$94+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Aug 2 — Aug 91
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 July 3, 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 July 3, 2026.
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/287:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:30 pm
ORD
- BOS
Nonstop2h 41m
Delta
Wed 9/98:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 7/3![Delta logo]()
$173
This Jetabroad deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 6/30![JetBlue logo]()
$174
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:20 pm
ORD
- BOS
Nonstop2h 56m
JetBlue
Tue 9/812:42 pm
BOS
- ORD
1 stop5h 38m
JetBlue
Deal found 7/3![JetBlue logo]()
$175
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 8/35:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/30![Southwest logo]()
$175
This Jetabroad deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/28![JetBlue logo]()
$176
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:35 am
ORD
- BOS
1 stop8h 24m
JetBlue
Tue 9/112:57 pm
BOS
- ORD
1 stop5h 38m
JetBlue
Deal found 6/30![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/3![United Airlines logo]()
$178
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$178
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Wed 7/228:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/1![Delta logo]()
$179
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 7/315:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$179
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Fri 8/147:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 6/30![United Airlines logo]()
$180
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 July 3, 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 July 3, 2026.
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 8/178:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 7/3![Southwest logo]()
$175
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:30 am
ORD
- BOS
Nonstop2h 37m
United Airlines
Wed 7/158:15 pm
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 6/28![United Airlines logo]()
$191
This Delta deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/67:30 pm
ORD
- BOS
Nonstop2h 30m
Delta
Sun 8/97:30 am
BOS
- ORD
Nonstop2h 56m
Delta
Deal found 6/28![Delta logo]()
$191
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:00 pm
ORD
- BOS
1 stop6h 49m
JetBlue
Wed 10/75:00 pm
BOS
- ORD
Nonstop3h 22m
JetBlue
Deal found 7/2![JetBlue logo]()
$199
This KAYAK deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:00 pm
ORD
- BOS
Nonstop2h 50m
American Airlines
Wed 8/1910:28 am
BOS
- ORD
Nonstop3h 01m
American Airlines
Deal found 7/1![American Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Thu 8/138:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$175
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:40 pm
ORD
- BOS
Nonstop2h 30m
United Airlines
Fri 9/118:30 pm
BOS
- ORD
1 stop4h 58m
United Airlines
Deal found 7/1![United Airlines logo]()
$192
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:30 am
ORD
- BOS
1 stop7h 10m
JetBlue
Sun 10/43:13 pm
BOS
- ORD
1 stop7h 53m
JetBlue
Deal found 7/2![JetBlue logo]()
$201
This Southwest deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/247:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/28![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:55 am
ORD
- BOS
Nonstop2h 29m
Delta
Fri 8/148:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 6/29![Delta logo]()
$217
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:40 am
ORD
- BOS
1 stop8h 19m
JetBlue
Wed 8/264:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/2![JetBlue logo]()
$201
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:30 pm
ORD
- BOS
Nonstop2h 39m
Delta
Mon 9/288:50 pm
BOS
- ORD
Nonstop2h 42m
Delta
Deal found 6/29![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:10 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Sat 8/225:50 am
BOS
- MDW
2 stops8h 15m
Southwest
Deal found 7/1![Southwest logo]()
$208
This JetBlue deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Sun 8/162:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 6/29![JetBlue logo]()
$211
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 9/176:40 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 6/29![Southwest logo]()
$211
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:05 pm
STL
- BGR
1 stop7h 53m
United Airlines
Sat 8/294:43 pm
BGR
- STL
1 stop6h 17m
United Airlines
Deal found 7/2![United Airlines logo]()
$267
This JetBlue deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Thu 8/204:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 6/29![JetBlue logo]()
$221
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/15:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Mon 8/35:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/30![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/121:59 pm
ORD
- BGR
2 stops8h 41m
Delta
Tue 8/185:00 pm
BGR
- ORD
1 stop6h 24m
Delta
Deal found 7/1![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/234:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 7/245:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$226
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:19 am
ORD
- BGR
2 stops8h 50m
Delta
Sat 10/244:10 pm
BGR
- ORD
1 stop6h 33m
Delta
Deal found 7/2![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:09 pm
MLI
- BOS
1 stop7h 01m
United Airlines
Tue 9/296:00 am
BOS
- MLI
1 stop5h 12m
United Airlines
Deal found 6/30![United Airlines logo]()
$319
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:59 pm
ORD
- BGR
2 stops8h 41m
Delta
Tue 8/185:00 pm
BGR
- ORD
1 stop6h 24m
Delta
Deal found 6/30![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 8/235:20 am
BOS
- MDW
2 stops9h 00m
Southwest
Deal found 7/2![Southwest logo]()
$247
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:59 pm
STL
- BGR
1 stop7h 48m
United Airlines
Sat 9/126:00 am
BGR
- STL
2 stops10h 38m
United Airlines
Deal found 6/28![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/251:50 pm
ORD
- BGR
2 stops8h 50m
Delta
Tue 9/15:20 am
BGR
- ORD
1 stop6h 03m
Delta
Deal found 7/2![Delta logo]()
$286
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:40 pm
MDW
- BOS
1 stop4h 35m
Southwest
Tue 8/188:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Deal found 6/30![Southwest logo]()
$248
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2210:50 am
ORD
- PWM
1 stop7h 34m
United Airlines
Sun 9/276:00 am
PWM
- ORD
Nonstop2h 57m
United Airlines
Deal found 6/30![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:25 pm
STL
- BGR
1 stop5h 15m
Delta
Mon 9/74:55 pm
BGR
- STL
1 stop4h 47m
Delta
Deal found 6/29![Delta logo]()
$288
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:00 am
ORD
- PWM
1 stop5h 16m
JetBlue
Fri 8/72:45 pm
PWM
- ORD
1 stop8h 13m
JetBlue
Deal found 7/2![JetBlue logo]()
$371
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated July 3, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Wed 7/228:45 pm
BOS
- ORD
Nonstop2h 54m
Delta
Deal found 7/1![Delta logo]()
$179
This Jetabroad deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
- BOS
1 stop7h 22m
JetBlue
Sun 7/265:01 am
BOS
- ORD
1 stop4h 49m
JetBlue
Deal found 6/28![JetBlue logo]()
$176
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Sun 7/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 7/3![United Airlines logo]()
$178
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/259:41 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Tue 7/287:27 pm
BOS
- ORD
1 stop5h 04m
United Airlines
Deal found 7/3![United Airlines logo]()
$172
This Southwest deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Mon 7/275:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/29![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:40 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Fri 7/315:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 7/1![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:35 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Mon 8/35:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 6/30![Southwest logo]()
$175
This Jetabroad deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:35 am
ORD
- BOS
1 stop6h 32m
JetBlue
Tue 8/112:45 pm
BOS
- ORD
1 stop8h 13m
JetBlue
Deal found 6/30![JetBlue logo]()
$174
This Southwest deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Wed 8/125:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Deal found 7/1![Southwest logo]()
$180
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:16 pm
ORD
- BOS
1 stop4h 36m
United Airlines
Fri 8/147:05 am
BOS
- ORD
Nonstop2h 59m
United Airlines
Deal found 6/30![United Airlines logo]()
$180
This JetBlue deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Tue 9/18:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 6/30![JetBlue logo]()
$175
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Sat 9/1210:30 am
BOS
- ORD
Nonstop3h 02m
American Airlines
Deal found 7/1![American Airlines logo]()
$173
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 July 3, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated July 3, 2026.
This SmartFares deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 7/1![JetBlue logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:10 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 7/3![JetBlue logo]()
$95
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:15 am
ORD
- BOS
Nonstop2h 42m
United Airlines
Deal found 6/30![United Airlines logo]()
$96
This Southwest deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/185:45 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 7/3![Southwest logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
ORD
- BOS
1 stop7h 43m
JetBlue
Deal found 6/28![JetBlue logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:24 pm
ORD
- BOS
Nonstop2h 34m
JetBlue
Deal found 6/28![JetBlue logo]()
$98
This Southwest deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/298:10 am
MDW
- BOS
1 stop6h 30m
Southwest
Deal found 6/30![Southwest logo]()
$98
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:30 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 6/30![Delta logo]()
$99
This Southwest deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/2![Southwest logo]()
$99
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
ORD
- BOS
1 stop7h 49m
JetBlue
Deal found 7/2![JetBlue logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:25 pm
MDW
- BOS
1 stop11h 44m
Allegiant Air
Deal found 6/30![Allegiant Air logo]()
$101
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/3![JetBlue logo]()
$102
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 July 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $172 (United Airlines) |
One-way from | $94 (SmartFares) |
Popular in | July |
Cheapest in | May |
Average price | $427 |
Good round-trip deal | $337 or less |
Good one-way deal | $153 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 July 3, 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
MDW - BOS
MDWBOS
Chicago Midway
Sat 8/15
3:10 pm-6:30 pm
Nonstop2h 20m
Boston Logan Intl
Mon 8/17
8:20 pm-10:00 pm
Nonstop2h 40m
$175
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Tue 8/11
6:00 pm-9:20 pm
Nonstop2h 20m
Boston Logan Intl
Thu 8/13
8:20 pm-10:00 pm
Nonstop2h 40m
$175
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 7/24
7:35 pm-10:55 pm
Nonstop2h 20m
Boston Logan Intl
Mon 7/27
5:25 am-7:00 am
Nonstop2h 35m
$187
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 7/14
10:30 am-2:07 pm
Nonstop2h 37m
Boston Logan Intl
Wed 7/15
8:15 pm-10:15 pm
Nonstop3h 00m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 8/6
7:30 pm-11:00 pm
Nonstop2h 30m
Boston Logan Intl
Sun 8/9
7:30 am-9:26 am
Nonstop2h 56m
$191
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 9/5
9:40 pm-1:10 am
Nonstop2h 30m
Boston Logan Intl
Fri 9/11
8:30 pm-12:28 am
1 stop4h 58m
$192
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Thu 10/1
1:00 pm-8:49 pm
1 stop6h 49m
Boston Logan Intl
Wed 10/7
5:00 pm-7:22 pm
Nonstop3h 22m
$199
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 9/29
6:30 am-2:40 pm
1 stop7h 10m
Boston Logan Intl
Sun 10/4
3:13 pm-10:06 pm
1 stop7h 53m
$201
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 8/25
9:40 am-6:59 pm
1 stop8h 19m
Boston Logan Intl
Wed 8/26
4:30 pm-9:58 pm
1 stop6h 28m
$201
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Sat 8/15
3:10 pm-6:30 pm
Nonstop2h 20m
Boston Logan Intl
Sat 8/22
5:50 am-1:05 pm
2 stops8h 15m
$208
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
STL-BGR
ORD-BGR
MLI-BOS
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
STL-BGR
ORD-BGR
What is the cheapest month to book a flight from Illinois to Maine?
Currently, September is the cheapest month in which you can book a flight from Illinois to Maine (average of $133). Flying from Illinois to Maine in July is currently the most expensive (average of $236). 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 July 3, 2026.
It’s optimal to fly from Illinois to Maine at noon. By choosing this option you can save up to 8% on the cost of your flight, compared to a flight in the morning.
How much does it cost to fly round-trip from Illinois to Maine?
How far ahead should I book a flight from Illinois to Maine?
Booking 76 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Maine. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Illinois to Maine?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Maine. Price data was last updated on June 27, 2026.
Travelers seeking maximum savings on their Illinois to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Maine
Get insights into the airlines that provide service to Maine. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Maine. Reviews last updated July 3, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Illinois to Maine. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Overall
7.9
Food
7.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from Illinois to Maine. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Illinois to Maine
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maine by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Maine by cabin class
Find flights from Illinois to Maine, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Maine flights
Browse other Illinois and Maine flight options. Last updated on July 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Maine
Find the right flight back to Illinois after your stay in Maine
Illinois to Maine flights
Consider these flights traveling from Illinois to Maine.
Top 2 airlines flying from Illinois to Maine
Discover the top 2 airlines that operate flights from Illinois to Maine. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$460 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$404 | FlexibilityNo cancel fee | On-time69% |