$65+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
May 10 — May 171
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 April 10, 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 April 10, 2026.
This Frontier deal was found by Cheapflights users on 4/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Tue 5/129:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/7![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Tue 5/126:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 4/6![Frontier logo]()
$140
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 pm
ORD
- BOS
1 stop14h 00m
Multiple Airlines
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Tue 5/59:31 am
BOS
- ORD
1 stop23h 24m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$146
This Expedia deal was found by Cheapflights users on 4/8. 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 Expedia 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 4/8![JetBlue logo]()
$147
This Southwest deal was found by Cheapflights users on 4/7. 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 5/1212:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/126:00 pm
BOS
- MDW
1 stop5h 15m
Southwest
Deal found 4/7![Southwest logo]()
$149
This Cheapflightsfares deal was found by Cheapflights users on 4/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 pm
ORD
- BOS
1 stop14h 00m
Spirit Airlines
Wed 4/228:16 pm
BOS
- ORD
1 stop14h 20m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$150
This SmartFares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Sat 5/26:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/6![JetBlue logo]()
$151
This CheapOair deal was found by Cheapflights users on 4/9. 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 5/612:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/1312:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/9![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/287:15 pm
ORD
- BOS
2 stops29h 16m
Multiple Airlines
Sat 5/210:25 am
BOS
- ORD
1 stop11h 47m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$152
This Delta deal was found by Cheapflights users on 4/8. 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 5/26:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Wed 5/64:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 4/8![Delta logo]()
$153
This Southwest deal was found by Cheapflights users on 4/7. 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 5/56:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 5/93:30 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/7![Southwest logo]()
$153
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 April 10, 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 April 10, 2026.
This United Airlines deal was found by Cheapflights users on 4/8. 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 5/233:55 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sat 5/307:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/8![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 4/7. 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.
Tue 5/1210:30 am
ORD
- BOS
Nonstop2h 27m
Delta
Thu 5/147:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 4/7![Delta logo]()
$176
This Southwest deal was found by Cheapflights users on 4/7. 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.
Sun 6/75:15 am
MDW
- BOS
Nonstop2h 10m
Southwest
Mon 6/85:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/7![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/286:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Tue 5/123:00 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/6![United Airlines logo]()
$167
This JetBlue deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/23:27 pm
ORD
- PWM
1 stop7h 31m
JetBlue
Wed 6/32:37 pm
PWM
- ORD
1 stop9h 21m
JetBlue
Deal found 4/5![JetBlue logo]()
$351
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Sun 5/37:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 5/106:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/5![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/299:15 am
ORD
- BOS
Nonstop2h 31m
United Airlines
Fri 5/18:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
Deal found 4/10![United Airlines logo]()
$182
This Delta deal was found by Cheapflights users on 4/7. 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.
Thu 5/147:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 5/206:51 am
BOS
- ORD
1 stop7h 56m
Delta
Deal found 4/7![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/78:00 am
MDW
- BOS
1 stop6h 10m
Southwest
Sun 5/105:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 4/5![Southwest logo]()
$197
This American Airlines deal was found by Cheapflights users on 4/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:16 am
ORD
- BGR
1 stop5h 20m
American Airlines
Sun 10/45:48 pm
BGR
- ORD
Nonstop3h 02m
American Airlines
Deal found 4/9![American Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 4/9. 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.
Fri 6/57:40 pm
ORD
- BOS
Nonstop2h 35m
United Airlines
Sun 6/75:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 4/9![United Airlines logo]()
$187
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/82:40 pm
ORD
- BOS
2 stops8h 15m
Southwest
Sat 5/95:25 am
BOS
- ORD
2 stops11h 05m
Southwest
Deal found 4/5![Southwest logo]()
$202
This Southwest deal was found by Cheapflights users on 4/9. 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 5/161:55 pm
ORD
- BOS
1 stop7h 10m
Southwest
Sun 5/178:15 am
BOS
- ORD
1 stop5h 35m
Southwest
Deal found 4/9![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/299:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 5/315:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 4/6![United Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Thu 4/238:26 am
MDW
- BGR
1 stop9h 47m
Multiple Airlines
Sun 4/267:53 pm
BGR
- MDW
1 stop13h 11m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$561
This Southwest deal was found by Cheapflights users on 4/9. 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 4/292:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Sat 5/212:50 pm
BOS
- ORD
2 stops10h 05m
Southwest
Deal found 4/9![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 4/9. 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 5/86:07 am
ORD
- PWM
1 stop6h 51m
Delta
Sun 5/106:02 am
PWM
- ORD
1 stop5h 37m
Delta
Deal found 4/9![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/112:10 pm
MDW
- BOS
2 stops6h 40m
Southwest
Thu 5/147:20 am
BOS
- MDW
2 stops6h 50m
Southwest
Deal found 4/5![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 4/9. 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 5/156:31 pm
ORD
- PWM
1 stop5h 12m
Delta
Tue 5/196:02 am
PWM
- ORD
2 stops7h 59m
Delta
Deal found 4/9![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/7. 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.
Sun 5/32:00 pm
ORD
- BOS
2 stops17h 05m
Southwest
Wed 5/65:35 am
BOS
- ORD
1 stop10h 25m
Southwest
Deal found 4/7![Southwest logo]()
$208
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/91:16 pm
MDW
- PWM
2 stops9h 13m
Delta
Tue 6/166:00 am
PWM
- MDW
2 stops11h 16m
Delta
Deal found 4/6![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/233:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 5/246:20 am
BOS
- MDW
1 stop6h 45m
Southwest
Deal found 4/6![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 4/9. 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 5/114:25 pm
ORD
- PWM
1 stop6h 34m
United Airlines
Sat 5/307:16 pm
PWM
- ORD
1 stop5h 10m
United Airlines
Deal found 4/9![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 4/7. 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 5/26:23 pm
ORD
- PWM
1 stop5h 23m
Delta
Tue 5/511:35 am
PWM
- ORD
2 stops8h 17m
Delta
Deal found 4/7![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/286:12 pm
ORD
- PWM
1 stop4h 39m
United Airlines
Sat 5/305:15 am
PWM
- ORD
1 stop5h 21m
United Airlines
Deal found 4/5![United Airlines logo]()
$289
This Southwest deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/117:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 6/245:50 am
BOS
- MDW
1 stop5h 55m
Southwest
Deal found 4/6![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 4/10. 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.
Wed 4/296:21 pm
ORD
- PWM
1 stop5h 25m
Delta
Fri 5/12:51 pm
PWM
- ORD
2 stops10h 08m
Delta
Deal found 4/10![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 4/7. 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 5/13:47 pm
ORD
- PWM
1 stop6h 36m
United Airlines
Sun 5/34:50 pm
PWM
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/7![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/1611:40 am
MDW
- BOS
1 stop5h 25m
Southwest
Thu 4/231:20 pm
BOS
- MDW
2 stops7h 45m
Southwest
Deal found 4/5![Southwest logo]()
$236
This Delta deal was found by Cheapflights users on 4/7. 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.
Tue 6/91:46 pm
ORD
- PWM
2 stops10h 06m
Delta
Tue 6/166:00 am
PWM
- ORD
2 stops8h 04m
Delta
Deal found 4/7![Delta logo]()
$319
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated April 10, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 pm
ORD
- BOS
1 stop14h 00m
Multiple Airlines
Tue 4/286:00 am
BOS
- ORD
1 stop12h 00m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$145
This Cheapflightsfares deal was found by Cheapflights users on 4/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 pm
ORD
- BOS
1 stop14h 00m
Spirit Airlines
Wed 4/228:16 pm
BOS
- ORD
1 stop14h 20m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$150
This Expedia deal was found by Cheapflights users on 4/8. 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 Expedia 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 4/8![JetBlue logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 4/287:15 pm
ORD
- BOS
2 stops29h 16m
Multiple Airlines
Sat 5/210:25 am
BOS
- ORD
1 stop11h 47m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Tue 5/59:31 am
BOS
- ORD
1 stop23h 24m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$146
This SmartFares deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Sat 5/26:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Sun 5/37:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Deal found 4/6![JetBlue logo]()
$151
This Delta deal was found by Cheapflights users on 4/8. 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 5/26:00 am
ORD
- BOS
Nonstop2h 26m
Delta
Wed 5/64:55 pm
BOS
- ORD
Nonstop3h 04m
Delta
Deal found 4/8![Delta logo]()
$153
This Frontier deal was found by Cheapflights users on 4/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Tue 5/129:31 am
BOS
- ORD
1 stop11h 20m
Frontier
Deal found 4/7![Frontier logo]()
$140
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Tue 5/126:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 4/6![Frontier logo]()
$140
This Southwest deal was found by Cheapflights users on 4/7. 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 5/56:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 5/93:30 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/7![Southwest logo]()
$153
This CheapOair deal was found by Cheapflights users on 4/9. 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 5/612:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Wed 5/1312:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/9![Frontier logo]()
$151
This Southwest deal was found by Cheapflights users on 4/7. 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 5/1212:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/126:00 pm
BOS
- MDW
1 stop5h 15m
Southwest
Deal found 4/7![Southwest logo]()
$149
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 April 10, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Trip.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/65:27 pm
STL
- BOS
1 stop6h 57m
Frontier
Deal found 4/6![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:27 pm
STL
- BOS
1 stop6h 57m
Frontier
Deal found 4/6![Frontier logo]()
$70
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/51:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/6![Frontier logo]()
$76
This Frontier deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/292:15 pm
MDW
- BOS
1 stop10h 16m
Frontier
Deal found 4/6![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 4/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BOS
1 stop14h 42m
Frontier
Deal found 4/8![Frontier logo]()
$77
This Expedia deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Fri 5/84:52 pm
MDW
- BOS
1 stop15h 20m
Frontier
Deal found 4/6![Frontier logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:23 pm
STL
- BOS
1 stop11h 11m
Frontier
Deal found 4/6![Frontier logo]()
$77
This Delta deal was found by Cheapflights users on 4/7. 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.
Tue 4/287:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 4/7![Delta logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/5![Frontier logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 4/7. 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.
Wed 4/2211:28 am
ORD
- BOS
1 stop13h 03m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$79
This Southwest deal was found by Cheapflights users on 4/7. 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 5/122:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 4/7![Southwest logo]()
$80
This Southwest deal was found by Cheapflights users on 4/8. 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 4/299:10 am
MDW
- BOS
1 stop5h 45m
Southwest
Deal found 4/8![Southwest logo]()
$80
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 April 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $65 (Trip.com) |
Popular in | December |
Cheapest in | September |
Average price | $396 |
Good round-trip deal | $307 or less |
Good one-way deal | $193 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 April 10, 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
Sat 5/23
3:55 pm-7:30 pm
Nonstop2h 35m
Boston Logan Intl
Sat 5/30
7:19 am-9:17 am
Nonstop2h 58m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 4/28
6:23 pm-9:59 pm
Nonstop2h 36m
Boston Logan Intl
Tue 5/12
3:00 pm-4:58 pm
Nonstop2h 58m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/12
10:30 am-1:57 pm
Nonstop2h 27m
Boston Logan Intl
Thu 5/14
7:35 am-9:27 am
Nonstop2h 52m
$176
Quickest round-trip
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sun 6/7
5:15 am-8:25 am
Nonstop2h 10m
Boston Logan Intl
Mon 6/8
5:25 am-7:00 am
Nonstop2h 35m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 4/29
9:15 am-12:46 pm
Nonstop2h 31m
Boston Logan Intl
Fri 5/1
8:25 pm-10:20 pm
Nonstop2h 55m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 6/5
7:40 pm-11:15 pm
Nonstop2h 35m
Boston Logan Intl
Sun 6/7
5:45 am-9:36 am
1 stop4h 51m
$187
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sun 5/3
7:40 am-10:55 am
Nonstop2h 15m
Boston Logan Intl
Sun 5/10
6:10 am-7:55 am
Nonstop2h 45m
$197
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Thu 5/7
8:00 am-3:10 pm
1 stop6h 10m
Boston Logan Intl
Sun 5/10
5:30 am-8:45 am
1 stop4h 15m
$197
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/8
2:40 pm-11:55 pm
2 stops8h 15m
Boston Logan Intl
Sat 5/9
5:25 am-3:30 pm
2 stops11h 05m
$202
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/16
1:55 pm-10:05 pm
1 stop7h 10m
Boston Logan Intl
Sun 5/17
8:15 am-12:50 pm
1 stop5h 35m
$202
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
ORD-PWM
ORD-BGR
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
ORD-BOS
MDW-BOS
ORD-PWM
ORD-BGR
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 $205). 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 April 10, 2026.
It’s optimal to fly from Illinois to Maine in the evening. By choosing this option you can save up to 14% on the cost of your flight, compared to a flight in the morning.
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 April 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. Thursday mornings 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 April 10, 2026.
The most flights from USIL to USME are scheduled on a Wednesday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Illinois to Maine?
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 April 10, 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.
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 10, 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 April 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$210 | Average$411 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$460 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$263 | Average$399 | FlexibilityNo cancel fee | On-timeN/A |