$69+ Cheap flights from Chicago (CHI) 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Apr 16 — Apr 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Massachusetts with Cheapflights
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Cheapest flights from Chicago to MassachusettsExplore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 17, 2026.
Explore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 17, 2026.
This SmartFares deal was found by Cheapflights users on 3/16. 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.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/16![JetBlue logo]()
$137
This Flysmarter deal was found by Cheapflights users on 3/13. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:55 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/13![JetBlue logo]()
$144
This SmartFares deal was found by Cheapflights users on 3/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Wed 4/227:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$147
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Multiple Airlines
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 3/13. 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.
Wed 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/13![JetBlue logo]()
$150
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Wed 4/88:05 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Wed 4/83:16 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/13![American Airlines logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/17![JetBlue logo]()
$152
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/99:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 4/133:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/13![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/13![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 3/13. 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.
Tue 3/312:35 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 4/86:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/13![Southwest logo]()
$171
This Southwest deal was found by Cheapflights users on 3/13. 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.
Tue 5/127:50 am
MDW
- BOS
2 stops7h 05m
Southwest
Tue 5/192:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/13![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 3/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:10 pm
MDW
- BOS
1 stop8h 00m
Southwest
Tue 6/22:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/14![Southwest logo]()
$173
Best flights from Chicago to MassachusettsDiscover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 17, 2026.
Discover carefully curated flight deals from Chicago to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 17, 2026.
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/307:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 5/410:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/13![Southwest logo]()
$157
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/219:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Thu 4/307:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 3/12![JetBlue logo]()
$167
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Fri 5/18:00 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 5/35:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Deal found 3/12![United Airlines logo]()
$177
This Delta deal was found by Cheapflights users on 3/15. 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 8/67:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Wed 8/127:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 3/15![Delta logo]()
$177
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Tue 4/287:15 pm
ORD
- ORH
1 stop17h 59m
American Airlines
Thu 4/302:39 pm
ORH
- ORD
1 stop19h 15m
American Airlines
Deal found 3/15![American Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 3/15. 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.
Thu 4/307:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 5/77:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/15![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 3/14. 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 4/286:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Mon 5/47:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 3/14![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 3/12. 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.
Tue 4/217:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 4/2812:55 pm
BOS
- MDW
1 stop8h 05m
Southwest
Deal found 3/12![Southwest logo]()
$167
This JetBlue deal was found by Cheapflights users on 3/12. 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 4/218:31 am
ORD
- BOS
1 stop4h 47m
JetBlue
Sat 4/257:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$187
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Fri 3/276:48 pm
ORD
- ORH
1 stop17h 31m
American Airlines
Mon 3/301:44 pm
ORH
- ORD
1 stop21h 16m
American Airlines
Deal found 3/14![American Airlines logo]()
$200
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 6/23:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 6/63:10 pm
BOS
- MDW
1 stop9h 30m
Southwest
Deal found 3/15![Southwest logo]()
$167
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Sun 6/76:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/17![United Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:48 pm
ORD
- ORH
1 stop17h 31m
American Airlines
Sat 4/41:44 pm
ORH
- ORD
1 stop20h 05m
American Airlines
Deal found 3/16![American Airlines logo]()
$200
This Delta deal was found by Cheapflights users on 3/16. 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.
Wed 6/107:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Sat 6/137:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 3/16![Delta logo]()
$207
This Southwest deal was found by Cheapflights users on 3/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:50 pm
MDW
- BOS
2 stops5h 50m
Southwest
Mon 4/1310:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/14![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Tue 6/95:00 am
ORD
- BOS
1 stop5h 16m
United Airlines
Tue 6/97:27 pm
BOS
- ORD
1 stop4h 59m
United Airlines
Deal found 3/12![United Airlines logo]()
$219
This JetBlue deal was found by Cheapflights users on 3/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/318:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/28:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 3/14![JetBlue logo]()
$222
This Southwest deal was found by Cheapflights users on 3/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:40 pm
ORD
- BOS
1 stop7h 35m
Southwest
Mon 4/138:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Deal found 3/14![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:00 am
ORD
- ORH
2 stops8h 43m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/12![Delta logo]()
$222
This Southwest deal was found by Cheapflights users on 3/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Sun 5/315:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 3/14![Southwest logo]()
$177
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Fri 3/208:55 pm
ORD
- ORH
1 stop15h 24m
American Airlines
Sun 3/221:44 pm
ORH
- ORD
1 stop21h 28m
American Airlines
Deal found 3/13![American Airlines logo]()
$236
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:15 am
ORD
- ORH
2 stops10h 28m
Delta
Wed 5/65:24 pm
ORH
- ORD
1 stop5h 51m
Delta
Deal found 3/12![Delta logo]()
$222
This Priceline deal was found by Cheapflights users on 3/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:50 am
ORD
- HYA
1 stop7h 30m
Multiple Airlines
Sun 5/317:05 am
HYA
- ORD
2 stops8h 25m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$595
This Delta deal was found by Cheapflights users on 3/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:15 am
ORD
- ORH
2 stops10h 28m
Delta
Fri 5/84:15 pm
ORH
- ORD
2 stops8h 44m
Delta
Deal found 3/12![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 3/16. 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.
Thu 4/92:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Sun 4/129:55 pm
BOS
- ORD
2 stops15h 55m
Southwest
Deal found 3/16![Southwest logo]()
$193
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Fri 5/15:00 am
ORD
- ORH
1 stop8h 14m
American Airlines
Sun 5/32:39 pm
ORH
- ORD
1 stop18h 00m
American Airlines
Deal found 3/14![American Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Tue 4/147:10 am
ORD
- ALB
Nonstop2h 15m
United Airlines
Wed 4/157:33 pm
ALB
- ORD
1 stop5h 10m
United Airlines
Deal found 3/16![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 3/12. 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 5/163:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 5/196:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/12![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Thu 4/95:00 am
ORD
- ORH
1 stop8h 14m
American Airlines
Sun 4/122:39 pm
ORH
- ORD
2 stops19h 05m
American Airlines
Deal found 3/14![American Airlines logo]()
$272
This Southwest deal was found by Cheapflights users on 3/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:00 am
MDW
- BOS
1 stop6h 05m
Southwest
Mon 4/134:45 pm
BOS
- MDW
1 stop6h 35m
Southwest
Deal found 3/17![Southwest logo]()
$197
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated March 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated March 17, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/13. 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.
Tue 3/312:35 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Wed 4/86:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/13![Southwest logo]()
$171
This Priceline deal was found by Cheapflights users on 3/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Multiple Airlines
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$149
This Super.com deal was found by Cheapflights users on 3/13. 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.
Wed 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/13![JetBlue logo]()
$150
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Wed 4/88:05 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Wed 4/83:16 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/13![American Airlines logo]()
$151
This SmartFares deal was found by Cheapflights users on 3/16. 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.
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/16![JetBlue logo]()
$137
This American Airlines deal was found by Cheapflights users on 3/15. 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 4/910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Sun 4/126:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/15![American Airlines logo]()
$154
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/99:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 4/133:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/13![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 3/13. 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.
Thu 4/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/13![Southwest logo]()
$167
This Southwest deal was found by Cheapflights users on 3/13. 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.
Fri 4/102:10 pm
MDW
- BOS
2 stops6h 40m
Southwest
Mon 4/133:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/13![Southwest logo]()
$172
This JetBlue deal was found by Cheapflights users on 3/16. 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.
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Deal found 3/16![JetBlue logo]()
$155
This SmartFares deal was found by Cheapflights users on 3/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Wed 4/227:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/12![JetBlue logo]()
$147
This Cheapflightsfares deal was found by Cheapflights users on 3/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/306:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Sun 5/36:52 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 3/12![JetBlue logo]()
$152
One-way flights from Chicago to MassachusettsSearch for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 17, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated March 17, 2026.
This Super.com deal was found by Cheapflights users on 3/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/812:45 pm
ORD
- BOS
1 stop7h 48m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$69
This Super.com deal was found by Cheapflights users on 3/12. 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.
Mon 4/206:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/12![JetBlue logo]()
$77
This Super.com deal was found by Cheapflights users on 3/13. 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.
Tue 6/238:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 3/13![JetBlue logo]()
$78
This United Airlines deal was found by Cheapflights users on 3/13. 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.
Sun 4/127:30 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 3/13![United Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 3/12. 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.
Tue 4/143:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/12![Southwest logo]()
$79
This Super.com deal was found by Cheapflights users on 3/16. 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 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 3/16![Spirit Airlines logo]()
$80
This Jettzy deal was found by Cheapflights users on 3/13. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/13![JetBlue logo]()
$82
This Super.com deal was found by Cheapflights users on 3/12. 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.
Fri 4/176:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/12![JetBlue logo]()
$87
This Super.com deal was found by Cheapflights users on 3/15. 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.
Thu 4/236:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
Deal found 3/15![JetBlue logo]()
$88
This Delta deal was found by Cheapflights users on 3/17. 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.
Thu 4/166:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/17![Delta logo]()
$89
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- BDL
1 stop5h 49m
Frontier
Deal found 3/13![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
MDW
- BDL
1 stop6h 58m
Frontier
Deal found 3/13![Frontier logo]()
$90
Find flight deals from Chicago to Massachusetts
Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated March 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (SmartFares) |
One-way from | $69 (Super.com) |
Popular in | April |
Cheapest in | January |
Average price | $225 |
Good round-trip deal | $145 or less |
Good one-way deal | $88 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 17, 2026.
Use the filters below to find and compare flights from Chicago to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 4/30
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Mon 5/4
10:40 am-12:20 pm
Nonstop2h 40m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 4/30
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Thu 5/7
7:10 am-9:00 am
Nonstop2h 50m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/21
9:41 am-1:07 pm
Nonstop2h 26m
Boston Logan Intl
Thu 4/30
7:02 am-8:59 am
Nonstop2h 57m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 4/21
7:45 am-11:00 am
Nonstop2h 15m
Boston Logan Intl
Tue 4/28
12:55 pm-8:00 pm
1 stop8h 05m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 6/2
3:15 pm-6:35 pm
Nonstop2h 20m
Boston Logan Intl
Sat 6/6
3:10 pm-11:40 pm
1 stop9h 30m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 4/7
12:50 pm-7:40 pm
2 stops5h 50m
Boston Logan Intl
Mon 4/13
10:40 am-12:20 pm
Nonstop2h 40m
$172
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/1
8:00 pm-11:35 pm
Nonstop2h 35m
Boston Logan Intl
Sun 5/3
5:45 am-9:37 am
1 stop4h 52m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/6
7:00 am-10:28 am
Nonstop2h 28m
Boston Logan Intl
Wed 8/12
7:00 am-8:58 am
Nonstop2h 58m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/28
6:50 am-10:11 am
Nonstop2h 21m
Boston Logan Intl
Mon 5/4
7:35 pm-9:29 pm
Nonstop2h 54m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 4/9
2:40 pm-11:15 pm
1 stop7h 35m
Boston Logan Intl
Mon 4/13
8:25 am-12:50 pm
1 stop5h 25m
$177
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Chicago with our price prediction graph.
ORD-BOS
MDW-BOS
ORD-BDL
MDW-BDL
ORD-ORH
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 to Massachusetts
CHI-USMA
ORD-BOS
MDW-BOS
ORD-BDL
MDW-BDL
What is the cheapest month to book a flight from Chicago to Massachusetts?
Currently, September is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $91). Flying from Chicago 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 CHI to MA?
Find hourly flight availability from Chicago 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 17, 2026.
One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 44% on airfare.
What is the cheapest day to fly from Chicago to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Massachusetts. Price data was last updated on March 14, 2026.
Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Massachusetts
Explore weekly flight availability from Chicago 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 17, 2026.
The most flights from CHI to USMA are scheduled on a Friday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (47 on average).
How much does it cost to fly round-trip from Chicago 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 17, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Chicago to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 Chicago to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Massachusetts by cabin class
Find flights from Chicago to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Massachusetts flights
Browse other Chicago and Massachusetts flight options. Last updated on March 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Massachusetts flights
Consider these flights traveling from Chicago to Massachusetts.
Top 6 airlines flying from Chicago to Massachusetts
Discover the top 6 airlines that operate flights from Chicago 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$253 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$248 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$117 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$124 | Average$243 | FlexibilityNo cancel fee | On-time63% |