$115+ Cheap flights from Massachusetts to Illinois
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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Massachusetts to Illinois 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Illinois
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Cheapest flights from Massachusetts to IllinoisExplore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Thu 12/1710:25 am -
1 stop10h 05m
Sat 12/198:35 pm -
1 stop11h 55m
Deal found 11/4![Frontier logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:15 pm -
1 stop6h 32m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/2![Frontier logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Wed 11/1812:39 pm -
1 stop6h 51m
Wed 11/255:40 am -
1 stop27h 31m
Deal found 11/3![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2111:06 am -
1 stop9h 41m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/3![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 11/1812:39 pm -
1 stop12h 08m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 11/4![Frontier logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 11/1912:39 pm -
1 stop12h 08m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 10/31![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 11/1912:39 pm -
1 stop7h 06m
Wed 11/255:40 am -
1 stop27h 31m
Deal found 10/31![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/1411:08 am -
1 stop15h 00m
Wed 12/165:24 pm -
1 stop15h 06m
Deal found 10/31![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2011:06 am -
1 stop9h 41m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/3![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:34 am -
1 stop11h 26m
Sun 12/610:29 pm -
1 stop11h 10m
Deal found 11/1![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:06 am -
1 stop9h 41m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/2![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:34 am -
1 stop11h 26m
Sun 12/1310:29 pm -
1 stop11h 10m
Deal found 11/1![Frontier logo]()
$229
Best flights from Massachusetts to IllinoisDiscover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Massachusetts to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/145:36 pm -
1 stop14h 51m
Wed 11/188:30 am -
1 stop7h 37m
Deal found 10/30![American Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/144:29 pm -
1 stop5h 45m
Tue 1/1910:05 am -
1 stop4h 44m
Deal found 11/3![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1810:25 pm -
Nonstop3h 00m
Mon 1/47:50 am -
2 stops6h 50m
Deal found 11/1![Southwest logo]()
$302
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/285:45 am -
Nonstop3h 06m
Thu 12/317:55 am -
1 stop4h 31m
Deal found 11/3![United Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 2/194:25 pm -
1 stop6h 54m
Mon 2/227:20 am -
1 stop7h 23m
Deal found 11/3![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/114:12 pm -
1 stop8h 18m
Fri 1/158:30 am -
1 stop6h 17m
Deal found 10/31![American Airlines logo]()
$300
This Southwest deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/55:55 pm -
Nonstop2h 45m
Thu 1/71:25 pm -
Nonstop2h 15m
Deal found 11/2![Southwest logo]()
$313
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/308:25 pm -
Nonstop3h 04m
Thu 12/310:28 am -
Nonstop2h 26m
Deal found 11/2![United Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/154:29 pm -
1 stop5h 45m
Tue 1/198:55 am -
1 stop5h 54m
Deal found 11/3![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2810:25 pm -
Nonstop3h 00m
Sun 1/37:00 pm -
Nonstop2h 25m
Deal found 11/1![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/44:29 pm -
1 stop5h 45m
Sun 2/710:05 am -
1 stop4h 44m
Deal found 11/1![Delta logo]()
$300
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/175:51 am -
1 stop6h 01m
Wed 1/135:42 am -
1 stop7h 38m
Deal found 10/30![American Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/217:00 am -
Nonstop2h 45m
Mon 12/287:45 am -
Nonstop2h 15m
Deal found 11/3![Southwest logo]()
$322
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/154:29 pm -
1 stop5h 45m
Mon 1/188:55 am -
1 stop5h 54m
Deal found 11/3![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:25 pm -
Nonstop3h 00m
Wed 12/212:50 pm -
1 stop5h 00m
Deal found 11/1![Southwest logo]()
$323
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/76:36 pm -
1 stop5h 23m
Sun 11/226:30 am -
1 stop5h 11m
Deal found 10/30![United Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/265:30 am -
1 stop5h 19m
Fri 1/18:05 am -
Nonstop2h 33m
Deal found 10/30![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/85:35 pm -
1 stop4h 55m
Tue 12/156:25 pm -
Nonstop2h 20m
Deal found 11/3![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/84:08 pm -
1 stop5h 37m
Sun 12/137:00 am -
1 stop7h 07m
Deal found 11/4![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/276:36 pm -
1 stop5h 23m
Tue 12/13:45 pm -
2 stops7h 14m
Deal found 10/31![United Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/204:20 pm -
Nonstop2h 45m
Sun 11/227:50 am -
2 stops6h 50m
Deal found 10/31![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/275:26 pm -
1 stop7h 38m
Tue 12/16:00 am -
1 stop4h 54m
Deal found 10/30![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/159:05 am -
1 stop5h 51m
Tue 12/2212:35 pm -
Nonstop2h 30m
Deal found 10/30![Delta logo]()
$310
This Mytrip deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:20 am -
2 stops10h 10m
Sat 11/215:26 pm -
3 stops22h 44m
Deal found 11/3![Multiple Airlines logo]()
$1,111
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/77:10 am -
Nonstop2h 45m
Mon 12/71:15 pm -
2 stops7h 40m
Deal found 11/3![Southwest logo]()
$328
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/286:00 am -
1 stop5h 05m
Wed 12/26:42 am -
2 stops8h 10m
Deal found 10/30![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:08 pm -
2 stops8h 48m
Tue 12/85:30 am -
2 stops8h 37m
Deal found 11/1![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/137:40 pm -
1 stop5h 19m
Mon 11/162:34 pm -
1 stop5h 52m
Deal found 10/31![American Airlines logo]()
$464
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/1612:30 pm -
Nonstop2h 45m
Mon 1/183:20 pm -
2 stops7h 45m
Deal found 10/31![Southwest logo]()
$328
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/611:52 am -
1 stop7h 07m
Sat 1/92:28 pm -
1 stop6h 25m
Deal found 11/2![United Airlines logo]()
$449
Last-minute flights from Massachusetts to IllinoisDiscover last-minute flight deals from Massachusetts to Illinois. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Massachusetts to Illinois. Data last updated November 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:15 pm -
1 stop6h 32m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/2![Frontier logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Wed 11/1812:39 pm -
1 stop6h 51m
Wed 11/255:40 am -
1 stop27h 31m
Deal found 11/3![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 11/1812:39 pm -
1 stop12h 08m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 11/4![Frontier logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 11/1912:39 pm -
1 stop12h 08m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 10/31![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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.
Thu 11/1912:39 pm -
1 stop7h 06m
Wed 11/255:40 am -
1 stop27h 31m
Deal found 10/31![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2011:06 am -
1 stop9h 41m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/3![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2111:06 am -
1 stop9h 41m
Wed 11/258:42 pm -
1 stop12h 29m
Deal found 11/3![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:06 am -
1 stop9h 41m
Tue 11/248:42 pm -
1 stop12h 29m
Deal found 11/2![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:34 am -
1 stop11h 26m
Sun 12/610:29 pm -
1 stop11h 10m
Deal found 11/1![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1211:34 am -
1 stop11h 26m
Sun 12/1310:29 pm -
1 stop11h 10m
Deal found 11/1![Frontier logo]()
$229
This CheapOair deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 12/1411:08 am -
1 stop15h 00m
Wed 12/165:24 pm -
1 stop15h 06m
Deal found 10/31![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Thu 12/1710:25 am -
1 stop10h 05m
Sat 12/198:35 pm -
1 stop11h 55m
Deal found 11/4![Frontier logo]()
$217
One-way flights from Massachusetts to IllinoisSearch for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Massachusetts to Illinois. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1011:08 am -
1 stop9h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/411:57 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2311:06 am -
1 stop9h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$116
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Thu 12/1710:25 am -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$117
This Cheapflightsfares deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/1411:27 am -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:15 pm -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$118
This iWofly deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:15 pm -
1 stop6h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$119
This Super.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/1411:27 am -
1 stop8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$119
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/2111:06 am -
1 stop9h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1111:34 am -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1910:25 am -
1 stop10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/14:45 pm -
Nonstop3h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$122
Find flight deals from Massachusetts to Illinois
Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Frontier) |
One-way from | $115 (Cheapflightsfares) |
Popular in | October |
Cheapest in | January |
Average price | $297 |
Good round-trip deal | $335 or less |
Good one-way deal | $192 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Illinois 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 November 4, 2026.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Wed 12/23
10:25 pm-12:25 am
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Thu 11/19
1:29 pm-3:32 pm
Nonstop3h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 12/18
10:25 pm-12:25 am
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sun 12/20
10:25 pm-12:25 am
Nonstop3h 00m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$144
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 11/20
4:00 pm-10:18 pm
1 stop7h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$148
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 11/20
2:30 pm-10:00 pm
1 stop8h 30m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$154
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Wed 12/9
7:10 am-8:55 am
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 12/4
12:50 pm-2:40 pm
Nonstop2h 50m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Fri 11/27
7:05 am-8:50 am
Nonstop2h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$157
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Wed 11/18
4:00 pm-11:54 pm
2 stops8h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$158
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Massachusetts to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Massachusetts with our price prediction graph.
BOS-MDW
BOS-ORD
ORH-ORD
BOS-PIA
BOS-CMI
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 Massachusetts to Illinois
USMA-USIL
BOS-MDW
BOS-ORD
ORH-ORD
BOS-PIA
What is the cheapest month to book a flight from Massachusetts to Illinois?
Currently, January is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $201). Flying from Massachusetts to Illinois in October is currently the most expensive (average of $357). 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 MA to IL?
Find hourly flight availability from Massachusetts to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2026.
A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Massachusetts to Illinois
Explore weekly flight availability from Massachusetts to Illinois. 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 November 4, 2026.
The most flights from USMA to USIL are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).
How much does it cost to fly round-trip from Massachusetts to Illinois?
Airfare is below average for this route at the moment.
Massachusetts to Illinois flights typically cost between $225 and $426 in November.The cheapest round-trip price found within the last 5 days was $218 on Frontier (Nov 18-Nov 25).
How far ahead should I book a flight from Massachusetts to Illinois?
Booking 63 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Illinois. 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 Massachusetts to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on June 8, 2026.
Travelers seeking maximum savings on their Massachusetts to Illinois flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated November 4, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Massachusetts to Illinois have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Illinois. 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 Massachusetts to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Massachusetts to Illinois by cabin class
Find flights from Massachusetts to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Massachusetts and Illinois flights
Browse other Massachusetts and Illinois flight options. Last updated on November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Massachusetts after your stay in Illinois
Massachusetts to Illinois flights
Consider these flights traveling from Massachusetts to Illinois.
Top 5 airlines flying from Massachusetts to Illinois
Discover the top 5 airlines that operate flights from Massachusetts to Illinois. 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 November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$79 | Average$239 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$331 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$365 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$153 | Average$443 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$313 | FlexibilityNo cancel fee | On-time63% |