stop4h 51m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/1
3:00 pm-6:35 pm
Nonstop2h 35m
Boston Logan Intl
Thu 9/10
7:30 am-9:28 am
Nonstop2h 58m
$186
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 5/14
6:00 am-9:25 am
Nonstop2h 25m
Boston Logan Intl
Sat 5/16
7:30 am-9:30 am
Nonstop3h 00m
$194
Quickest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 9/17
6:00 am-9:23 am
Nonstop2h 23m
Boston Logan Intl
Wed 9/23
6:42 pm-8:39 pm
Nonstop2h 57m
$205
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-ACK
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Massachusetts
ORD-USMA
ORD-BOS
ORD-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 April is currently the most expensive (average of $538). 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 April 17, 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 49% 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 April 17, 2026.
The most flights from ORD to USMA are scheduled on a Thursday (62 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 April 17, 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
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
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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Alternative routes for O'Hare Intl to Massachusetts
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Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
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O'Hare Intl and Massachusetts flights
Browse other O'Hare Intl and Massachusetts flight options. Last updated on April 17, 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 April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$65 | Average$366 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$79 | Average$166 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$86 | Average$257 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$250 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$118 | Average$440 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$144 | Average$206 | FlexibilityNo cancel fee | On-time63% |