$87+ Cheap flights from Illinois to Maine
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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Sep 1 — Sep 81
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Maine with Cheapflights
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Cheapest flights from Illinois to MaineExplore the most affordable flight options available from Illinois to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
Explore the most affordable flight options available from Illinois to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2026.
This Frontier deal was found by Cheapflights users on 8/1. 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.
Fri 10/239:33 pm
ORD
- BOS
1 stop12h 19m
Frontier
Tue 10/2712:35 pm
BOS
- ORD
1 stop8h 09m
Frontier
Deal found 8/1![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 8/1. 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 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 8/1![Frontier logo]()
$167
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/30![Frontier logo]()
$169
This Expedia deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Sun 9/612:45 pm
BOS
- ORD
1 stop8h 19m
Frontier
Deal found 7/29![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:15 am
ORD
- BOS
1 stop22h 36m
Frontier
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/31![Frontier logo]()
$172
This Trip.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/125:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Wed 8/1912:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/29![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Mon 8/319:36 am
BOS
- ORD
1 stop11h 23m
Frontier
Deal found 7/31![Frontier logo]()
$176
This Trip.com deal was found by Cheapflights users on 7/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Sat 9/1912:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Deal found 7/31![Frontier logo]()
$180
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Fri 8/2112:45 pm
BOS
- ORD
1 stop8h 14m
Frontier
Deal found 7/31![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/166:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 9/233:20 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/29![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 9/146:40 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 7/29![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/266:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 8/313:55 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/29![Southwest logo]()
$235
Best flights from Illinois to MaineDiscover carefully curated flight deals from Illinois to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
Discover carefully curated flight deals from Illinois to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 2, 2026.
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:29 am
ORD
- BOS
Nonstop2h 36m
Delta
Wed 9/2312:15 pm
BOS
- ORD
Nonstop2h 49m
Delta
Deal found 8/2![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 8/2. 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 10/67:50 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 10/177:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 8/2![Southwest logo]()
$217
This United Airlines deal was found by Cheapflights users on 8/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:00 am
ORD
- BOS
1 stop5h 24m
United Airlines
Sat 9/266:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 8/1![United Airlines logo]()
$227
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Tue 9/226:19 am
BOS
- ORD
1 stop8h 26m
JetBlue
Deal found 7/31![JetBlue logo]()
$234
This American Airlines deal was found by Cheapflights users on 8/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am
MLI
- BOS
2 stops7h 26m
American Airlines
Sat 10/35:35 pm
BOS
- MLI
2 stops7h 30m
American Airlines
Deal found 8/2![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:30 am
ORD
- BOS
Nonstop2h 31m
Delta
Mon 9/148:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/29![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Sun 10/186:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Tue 10/208:00 am
BOS
- ORD
Nonstop2h 56m
United Airlines
Deal found 7/31![United Airlines logo]()
$231
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/197:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 9/209:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/29![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/233:05 pm
ORD
- BOS
Nonstop2h 47m
Delta
Mon 9/288:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/28![Delta logo]()
$226
This JetBlue deal was found by Cheapflights users on 8/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:00 pm
ORD
- BOS
1 stop7h 39m
JetBlue
Sun 9/136:19 am
BOS
- ORD
1 stop8h 26m
JetBlue
Deal found 8/1![JetBlue logo]()
$252
This Southwest deal was found by Cheapflights users on 8/2. 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.
Wed 9/162:00 pm
MDW
- BOS
2 stops7h 15m
Southwest
Wed 9/2310:50 am
BOS
- MDW
1 stop6h 00m
Southwest
Deal found 8/2![Southwest logo]()
$242
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/298:00 am
STL
- BGR
1 stop5h 23m
United Airlines
Sat 9/56:00 am
BGR
- STL
1 stop5h 12m
United Airlines
Deal found 7/30![United Airlines logo]()
$249
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Fri 9/44:40 pm
BOS
- ORD
1 stop6h 18m
JetBlue
Deal found 7/31![JetBlue logo]()
$252
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:30 am
ORD
- BOS
Nonstop2h 31m
Delta
Mon 9/218:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 8/2![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 7/31. 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.
Wed 8/1912:50 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 8/237:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/31![Southwest logo]()
$245
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Sun 10/2511:15 am
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 7/30![JetBlue logo]()
$262
This Delta deal was found by Cheapflights users on 7/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Tue 9/87:30 am
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/31![Delta logo]()
$245
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:55 am
MDW
- BOS
2 stops7h 10m
Southwest
Thu 10/225:20 pm
BOS
- MDW
1 stop7h 55m
Southwest
Deal found 7/28![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/57:25 am
STL
- BGR
1 stop5h 58m
United Airlines
Sat 9/126:14 am
BGR
- STL
2 stops10h 29m
United Airlines
Deal found 7/30![United Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/112:45 pm
MDW
- BOS
2 stops7h 40m
Southwest
Sat 9/58:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/29![Southwest logo]()
$250
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 9/185:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Mon 9/216:00 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/29![United Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 7/31. 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.
Mon 9/147:55 pm
MDW
- BOS
1 stop11h 05m
Southwest
Wed 9/168:15 am
BOS
- MDW
2 stops5h 50m
Southwest
Deal found 7/31![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:22 am
ORD
- PWM
2 stops10h 51m
Delta
Sat 9/56:00 am
PWM
- ORD
2 stops9h 48m
Delta
Deal found 8/2![Delta logo]()
$292
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 9/35:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Sun 9/66:03 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 8/2![United Airlines logo]()
$295
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:20 am
STL
- BGR
2 stops8h 48m
Delta
Wed 10/214:10 pm
BGR
- STL
2 stops8h 44m
Delta
Deal found 8/2![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/222:50 pm
MDW
- BOS
2 stops5h 30m
Southwest
Sun 10/2510:50 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/29![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 7/30. 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 8/225:50 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Tue 8/256:00 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 7/30![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
ORD
- PWM
1 stop5h 32m
Delta
Sat 8/296:00 am
PWM
- ORD
2 stops11h 51m
Delta
Deal found 8/2![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 7/31. 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.
Tue 9/86:50 pm
MDW
- PWM
Nonstop2h 20m
Southwest
Thu 9/107:40 am
PWM
- MDW
Nonstop2h 30m
Southwest
Deal found 7/31![Southwest logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Tue 11/106:30 am
MLI
- BOS
1 stop5h 16m
United Airlines
Thu 11/197:15 am
BOS
- MLI
2 stops7h 40m
United Airlines
Deal found 8/2![United Airlines logo]()
$334
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated August 2, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated August 2, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 8/125:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Wed 8/1912:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/29![Frontier logo]()
$175
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Fri 8/2112:45 pm
BOS
- ORD
1 stop8h 14m
Frontier
Deal found 7/31![Frontier logo]()
$182
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:59 pm
ORD
- BOS
1 stop14h 10m
Frontier
Wed 8/2612:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/30![Frontier logo]()
$201
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:20 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Sat 8/2212:45 pm
BOS
- ORD
1 stop8h 23m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$211
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:20 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Mon 8/2412:45 pm
BOS
- ORD
1 stop8h 14m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$196
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- BOS
1 stop7h 24m
Multiple Airlines
Mon 8/2412:45 pm
BOS
- ORD
1 stop8h 14m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$208
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Mon 8/319:36 am
BOS
- ORD
1 stop11h 23m
Frontier
Deal found 7/31![Frontier logo]()
$176
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:20 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Fri 8/2812:45 pm
BOS
- ORD
1 stop8h 14m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$206
This Priceline deal was found by Cheapflights users on 8/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/289:10 pm
ORD
- BOS
1 stop10h 59m
Frontier
Mon 8/3112:45 pm
BOS
- ORD
1 stop8h 14m
Frontier
Deal found 8/1![Frontier logo]()
$204
This Priceline deal was found by Cheapflights users on 7/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/291:55 pm
ORD
- BOS
Nonstop2h 36m
Multiple Airlines
Wed 9/212:45 pm
BOS
- ORD
1 stop8h 23m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$207
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Tue 9/112:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Deal found 7/30![Frontier logo]()
$199
This Travelocity deal was found by Cheapflights users on 8/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:35 pm
ORD
- BOS
1 stop8h 57m
Multiple Airlines
Sun 9/612:45 pm
BOS
- ORD
1 stop8h 19m
Multiple Airlines
Deal found 8/1![Multiple Airlines logo]()
$209
One-way flights from Illinois to MaineSearch for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated August 2, 2026.
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Deal found 7/30![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 7/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:50 pm
ORD
- BOS
1 stop18h 01m
Frontier
Deal found 7/31![Frontier logo]()
$88
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Deal found 7/31![Frontier logo]()
$89
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:33 pm
ORD
- BOS
1 stop12h 19m
Frontier
Deal found 7/30![Frontier logo]()
$90
This Trip.com deal was found by Cheapflights users on 8/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:50 pm
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 8/1![Frontier logo]()
$93
This Super.com deal was found by Cheapflights users on 8/2. 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.
Sat 10/314:44 pm
ORD
- BOS
1 stop16h 32m
Frontier
Deal found 8/2![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 7/30. 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.
Fri 8/145:13 pm
ORD
- BOS
1 stop14h 56m
Frontier
Deal found 7/30![Frontier logo]()
$98
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/119:33 pm
ORD
- BOS
1 stop12h 19m
Frontier
Deal found 7/31![Frontier logo]()
$99
This Trip.com deal was found by Cheapflights users on 8/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:15 am
ORD
- BOS
1 stop22h 36m
Frontier
Deal found 8/1![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” 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 10/138:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/29![JetBlue logo]()
$107
This Super.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/710:59 am
ORD
- BOS
1 stop5h 25m
JetBlue
Deal found 7/28![JetBlue logo]()
$108
This JetBlue deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:24 pm
ORD
- BOS
Nonstop2h 45m
JetBlue
Deal found 7/29![JetBlue logo]()
$109
Find flight deals from Illinois to Maine
Keep the following information in mind while searching for Illinois to Maine flight deals. Data was last updated August 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Frontier) |
One-way from | $87 (Trip.com) |
Popular in | July |
Cheapest in | May |
Average price | $377 |
Good round-trip deal | $336 or less |
Good one-way deal | $162 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Maine 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 2,558,603 searches. Data last updated August 2, 2026.
Use the filters below to find and compare flights from Illinois to Maine that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/16
10:29 am-2:05 pm
Nonstop2h 36m
Boston Logan Intl
Wed 9/23
12:15 pm-2:04 pm
Nonstop2h 49m
$217
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 10/6
7:50 am-11:10 am
Nonstop2h 20m
Boston Logan Intl
Sat 10/17
7:40 am-9:15 am
Nonstop2h 35m
$217
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/12
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Mon 9/14
8:50 pm-10:32 pm
Nonstop2h 42m
$226
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 9/23
3:05 pm-6:52 pm
Nonstop2h 47m
Boston Logan Intl
Mon 9/28
8:50 pm-10:32 pm
Nonstop2h 42m
$226
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/26
5:00 am-11:24 am
1 stop5h 24m
Boston Logan Intl
Sat 9/26
6:43 pm-8:40 pm
Nonstop2h 57m
$227
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sun 10/18
6:10 am-9:33 am
Nonstop2h 23m
Boston Logan Intl
Tue 10/20
8:00 am-9:56 am
Nonstop2h 56m
$231
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/12
7:30 am-11:01 am
Nonstop2h 31m
Boston Logan Intl
Mon 9/21
8:50 pm-10:32 pm
Nonstop2h 42m
$231
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/19
8:24 pm-12:09 am
Nonstop2h 45m
Boston Logan Intl
Tue 9/22
6:19 am-1:45 pm
1 stop8h 26m
$234
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 9/19
7:40 am-11:00 am
Nonstop2h 20m
Boston Logan Intl
Sun 9/20
9:05 pm-10:45 pm
Nonstop2h 40m
$241
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 9/16
2:00 pm-10:15 pm
2 stops7h 15m
Boston Logan Intl
Wed 9/23
10:50 am-3:50 pm
1 stop6h 00m
$242
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Maine
Have a flexible travel schedule? Discover the best time to fly to Maine from Illinois with our price prediction graph.
ORD-BOS
MDW-BOS
MDW-BGR
STL-BGR
MDW-PWM
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 Maine
USIL-USME
ORD-BOS
MDW-BOS
MDW-BGR
STL-BGR
What is the cheapest month to book a flight from Illinois to Maine?
Currently, March is the cheapest month in which you can book a flight from Illinois to Maine (average of $317). Flying from Illinois to Maine in December is currently the most expensive (average of $438). 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 ME?
Find hourly flight availability from Illinois to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2026.
It’s optimal to fly from Illinois to Maine in the afternoon. By choosing this option you can save up to 16% on the cost of your flight, compared to a flight at noon.
Weekly flight availability from Illinois to Maine
Explore weekly flight availability from Illinois to Maine. 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 2, 2026.
The most flights from USIL to USME are scheduled on a Friday (8 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Illinois to Maine?
Airfare is below average for this route at the moment.
Illinois to Maine flights typically cost between $308 and $467 in September.The cheapest round-trip price found within the last 5 days was $279 on United Airlines (Sep 3-Sep 8).
How far ahead should I book a flight from Illinois to Maine?
Booking 46 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Maine. 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 Illinois to Maine?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Maine. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Illinois to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Maine
Get insights into the airlines that provide service to Maine. 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 Maine. Reviews last updated August 2, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Illinois to Maine. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Illinois to Maine. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Illinois to Maine
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maine by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Maine by cabin class
Find flights from Illinois to Maine, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Maine flights
Browse other Illinois and Maine flight options. Last updated on August 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Maine
Find the right flight back to Illinois after your stay in Maine
Illinois to Maine flights
Consider these flights traveling from Illinois to Maine.
Top 2 airlines flying from Illinois to Maine
Discover the top 2 airlines that operate flights from Illinois to Maine. 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 2,558,603 searches. Data last updated August 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$475 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$230 | Average$404 | FlexibilityNo cancel fee | On-time69% |