$79+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
May 22 — May 291
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 22, 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 22, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/510:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Tue 8/118:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/21![JetBlue logo]()
$146
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Deal found 4/20![Delta logo]()
$147
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Sat 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Tue 5/266:36 pm
BOS
- ORD
Nonstop3h 24m
American Airlines
Deal found 4/20![American Airlines logo]()
$148
This Southwest deal was found by Cheapflights users on 4/20. 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 5/197:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 5/267:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/20![Southwest logo]()
$148
This Delta deal was found by Cheapflights users on 4/20. 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.
Thu 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Mon 6/16:00 pm
BOS
- ORD
1 stop5h 36m
Delta
Deal found 4/20![Delta logo]()
$149
This Priceline deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Deal found 4/18![Frontier logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Tue 8/118:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/21![JetBlue logo]()
$151
This Southwest deal was found by Cheapflights users on 4/20. 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 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/1910:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/20![Southwest logo]()
$151
This Jetabroad deal was found by Cheapflights users on 4/21. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/21![JetBlue logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/21![JetBlue logo]()
$153
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Mon 8/318:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/21![JetBlue logo]()
$154
This SmartFares deal was found by Cheapflights users on 4/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/20![JetBlue logo]()
$155
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 22, 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 22, 2026.
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/193:55 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Wed 5/207:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 4/19![United Airlines logo]()
$167
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Sat 5/165:30 pm
BOS
- ORD
Nonstop3h 03m
Delta
Deal found 4/17![Delta logo]()
$167
This Southwest deal was found by Cheapflights users on 4/21. 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 5/291:55 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 6/211:40 am
BOS
- MDW
1 stop5h 35m
Southwest
Deal found 4/21![Southwest logo]()
$190
This American Airlines deal was found by Cheapflights users on 4/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:54 pm
ORD
- PWM
Nonstop2h 43m
American Airlines
Sun 6/287:15 am
PWM
- ORD
1 stop6h 05m
American Airlines
Deal found 4/21![American Airlines logo]()
$325
This Delta deal was found by Cheapflights users on 4/21. 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 5/296:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Tue 6/25:40 am
BOS
- MDW
1 stop4h 03m
Delta
Deal found 4/21![Delta logo]()
$169
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/296:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Sun 5/315:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Deal found 4/21![United Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 4/21. 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 5/227:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Wed 5/278:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Deal found 4/21![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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
Mon 6/155:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/19![Southwest logo]()
$197
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/97:00 am
ORD
- BOS
1 stop4h 51m
United Airlines
Sat 8/228:22 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 4/18![United Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/99:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Fri 8/218:22 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Deal found 4/18![United Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 4/21. 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.
Mon 5/187:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Wed 5/209:05 am
BOS
- ORD
1 stop4h 56m
Delta
Deal found 4/21![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/194:40 pm
MDW
- BOS
1 stop4h 40m
Southwest
Wed 5/277:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/19![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/26:23 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Sun 5/37:30 am
BOS
- ORD
Nonstop3h 01m
United Airlines
Deal found 4/17![United Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/285:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Sun 5/315:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Deal found 4/19![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 6/27:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Sun 6/147:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Deal found 4/21![Delta logo]()
$237
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/156:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Fri 7/177:19 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 4/19![United Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 4/20. 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.
Mon 6/87:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Thu 6/112:20 pm
BOS
- MDW
1 stop8h 00m
Southwest
Deal found 4/20![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 6/37:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Mon 6/85:30 am
BOS
- ORD
1 stop6h 15m
Delta
Deal found 4/17![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 6/15:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Mon 6/85:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/17![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 4/20. 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 6/267:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Sun 6/2810:05 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/20![Southwest logo]()
$267
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 8/1110:55 am
ORD
- PWM
Nonstop2h 33m
United Airlines
Wed 8/196:00 am
PWM
- ORD
Nonstop2h 55m
United Airlines
Deal found 4/17![United Airlines logo]()
$269
This Delta deal was found by Cheapflights users on 4/21. 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 6/52:00 pm
ORD
- PWM
2 stops8h 18m
Delta
Sun 6/711:48 am
PWM
- ORD
1 stop8h 43m
Delta
Deal found 4/21![Delta logo]()
$282
This American Airlines deal was found by Cheapflights users on 4/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
STL
- PWM
1 stop5h 40m
American Airlines
Mon 6/226:54 pm
PWM
- STL
1 stop6h 05m
American Airlines
Deal found 4/21![American Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/233:40 pm
ORD
- BGR
1 stop6h 35m
United Airlines
Wed 5/274:15 pm
BGR
- ORD
Nonstop3h 22m
United Airlines
Deal found 4/21![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/1811:40 am
MDW
- BOS
1 stop5h 25m
Southwest
Sun 5/248:10 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/17![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/3011:09 am
ORD
- PWM
1 stop3h 58m
Delta
Sat 6/68:05 am
PWM
- ORD
2 stops11h 36m
Delta
Deal found 4/18![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/29:15 am
MDW
- BOS
1 stop7h 05m
Southwest
Tue 5/511:40 am
BOS
- MDW
2 stops8h 45m
Southwest
Deal found 4/19![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 6/161:46 pm
ORD
- PWM
2 stops8h 43m
Delta
Tue 7/216:57 pm
PWM
- ORD
1 stop5h 56m
Delta
Deal found 4/21![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 4/21. 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 6/166:15 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Tue 7/215:30 am
PWM
- MDW
1 stop6h 30m
Southwest
Deal found 4/21![Southwest logo]()
$279
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/1911:57 am
MLI
- BOS
1 stop4h 25m
United Airlines
Tue 5/267:19 am
BOS
- MLI
1 stop6h 21m
United Airlines
Deal found 4/18![United Airlines logo]()
$308
Last-minute flights from Illinois to MaineDiscover last-minute flight deals from Illinois to Maine. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Maine. Data last updated April 22, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/97:20 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Mon 5/116:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/19![JetBlue logo]()
$156
This Priceline deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Sat 5/1612:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Deal found 4/18![Frontier logo]()
$150
This American Airlines deal was found by Cheapflights users on 4/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Sat 5/165:35 pm
BOS
- ORD
Nonstop3h 17m
American Airlines
Deal found 4/21![American Airlines logo]()
$151
This Southwest deal was found by Cheapflights users on 4/20. 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 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Tue 5/1910:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/20![Southwest logo]()
$151
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
ORD
- BOS
Nonstop2h 17m
JetBlue
Tue 5/196:47 pm
BOS
- ORD
Nonstop3h 06m
JetBlue
Deal found 4/21![JetBlue logo]()
$153
This Southwest deal was found by Cheapflights users on 4/20. 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 5/197:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Tue 5/267:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Deal found 4/20![Southwest logo]()
$148
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Sat 5/237:20 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Tue 5/266:36 pm
BOS
- ORD
Nonstop3h 24m
American Airlines
Deal found 4/20![American Airlines logo]()
$148
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 5/235:19 pm
ORD
- BOS
1 stop5h 10m
Delta
Tue 5/262:00 pm
BOS
- ORD
1 stop7h 26m
Delta
Deal found 4/20![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 4/20. 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.
Thu 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Mon 6/16:00 pm
BOS
- ORD
1 stop5h 36m
Delta
Deal found 4/20![Delta logo]()
$149
This Jetabroad deal was found by Cheapflights users on 4/21. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Sun 5/316:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/21![JetBlue logo]()
$152
This SmartFares deal was found by Cheapflights users on 4/20. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Mon 6/16:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/20![JetBlue logo]()
$155
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Wed 6/35:35 am
BOS
- ORD
1 stop5h 41m
Delta
Deal found 4/20![Delta logo]()
$147
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 22, 2026.
Search for one-way flight options from Illinois to Maine. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This Delta deal was found by Cheapflights users on 4/20. 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 5/207:05 am
ORD
- BOS
1 stop5h 15m
Delta
Deal found 4/20![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/20. 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.
Sat 6/66:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/20![Delta logo]()
$79
This Delta deal was found by Cheapflights users on 4/20. 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.
Mon 6/16:06 pm
ORD
- BOS
1 stop6h 22m
Delta
Deal found 4/20![Delta logo]()
$80
This Delta deal was found by Cheapflights users on 4/21. 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.
Mon 6/16:36 pm
MDW
- BOS
1 stop3h 53m
Delta
Deal found 4/21![Delta logo]()
$80
This JetBlue deal was found by Cheapflights users on 4/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 4/21![JetBlue logo]()
$81
This Southwest deal was found by Cheapflights users on 4/20. 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.
Mon 9/145:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/20![Southwest logo]()
$81
This SmartFares deal was found by Cheapflights users on 4/21. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:21 am
ORD
- BOS
Nonstop2h 28m
JetBlue
Deal found 4/21![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 7/148:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/17![JetBlue logo]()
$83
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/1912:45 pm
ORD
- BOS
Nonstop2h 31m
United Airlines
Deal found 4/19![United Airlines logo]()
$84
This Southwest deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/123:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/17![Southwest logo]()
$84
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Wed 6/246:00 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 4/20![American Airlines logo]()
$85
This Super.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 4/16![JetBlue logo]()
$86
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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $147 (Delta) |
One-way from | $79 (Delta) |
Popular in | December |
Cheapest in | September |
Average price | $393 |
Good round-trip deal | $327 or less |
Good one-way deal | $174 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 22, 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
Tue 5/19
3:55 pm-7:26 pm
Nonstop2h 31m
Boston Logan Intl
Wed 5/20
7:30 am-9:30 am
Nonstop3h 00m
$167
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Tue 5/12
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Sat 5/16
5:30 pm-7:33 pm
Nonstop3h 03m
$167
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 5/29
6:36 pm-11:29 pm
1 stop3h 53m
Boston Logan Intl
Tue 6/2
5:40 am-8:43 am
1 stop4h 03m
$169
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/22
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Wed 5/27
8:40 pm-10:35 pm
Nonstop2h 55m
$177
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Fri 5/29
6:15 am-9:39 am
Nonstop2h 24m
Boston Logan Intl
Sun 5/31
5:45 am-9:36 am
1 stop4h 51m
$179
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/9
7:00 am-12:51 pm
1 stop4h 51m
Boston Logan Intl
Sat 8/22
8:22 pm-10:19 pm
Nonstop2h 57m
$182
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/9
9:30 pm-12:59 am
Nonstop2h 29m
Boston Logan Intl
Fri 8/21
8:22 pm-10:19 pm
Nonstop2h 57m
$186
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Mon 5/18
7:16 pm-10:50 pm
Nonstop2h 34m
Boston Logan Intl
Wed 5/20
9:05 am-1:01 pm
1 stop4h 56m
$187
ChicagoBoston
MDW - BOS
MDWBOS
Chicago Midway
Fri 5/29
1:55 pm-5:10 pm
Nonstop2h 15m
Boston Logan Intl
Tue 6/2
11:40 am-4:15 pm
1 stop5h 35m
$190
ChicagoBoston
ORD - BOS
ORDBOS
Chicago O'Hare Intl
Sat 5/2
6:23 pm-9:59 pm
Nonstop2h 36m
Boston Logan Intl
Sun 5/3
7:30 am-9:31 am
Nonstop3h 01m
$192
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
MLI-BOS
STL-PWM
ORD-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
MLI-BOS
STL-PWM
What is the cheapest month to book a flight from Illinois to Maine?
Currently, July is the cheapest month in which you can book a flight from Illinois to Maine (average of $101). Flying from Illinois to Maine in January is currently the most expensive (average of $209). 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 22, 2026.
It’s optimal to fly from Illinois to Maine in the afternoon. By choosing this option you can save up to 15% 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 18, 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 22, 2026.
The most flights from USIL to USME are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 22, 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.
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
8.0
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
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 22, 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$221 | Average$411 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$229 | Average$430 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$460 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$263 | Average$469 | FlexibilityNo cancel fee | On-timeN/A |