$82+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
May 31 — Jun 71
Round-trip
1 adult, Economy
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Find cheap flights from Maine to Illinois with Cheapflights
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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 May 1, 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 May 1, 2026.
This Expedia deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:17 am
BOS
- ORD
1 stop13h 56m
Multiple Airlines
Sat 5/231:56 pm
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$159
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Tue 5/1912:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/27![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:07 am
BOS
- ORD
1 stop14h 06m
Frontier
Tue 5/191:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/28![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 7/2110:56 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 4/30![JetBlue logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Tue 5/265:45 am
BOS
- ORD
1 stop31h 52m
Multiple Airlines
Tue 6/91:29 pm
ORD
- BOS
1 stop10h 58m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$164
This Super.com deal was found by Cheapflights users on 4/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/78:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Tue 7/78:20 pm
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/29![JetBlue logo]()
$165
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 6/167:46 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Wed 6/177:00 am
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 4/29![American Airlines logo]()
$166
This Southwest deal was found by Cheapflights users on 4/28. 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.
Tue 6/27:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Sat 6/65:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/28![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 5/278:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Sat 5/307:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 4/28![Delta logo]()
$167
This SmartFares deal was found by Cheapflights users on 4/28. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2311:00 am
BOS
- ORD
Nonstop3h 01m
JetBlue
Sun 5/248:50 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 4/28![JetBlue logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:12 am
BOS
- MDW
1 stop13h 50m
Frontier
Tue 6/212:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 4/28![Frontier logo]()
$169
This Priceline deal was found by Cheapflights users on 4/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:47 pm
BOS
- ORD
Nonstop3h 06m
Multiple Airlines
Wed 5/201:59 pm
ORD
- BOS
1 stop10h 25m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$169
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 May 1, 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 May 1, 2026.
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/272:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Sat 5/307:45 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/26![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/207:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Thu 5/2810:25 am
ORD
- BOS
Nonstop2h 24m
Delta
Deal found 4/30![Delta logo]()
$182
This United Airlines deal was found by Cheapflights users on 4/28. 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.
Mon 5/256:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Thu 5/286:00 am
ORD
- BOS
1 stop4h 16m
United Airlines
Deal found 4/28![United Airlines logo]()
$187
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Fri 5/226:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Thu 5/288:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 4/30![JetBlue logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:33 pm
BOS
- RFD
1 stop20h 44m
Multiple Airlines
Sun 6/711:27 am
RFD
- BOS
1 stop11h 27m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$296
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 6/165:25 am
BOS
- ORD
2 stops8h 50m
Southwest
Wed 6/172:40 pm
ORD
- BOS
2 stops7h 40m
Southwest
Deal found 4/30![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 4/28. 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.
Sun 6/77:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Fri 6/127:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 4/28![Delta logo]()
$201
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Mon 6/19:26 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/29![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 4/29. 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 6/35:45 am
BOS
- MDW
1 stop6h 50m
Southwest
Thu 6/47:45 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/29![Southwest logo]()
$212
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/15:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Mon 7/69:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/27![United Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/58:03 am
BOS
- BMI
1 stop7h 13m
American Airlines
Sat 5/911:16 am
BMI
- BOS
1 stop4h 29m
American Airlines
Deal found 4/29![American Airlines logo]()
$507
This JetBlue deal was found by Cheapflights users on 4/30. 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.
Sun 5/107:02 am
BOS
- ORD
Nonstop2h 57m
JetBlue
Tue 5/129:49 am
ORD
- BOS
Nonstop2h 31m
JetBlue
Deal found 4/30![JetBlue logo]()
$257
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/267:30 am
BOS
- ORD
Nonstop2h 58m
Delta
Mon 6/297:10 am
ORD
- BOS
Nonstop2h 36m
Delta
Deal found 4/26![Delta logo]()
$236
This Delta deal was found by Cheapflights users on 4/28. 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.
Wed 6/109:15 am
BOS
- ORD
1 stop4h 49m
Delta
Wed 6/107:25 pm
ORD
- BOS
Nonstop2h 37m
Delta
Deal found 4/28![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Sun 6/289:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 4/26![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/117:30 am
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 6/125:05 pm
MDW
- BOS
1 stop6h 05m
Southwest
Deal found 4/27![Southwest logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/312:37 pm
BOS
- RFD
1 stop20h 38m
Multiple Airlines
Thu 7/911:27 am
RFD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/810:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 5/117:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/26![Southwest logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Sun 7/1911:27 am
RFD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/48:25 pm
BOS
- ORD
Nonstop2h 55m
United Airlines
Thu 5/76:00 am
ORD
- BOS
Nonstop2h 25m
United Airlines
Deal found 4/30![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 4/29. 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 7/304:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 8/15:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 4/29![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/104:22 pm
BGR
- ORD
1 stop6h 26m
Delta
Wed 6/175:30 am
ORD
- BGR
2 stops9h 12m
Delta
Deal found 4/27![Delta logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 6/1012:01 pm
BOS
- RFD
2 stops23h 36m
Multiple Airlines
Mon 6/157:53 pm
RFD
- BOS
1 stop23h 07m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/145:15 am
PWM
- ORD
1 stop5h 18m
United Airlines
Sun 8/166:25 pm
ORD
- PWM
Nonstop2h 36m
United Airlines
Deal found 4/29![United Airlines logo]()
$279
This Southwest deal was found by Cheapflights users on 4/30. 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.
Tue 5/57:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 5/63:15 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/30![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 7/224:22 pm
BGR
- ORD
1 stop6h 30m
Delta
Tue 7/281:44 pm
ORD
- BGR
2 stops8h 27m
Delta
Deal found 4/30![Delta logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Wed 7/156:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Mon 7/207:50 pm
RFD
- BOS
1 stop25h 51m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/307:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 6/15:40 pm
MDW
- BOS
1 stop4h 30m
Southwest
Deal found 4/27![Southwest logo]()
$262
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/1011:48 am
PWM
- ORD
1 stop8h 43m
Delta
Mon 6/157:01 am
ORD
- PWM
1 stop3h 54m
Delta
Deal found 4/26![Delta logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
BOS
- RFD
1 stop29h 37m
Multiple Airlines
Mon 8/37:50 pm
RFD
- BOS
1 stop25h 51m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$327
Last-minute flights from Maine to IllinoisDiscover last-minute flight deals from Maine to Illinois. Data last updated May 1, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Illinois. Data last updated May 1, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/1112:01 pm
BOS
- ORD
1 stop8h 50m
Frontier
Tue 5/121:59 pm
ORD
- BOS
1 stop10h 25m
Frontier
Deal found 4/27![Frontier logo]()
$180
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/1112:01 pm
BOS
- ORD
1 stop8h 50m
Multiple Airlines
Wed 5/139:49 am
ORD
- BOS
Nonstop2h 31m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$184
This Orbitz deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Tue 5/1912:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/27![Frontier logo]()
$160
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1612:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Tue 5/1912:24 pm
MDW
- BOS
1 stop12h 00m
Frontier
Deal found 4/27![Frontier logo]()
$181
This Southwest deal was found by Cheapflights users on 4/28. 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.
Tue 5/1910:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Wed 5/206:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/28![Southwest logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:12 am
BOS
- MDW
1 stop13h 50m
Frontier
Tue 6/212:27 pm
MDW
- BOS
1 stop11h 57m
Frontier
Deal found 4/28![Frontier logo]()
$169
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2610:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Fri 5/297:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/27![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 4/29. 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 5/267:20 am
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 6/36:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/29![Southwest logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:12 am
BOS
- MDW
1 stop13h 50m
Frontier
Mon 6/112:04 pm
MDW
- BOS
1 stop18h 45m
Frontier
Deal found 4/28![Frontier logo]()
$186
This Expedia deal was found by Cheapflights users on 4/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Wed 6/312:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/28![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 4/28. 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 5/287:10 am
BOS
- MDW
Nonstop2h 50m
Southwest
Wed 6/36:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 4/28![Southwest logo]()
$187
This Travelocity deal was found by Cheapflights users on 4/28. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Mon 6/112:04 pm
MDW
- BOS
1 stop12h 20m
Frontier
Deal found 4/28![Frontier logo]()
$185
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 May 1, 2026.
Search for one-way flight options from Maine to Illinois. Find affordable one-way fares based on user searches. Data last updated May 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Tue 5/269:12 am
BOS
- STL
1 stop24h 43m
Frontier
Deal found 4/29![Frontier logo]()
$82
This Super.com deal was found by Cheapflights users on 4/29. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/266:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/29![JetBlue logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:10 am
BOS
- ORD
Nonstop2h 56m
JetBlue
Deal found 4/30![JetBlue logo]()
$83
This Southwest deal was found by Cheapflights users on 4/28. 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 5/2710:45 am
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 4/28![Southwest logo]()
$84
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:25 pm
BOS
- ORD
Nonstop3h 10m
JetBlue
Deal found 4/28![JetBlue logo]()
$84
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:00 am
BOS
- STL
1 stop12h 33m
Frontier
Deal found 4/29![Frontier logo]()
$86
This Super.com deal was found by Cheapflights users on 4/28. 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.
Thu 6/115:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Deal found 4/28![JetBlue logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/35:45 am
BOS
- RFD
1 stop29h 52m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:01 pm
BOS
- MDW
1 stop11h 01m
Frontier
Deal found 4/27![Frontier logo]()
$88
This Super.com deal was found by Cheapflights users on 4/30. 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.
Mon 5/256:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 4/30![JetBlue logo]()
$88
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 5/2712:01 pm
BOS
- STL
1 stop30h 32m
Frontier
Deal found 4/30![Frontier logo]()
$89
This Southwest deal was found by Cheapflights users on 4/29. 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 6/185:25 am
BOS
- MDW
Nonstop2h 35m
Southwest
Deal found 4/29![Southwest logo]()
$89
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 May 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $159 (Expedia) |
One-way from | $82 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $289 |
Good round-trip deal | $371 or less |
Good one-way deal | $193 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 May 1, 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
Wed 5/27
2:25 pm-4:05 pm
Nonstop2h 40m
Chicago Midway
Sat 5/30
7:45 am-11:00 am
Nonstop2h 15m
$167
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/20
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Thu 5/28
10:25 am-1:49 pm
Nonstop2h 24m
$182
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 5/25
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Thu 5/28
6:00 am-11:16 am
1 stop4h 16m
$187
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 6/16
5:25 am-1:15 pm
2 stops8h 50m
Chicago O'Hare Intl
Wed 6/17
2:40 pm-11:20 pm
2 stops7h 40m
$197
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 6/7
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
Fri 6/12
7:25 pm-11:02 pm
Nonstop2h 37m
$201
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 5/31
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Mon 6/1
9:26 pm-12:59 am
Nonstop2h 33m
$209
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 6/3
5:45 am-11:35 am
1 stop6h 50m
Chicago Midway
Thu 6/4
7:45 pm-11:00 pm
Nonstop2h 15m
$212
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/1
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Mon 7/6
9:35 pm-1:08 am
Nonstop2h 33m
$219
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/22
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Thu 5/28
8:30 pm-11:59 pm
Nonstop2h 29m
$232
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 6/26
7:30 am-9:28 am
Nonstop2h 58m
Chicago O'Hare Intl
Mon 6/29
7:10 am-10:46 am
Nonstop2h 36m
$236
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-STL
BOS-ORD
BOS-MDW
BOS-RFD
BOS-BMI
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-STL
BOS-ORD
BOS-MDW
BOS-RFD
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.
What is the cheapest month to book a flight from Maine to Illinois?
Currently, May is the cheapest month in which you can book a flight from Maine to Illinois (average of $102). Flying from Maine to Illinois 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 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 May 1, 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 at noon could potentially save you up to 19% 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 May 1, 2026.
The most flights from USME to USIL are scheduled on a Friday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Maine to Illinois?
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 May 1, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican 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.
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from 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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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 May 1, 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 3 airlines flying from Maine to Illinois
Discover the top 3 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 May 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$353 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$420 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$267 | Average$397 | FlexibilityNo cancel fee | On-time63% |