$78+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — ORD
Apr 18 — Apr 251
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 March 19, 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 March 19, 2026.
This flygcity.se deal was found by Cheapflights users on 3/16. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Sun 4/128:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/16![JetBlue logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Thu 5/285:26 pm
BOS
- ORD
Nonstop3h 09m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/17![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:03 am
BOS
- ORD
Nonstop3h 09m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/15![American Airlines logo]()
$154
This SmartFares deal was found by Cheapflights users on 3/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sun 4/128:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/17![JetBlue logo]()
$155
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/16![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:15 am
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 4/207:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/14![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 3/18. 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.
Fri 5/17:35 pm
BOS
- ORD
Nonstop2h 54m
Delta
Mon 5/46:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/18![Delta logo]()
$157
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:59 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Wed 4/151:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 3/17![American Airlines logo]()
$158
This Cheapflightsfares deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/76:52 am
BOS
- ORD
Nonstop2h 59m
JetBlue
Sat 5/96:00 am
ORD
- BOS
Nonstop2h 15m
JetBlue
Deal found 3/14![JetBlue logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Thu 6/46:00 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
- BOS
Nonstop2h 29m
JetBlue
Deal found 3/17![JetBlue logo]()
$162
This Super.com deal was found by Cheapflights users on 3/16. 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.
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Tue 4/149:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/16![JetBlue logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Mon 4/68:58 am
ORD
- BOS
Nonstop2h 27m
JetBlue
Deal found 3/16![JetBlue logo]()
$166
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 March 19, 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 March 19, 2026.
This Delta deal was found by Cheapflights users on 3/17. 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 5/207:35 am
BOS
- ORD
Nonstop2h 52m
Delta
Sun 5/247:00 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 3/17![Delta logo]()
$157
This United Airlines deal was found by Cheapflights users on 3/18. 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.
Thu 5/286:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Wed 6/36:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 3/18![United Airlines logo]()
$157
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:25 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Wed 5/67:50 am
MDW
- BOS
2 stops7h 05m
Southwest
Deal found 3/15![Southwest logo]()
$172
This JetBlue deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/97:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Tue 5/128:31 am
ORD
- BOS
1 stop4h 45m
JetBlue
Deal found 3/14![JetBlue logo]()
$187
This American Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:30 am
BOS
- MLI
1 stop6h 51m
American Airlines
Tue 4/283:48 pm
MLI
- BOS
1 stop7h 16m
American Airlines
Deal found 3/14![American Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:15 am
BOS
- RFD
1 stop29h 22m
Multiple Airlines
Sun 5/3111:27 am
RFD
- BOS
1 stop11h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:30 am
BOS
- MDW
1 stop4h 15m
Southwest
Sat 5/1612:45 pm
MDW
- BOS
2 stops9h 55m
Southwest
Deal found 3/14![Southwest logo]()
$192
This Delta deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/25:10 pm
BOS
- ORD
Nonstop3h 07m
Delta
Sun 5/36:50 am
ORD
- BOS
Nonstop2h 21m
Delta
Deal found 3/14![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/68:00 am
BOS
- ORD
1 stop5h 06m
United Airlines
Thu 7/99:35 pm
ORD
- BOS
Nonstop2h 33m
United Airlines
Deal found 3/16![United Airlines logo]()
$210
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 4/127:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/15![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 3/17. 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.
Fri 5/298:40 pm
BOS
- ORD
Nonstop2h 55m
Delta
Tue 6/27:16 pm
ORD
- BOS
Nonstop2h 34m
Delta
Deal found 3/17![Delta logo]()
$217
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/105:45 am
BOS
- ORD
1 stop4h 51m
United Airlines
Tue 7/146:20 pm
ORD
- BOS
Nonstop2h 36m
United Airlines
Deal found 3/16![United Airlines logo]()
$220
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:45 pm
BOS
- MDW
1 stop5h 00m
Southwest
Wed 6/312:50 pm
MDW
- BOS
2 stops5h 50m
Southwest
Deal found 3/18![Southwest logo]()
$222
This United Airlines deal was found by Cheapflights users on 3/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Thu 4/309:30 pm
ORD
- BOS
Nonstop2h 29m
United Airlines
Deal found 3/16![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 3/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/308:45 am
BOS
- MDW
1 stop7h 20m
Southwest
Thu 5/79:25 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/16![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 3/17. 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 8/266:00 am
BOS
- ORD
1 stop5h 00m
Delta
Sat 8/297:00 am
ORD
- BOS
Nonstop2h 28m
Delta
Deal found 3/17![Delta logo]()
$256
This American Airlines deal was found by Cheapflights users on 3/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:27 pm
BGR
- ORD
1 stop6h 07m
American Airlines
Sun 5/37:15 am
ORD
- BGR
1 stop6h 18m
American Airlines
Deal found 3/18![American Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/145:50 pm
BOS
- MDW
1 stop7h 05m
Southwest
Mon 5/187:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 3/15![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 6/136:00 am
BOS
- ORD
1 stop6h 04m
United Airlines
Sun 6/146:15 am
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 3/15![United Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/66:15 am
BOS
- RFD
1 stop28h 32m
Multiple Airlines
Sun 5/1010:37 am
RFD
- BOS
1 stop12h 07m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 5/295:30 am
BOS
- ORD
2 stops9h 50m
Southwest
Tue 6/22:40 pm
ORD
- BOS
1 stop6h 50m
Southwest
Deal found 3/14![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 3/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:26 pm
PWM
- ORD
1 stop5h 49m
Delta
Tue 4/216:21 pm
ORD
- PWM
1 stop5h 25m
Delta
Deal found 3/16![Delta logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/15:49 pm
BOS
- RFD
1 stop16h 58m
Multiple Airlines
Fri 4/310:44 am
RFD
- BOS
1 stop22h 10m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:36 pm
PWM
- ORD
1 stop5h 07m
United Airlines
Sun 4/126:10 pm
ORD
- PWM
Nonstop2h 30m
United Airlines
Deal found 3/14![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 3/17. 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 5/266:00 am
PWM
- ORD
1 stop8h 47m
Delta
Fri 5/292:00 pm
ORD
- PWM
2 stops9h 43m
Delta
Deal found 3/17![Delta logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/206:15 am
BOS
- RFD
1 stop29h 22m
Multiple Airlines
Sun 5/2411:27 am
RFD
- BOS
1 stop11h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 6/115:20 pm
PWM
- MDW
1 stop5h 40m
Southwest
Mon 6/156:55 pm
MDW
- PWM
Nonstop2h 15m
Southwest
Deal found 3/15![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” 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 6/46:00 am
PWM
- ORD
Nonstop3h 00m
United Airlines
Sun 6/76:18 pm
ORD
- PWM
Nonstop2h 33m
United Airlines
Deal found 3/14![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 3/18. 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.
Fri 5/2912:55 pm
PWM
- MDW
1 stop6h 38m
Delta
Mon 6/11:22 pm
MDW
- PWM
2 stops8h 47m
Delta
Deal found 3/18![Delta logo]()
$294
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/15:50 am
BOS
- MDW
1 stop5h 55m
Southwest
Sat 7/46:30 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/18![Southwest logo]()
$261
Last-minute flights from Maine to IllinoisDiscover last-minute flight deals from Maine to Illinois. Data last updated March 19, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Illinois. Data last updated March 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 4/1111:25 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/15![Southwest logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/16:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sat 4/118:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/16![JetBlue logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/26:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Tue 4/78:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/15![JetBlue logo]()
$162
This Cheapflightsfares deal was found by Cheapflights users on 3/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Thu 4/98:55 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/16![JetBlue logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:59 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Wed 4/151:11 pm
ORD
- BOS
Nonstop2h 34m
American Airlines
Deal found 3/17![American Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:03 am
BOS
- ORD
Nonstop3h 09m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/15![American Airlines logo]()
$154
This SmartFares deal was found by Cheapflights users on 3/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Sun 4/128:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/17![JetBlue logo]()
$155
This flygcity.se deal was found by Cheapflights users on 3/16. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Sun 4/128:58 am
ORD
- BOS
Nonstop2h 30m
JetBlue
Deal found 3/16![JetBlue logo]()
$142
This American Airlines deal was found by Cheapflights users on 3/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:40 pm
BOS
- ORD
Nonstop3h 10m
American Airlines
Sun 4/126:00 am
ORD
- BOS
Nonstop2h 27m
American Airlines
Deal found 3/16![American Airlines logo]()
$156
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/119:25 am
BOS
- MDW
Nonstop2h 40m
Southwest
Mon 4/137:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 3/14![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 3/18. 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 4/115:35 pm
BOS
- ORD
Nonstop3h 08m
Delta
Mon 4/1310:15 am
ORD
- BOS
Nonstop2h 20m
Delta
Deal found 3/18![Delta logo]()
$157
This Super.com deal was found by Cheapflights users on 3/16. 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.
Sun 4/126:05 am
BOS
- ORD
Nonstop3h 03m
JetBlue
Tue 4/149:41 am
ORD
- BOS
Nonstop2h 26m
JetBlue
Deal found 3/16![JetBlue logo]()
$165
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 March 19, 2026.
Search for one-way flight options from Maine to Illinois. Find affordable one-way fares based on user searches. Data last updated March 19, 2026.
This Super.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/27:35 pm
BOS
- ORD
Nonstop3h 01m
JetBlue
Deal found 3/15![JetBlue logo]()
$78
This Southwest deal was found by Cheapflights users on 3/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:50 pm
BOS
- MDW
Nonstop2h 40m
Southwest
Deal found 3/16![Southwest logo]()
$79
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:30 am
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/17![American Airlines logo]()
$79
This American Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 5/203:59 pm
BOS
- ORD
Nonstop3h 14m
American Airlines
Deal found 3/15![American Airlines logo]()
$80
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Sun 5/316:00 am
BOS
- ORD
Nonstop2h 58m
United Airlines
Deal found 3/17![United Airlines logo]()
$86
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Sun 5/36:00 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/17![United Airlines logo]()
$87
This Super.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” 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 4/26:05 am
BOS
- ORD
Nonstop3h 00m
JetBlue
Deal found 3/15![JetBlue logo]()
$88
This Southwest deal was found by Cheapflights users on 3/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:20 am
BOS
- MDW
1 stop5h 20m
Southwest
Deal found 3/16![Southwest logo]()
$89
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Thu 5/77:30 am
BOS
- ORD
Nonstop3h 00m
United Airlines
Deal found 3/17![United Airlines logo]()
$89
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
BOS
- MDW
1 stop6h 09m
Frontier
Deal found 3/17![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 3/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3112:36 pm
BOS
- ORD
1 stop6h 57m
Frontier
Deal found 3/16![Frontier logo]()
$90
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
BOS
- MDW
1 stop6h 12m
Frontier
Deal found 3/17![Frontier logo]()
$91
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 March 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $142 (flygcity.se) |
One-way from | $78 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $391 |
Good round-trip deal | $338 or less |
Good one-way deal | $198 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 March 19, 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
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 5/20
7:35 am-9:27 am
Nonstop2h 52m
Chicago O'Hare Intl
Sun 5/24
7:00 am-10:35 am
Nonstop2h 35m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 5/28
6:00 am-7:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Wed 6/3
6:15 am-9:39 am
Nonstop2h 24m
$157
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 4/29
2:25 pm-4:05 pm
Nonstop2h 40m
Chicago Midway
Wed 5/6
7:50 am-3:55 pm
2 stops7h 05m
$172
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/9
7:35 pm-9:36 pm
Nonstop3h 01m
Chicago O'Hare Intl
Tue 5/12
8:31 am-2:16 pm
1 stop4h 45m
$187
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sun 5/10
5:30 am-8:45 am
1 stop4h 15m
Chicago Midway
Sat 5/16
12:45 pm-11:40 pm
2 stops9h 55m
$192
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
5:10 pm-7:17 pm
Nonstop3h 07m
Chicago O'Hare Intl
Sun 5/3
6:50 am-10:11 am
Nonstop2h 21m
$207
Quickest round-trip
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 4/11
9:25 am-11:05 am
Nonstop2h 40m
Chicago Midway
Sun 4/12
7:40 am-10:55 am
Nonstop2h 15m
$207
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 7/6
8:00 am-12:06 pm
1 stop5h 06m
Chicago O'Hare Intl
Thu 7/9
9:35 pm-1:08 am
Nonstop2h 33m
$210
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 5/29
8:40 pm-10:35 pm
Nonstop2h 55m
Chicago O'Hare Intl
Tue 6/2
7:16 pm-10:50 pm
Nonstop2h 34m
$217
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 7/10
5:45 am-9:36 am
1 stop4h 51m
Chicago O'Hare Intl
Tue 7/14
6:20 pm-9:56 pm
Nonstop2h 36m
$220
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
BOS-MLI
BOS-RFD
BGR-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
BOS-MLI
BOS-RFD
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 $182). Flying from Maine to Illinois in December is currently the most expensive (average of $259). 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 March 19, 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 evening tend to be the most expensive. A flight at noon could potentially save you up to 46% 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 March 19, 2026.
The most flights from USME to USIL are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).
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 March 19, 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.
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
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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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 March 19, 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 March 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$373 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$358 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$224 | Average$435 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$264 | Average$387 | FlexibilityNo cancel fee | On-time63% |