$97+ Cheap flights from Maine to Illinois
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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Sep 2 — Sep 91
Round-trip
1 adult, Economy
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Find cheap flights from Maine to Illinois with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Maine to IllinoisExplore the most affordable flight options available from Maine to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.
Explore the most affordable flight options available from Maine to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:28 am
BOS
- ORD
1 stop10h 00m
Frontier
Fri 10/239:33 pm
ORD
- BOS
1 stop12h 19m
Frontier
Deal found 7/30![Frontier logo]()
$161
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:04 am
BOS
- ORD
1 stop14h 04m
Frontier
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Deal found 7/31![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Sat 9/57:44 pm
ORD
- BOS
1 stop12h 25m
Frontier
Deal found 8/1![Frontier logo]()
$167
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Fri 9/183:50 pm
ORD
- BOS
1 stop18h 01m
Frontier
Deal found 7/30![Frontier logo]()
$168
This CheapTickets deal was found by Cheapflights users on 8/1. 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 CheapTickets is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Wed 9/93:50 pm
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 8/1![Frontier logo]()
$170
This CheapOair deal was found by Cheapflights users on 7/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:54 pm
BOS
- ORD
1 stop6h 29m
Frontier
Fri 9/183:50 pm
ORD
- BOS
1 stop18h 01m
Frontier
Deal found 7/29![Frontier logo]()
$171
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Deal found 8/2![Frontier logo]()
$172
This Jettzy deal was found by Cheapflights users on 8/1. 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 Jettzy is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:45 pm
BOS
- ORD
1 stop8h 23m
Frontier
Wed 9/93:50 pm
ORD
- BOS
1 stop17h 32m
Frontier
Deal found 8/1![Frontier logo]()
$175
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:17 am
BOS
- ORD
1 stop12h 42m
Frontier
Sat 9/123:50 pm
ORD
- BOS
1 stop18h 08m
Frontier
Deal found 7/31![Frontier logo]()
$181
This CheapOair deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Thu 10/159:15 am
BOS
- ORD
1 stop29h 01m
Frontier
Sun 10/186:05 am
ORD
- BOS
1 stop25h 15m
Frontier
Deal found 7/31![Frontier logo]()
$186
This Southwest deal was found by Cheapflights users on 7/29. 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.
Wed 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Sat 9/197:40 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/29![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 7/29. 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 9/121:00 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/29![Southwest logo]()
$222
Best flights from Maine to IllinoisDiscover carefully curated flight deals from Maine to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
Discover carefully curated flight deals from Maine to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
This Southwest deal was found by Cheapflights users on 8/2. 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.
Sat 9/128:40 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 9/136:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$231
This Delta deal was found by Cheapflights users on 7/29. 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.
Thu 8/208:50 pm
BOS
- ORD
Nonstop2h 54m
Delta
Mon 8/243:19 pm
ORD
- BOS
Nonstop2h 40m
Delta
Deal found 7/29![Delta logo]()
$235
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Fri 9/46:42 pm
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 9/63:35 pm
ORD
- BOS
Nonstop2h 44m
United Airlines
Deal found 7/30![United Airlines logo]()
$245
This JetBlue deal was found by Cheapflights users on 8/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:10 am
BOS
- ORD
1 stop9h 29m
JetBlue
Wed 9/211:01 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 8/1![JetBlue logo]()
$248
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:46 pm
PWM
- STL
1 stop5h 48m
American Airlines
Tue 8/256:00 am
STL
- PWM
1 stop4h 46m
American Airlines
Deal found 7/28![American Airlines logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:30 pm
BGR
- STL
2 stops15h 10m
Multiple Airlines
Sat 10/318:34 pm
STL
- BGR
1 stop22h 06m
Multiple Airlines
Deal found 7/29![Multiple Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 7/28. 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.
Thu 9/177:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 9/213:15 pm
MDW
- BOS
1 stop6h 20m
Southwest
Deal found 7/28![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 7/30. 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.
Sat 9/127:00 am
BOS
- ORD
Nonstop2h 48m
JetBlue
Mon 9/1410:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Deal found 7/30![JetBlue logo]()
$250
This Delta deal was found by Cheapflights users on 7/30. 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 12/811:40 am
PWM
- ORD
2 stops7h 53m
Delta
Tue 12/157:00 am
ORD
- PWM
1 stop4h 08m
Delta
Deal found 7/30![Delta logo]()
$260
This Southwest deal was found by Cheapflights users on 7/28. 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.
Wed 8/195:35 am
BOS
- MDW
1 stop7h 15m
Southwest
Thu 8/205:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/28![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 7/29. 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.
Sat 9/54:09 pm
BOS
- ORD
1 stop6h 49m
JetBlue
Tue 9/811:01 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 7/29![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 8/2. 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 9/56:00 am
PWM
- MDW
2 stops10h 44m
Delta
Sun 9/69:24 am
MDW
- PWM
1 stop5h 37m
Delta
Deal found 8/2![Delta logo]()
$260
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/86:43 pm
BOS
- ORD
Nonstop2h 57m
United Airlines
Sat 8/157:05 am
ORD
- BOS
1 stop4h 45m
United Airlines
Deal found 7/30![United Airlines logo]()
$286
This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 8/245:25 am
BOS
- MDW
1 stop6h 35m
Southwest
Sat 8/2911:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/29![Southwest logo]()
$237
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Wed 9/3010:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Deal found 7/31![JetBlue logo]()
$259
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/119:32 am
BGR
- ORD
Nonstop3h 02m
United Airlines
Sun 9/135:55 pm
ORD
- BGR
Nonstop2h 52m
United Airlines
Deal found 7/31![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 7/30. 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.
Thu 8/208:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 8/243:20 pm
MDW
- BOS
1 stop6h 00m
Southwest
Deal found 7/30![Southwest logo]()
$250
This KAYAK deal was found by Cheapflights users on 7/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:15 pm
BOS
- ORD
Nonstop2h 49m
Delta
Fri 9/183:05 pm
ORD
- BOS
Nonstop2h 47m
Delta
Deal found 7/30![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 7/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
BGR
- ORD
1 stop7h 54m
American Airlines
Sat 8/224:00 pm
ORD
- BGR
1 stop5h 13m
American Airlines
Deal found 7/28![American Airlines logo]()
$344
This JetBlue deal was found by Cheapflights users on 7/29. 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.
Sat 9/124:11 pm
BOS
- ORD
1 stop6h 47m
JetBlue
Sun 9/137:00 am
ORD
- BOS
1 stop7h 14m
JetBlue
Deal found 7/29![JetBlue logo]()
$261
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 10/297:30 pm
PWM
- ORD
1 stop5h 09m
United Airlines
Mon 11/26:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 8/2![United Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 8/2. 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.
Tue 9/15:50 pm
BOS
- MDW
1 stop5h 30m
Southwest
Thu 9/35:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 8/2![Southwest logo]()
$255
This Delta deal was found by Cheapflights users on 7/29. 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 9/811:50 am
PWM
- MDW
1 stop7h 29m
Delta
Fri 9/114:30 pm
MDW
- PWM
1 stop5h 59m
Delta
Deal found 7/29![Delta logo]()
$292
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:58 am
BOS
- MLI
1 stop7h 13m
American Airlines
Thu 8/276:00 am
MLI
- BOS
2 stops7h 42m
American Airlines
Deal found 7/30![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/28:15 am
BOS
- MDW
2 stops6h 15m
Southwest
Sun 9/611:55 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/31![Southwest logo]()
$255
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/305:15 am
BOS
- ORD
1 stop5h 43m
JetBlue
Thu 10/110:59 am
ORD
- BOS
1 stop5h 22m
JetBlue
Deal found 7/31![JetBlue logo]()
$286
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/238:15 am
BOS
- MDW
2 stops5h 50m
Southwest
Mon 9/289:00 am
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 7/31![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 8/2. 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 10/206:28 am
PWM
- ORD
2 stops7h 31m
Delta
Tue 10/206:00 pm
ORD
- PWM
1 stop5h 10m
Delta
Deal found 8/2![Delta logo]()
$314
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Sun 1/104:48 pm
PWM
- ORD
Nonstop2h 57m
United Airlines
Wed 1/136:00 pm
ORD
- PWM
Nonstop2h 27m
United Airlines
Deal found 7/31![United Airlines logo]()
$355
This Delta deal was found by Cheapflights users on 8/2. 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.
Thu 10/291:52 pm
PWM
- ORD
1 stop5h 28m
Delta
Mon 11/211:19 am
ORD
- PWM
2 stops8h 41m
Delta
Deal found 8/2![Delta logo]()
$314
Last-minute flights from Maine to IllinoisDiscover last-minute flight deals from Maine to Illinois. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Illinois. Data last updated August 3, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:15 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Wed 8/199:35 am
ORD
- BOS
1 stop6h 42m
JetBlue
Deal found 7/29![JetBlue logo]()
$237
This Southwest deal was found by Cheapflights users on 7/29. 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.
Wed 8/127:15 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 8/196:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/29![Southwest logo]()
$240
This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:53 pm
BOS
- ORD
Nonstop3h 11m
American Airlines
Wed 8/193:00 pm
ORD
- BOS
Nonstop2h 40m
American Airlines
Deal found 7/29![American Airlines logo]()
$240
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:27 am
BOS
- ORD
Nonstop3h 03m
American Airlines
Sun 8/166:05 am
ORD
- BOS
Nonstop2h 32m
American Airlines
Deal found 7/30![American Airlines logo]()
$245
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/138:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 8/306:00 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/29![Southwest logo]()
$236
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/207:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/26:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/29![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/208:40 am
BOS
- MDW
2 stops9h 25m
Southwest
Mon 8/246:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/29![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 7/29. 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.
Fri 8/217:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Sun 8/237:55 am
MDW
- BOS
Nonstop2h 30m
Southwest
Deal found 7/29![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 8/248:20 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Wed 9/29:25 am
MDW
- BOS
1 stop5h 35m
Southwest
Deal found 7/29![Southwest logo]()
$237
This Southwest deal was found by Cheapflights users on 8/1. 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 8/257:30 am
BOS
- MDW
Nonstop2h 35m
Southwest
Tue 9/296:00 pm
MDW
- BOS
Nonstop2h 25m
Southwest
Deal found 8/1![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 8/273:55 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Wed 9/26:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 7/29![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 7/29. 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.
Mon 8/313:55 pm
BOS
- MDW
Nonstop2h 35m
Southwest
Mon 8/316:30 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 7/29![Southwest logo]()
$222
One-way flights from Maine to IllinoisSearch for one-way flight options from Maine to Illinois. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
Search for one-way flight options from Maine to Illinois. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:45 pm
BOS
- MDW
1 stop11h 02m
Frontier
Deal found 8/2![Frontier logo]()
$97
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:45 pm
BOS
- MDW
1 stop11h 02m
Frontier
Deal found 7/31![Frontier logo]()
$98
This Super.com deal was found by Cheapflights users on 7/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:45 pm
BOS
- MDW
1 stop11h 02m
Frontier
Deal found 7/30![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:36 am
BOS
- ORD
1 stop12h 23m
Frontier
Deal found 7/31![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 8/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/911:28 am
BOS
- MDW
1 stop11h 30m
Frontier
Deal found 8/2![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/310:19 am
BOS
- RFD
1 stop23h 59m
Allegiant Air
Deal found 8/2![Allegiant Air logo]()
$100
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:04 am
BOS
- ORD
1 stop14h 04m
Frontier
Deal found 7/30![Frontier logo]()
$101
This Travelocity deal was found by Cheapflights users on 8/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/710:04 am
BOS
- ORD
1 stop14h 04m
Frontier
Deal found 8/2![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:30 pm
BOS
- ORD
1 stop6h 28m
JetBlue
Deal found 7/28![JetBlue logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:00 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 7/29![JetBlue logo]()
$107
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:55 am
BOS
- ORD
1 stop5h 52m
JetBlue
Deal found 7/28![JetBlue logo]()
$108
This Southwest deal was found by Cheapflights users on 7/29. 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.
Wed 9/1610:05 am
BOS
- MDW
Nonstop2h 30m
Southwest
Deal found 7/29![Southwest logo]()
$109
Find flight deals from Maine to Illinois
Keep the following information in mind while searching for Maine to Illinois flight deals. Data was last updated August 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $161 (Frontier) |
One-way from | $97 (Super.com) |
Popular in | July |
Cheapest in | September |
Average price | $354 |
Good round-trip deal | $382 or less |
Good one-way deal | $241 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maine to Illinois 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 August 3, 2026.
Use the filters below to find and compare flights from Maine to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 9/12
8:40 am-10:15 am
Nonstop2h 35m
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
$231
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 8/20
8:50 pm-10:44 pm
Nonstop2h 54m
Chicago O'Hare Intl
Mon 8/24
3:19 pm-6:59 pm
Nonstop2h 40m
$235
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 9/17
7:30 am-9:05 am
Nonstop2h 35m
Chicago Midway
Mon 9/21
3:15 pm-10:35 pm
1 stop6h 20m
$237
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 8/19
5:35 am-11:50 am
1 stop7h 15m
Chicago Midway
Thu 8/20
5:45 am-9:00 am
Nonstop2h 15m
$237
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 8/24
5:25 am-11:00 am
1 stop6h 35m
Chicago Midway
Sat 8/29
11:25 am-2:45 pm
Nonstop2h 20m
$237
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 9/4
6:42 pm-8:40 pm
Nonstop2h 58m
Chicago O'Hare Intl
Sun 9/6
3:35 pm-7:19 pm
Nonstop2h 44m
$245
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 8/26
5:10 am-1:39 pm
1 stop9h 29m
Chicago O'Hare Intl
Wed 9/2
11:01 am-2:28 pm
Nonstop2h 27m
$248
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 9/12
7:00 am-8:48 am
Nonstop2h 48m
Chicago O'Hare Intl
Mon 9/14
10:59 am-5:21 pm
1 stop5h 22m
$250
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 8/20
8:20 pm-10:00 pm
Nonstop2h 40m
Chicago Midway
Mon 8/24
3:20 pm-10:20 pm
1 stop6h 00m
$250
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 9/1
5:50 pm-10:20 pm
1 stop5h 30m
Chicago Midway
Thu 9/3
5:45 am-9:00 am
Nonstop2h 15m
$255
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Maine to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Maine with our price prediction graph.
BOS-ORD
BOS-MDW
PWM-STL
BOS-RFD
PWM-ORD
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 Maine to Illinois
USME-USIL
BOS-ORD
BOS-MDW
PWM-STL
BOS-RFD
What is the cheapest month to book a flight from Maine to Illinois?
Currently, September is the cheapest month in which you can book a flight from Maine to Illinois (average of $314). Flying from Maine to Illinois in December is currently the most expensive (average of $443). 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 ME to IL?
Find hourly flight availability from Maine to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 3, 2026.
One of the essential ways to save on airfare from Maine to Illinois is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 29% on airfare.
Weekly flight availability from Maine to Illinois
Explore weekly flight availability from Maine to Illinois. 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 August 3, 2026.
The most flights from USME to USIL are scheduled on a Friday (8 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Maine to Illinois?
Airfare is below average for this route at the moment.
Maine to Illinois flights typically cost between $281 and $378 in September.The cheapest round-trip price found within the last 5 days was $257 on American Airlines (Sep 5-Sep 6).
How far ahead should I book a flight from Maine to Illinois?
The best time to book flights from Maine to Illinois is 83 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated August 3, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Maine to Illinois have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Maine to Illinois. 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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Complete your trip
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Top destinations
Alternative routes for Maine to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Illinois by cabin class
Find flights from Maine to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maine and Illinois flights
Browse other Maine and Illinois flight options. Last updated on August 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Maine after your stay in Illinois
Maine to Illinois flights
Consider these flights traveling from Maine to Illinois.
Top 4 airlines flying from Maine to Illinois
Discover the top 4 airlines that operate flights from Maine to Illinois. 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 August 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$361 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$434 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$378 | FlexibilityNo cancel fee | On-time63% |