$105+ Cheap flights from Chicago (CHI) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Oct 16 — Oct 231
Round-trip
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 September 16, 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 September 16, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/268:36 am -
1 stop5h 51m
Fri 10/304:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 9/13. 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 12/91:15 pm -
2 stops7h 35m
Sat 12/1211:35 am -
2 stops6h 30m
Deal found 9/13![Southwest logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 51m
Sun 10/116:55 am -
Nonstop2h 52m
Deal found 9/15![Multiple Airlines logo]()
$224
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/226:00 am -
1 stop5h 21m
Mon 10/267:40 pm -
Nonstop2h 51m
Deal found 9/14![Delta logo]()
$225
This Southwest deal was found by Cheapflights users on 9/13. 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 10/217:55 am -
2 stops7h 10m
Sat 10/245:15 am -
2 stops13h 45m
Deal found 9/13![Southwest logo]()
$225
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 51m
Tue 10/136:55 am -
Nonstop2h 52m
Deal found 9/15![Multiple Airlines logo]()
$226
This Southwest deal was found by Cheapflights users on 9/14. 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 10/295:30 am -
Nonstop2h 25m
Thu 11/52:30 pm -
1 stop8h 30m
Deal found 9/14![Southwest logo]()
$226
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 9/15![Multiple Airlines logo]()
$227
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 11/111:15 pm -
2 stops7h 40m
Mon 11/161:10 pm -
1 stop5h 40m
Deal found 9/14![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/306:59 am -
Nonstop2h 19m
Mon 11/26:36 pm -
Nonstop3h 04m
Deal found 9/15![United Airlines logo]()
$228
This Southwest deal was found by Cheapflights users on 9/14. 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 11/1210:20 am -
1 stop5h 50m
Sat 11/148:10 am -
2 stops10h 15m
Deal found 9/14![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 9/14. 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 11/126:45 pm -
Nonstop2h 20m
Fri 11/134:20 pm -
Nonstop2h 45m
Deal found 9/14![Southwest logo]()
$229
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 September 16, 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 September 16, 2026.
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/2710:05 am -
1 stop4h 22m
Thu 10/294:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$204
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 12/286:50 am -
Nonstop2h 27m
Sat 1/99:12 am -
Nonstop3h 05m
Deal found 9/15![United Airlines logo]()
$242
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Sat 10/310:59 am -
1 stop6h 01m
Mon 10/54:10 pm -
1 stop6h 50m
Deal found 9/14![JetBlue logo]()
$284
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/167:37 pm -
1 stop20h 12m
Sat 10/245:19 pm -
1 stop6h 11m
Deal found 9/15![American Airlines logo]()
$284
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 10/147:45 am -
Nonstop2h 10m
Mon 10/265:50 pm -
1 stop5h 10m
Deal found 9/15![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/277:00 am -
2 stops7h 27m
Wed 10/284:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 9/15. 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.
Tue 10/275:27 am -
2 stops9h 00m
Fri 10/304:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 9/15. 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.
Wed 10/287:00 am -
2 stops7h 27m
Fri 10/304:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/176:06 pm -
1 stop4h 53m
Tue 10/207:40 pm -
1 stop4h 52m
Deal found 9/14![United Airlines logo]()
$277
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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.
Thu 10/2212:38 pm -
1 stop7h 11m
Sun 10/259:59 am -
Nonstop3h 01m
Deal found 9/11![JetBlue logo]()
$288
This Southwest deal was found by Cheapflights users on 9/13. 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 10/279:35 am -
2 stops7h 35m
Wed 10/2812:55 pm -
2 stops10h 05m
Deal found 9/13![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/157:00 am -
1 stop6h 58m
Mon 10/194:15 pm -
1 stop7h 02m
Deal found 9/14![Delta logo]()
$230
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/179:38 am -
1 stop7h 25m
Sat 10/241:32 pm -
1 stop6h 42m
Deal found 9/15![Multiple Airlines logo]()
$620
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Sat 11/216:29 am -
1 stop9h 52m
Sun 11/225:46 pm -
1 stop6h 45m
Deal found 9/12![American Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 11/66:00 am -
1 stop5h 26m
Sun 11/86:00 am -
2 stops8h 04m
Deal found 9/15![United Airlines logo]()
$294
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Thu 10/2212:38 pm -
1 stop7h 11m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 9/14![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 10/166:45 pm -
Nonstop2h 20m
Mon 10/1910:00 pm -
Nonstop2h 40m
Deal found 9/12![Southwest logo]()
$295
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Thu 10/158:04 pm -
Nonstop2h 55m
Mon 10/193:41 pm -
1 stop7h 29m
Deal found 9/14![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 10/203:15 pm -
Nonstop2h 20m
Sat 10/241:25 pm -
Nonstop2h 35m
Deal found 9/11![Southwest logo]()
$295
This JetBlue deal was found by Cheapflights users on 9/12. 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.
Sat 9/269:38 am -
Nonstop2h 28m
Tue 9/295:15 am -
1 stop5h 43m
Deal found 9/12![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/12. 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.
Sun 1/101:25 pm -
Nonstop2h 10m
Tue 1/121:10 pm -
Nonstop2h 45m
Deal found 9/12![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Fri 10/96:10 pm -
Nonstop2h 12m
Mon 10/126:20 am -
Nonstop2h 33m
Deal found 9/14![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/187:00 am -
1 stop7h 19m
Fri 11/204:00 pm -
1 stop7h 18m
Deal found 9/11![Delta logo]()
$280
This JetBlue deal was found by Cheapflights users on 9/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:55 pm -
1 stop8h 03m
Wed 10/216:25 am -
1 stop5h 59m
Deal found 9/13![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 9/15. 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.
Wed 9/309:25 am -
1 stop5h 35m
Sat 10/31:25 pm -
Nonstop2h 35m
Deal found 9/15![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 9/14. 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 9/299:30 am -
1 stop5h 07m
Fri 10/24:20 pm -
1 stop6h 58m
Deal found 9/14![Delta logo]()
$280
This JetBlue deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 9/268:24 pm -
Nonstop2h 45m
Mon 9/285:30 pm -
1 stop5h 28m
Deal found 9/11![JetBlue logo]()
$299
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 11/66:30 pm -
2 stops12h 40m
Sat 11/79:30 am -
2 stops8h 35m
Deal found 9/15![Southwest logo]()
$305
This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/227:00 am -
1 stop7h 23m
Mon 11/234:00 pm -
1 stop7h 18m
Deal found 9/11![Delta logo]()
$280
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” 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 11/2110:57 am -
Nonstop2h 18m
Tue 11/2412:37 pm -
Nonstop2h 52m
Deal found 9/11![United Airlines logo]()
$391
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated September 16, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm -
Nonstop2h 45m
Mon 10/56:50 am -
Nonstop2h 52m
Deal found 9/15![JetBlue logo]()
$230
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 51m
Sun 10/116:55 am -
Nonstop2h 52m
Deal found 9/15![Multiple Airlines logo]()
$224
This Expedia deal was found by Cheapflights users on 9/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:11 pm -
1 stop13h 51m
Tue 10/136:55 am -
Nonstop2h 52m
Deal found 9/15![Multiple Airlines logo]()
$226
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/157:00 am -
1 stop6h 58m
Mon 10/194:15 pm -
1 stop7h 02m
Deal found 9/14![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 9/13. 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 10/219:25 am -
1 stop5h 10m
Sat 10/245:15 am -
2 stops13h 45m
Deal found 9/13![Southwest logo]()
$220
This Delta deal was found by Cheapflights users on 9/14. 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.
Thu 10/226:00 am -
1 stop5h 21m
Mon 10/267:40 pm -
Nonstop2h 51m
Deal found 9/14![Delta logo]()
$225
This CheapOair deal was found by Cheapflights users on 9/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:11 pm -
1 stop13h 51m
Mon 10/265:15 pm -
Nonstop3h 14m
Deal found 9/15![Multiple Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/268:36 am -
1 stop5h 51m
Wed 10/284:10 pm -
1 stop5h 33m
Deal found 9/15![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/266:30 am -
2 stops7h 57m
Thu 10/294:10 pm -
1 stop7h 07m
Deal found 9/15![Delta logo]()
$214
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 10/265:27 am -
2 stops9h 00m
Fri 10/304:10 pm -
2 stops8h 47m
Deal found 9/15![Delta logo]()
$219
This Southwest deal was found by Cheapflights users on 9/14. 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 10/295:30 am -
Nonstop2h 25m
Thu 11/52:30 pm -
1 stop8h 30m
Deal found 9/14![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/306:59 am -
Nonstop2h 19m
Mon 11/26:36 pm -
Nonstop3h 04m
Deal found 9/15![United Airlines logo]()
$228
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 September 16, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Delta deal was found by Cheapflights users on 9/16. 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 10/278:36 am -
1 stop5h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/148:04 am -
1 stop25h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$107
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 10/267:00 am -
1 stop7h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$118
This Southwest deal was found by Cheapflights users on 9/14. 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.
Mon 10/262:50 pm -
2 stops5h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Southwest logo]()
$118
This Delta deal was found by Cheapflights users on 9/14. 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.
Mon 10/59:30 am -
1 stop5h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$118
This KAYAK deal was found by Cheapflights users on 9/14. 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.
Fri 10/238:00 pm -
Nonstop2h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![JetBlue logo]()
$119
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/248:43 pm -
Nonstop2h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 9/16. 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.
Tue 10/206:05 pm -
Nonstop2h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Southwest logo]()
$119
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:39 pm -
1 stop5h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$120
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/212:39 pm -
1 stop5h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$120
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/157:50 pm -
Nonstop2h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$121
This Southwest deal was found by Cheapflights users on 9/13. 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 11/136:45 pm -
Nonstop2h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Southwest logo]()
$121
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 September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $204 (Delta) |
One-way from | $105 (Delta) |
Popular in | August |
Cheapest in | January |
Average price | $271 |
Good round-trip deal | $258 or less |
Good one-way deal | $158 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 7,457,451 searches. Data last updated September 16, 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
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Tue 10/27
8:36 am-3:27 pm
1 stop5h 51m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/31
8:05 am-2:54 pm
1 stop5h 49m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/14
1:41 pm-7:58 pm
1 stop5h 17m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$118
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/31
8:30 pm-11:58 pm
Nonstop2h 28m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Sun 11/15
7:00 am-3:23 pm
1 stop7h 23m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Tue 10/13
8:36 am-2:58 pm
1 stop5h 22m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Thu 10/8
7:00 am-2:58 pm
1 stop6h 58m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoAlbany
MDW Chicago Midway - ALB Albany Intl
MDWALB
Chicago Midway
Mon 11/23
5:13 pm-11:53 pm
1 stop5h 40m
Albany Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$147
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 10/2
10:59 am-7:27 pm
1 stop7h 28m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 10/31
10:20 am-1:40 pm
Nonstop2h 20m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$148
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-ORH
MDW-BOS
ORD-BOS
MDW-BDL
ORD-BDL
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-ORH
MDW-BOS
ORD-BOS
MDW-BDL
What is the cheapest month to book a flight from Chicago to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $201). Flying from Chicago to Massachusetts in August is currently the most expensive (average of $293). 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 September 16, 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.
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 September 16, 2026.
The most flights from CHI to USMA are scheduled on a Monday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).
How much does it cost to fly round-trip from Chicago to Massachusetts?
Airfare is below average for this route at the moment.
Chicago to Massachusetts flights typically cost between $221 and $330 in December.The cheapest round-trip price found within the last 5 days was $220 on Southwest (Dec 9-Dec 12).
How far ahead should I book a flight from Chicago to Massachusetts?
Booking 60 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Massachusetts. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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 September 12, 2026.
Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Thursday afternoons 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.
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 September 16, 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.
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
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 September 16, 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 5 airlines flying from Chicago to Massachusetts
Discover the top 5 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 7,457,451 searches. Data last updated September 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$371 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$92 | Average$316 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$133 | Average$297 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$320 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$138 | Average$373 | FlexibilityNo cancel fee | On-time71% |