$90+ Cheap flights from Illinois 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.
ORD — BOS
Sep 22 — Sep 291
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Massachusetts with Cheapflights
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Cheapest flights from Illinois to MassachusettsExplore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 23, 2026.
Explore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 23, 2026.
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/193:50 pm -
1 stop18h 08m
Tue 9/2212:52 pm -
1 stop6h 31m
Deal found 8/19![Frontier logo]()
$183
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 8/19. Clicking the “Pick Dates” 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 10/2812:35 pm -
1 stop8h 09m
Deal found 8/19![Frontier logo]()
$186
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.
Fri 10/238:11 pm -
1 stop13h 51m
Tue 10/2712:15 pm -
1 stop7h 30m
Deal found 8/22![Frontier logo]()
$187
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 CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Wed 9/27:44 pm -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/19![Frontier logo]()
$196
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
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/22![Frontier logo]()
$197
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:38 am -
Nonstop2h 28m
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/22![Multiple Airlines logo]()
$198
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
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 10/311:25 am -
1 stop8h 05m
Wed 10/77:20 am -
Nonstop2h 35m
Deal found 8/21![Southwest logo]()
$233
Best flights from Illinois to MassachusettsDiscover carefully curated flight deals from Illinois to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 23, 2026.
Discover carefully curated flight deals from Illinois to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 23, 2026.
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.
Wed 11/113:05 pm -
Nonstop2h 24m
Mon 11/168:40 pm -
Nonstop2h 56m
Deal found 8/21![Delta logo]()
$217
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 8/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/149:07 am -
Nonstop2h 43m
Fri 9/188:31 pm -
Nonstop2h 59m
Deal found 8/21![United Airlines logo]()
$226
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.
Sat 10/33:00 pm -
1 stop7h 39m
Wed 10/146:55 am -
Nonstop2h 51m
Deal found 8/22![JetBlue logo]()
$249
This American Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 12/45:00 am -
1 stop5h 27m
Fri 12/118:00 am -
1 stop5h 43m
Deal found 8/19![American Airlines logo]()
$325
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 8/22. 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.
Sun 12/279:49 pm -
Nonstop2h 29m
Thu 12/315:45 am -
Nonstop3h 06m
Deal found 8/22![United Airlines logo]()
$242
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.
Sun 9/68:20 pm -
Nonstop2h 56m
Thu 9/105:00 pm -
Nonstop3h 01m
Deal found 8/22![JetBlue logo]()
$255
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 9/97:35 am -
Nonstop2h 33m
Fri 9/118:50 pm -
Nonstop2h 42m
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.
Wed 11/118:50 am -
1 stop6h 00m
Mon 11/1611:20 am -
2 stops9h 25m
Deal found 8/23![Southwest logo]()
$242
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.
Fri 9/119:07 am -
Nonstop2h 43m
Sun 9/136:00 am -
Nonstop2h 59m
Deal found 8/22![United Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/209:38 am -
Nonstop2h 28m
Mon 10/265:00 pm -
Nonstop3h 12m
Deal found 8/18![JetBlue logo]()
$255
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 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 8/20. 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.
Fri 9/1110:29 am -
Nonstop2h 36m
Mon 9/148:50 pm -
Nonstop2h 42m
Deal found 8/20![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/55:30 am -
Nonstop2h 25m
Thu 10/85:50 am -
Nonstop2h 35m
Deal found 8/19![Southwest logo]()
$255
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:29 am -
1 stop10h 24m
Mon 10/197:20 pm -
1 stop5h 59m
Deal found 8/18![American Airlines logo]()
$341
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 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.
Sat 9/1212:29 pm -
1 stop5h 46m
Mon 9/148:50 pm -
Nonstop2h 42m
Deal found 8/23![Delta logo]()
$266
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 JetBlue deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/32:35 pm -
1 stop8h 23m
Sun 9/65:07 pm -
1 stop7h 37m
Deal found 8/18![JetBlue logo]()
$295
This Southwest deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/178:40 am -
2 stops8h 40m
Sat 10/249:40 am -
Nonstop2h 35m
Deal found 8/18![Southwest logo]()
$270
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.
Thu 10/225:29 pm -
1 stop4h 58m
Mon 10/267:06 pm -
1 stop5h 51m
Deal found 8/20![Delta logo]()
$277
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/143:51 pm -
1 stop6h 50m
Mon 1/1811:49 am -
1 stop6h 34m
Deal found 8/22![American Airlines logo]()
$371
This JetBlue deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/253:00 pm -
1 stop7h 14m
Fri 10/27:00 am -
1 stop7h 45m
Deal found 8/19![JetBlue logo]()
$309
This JetBlue deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/243:00 pm -
1 stop7h 14m
Fri 10/27:00 am -
1 stop7h 45m
Deal found 8/19![JetBlue logo]()
$309
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 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.
Sat 9/269:50 am -
1 stop9h 05m
Tue 9/297:15 pm -
Nonstop2h 40m
Deal found 8/22![Southwest logo]()
$293
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 9/53:44 pm -
1 stop7h 13m
Wed 9/96:28 pm -
1 stop6h 14m
Deal found 8/21![Delta logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:14 am -
2 stops7h 12m
Sun 11/17:40 pm -
1 stop5h 19m
Deal found 8/18![American Airlines logo]()
$432
Last-minute flights from Illinois to MassachusettsDiscover last-minute flight deals from Illinois to Massachusetts. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Massachusetts. Data last updated August 23, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Wed 9/27:44 pm -
1 stop12h 25m
Sat 9/512:45 pm -
1 stop8h 23m
Deal found 8/19![Frontier logo]()
$196
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.
Tue 9/86:00 pm -
Nonstop2h 25m
Fri 9/116:40 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$245
This Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 8/18![Frontier logo]()
$186
This CheapOair deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Wed 9/93:50 pm -
1 stop17h 32m
Fri 9/1111:36 am -
1 stop12h 23m
Deal found 8/18![Frontier logo]()
$192
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 9/98:45 am -
Nonstop2h 30m
Sat 9/128:40 am -
Nonstop2h 35m
Deal found 8/21![Southwest logo]()
$236
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
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/22![Frontier logo]()
$197
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:38 am -
Nonstop2h 28m
Tue 9/1512:52 pm -
1 stop6h 31m
Deal found 8/22![Multiple Airlines logo]()
$198
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 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 Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/193:50 pm -
1 stop18h 08m
Tue 9/2212:52 pm -
1 stop6h 31m
Deal found 8/19![Frontier logo]()
$183
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.
Mon 9/288:24 pm -
Nonstop2h 45m
Sat 10/312:54 pm -
1 stop6h 29m
Deal found 8/22![Multiple Airlines logo]()
$203
One-way flights from Illinois to MassachusettsSearch for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
Search for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated August 23, 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 Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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
Deal found 8/18![Frontier logo]()
$94
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 Trip.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 10/43:50 pm -
1 stop18h 01m
Deal found 8/18![Frontier logo]()
$97
This CheapOair deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/19![Frontier logo]()
$99
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/302:29 pm -
2 stops19h 26m
Deal found 8/23![Multiple Airlines logo]()
$100
This Kiwi.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 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 8/22![Multiple Airlines logo]()
$101
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/57:44 pm -
1 stop12h 25m
Deal found 8/19![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/27:44 pm -
1 stop12h 25m
Deal found 8/19![Frontier logo]()
$103
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 9/168:24 pm -
Nonstop2h 45m
Deal found 8/22![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
Find flight deals from Illinois to Massachusetts
Keep the following information in mind while searching for Illinois to Massachusetts flight deals. Data was last updated August 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $183 (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 Illinois 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 23, 2026.
Use the filters below to find and compare flights from Illinois to Massachusetts that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 11/11
3:05 pm-6:29 pm
Nonstop2h 24m
Boston Logan Intl
Mon 11/16
8:40 pm-10:36 pm
Nonstop2h 56m
$217
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
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 9/14
9:07 am-12:50 pm
Nonstop2h 43m
Boston Logan Intl
Fri 9/18
8:31 pm-10:30 pm
Nonstop2h 59m
$226
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
Sun 12/27
9:49 pm-1:18 am
Nonstop2h 29m
Boston Logan Intl
Thu 12/31
5:45 am-7:51 am
Nonstop3h 06m
$242
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 11/11
8:50 am-3:50 pm
1 stop6h 00m
Boston Logan Intl
Mon 11/16
11:20 am-7:45 pm
2 stops9h 25m
$242
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/3
3:00 pm-11:39 pm
1 stop7h 39m
Boston Logan Intl
Wed 10/14
6:55 am-8:46 am
Nonstop2h 51m
$249
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 9/6
8:20 pm-12:16 am
Nonstop2h 56m
Boston Logan Intl
Thu 9/10
5:00 pm-7:01 pm
Nonstop3h 01m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 9/9
7:35 am-11:08 am
Nonstop2h 33m
Boston Logan Intl
Fri 9/11
8:50 pm-10:32 pm
Nonstop2h 42m
$255
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/11
9:07 am-12:50 pm
Nonstop2h 43m
Boston Logan Intl
Sun 9/13
6:00 am-7:59 am
Nonstop2h 59m
$255
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Illinois with our price prediction graph.
ORD-BOS
MDW-BOS
STL-ALB
ORD-ALB
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 Illinois to Massachusetts
USIL-USMA
ORD-BOS
MDW-BOS
STL-ALB
ORD-ALB
What is the cheapest month to book a flight from Illinois to Massachusetts?
Currently, January is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $203). Flying from Illinois to Massachusetts in August is currently the most expensive (average of $292). 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 IL to MA?
Find hourly flight availability from Illinois 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 23, 2026.
When flying from Illinois to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 44% versus a flight in the morning.
Weekly flight availability from Illinois to Massachusetts
Explore weekly flight availability from Illinois 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 23, 2026.
The most flights from USIL to USMA are scheduled on a Friday (68 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (50 on average).
How much does it cost to fly round-trip from Illinois to Massachusetts?
Airfare is below average for this route at the moment.
Illinois to Massachusetts flights typically cost between $188 and $340 in September.The cheapest round-trip price found within the last 5 days was $183 on Frontier (Sep 9-Sep 12).
How far ahead should I book a flight from Illinois to Massachusetts?
To ensure you get the cheapest price possible for a flight from Illinois to Massachusetts, you should look to book at least 60 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Illinois to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Massachusetts. Price data was last updated on August 22, 2026.
Travelers seeking maximum savings on their Illinois 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 23, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Illinois to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Entertainment
7.5
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Related info for your journey
Find useful and relevant information for your journey from Illinois 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 Illinois 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 Illinois to Massachusetts by cabin class
Find flights from Illinois to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Massachusetts flights
Browse other Illinois and Massachusetts flight options. Last updated on August 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Illinois after your stay in Massachusetts
Illinois to Massachusetts flights
Consider these flights traveling from Illinois to Massachusetts.
Top 5 airlines flying from Illinois to Massachusetts
Discover the top 5 airlines that operate flights from Illinois 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 23, 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$380 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$323 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$137 | Average$430 | FlexibilityNo cancel fee | On-time71% |