$90+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Sep 24 — Oct 11
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Massachusetts with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 August 25, 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 August 25, 2026.
This Super.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/163:50 pm -
1 stop17h 32m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/22![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Fri 10/238:11 pm -
1 stop13h 51m
Wed 10/2812:39 pm -
1 stop7h 06m
Deal found 8/23![Frontier logo]()
$187
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/33:50 pm -
1 stop18h 08m
Tue 10/612:52 pm -
1 stop6h 31m
Deal found 8/24![Frontier logo]()
$194
This Frontier deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Sat 9/123:50 pm -
1 stop18h 08m
Mon 9/1412:54 pm -
1 stop6h 29m
Deal found 8/22![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Sat 9/128:24 pm -
Nonstop2h 45m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/21![Multiple Airlines logo]()
$197
This Priceline deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Sat 10/2411:42 am -
1 stop7h 49m
Deal found 8/23![Multiple Airlines logo]()
$198
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Mon 9/288:24 pm -
Nonstop2h 45m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 8/23![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:04 am -
1 stop24h 25m
Sat 10/2411:42 am -
1 stop7h 49m
Deal found 8/25![Multiple Airlines logo]()
$201
This deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:00 pm -
1 stop6h 49m
Sun 10/116:55 am -
Nonstop2h 51m
Deal found 8/20![JetBlue logo]()
$202
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Thu 10/228:04 pm -
Nonstop2h 55m
Tue 10/2712:15 pm -
1 stop7h 30m
Deal found 8/23![Multiple Airlines logo]()
$203
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/127:40 am -
Nonstop2h 20m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/23:30 pm -
Nonstop2h 20m
Tue 10/610:55 am -
Nonstop2h 35m
Deal found 8/22![Southwest logo]()
$226
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 August 25, 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 August 25, 2026.
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/127:40 am -
Nonstop2h 20m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/176:00 am -
1 stop5h 43m
Sat 10/178:31 pm -
Nonstop2h 59m
Deal found 8/23![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 10/227:25 am -
Nonstop2h 35m
Sun 10/257:30 am -
Nonstop2h 54m
Deal found 8/23![Delta logo]()
$236
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/102:35 pm -
1 stop8h 44m
Wed 11/185:00 pm -
Nonstop3h 12m
Deal found 8/24![JetBlue logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/45:00 am -
1 stop10h 58m
Tue 9/85:23 pm -
1 stop5h 07m
Deal found 8/20![American Airlines logo]()
$260
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/306:45 pm -
Nonstop2h 15m
Thu 11/512:45 pm -
Nonstop2h 45m
Deal found 8/24![Southwest logo]()
$226
This United Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/117:00 am -
1 stop4h 26m
Mon 11/165:00 pm -
Nonstop3h 01m
Deal found 8/24![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/165:30 am -
2 stops9h 07m
Wed 9/234:20 pm -
1 stop6h 58m
Deal found 8/23![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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
Mon 11/28:40 am -
1 stop6h 00m
Deal found 8/21![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Mon 12/289:49 pm -
Nonstop2h 29m
Sat 1/96:33 pm -
Nonstop2h 52m
Deal found 8/25![United Airlines logo]()
$236
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 10/169:38 am -
Nonstop2h 28m
Sun 10/2511:15 am -
Nonstop3h 05m
Deal found 8/22![JetBlue logo]()
$265
This Delta deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/237:30 pm -
Nonstop2h 39m
Sat 9/266:00 pm -
Nonstop2h 59m
Deal found 8/20![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/215:45 am -
Nonstop2h 15m
Wed 9/231:20 pm -
2 stops6h 45m
Deal found 8/23![Southwest logo]()
$241
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/511:15 am -
Nonstop2h 42m
Sun 9/612:42 pm -
1 stop8h 04m
Deal found 8/20![American Airlines logo]()
$300
This JetBlue deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/162:35 pm -
1 stop8h 50m
Mon 10/196:55 am -
Nonstop2h 51m
Deal found 8/20![JetBlue logo]()
$278
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/191:55 pm -
Nonstop2h 41m
Sun 9/206:00 am -
Nonstop2h 59m
Deal found 8/20![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:30 am -
Nonstop2h 31m
Mon 9/148:50 pm -
Nonstop2h 42m
Deal found 8/21![Delta logo]()
$255
This United deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:45 pm -
1 stop16h 10m
Tue 9/811:02 am -
2 stops12h 13m
Deal found 8/22![Multiple Airlines logo]()
$629
This Southwest deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/175:45 am -
Nonstop2h 15m
Sun 9/209:05 pm -
Nonstop2h 40m
Deal found 8/23![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/2111:59 am -
Nonstop2h 05m
Mon 9/287:35 pm -
1 stop4h 57m
Deal found 8/20![United Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 11/257:05 am -
Nonstop2h 27m
Mon 11/308:40 pm -
Nonstop2h 56m
Deal found 8/24![Delta logo]()
$275
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/911:55 am -
2 stops5h 40m
Sat 9/124:35 pm -
1 stop5h 00m
Deal found 8/21![Southwest logo]()
$261
This JetBlue deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 10/16:00 am -
1 stop8h 24m
Sun 10/44:55 pm -
1 stop7h 13m
Deal found 8/21![JetBlue logo]()
$318
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 11/258:45 am -
1 stop5h 34m
Thu 12/34:08 pm -
1 stop7h 05m
Deal found 8/22![Delta logo]()
$282
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/113:00 pm -
1 stop7h 14m
Sun 9/137:00 am -
1 stop7h 45m
Deal found 8/22![JetBlue logo]()
$335
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/175:45 am -
Nonstop2h 15m
Mon 9/215:50 am -
2 stops7h 30m
Deal found 8/24![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/242:30 pm -
Nonstop2h 12m
Sun 9/276:20 am -
Nonstop2h 33m
Deal found 8/22![United Airlines logo]()
$318
This JetBlue deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/53:20 pm -
1 stop7h 38m
Wed 9/96:25 am -
1 stop4h 33m
Deal found 8/23![JetBlue logo]()
$335
This Southwest deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/66:05 pm -
Nonstop1h 55m
Thu 11/56:50 pm -
Nonstop2h 30m
Deal found 8/20![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/119:30 am -
1 stop5h 07m
Sun 9/134:20 pm -
1 stop6h 58m
Deal found 8/23![Delta logo]()
$326
Last-minute flights from Chicago to MassachusettsDiscover last-minute flight deals from Chicago to Massachusetts. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Massachusetts. Data last updated August 25, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Wed 9/93:50 pm -
1 stop17h 32m
Sat 9/1212:54 pm -
1 stop6h 29m
Deal found 8/20![Frontier logo]()
$188
This Super.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 9/93:50 pm -
1 stop17h 32m
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/24![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Sat 9/123:50 pm -
1 stop18h 08m
Mon 9/1412:54 pm -
1 stop6h 29m
Deal found 8/22![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Sat 9/128:24 pm -
Nonstop2h 45m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/21![Multiple Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/127:40 am -
Nonstop2h 20m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$217
This Super.com deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/163:50 pm -
1 stop17h 32m
Sat 9/1912:54 pm -
1 stop6h 29m
Deal found 8/22![Frontier logo]()
$185
This Super.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/169:38 am -
Nonstop2h 28m
Sat 9/197:00 am -
Nonstop2h 48m
Deal found 8/23![JetBlue logo]()
$209
This CheapOair deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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 9/188:24 pm -
Nonstop2h 45m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 8/22![Multiple Airlines logo]()
$206
This CheapOair deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Sat 9/193:50 pm -
1 stop18h 08m
Wed 9/235:00 pm -
Nonstop3h 01m
Deal found 8/24![Multiple Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Sat 9/193:50 pm -
1 stop18h 08m
Sat 9/265:00 pm -
Nonstop3h 01m
Deal found 8/23![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/228:24 pm -
Nonstop2h 45m
Tue 9/2912:52 pm -
1 stop6h 31m
Deal found 8/23![Multiple Airlines logo]()
$198
This CheapOair deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Mon 9/288:24 pm -
Nonstop2h 45m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 8/23![Multiple Airlines logo]()
$199
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 August 25, 2026.
Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/307:11 am -
1 stop26h 44m
Deal found 8/20![Multiple Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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 9/237:11 am -
1 stop26h 14m
Deal found 8/21![Multiple Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/218:04 am -
1 stop26h 01m
Deal found 8/24![Multiple Airlines logo]()
$101
This Frontier deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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.
Fri 10/98:11 pm -
1 stop13h 51m
Deal found 8/23![Frontier logo]()
$104
This Super.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/158:24 pm -
Nonstop2h 45m
Deal found 8/23![JetBlue logo]()
$105
This CheapOair deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” 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.
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/22![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” 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.
Sat 9/197:11 am -
1 stop26h 14m
Deal found 8/21![Multiple Airlines logo]()
$106
This Super.com deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” 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 9/269:38 am -
Nonstop2h 28m
Deal found 8/23![JetBlue logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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.
Sat 9/1912:56 pm -
2 stops21h 02m
Deal found 8/24![Frontier logo]()
$108
This Delta deal was found by Cheapflights users on 8/25. 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.
Mon 9/217:30 pm -
Nonstop2h 39m
Deal found 8/25![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” 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 10/211:10 pm -
Nonstop2h 20m
Deal found 8/24![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Sat 10/312:56 pm -
2 stops21h 02m
Deal found 8/20![Frontier logo]()
$110
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 August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $185 (Super.com) |
One-way from | $90 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $283 |
Good round-trip deal | $248 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 August 25, 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
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 9/12
7:40 am-11:00 am
Nonstop2h 20m
Boston Logan Intl
Mon 9/14
6:40 pm-8:25 pm
Nonstop2h 45m
$217
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Fri 10/30
6:45 pm-10:00 pm
Nonstop2h 15m
Boston Logan Intl
Thu 11/5
12:45 pm-2:30 pm
Nonstop2h 45m
$226
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/17
6:00 am-12:43 pm
1 stop5h 43m
Boston Logan Intl
Sat 10/17
8:31 pm-10:30 pm
Nonstop2h 59m
$227
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 11/11
7:00 am-12:26 pm
1 stop4h 26m
Boston Logan Intl
Mon 11/16
5:00 pm-7:01 pm
Nonstop3h 01m
$227
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 10/29
5:30 am-8:55 am
Nonstop2h 25m
Boston Logan Intl
Mon 11/2
8:40 am-1:40 pm
1 stop6h 00m
$227
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/22
7:25 am-11:00 am
Nonstop2h 35m
Boston Logan Intl
Sun 10/25
7:30 am-9:24 am
Nonstop2h 54m
$236
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 12/28
9:49 pm-1:18 am
Nonstop2h 29m
Boston Logan Intl
Sat 1/9
6:33 pm-8:25 pm
Nonstop2h 52m
$236
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 9/21
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Wed 9/23
1:20 pm-7:05 pm
2 stops6h 45m
$241
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Wed 9/16
5:30 am-3:37 pm
2 stops9h 07m
Worcester
Wed 9/23
4:20 pm-10:18 pm
1 stop6h 58m
$242
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 9/17
5:45 am-9:00 am
Nonstop2h 15m
Boston Logan Intl
Sun 9/20
9:05 pm-10:45 pm
Nonstop2h 40m
$246
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-ALB
ORD-BOS
MDW-BOS
ORD-ORH
ORD-HYA
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-ALB
ORD-BOS
MDW-BOS
ORD-ORH
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 $200). Flying from Chicago to Massachusetts in August is currently the most expensive (average of $288). 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 August 25, 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 August 25, 2026.
The most flights from CHI to USMA are scheduled on a Sunday (77 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (55 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 $204 and $332 in September.The cheapest round-trip price found within the last 5 days was $185 on Frontier (Sep 16-Sep 19).
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 August 22, 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 August 25, 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.
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Food
7.0
Comfort
8.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
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 August 25, 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 August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$78 | Average$349 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$89 | Average$313 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$131 | Average$289 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$323 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$372 | FlexibilityNo cancel fee | On-time71% |