$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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Mar 26 — Apr 21
1 adult, Economy
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Find cheap flights from Illinois to Maine with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 February 24, 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 February 24, 2026.
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/257:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Wed 4/17:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/23![Delta logo]()
$127
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/256:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 4/12:00 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/23![Southwest logo]()
$127
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/258:45 pm
ORD
- BOS
Nonstop2h 20m
American Airlines
Wed 4/16:30 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Deal found 2/23![American Airlines logo]()
$128
This CheapOair deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 6/33:31 pm
ORD
- BOS
1 stop6h 47m
Multiple Airlines
Mon 6/86:00 am
BOS
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 2/24![Multiple Airlines logo]()
$129
This American Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/93:16 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Mon 4/137:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Deal found 2/24![American Airlines logo]()
$130
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/44:35 pm
MDW
- BOS
1 stop6h 20m
Southwest
Tue 4/72:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 2/22![Southwest logo]()
$130
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/96:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Thu 8/209:30 am
BOS
- ORD
Nonstop2h 55m
United Airlines
Deal found 2/23![United Airlines logo]()
$131
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/912:30 pm
ORD
- BOS
1 stop5h 45m
Delta
Fri 8/217:00 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 2/23![Delta logo]()
$132
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Wed 4/157:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/21![Southwest logo]()
$132
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/166:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Mon 4/209:20 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/23![United Airlines logo]()
$133
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/286:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 4/27:15 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/22![Southwest logo]()
$133
This Expedia deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/69:41 am
ORD
- BOS
Nonstop2h 28m
Multiple Airlines
Fri 5/811:16 am
BOS
- ORD
1 stop29h 09m
Multiple Airlines
Deal found 2/23![Multiple Airlines logo]()
$134
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 February 24, 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 February 24, 2026.
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/21![Southwest logo]()
$133
This Delta deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:59 pm
ORD
- BOS
Nonstop2h 28m
Delta
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 09m
Delta
Deal found 2/21![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 5/61:55 pm
ORD
- BOS
Nonstop2h 27m
United Airlines
Fri 5/87:26 pm
BOS
- ORD
1 stop5h 11m
United Airlines
Deal found 2/22![United Airlines logo]()
$157
This JetBlue deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/11:55 pm
ORD
- BOS
Nonstop2h 36m
JetBlue
Sun 8/168:00 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 2/20![JetBlue logo]()
$276
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/232:56 pm
BMI
- BOS
1 stop8h 09m
American Airlines
Sat 3/286:52 am
BOS
- BMI
1 stop8h 41m
American Airlines
Deal found 2/23![American Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
ORD
- BOS
1 stop4h 10m
United Airlines
Sun 3/157:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Deal found 2/20![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:55 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 3/97:15 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/21![Southwest logo]()
$162
This Delta deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:15 pm
ORD
- BOS
Nonstop2h 34m
Delta
Sun 5/177:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Deal found 2/20![Delta logo]()
$177
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/283:40 pm
ORD
- BOS
1 stop6h 01m
United Airlines
Mon 3/306:00 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 2/23![United Airlines logo]()
$181
This Delta deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:30 pm
ORD
- BOS
Nonstop2h 33m
Delta
Mon 5/258:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 2/21![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:15 am
MDW
- BOS
2 stops8h 05m
Southwest
Tue 5/126:20 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/21![Southwest logo]()
$202
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/285:47 pm
ORD
- PWM
Nonstop2h 17m
United Airlines
Mon 3/306:04 am
PWM
- ORD
Nonstop2h 56m
United Airlines
Deal found 2/22![United Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/286:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 3/306:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Deal found 2/23![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/77:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Tue 3/1011:30 am
BOS
- ORD
Nonstop2h 57m
Delta
Deal found 2/21![Delta logo]()
$211
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Sun 4/56:18 pm
PWM
- ORD
Nonstop3h 10m
United Airlines
Deal found 2/21![United Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” 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 4/47:10 am
ORD
- PWM
1 stop3h 59m
Delta
Tue 4/74:48 pm
PWM
- ORD
1 stop4h 35m
Delta
Deal found 2/24![Delta logo]()
$213
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/203:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 3/233:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/20![Southwest logo]()
$226
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/113:20 pm
ORD
- BGR
1 stop5h 19m
American Airlines
Fri 8/144:58 pm
BGR
- ORD
1 stop7h 50m
American Airlines
Deal found 2/20![American Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Tue 4/77:12 pm
PWM
- ORD
1 stop5h 25m
United Airlines
Deal found 2/21![United Airlines logo]()
$219
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 6/205:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 6/255:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 2/22![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/11:55 pm
ORD
- PWM
Nonstop2h 37m
United Airlines
Tue 4/77:12 pm
PWM
- ORD
1 stop5h 25m
United Airlines
Deal found 2/21![United Airlines logo]()
$219
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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
1 stop6h 50m
Delta
Deal found 2/22![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:10 am
MDW
- PWM
1 stop5h 05m
Southwest
Tue 4/141:00 pm
PWM
- MDW
1 stop7h 30m
Southwest
Deal found 2/20![Southwest logo]()
$229
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/1711:31 am
BMI
- BOS
1 stop6h 52m
American Airlines
Thu 3/196:52 am
BOS
- BMI
1 stop15h 59m
American Airlines
Deal found 2/23![American Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/96:15 pm
ORD
- PWM
1 stop4h 44m
United Airlines
Mon 5/115:30 am
PWM
- ORD
1 stop7h 21m
United Airlines
Deal found 2/23![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/306:00 am
ORD
- BGR
1 stop5h 09m
Delta
Tue 5/55:15 am
BGR
- ORD
2 stops12h 27m
Delta
Deal found 2/23![Delta logo]()
$254
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sat 3/146:40 pm
BOS
- MDW
1 stop5h 00m
Southwest
Deal found 2/22![Southwest logo]()
$233
This American Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 5/25:00 am
BMI
- BOS
1 stop5h 32m
American Airlines
Sun 5/108:03 am
BOS
- BMI
1 stop7h 13m
American Airlines
Deal found 2/22![American Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 5/86:15 pm
ORD
- PWM
1 stop4h 44m
United Airlines
Mon 5/115:30 am
PWM
- ORD
1 stop7h 21m
United Airlines
Deal found 2/23![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
ORD
- BGR
2 stops9h 01m
Delta
Wed 9/23:00 pm
BGR
- ORD
2 stops9h 57m
Delta
Deal found 2/21![Delta logo]()
$259
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated February 24, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated February 24, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Sat 2/287:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/20![JetBlue logo]()
$140
This KAYAK deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Sun 3/17:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/20![JetBlue logo]()
$143
This KAYAK deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Wed 2/257:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/20![JetBlue logo]()
$144
This KAYAK deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Thu 3/57:00 am
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 2/23![JetBlue logo]()
$142
This Southwest deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 3/233:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/21![Southwest logo]()
$137
This United Airlines deal was found by Cheapflights users on 2/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:20 am
ORD
- BOS
Nonstop2h 29m
United Airlines
Sat 3/146:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/21![United Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/127:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Sun 3/156:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 2/20![United Airlines logo]()
$136
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/127:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Sat 3/147:16 am
BOS
- ORD
Nonstop3h 06m
United Airlines
Deal found 2/22![United Airlines logo]()
$137
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/257:00 am
ORD
- BOS
Nonstop2h 25m
Delta
Wed 4/17:15 am
BOS
- ORD
Nonstop3h 10m
Delta
Deal found 2/23![Delta logo]()
$127
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/256:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 4/12:00 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 2/23![Southwest logo]()
$127
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 3/258:45 pm
ORD
- BOS
Nonstop2h 20m
American Airlines
Wed 4/16:30 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Deal found 2/23![American Airlines logo]()
$128
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/286:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 4/27:15 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/22![Southwest logo]()
$133
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 February 24, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated February 24, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/20![JetBlue logo]()
$68
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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
Deal found 2/23![Southwest logo]()
$69
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 4/97:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/22![Southwest logo]()
$69
This Cheapflightsfares deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/15:05 am
ORD
- BOS
1 stop9h 23m
Spirit Airlines
Deal found 2/23![Spirit Airlines logo]()
$70
This Gotogate deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:17 am
ORD
- BOS
1 stop7h 11m
Spirit Airlines
Deal found 2/22![Spirit Airlines logo]()
$71
This KAYAK deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 2/20![JetBlue logo]()
$72
This Southwest deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” 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 4/44:35 pm
MDW
- BOS
1 stop6h 20m
Southwest
Deal found 2/23![Southwest logo]()
$72
This Delta deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:35 pm
ORD
- BOS
Nonstop2h 27m
Delta
Deal found 2/22![Delta logo]()
$73
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/35:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/22![Southwest logo]()
$73
This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:40 pm
ORD
- BOS
Nonstop2h 21m
American Airlines
Deal found 2/20![American Airlines logo]()
$74
This Southwest deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” 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 3/2412:10 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 2/22![Southwest logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:31 pm
ORD
- BOS
1 stop6h 47m
Spirit Airlines
Deal found 2/20![Spirit Airlines logo]()
$75
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 February 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $127 (Delta) |
One-way from | $68 (Cheapflightsfares) |
Popular in | April |
Cheapest in | January |
Average price | $246 |
Good round-trip deal | $279 or less |
Good one-way deal | $172 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 February 24, 2026.
Use the filters below to find and compare flights from Illinois to Maine that are best for you.
Fly from
Illinois
Fly to
Maine
Route
Depart
Return
Price
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 4/10
7:00 pm-10:20 pm
Nonstop2h 20m
Boston Logan Intl
Sat 4/11
7:15 am-9:05 am
Nonstop2h 50m
$133
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/1
7:59 pm-11:27 pm
Nonstop2h 28m
Boston Logan Intl
Sun 5/3
6:00 am-8:09 am
Nonstop3h 09m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/6
1:55 pm-5:22 pm
Nonstop2h 27m
Boston Logan Intl
Fri 5/8
7:26 pm-11:37 pm
1 stop5h 11m
$157
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 3/12
6:00 am-11:10 am
1 stop4h 10m
Boston Logan Intl
Sun 3/15
7:16 am-9:22 am
Nonstop3h 06m
$157
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 3/6
7:55 am-11:10 am
Nonstop2h 15m
Boston Logan Intl
Mon 3/9
7:15 am-9:10 am
Nonstop2h 55m
$162
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Wed 5/13
7:15 pm-10:49 pm
Nonstop2h 34m
Boston Logan Intl
Sun 5/17
7:35 am-9:27 am
Nonstop2h 52m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 3/28
3:40 pm-10:41 pm
1 stop6h 01m
Boston Logan Intl
Mon 3/30
6:00 am-7:59 am
Nonstop2h 59m
$181
ChicagoPortland
ORD - PWM
ORDPWM
Chicago O'Hare Intl
Sat 3/28
5:47 pm-9:04 pm
Nonstop2h 17m
Portland
Mon 3/30
6:04 am-8:00 am
Nonstop2h 56m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/23
4:30 pm-8:03 pm
Nonstop2h 33m
Boston Logan Intl
Mon 5/25
8:40 pm-10:35 pm
Nonstop2h 55m
$197
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 5/12
8:15 am-5:20 pm
2 stops8h 05m
Boston Logan Intl
Tue 5/12
6:20 pm-8:10 pm
Nonstop2h 50m
$202
Showing 1-10 of 60 results
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
BMI-BOS
ORD-PWM
STL-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
BMI-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 February 24, 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 February 24, 2026.
The most flights from USIL to USME are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 February 24, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Crew
8.6
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 February 24, 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 February 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$393 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$414 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$508 | FlexibilityNo cancel fee | On-time63% |