$68+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Apr 11 — Apr 181
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 March 12, 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 March 12, 2026.
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/46:25 am
MDW
- BOS
1 stop6h 20m
Southwest
Sat 4/111:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/7![Southwest logo]()
$125
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Tue 4/147:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 3/8![Delta logo]()
$126
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/1111:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 4/133:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/8![Southwest logo]()
$126
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/113:16 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Mon 4/137:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/7![American Airlines logo]()
$127
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/810:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Wed 4/84:34 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 3/10![American Airlines logo]()
$131
This SmartFares deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Wed 4/297:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/8![JetBlue logo]()
$134
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Wed 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/9![JetBlue logo]()
$135
This JetBlue deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Tue 5/197:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/8![JetBlue logo]()
$136
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/127:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Tue 5/124:15 pm
BOS
- ORD
Nonstop3h 00m
Delta
Deal found 3/9![Delta logo]()
$137
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/117:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 4/1410:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/9![Southwest logo]()
$137
This Priceline deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Sat 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$138
This CheapOair deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:17 am
ORD
- BOS
1 stop7h 11m
Multiple Airlines
Thu 4/26:05 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$139
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 March 12, 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 March 12, 2026.
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/207:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 4/3010:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/8![Southwest logo]()
$137
This JetBlue deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 6/128:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Wed 6/175:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 3/7![JetBlue logo]()
$147
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/309:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Sun 4/57:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/9![United Airlines logo]()
$165
This Delta deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 8/67:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Sun 8/97:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 3/11![Delta logo]()
$217
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/412:48 pm
PIA
- BOS
1 stop4h 07m
American Airlines
Sat 4/117:40 pm
BOS
- PIA
1 stop4h 53m
American Airlines
Deal found 3/7![American Airlines logo]()
$299
This JetBlue deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/139:41 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Sun 5/176:52 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Deal found 3/7![JetBlue logo]()
$157
This Southwest deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 5/136:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sun 5/176:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/11![Southwest logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/18:45 am
ORD
- BOS
1 stop4h 57m
United Airlines
Sun 4/57:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/8![United Airlines logo]()
$175
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/62:40 pm
ORD
- BOS
1 stop9h 05m
Southwest
Mon 4/138:25 am
BOS
- ORD
1 stop5h 25m
Southwest
Deal found 3/7![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/72:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Tue 4/146:20 am
BOS
- ORD
2 stops10h 45m
Southwest
Deal found 3/9![Southwest logo]()
$162
This JetBlue deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/68:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
Sat 5/97:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/9![JetBlue logo]()
$187
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 6/1112:53 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Mon 6/155:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 3/11![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/72:35 pm
MDW
- BOS
2 stops7h 05m
Southwest
Tue 4/1411:40 am
BOS
- MDW
1 stop5h 35m
Southwest
Deal found 3/9![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/163:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 5/315:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 3/9![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 8/291:15 pm
ORD
- PWM
1 stop8h 18m
Delta
Sun 9/66:00 am
PWM
- ORD
1 stop7h 08m
Delta
Deal found 3/9![Delta logo]()
$249
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/236:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Sat 5/306:25 pm
PWM
- ORD
Nonstop3h 09m
United Airlines
Deal found 3/8![United Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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.
Thu 4/95:01 am
MDW
- BGR
1 stop28h 09m
Multiple Airlines
Sun 4/1210:50 am
BGR
- MDW
1 stop14h 07m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$511
This Delta deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/49:35 am
MDW
- PWM
1 stop5h 31m
Delta
Sat 4/1112:51 pm
PWM
- MDW
1 stop6h 03m
Delta
Deal found 3/7![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/14:45 pm
MDW
- BOS
1 stop4h 25m
Southwest
Tue 4/75:35 am
BOS
- MDW
2 stops12h 00m
Southwest
Deal found 3/8![Southwest logo]()
$172
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/19:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Mon 4/67:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/9![United Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/66:25 pm
MDW
- BOS
1 stop5h 20m
Southwest
Wed 4/86:20 am
BOS
- MDW
1 stop5h 20m
Southwest
Deal found 3/12![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/15:59 pm
ORD
- BGR
1 stop4h 32m
Delta
Tue 5/512:49 pm
BGR
- ORD
2 stops10h 32m
Delta
Deal found 3/9![Delta logo]()
$270
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/284:30 pm
ORD
- BOS
1 stop5h 11m
United Airlines
Sun 3/296:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 3/9![United Airlines logo]()
$232
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 9/17:00 am
ORD
- PWM
1 stop5h 21m
Delta
Sat 9/511:25 am
PWM
- ORD
2 stops9h 59m
Delta
Deal found 3/10![Delta logo]()
$274
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 6/129:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Wed 6/176:00 am
BOS
- ORD
2 stops9h 41m
United Airlines
Deal found 3/7![United Airlines logo]()
$236
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 6/33:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 6/86:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 3/9![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 8/306:00 am
MDW
- BGR
1 stop6h 35m
Delta
Sat 9/52:40 pm
BGR
- MDW
1 stop8h 06m
Delta
Deal found 3/9![Delta logo]()
$285
This American Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 9/11:30 pm
STL
- BGR
1 stop7h 09m
American Airlines
Mon 9/74:58 pm
BGR
- STL
1 stop7h 57m
American Airlines
Deal found 3/8![American Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 8/86:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Fri 8/146:00 am
PWM
- ORD
Nonstop2h 55m
United Airlines
Deal found 3/11![United Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 6/162:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 6/245:35 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 3/7![Southwest logo]()
$212
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated March 12, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated March 12, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/17:17 am
ORD
- BOS
1 stop7h 11m
Multiple Airlines
Thu 4/26:05 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$139
This Southwest deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/46:25 am
MDW
- BOS
1 stop6h 20m
Southwest
Sat 4/111:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/7![Southwest logo]()
$125
This JetBlue deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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.
Mon 4/68:58 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Thu 4/96:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/9![JetBlue logo]()
$137
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” 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 4/810:55 am
ORD
- BOS
Nonstop2h 31m
American Airlines
Wed 4/84:34 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 3/10![American Airlines logo]()
$131
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/88:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Wed 4/157:35 pm
BOS
- ORD
Nonstop3h 04m
JetBlue
Deal found 3/9![JetBlue logo]()
$135
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/117:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Tue 4/147:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 3/8![Delta logo]()
$126
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/1111:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 4/133:45 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 3/8![Southwest logo]()
$126
This American Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/113:16 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Mon 4/137:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 3/7![American Airlines logo]()
$127
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/117:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 4/1410:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/9![Southwest logo]()
$137
This SmartFares deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Wed 4/297:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/8![JetBlue logo]()
$134
This JetBlue deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/289:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Tue 5/197:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/8![JetBlue logo]()
$136
This Priceline deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 4/296:08 pm
ORD
- BOS
1 stop6h 23m
Multiple Airlines
Sat 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$138
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 March 12, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated March 12, 2026.
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/149:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/9![JetBlue logo]()
$68
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/305:25 pm
MDW
- BOS
1 stop5h 15m
Southwest
Deal found 3/9![Southwest logo]()
$68
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/82:10 pm
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 3/9![Delta logo]()
$69
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/137:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/9![Southwest logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 3/3111:27 am
STL
- BOS
1 stop12h 46m
Frontier
Deal found 3/9![Frontier logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 4/812:45 pm
ORD
- BOS
1 stop7h 48m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$70
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/301:55 pm
ORD
- BOS
2 stops8h 45m
Southwest
Deal found 3/9![Southwest logo]()
$73
This Trip.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/15:15 am
ORD
- BOS
1 stop19h 11m
Frontier
Deal found 3/11![Frontier logo]()
$74
This Trip.com deal was found by Cheapflights users on 3/11. Clicking the “Pick Dates” 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 4/12:56 pm
MDW
- BOS
1 stop9h 30m
Frontier
Deal found 3/11![Frontier logo]()
$74
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” 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 5/236:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 3/8![United Airlines logo]()
$75
This Flysmarter deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:20 pm
ORD
- BOS
Nonstop2h 33m
JetBlue
Deal found 3/7![JetBlue logo]()
$76
This Super.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” 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 5/36:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/9![JetBlue logo]()
$78
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 March 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $125 (Southwest) |
One-way from | $68 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $320 |
Good round-trip deal | $284 or less |
Good one-way deal | $148 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 March 12, 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
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Mon 4/20
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Thu 4/30
10:40 am-12:20 pm
Nonstop2h 40m
$137
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/12
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Wed 6/17
5:20 pm-7:25 pm
Nonstop3h 05m
$147
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/13
9:41 am-1:09 pm
Nonstop2h 28m
Boston Logan Intl
Sun 5/17
6:52 am-8:51 am
Nonstop2h 59m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 5/13
6:00 pm-9:20 pm
Nonstop2h 20m
Boston Logan Intl
Sun 5/17
6:10 am-7:55 am
Nonstop2h 45m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 4/6
2:40 pm-12:45 am
1 stop9h 05m
Boston Logan Intl
Mon 4/13
8:25 am-12:50 pm
1 stop5h 25m
$162
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/7
2:40 pm-10:30 pm
1 stop6h 50m
Boston Logan Intl
Tue 4/14
6:20 am-4:05 pm
2 stops10h 45m
$162
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 4/7
2:35 pm-10:40 pm
2 stops7h 05m
Boston Logan Intl
Tue 4/14
11:40 am-4:15 pm
1 stop5h 35m
$162
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 3/30
9:30 pm-12:59 am
Nonstop2h 29m
Boston Logan Intl
Sun 4/5
7:00 am-9:00 am
Nonstop3h 00m
$165
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 5/16
3:30 pm-6:45 pm
Nonstop2h 15m
Boston Logan Intl
Sun 5/31
5:30 am-8:45 am
1 stop4h 15m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Wed 4/1
4:45 pm-10:10 pm
1 stop4h 25m
Boston Logan Intl
Tue 4/7
5:35 am-4:35 pm
2 stops12h 00m
$172
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.
MDW-BOS
ORD-BOS
PIA-BOS
ORD-PWM
MDW-BGR
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
MDW-BOS
ORD-BOS
PIA-BOS
ORD-PWM
What is the cheapest month to book a flight from Illinois to Maine?
Currently, October is the cheapest month in which you can book a flight from Illinois to Maine (average of $206). Flying from Illinois to Maine in November is currently the most expensive (average of $276). 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 March 12, 2026.
It’s optimal to fly from Illinois to Maine in the afternoon. By choosing this option you can save up to 21% on the cost of your flight, compared to a flight in the evening.
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 February 21, 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. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 12, 2026.
The most flights from USIL to USME are scheduled on a Wednesday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
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 March 12, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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.
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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 March 12, 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 4 airlines flying from Illinois to Maine
Discover the top 4 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 March 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$415 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$429 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$490 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$263 | Average$399 | FlexibilityNo cancel fee | On-timeN/A |