$65+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Apr 1 — Apr 81
1 adult, Economy
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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 März 2, 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 März 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.
Fr 5/87:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
Do 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.
Di 3/312:10 pm
ORD
- BOS
Nonstop2h 28m
Delta
Di 4/77:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 3/1![Delta logo]()
$127
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.
Fr 5/15:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Mo 5/46:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/2![Southwest 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.
Do 4/306:50 am
ORD
- BOS
Nonstop2h 21m
Delta
So 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.
Sa 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
Mi 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.
Mi 5/63:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Fr 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.
Di 3/177:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Do 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.
Fr 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mo 6/86:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/27![JetBlue logo]()
$132
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.
Di 5/127:50 am
MDW
- BOS
2 stops8h 25m
Southwest
Di 5/126:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/2![Southwest 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.
Do 4/910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
So 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 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.
Do 4/302:10 pm
MDW
- BOS
1 stop8h 00m
Southwest
Mo 5/43:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/27![Southwest 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.
Mi 5/62:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Sa 5/96:00 am
BOS
- ORD
2 stops10h 30m
Southwest
Deal found 3/1![Southwest logo]()
$134
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 März 2, 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 März 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.
Mi 4/11:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Mi 4/87:15 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/2![United Airlines logo]()
$127
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.
Mi 4/16:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mi 4/86:00 pm
BOS
- MDW
1 stop5h 15m
Southwest
Deal found 3/2![Southwest logo]()
$137
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.
Sa 5/28:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
Mi 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.
Mo 3/307:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Do 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.
Fr 5/18:00 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
So 5/35:45 am
BOS
- ORD
1 stop4h 52m
United Airlines
Deal found 3/1![United Airlines logo]()
$152
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.
Mi 4/87:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mi 4/157:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/27![Southwest logo]()
$157
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.
Di 4/77:38 pm
ORD
- BDL
Nonstop2h 19m
American Airlines
Sa 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.
Mi 3/2512:20 pm
ORD
- BOS
1 stop8h 05m
JetBlue
Mo 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.
Di 4/74:21 pm
ORD
- BDL
1 stop17h 40m
Frontier
Sa 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.
Sa 5/309:36 am
ORD
- MVY
1 stop4h 46m
Delta
Do 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.
So 6/218:09 pm
ORD
- BDL
1 stop13h 38m
Sun Country Air
Fr 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 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.
Sa 4/115:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
So 4/126:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/1![Southwest logo]()
$186
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.
Mi 5/137:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
So 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.
Di 3/317:00 am
ORD
- BOS
1 stop6h 26m
United Airlines
Di 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.
So 5/317:00 am
ORD
- MVY
2 stops7h 22m
Delta
Do 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.
Fr 5/299:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sa 6/66:00 am
BOS
- ORD
2 stops9h 41m
United Airlines
Deal found 2/28![United Airlines logo]()
$227
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.
Di 5/127:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Di 5/122:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/2![Southwest logo]()
$236
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.
Sa 3/287:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Do 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.
Mo 3/1611:00 am
ORD
- HYA
1 stop5h 20m
Multiple Airlines
Fr 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.
Mi 3/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Sa 3/145:35 pm
BOS
- ORD
Nonstop3h 08m
Delta
Deal found 3/2![Delta logo]()
$217
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.
Mo 4/137:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mo 4/203:50 pm
BOS
- MDW
1 stop6h 10m
Southwest
Deal found 2/27![Southwest logo]()
$250
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.
Sa 3/287:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Mi 4/17:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/27![Delta logo]()
$222
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 3/242:35 pm
MDW
- BOS
Nonstop2h 10m
Southwest
So 3/2911:40 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/25![Southwest logo]()
$251
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.
Fr 5/156:05 am
ORD
- ORH
2 stops7h 09m
American Airlines
Mo 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.
Fr 5/159:38 pm
ORD
- ALB
Nonstop2h 10m
United Airlines
So 5/176:00 am
ALB
- ORD
Nonstop2h 34m
United Airlines
Deal found 2/26![United Airlines logo]()
$308
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.
Fr 3/273:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
So 3/2911:40 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/27![Southwest logo]()
$260
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.
Fr 8/147:00 am
ORD
- ORH
1 stop6h 39m
Delta
Di 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.
Do 4/212:08 pm
ORD
- ALB
Nonstop2h 04m
United Airlines
So 4/54:50 pm
ALB
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/26![United Airlines logo]()
$309
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/197:50 am
MDW
- BOS
2 stops7h 05m
Southwest
Fr 5/225:50 pm
BOS
- MDW
1 stop7h 05m
Southwest
Deal found 2/28![Southwest logo]()
$261
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.
Mo 4/134:20 pm
ORD
- ALB
1 stop6h 39m
United Airlines
Mo 4/204:50 pm
ALB
- ORD
Nonstop2h 35m
United Airlines
Deal found 2/27![United Airlines logo]()
$309
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated März 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated März 2, 2026 and is based on user searches.
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.
Di 3/177:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Do 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.
Di 3/312:10 pm
ORD
- BOS
Nonstop2h 28m
Delta
Di 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.
Do 4/28:55 am
ORD
- BOS
Nonstop2h 32m
JetBlue
So 4/56:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/27![JetBlue logo]()
$134
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.
Di 4/712:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Di 4/148:10 am
BOS
- MDW
1 stop6h 20m
Southwest
Deal found 3/2![Southwest logo]()
$127
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.
Mi 4/88:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
Di 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.
Do 4/97:05 am
ORD
- BOS
Nonstop2h 34m
American Airlines
Mo 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.
Do 4/910:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
So 4/128:03 am
BOS
- ORD
Nonstop3h 09m
American Airlines
Deal found 2/26![American Airlines logo]()
$133
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.
Sa 4/118:58 am
ORD
- BOS
Nonstop2h 30m
Multiple Airlines
Mi 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.
Do 4/236:00 am
ORD
- BOS
Nonstop2h 13m
JetBlue
So 4/267:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 2/27![JetBlue logo]()
$132
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.
Mi 4/294:40 pm
MDW
- BOS
1 stop4h 40m
Southwest
Sa 5/25:15 am
BOS
- MDW
2 stops13h 00m
Southwest
Deal found 3/1![Southwest logo]()
$134
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.
Do 4/306:50 am
ORD
- BOS
Nonstop2h 21m
Delta
So 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 2/26![Delta logo]()
$128
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.
Do 4/302:10 pm
MDW
- BOS
1 stop8h 00m
Southwest
Mo 5/43:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/27![Southwest logo]()
$133
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 März 2, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated März 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.
Mo 5/45:50 am
ORD
- BDL
1 stop7h 59m
Frontier
Deal found 2/26![Frontier logo]()
$65
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.
Do 4/236:00 am
MDW
- BDL
1 stop7h 49m
Frontier
Deal found 2/26![Frontier logo]()
$65
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 4/306:00 am
MDW
- BDL
1 stop7h 49m
Frontier
Deal found 2/28![Frontier logo]()
$66
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.
Do 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.
Mi 4/17:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 3/2![Delta logo]()
$69
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.
Mi 4/155:00 pm
MDW
- BOS
1 stop4h 40m
Southwest
Deal found 3/2![Southwest logo]()
$69
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.
Mi 4/222:15 pm
MDW
- BDL
1 stop23h 34m
Frontier
Deal found 2/26![Frontier 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.
Mi 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 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.
Di 3/316:00 am
MDW
- BOS
1 stop18h 13m
Frontier
Deal found 3/1![Frontier 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.
Mi 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 2/26. 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.
Mi 4/292:15 pm
MDW
- BDL
1 stop23h 34m
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.
Mo 4/136:00 am
MDW
- BOS
1 stop28h 45m
Frontier
Deal found 2/27![Frontier logo]()
$71
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 März 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 | $147 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 März 2, 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
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mi 4/1
1:55 pm-5:26 pm
Nonstop2h 31m
Boston Logan Intl
Mi 4/8
7:15 am-9:14 am
Nonstop2h 59m
$127
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mi 4/1
6:10 pm-9:25 pm
Nonstop2h 15m
Boston Logan Intl
Mi 4/8
6:00 pm-10:15 pm
1 stop5h 15m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sa 5/2
8:31 am-2:16 pm
1 stop4h 45m
Boston Logan Intl
Mi 5/6
7:35 pm-9:36 pm
Nonstop3h 01m
$147
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fr 5/1
8:00 pm-11:35 pm
Nonstop2h 35m
Boston Logan Intl
So 5/3
5:45 am-9:37 am
1 stop4h 52m
$152
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mi 4/8
7:45 am-11:00 am
Nonstop2h 15m
Boston Logan Intl
Mi 4/15
7:20 am-9:05 am
Nonstop2h 45m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mi 3/25
12:20 pm-9:25 pm
1 stop8h 05m
Boston Logan Intl
Mo 3/30
3:20 pm-5:24 pm
Nonstop3h 04m
$172
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sa 4/11
5:25 pm-11:40 pm
1 stop5h 15m
Boston Logan Intl
So 4/12
6:10 am-7:55 am
Nonstop2h 45m
$186
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mo 3/30
7:35 pm-11:02 pm
Nonstop2h 27m
Boston Logan Intl
Do 4/2
7:15 am-9:25 am
Nonstop3h 10m
$187
ChicagoWest Tisbury
ORD - MVY
ORDMVY
Chicago O'Hare Intl
Sa 5/30
9:36 am-3:22 pm
1 stop4h 46m
West Tisbury Martha's Vineyard
Do 6/4
12:04 pm-6:07 pm
1 stop7h 03m
$196
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mi 5/13
7:15 pm-10:49 pm
Nonstop2h 34m
Boston Logan Intl
So 5/17
5:40 am-10:27 am
1 stop5h 47m
$207
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-ORH
ORD-ACK
ORD-MVY
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-ORH
ORD-ACK
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 März 2, 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 43% 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 February 21, 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 März 2, 2026.
The most flights from CHI to USMA are scheduled on a Monday (57 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (38 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 März 2, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
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 März 2, 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 März 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$62 | Average$309 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$91 | Average$254 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$91 | Average$158 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$117 | Average$379 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$117 | Average$252 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$126 | Average$247 | FlexibilityNo cancel fee | On-time63% |