$111+ Cheap flights from Illinois 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 20 — Nov 271
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 October 21, 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 October 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Fri 10/302:26 pm -
1 stop16h 46m
Tue 11/1012:15 pm -
1 stop6h 32m
Deal found 10/21![Multiple Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/219:20 pm -
Nonstop2h 26m
Sun 11/225:30 am -
1 stop5h 15m
Deal found 10/20![United Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am -
2 stops28h 30m
Wed 11/1812:39 pm -
1 stop6h 51m
Deal found 10/19![Frontier logo]()
$224
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop12h 29m
Thu 12/311:08 am -
1 stop28h 33m
Deal found 10/20![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 10/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/208:35 pm -
1 stop11h 58m
Tue 1/58:38 am -
1 stop8h 48m
Deal found 10/20![Frontier logo]()
$227
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 12/57:40 am -
Nonstop2h 15m
Sat 12/1211:35 am -
2 stops6h 30m
Deal found 10/20![Southwest logo]()
$228
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:46 pm -
Nonstop2h 28m
Sun 12/1311:08 am -
1 stop15h 00m
Deal found 10/20![Multiple Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 11/218:55 pm -
1 stop10h 10m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/20![Southwest logo]()
$229
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:40 am -
1 stop27h 31m
Fri 11/277:55 am -
Nonstop3h 04m
Deal found 10/20![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:16 pm -
1 stop16h 03m
Wed 11/1812:39 pm -
1 stop12h 08m
Deal found 10/19![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Tue 11/245:40 am -
1 stop27h 31m
Sat 12/511:34 am -
2 stops29h 30m
Deal found 10/20![Frontier logo]()
$231
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 October 21, 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 October 21, 2026.
This Delta deal was found by Cheapflights users on 10/20. 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.
Mon 12/2812:35 pm -
Nonstop2h 30m
Sat 1/912:00 pm -
1 stop6h 47m
Deal found 10/20![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Thu 11/125:00 am -
1 stop4h 51m
Sun 11/159:12 am -
Nonstop3h 03m
Deal found 10/20![United Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:29 am -
1 stop9h 52m
Sun 11/225:46 pm -
1 stop14h 39m
Deal found 10/17![American Airlines logo]()
$331
This JetBlue deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/187:55 pm -
Nonstop2h 26m
Sat 1/911:45 am -
Nonstop3h 04m
Deal found 10/17![JetBlue logo]()
$335
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 11/119:40 am -
1 stop6h 10m
Mon 11/167:10 am -
Nonstop2h 45m
Deal found 10/20![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 10/20. 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 11/117:05 am -
1 stop3h 48m
Fri 11/134:00 pm -
1 stop5h 45m
Deal found 10/20![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 12/41:15 pm -
2 stops7h 40m
Tue 12/85:55 pm -
Nonstop2h 45m
Deal found 10/19![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 10/20. 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 11/256:44 pm -
1 stop4h 10m
Fri 11/275:45 am -
1 stop5h 40m
Deal found 10/20![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 10/20. 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.
Thu 11/125:05 am -
1 stop6h 10m
Sun 11/155:10 am -
1 stop10h 00m
Deal found 10/20![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 10/20. 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.
Mon 12/2812:35 pm -
Nonstop2h 30m
Thu 12/319:00 am -
1 stop4h 46m
Deal found 10/20![Delta logo]()
$268
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/318:10 am -
1 stop4h 52m
Sun 4/47:10 am -
1 stop7h 41m
Deal found 10/16![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 10/20. 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.
Fri 11/136:45 pm -
Nonstop2h 20m
Sun 11/157:05 am -
Nonstop2h 45m
Deal found 10/20![Southwest logo]()
$274
This Delta deal was found by Cheapflights users on 10/20. 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 11/1211:27 am -
1 stop6h 31m
Sun 11/159:15 am -
1 stop4h 36m
Deal found 10/20![Delta logo]()
$278
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Fri 11/132:31 pm -
1 stop5h 59m
Sun 11/156:00 am -
1 stop5h 05m
Deal found 10/20![United Airlines logo]()
$349
This FlightHub deal was found by Cheapflights users on 10/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:46 pm -
1 stop19h 09m
Mon 12/1411:40 am -
1 stop6h 02m
Deal found 10/19![Multiple Airlines logo]()
$796
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:22 am -
1 stop9h 16m
Mon 12/77:04 pm -
2 stops14h 55m
Deal found 10/17![American Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:05 am -
1 stop4h 22m
Wed 11/44:10 pm -
1 stop7h 07m
Deal found 10/17![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Thu 11/198:39 am -
1 stop7h 42m
Mon 11/235:46 pm -
1 stop14h 39m
Deal found 10/19![American Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:43 am -
1 stop4h 28m
Wed 11/117:20 am -
2 stops7h 33m
Deal found 10/16![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 10/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:05 am -
1 stop4h 22m
Fri 11/64:10 pm -
1 stop7h 07m
Deal found 10/18![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/101:15 pm -
Nonstop2h 05m
Tue 11/174:15 pm -
1 stop7h 25m
Deal found 10/17![Southwest logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/136:07 pm -
1 stop4h 46m
Tue 3/1610:44 am -
2 stops7h 52m
Deal found 10/16![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/20. 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.
Wed 11/410:43 am -
2 stops6h 51m
Sun 11/86:00 am -
1 stop5h 08m
Deal found 10/20![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:05 am -
Nonstop2h 27m
Thu 11/197:30 am -
Nonstop3h 05m
Deal found 10/19![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 10/18. 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.
Mon 12/78:30 am -
Nonstop2h 30m
Thu 12/105:20 am -
1 stop7h 45m
Deal found 10/18![Southwest logo]()
$345
This American Airlines deal was found by Cheapflights users on 10/20. 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 10/316:00 am -
2 stops8h 06m
Tue 11/39:23 am -
2 stops8h 05m
Deal found 10/20![American Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 10/20. 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 11/135:29 pm -
1 stop5h 15m
Sun 11/155:30 am -
1 stop5h 16m
Deal found 10/20![Delta logo]()
$308
This American Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:01 pm -
1 stop5h 20m
Tue 12/87:47 am -
2 stops8h 03m
Deal found 10/17![American Airlines logo]()
$444
This United Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/78:15 am -
1 stop4h 55m
Sat 11/1412:14 pm -
1 stop6h 36m
Deal found 10/17![United Airlines logo]()
$449
Last-minute flights from Illinois to MassachusettsDiscover last-minute flight deals from Illinois to Massachusetts. Data last updated October 21, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Massachusetts. Data last updated October 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
Fri 10/302:26 pm -
1 stop16h 46m
Tue 11/1012:15 pm -
1 stop6h 32m
Deal found 10/21![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:00 am -
2 stops28h 30m
Tue 11/1712:15 pm -
1 stop7h 15m
Deal found 10/19![Frontier logo]()
$224
This Southwest deal was found by Cheapflights users on 10/20. 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.
Wed 11/117:35 am -
2 stops8h 35m
Mon 11/167:10 am -
Nonstop2h 45m
Deal found 10/20![Southwest logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/116:08 am -
2 stops28h 36m
Mon 11/1612:39 pm -
1 stop12h 08m
Deal found 10/20![Multiple Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 10/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:00 am -
1 stop5h 21m
Mon 11/166:00 pm -
1 stop5h 18m
Deal found 10/19![Delta logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:16 pm -
1 stop16h 03m
Wed 11/1812:39 pm -
1 stop12h 08m
Deal found 10/19![Multiple Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/219:20 pm -
Nonstop2h 26m
Sun 11/225:30 am -
1 stop5h 15m
Deal found 10/20![United Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 10/20. 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.
Sat 11/218:55 pm -
1 stop10h 10m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/20![Southwest logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/248:42 pm -
1 stop12h 29m
Thu 12/311:08 am -
1 stop28h 33m
Deal found 10/20![Frontier logo]()
$225
This CheapOair deal was found by Cheapflights users on 10/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:40 am -
1 stop27h 31m
Fri 11/277:55 am -
Nonstop3h 04m
Deal found 10/20![Multiple Airlines logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Tue 11/245:40 am -
1 stop27h 31m
Sat 12/511:34 am -
2 stops29h 30m
Deal found 10/20![Frontier logo]()
$231
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/268:40 am -
1 stop7h 25m
Mon 11/3010:25 pm -
Nonstop3h 00m
Deal found 10/19![Southwest logo]()
$223
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 October 21, 2026.
Search for one-way flight options from Illinois to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 21, 2026.
This CheapOair deal was found by Cheapflights users on 10/21. 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 12/125:24 pm -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:40 am -
1 stop27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/218:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 10/18. 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.
Tue 11/248:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$116
This United Airlines deal was found by Cheapflights users on 10/20. 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 11/95:00 am -
1 stop4h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![United Airlines logo]()
$117
This Southwest deal was found by Cheapflights users on 10/19. 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.
Wed 11/188:00 am -
1 stop8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:24 pm -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:36 pm -
1 stop17h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$121
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Tue 11/246:29 am -
1 stop9h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Fri 12/188:35 pm -
1 stop11h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/910:00 am -
2 stops22h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$124
This Super.com deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/228:42 pm -
1 stop12h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$124
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 October 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $223 (Delta) |
One-way from | $111 (CheapOair) |
Popular in | October |
Cheapest in | January |
Average price | $296 |
Good round-trip deal | $295 or less |
Good one-way deal | $174 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 October 21, 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
Thu 12/17
5:30 am-12:38 pm
1 stop6h 08m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Tue 12/8
12:55 pm-6:45 pm
1 stop4h 50m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Tue 12/1
3:50 pm-9:45 pm
1 stop4h 55m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 11/30
11:30 am-6:27 pm
1 stop5h 57m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 12/21
8:00 am-1:50 pm
1 stop4h 50m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 12/5
12:32 pm-6:35 pm
1 stop5h 03m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Thu 12/3
7:35 am-1:45 pm
1 stop5h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
ChicagoWorcester
ORD Chicago O'Hare Intl - ORH Worcester
ORDORH
Chicago O'Hare Intl
Tue 11/24
6:29 am-5:21 pm
1 stop9h 52m
Worcester
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Mon 11/30
9:05 pm-8:20 am
1 stop10h 15m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sun 11/22
6:15 am-9:34 am
Nonstop2h 19m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
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
ORD-ORH
MLI-BOS
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 Illinois to Massachusetts
USIL-USMA
ORD-BOS
MDW-BOS
ORD-ORH
MLI-BOS
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 $202). Flying from Illinois to Massachusetts in October is currently the most expensive (average of $323). 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 October 21, 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 41% 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 October 21, 2026.
The most flights from USIL to USMA are scheduled on a Monday (73 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (17 on average).
How much does it cost to fly round-trip from Illinois to Massachusetts?
Airfare is typical for this route at the moment.
Illinois to Massachusetts flights typically cost between $210 and $398 in November.The cheapest round-trip price found within the last 5 days was $223 on Delta (Nov 21-Nov 23).
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 October 17, 2026.
Travelers seeking maximum savings on their Illinois to Massachusetts flight should consider departing on Tuesday at noon 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 October 21, 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.
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
Reviews
1 / 20
2.0
MediocreBhoopal,Nov 2024
STL - BOS
Comfort
8.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Food
7.0
Overall
7.9
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 October 21, 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 October 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$358 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$98 | Average$318 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$392 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$442 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$334 | FlexibilityNo cancel fee | On-time63% |