$129+ Cheap flights from Maine to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Oct 24 — Oct 311
Round-trip
1 adult, Economy
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Find cheap flights from Maine to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Maine to ChicagoExplore the most affordable flight options available from Maine to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
Explore the most affordable flight options available from Maine to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 24, 2026.
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:50 pm -
Nonstop3h 19m
Sat 10/247:13 pm -
Nonstop2h 54m
Deal found 9/20![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:57 pm -
1 stop6h 34m
Tue 11/245:29 pm -
1 stop4h 49m
Deal found 9/21![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:45 pm -
2 stops9h 09m
Tue 11/245:50 pm -
1 stop4h 35m
Deal found 9/21![Delta logo]()
$336
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:50 pm -
Nonstop3h 19m
Thu 10/297:13 pm -
Nonstop2h 54m
Deal found 9/20![American Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:10 am -
2 stops9h 46m
Sat 12/55:30 am -
2 stops8h 35m
Deal found 9/19![Delta logo]()
$342
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:50 pm -
Nonstop3h 10m
Sat 11/148:25 am -
Nonstop2h 28m
Deal found 9/21![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:45 pm -
Nonstop3h 10m
Sat 10/248:45 am -
Nonstop2h 46m
Deal found 9/19![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:10 pm -
1 stop6h 33m
Wed 10/281:55 pm -
2 stops8h 30m
Deal found 9/21![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1012:50 pm -
Nonstop3h 10m
Mon 12/148:25 am -
Nonstop2h 28m
Deal found 9/20![American Airlines logo]()
$353
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
Nonstop2h 35m
Tue 10/277:45 am -
Nonstop2h 10m
Deal found 9/21![Southwest logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:27 pm -
1 stop7h 33m
Sat 10/247:59 pm -
Nonstop2h 44m
Deal found 9/19![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:10 pm -
1 stop7h 26m
Mon 10/197:55 am -
1 stop7h 03m
Deal found 9/19![American Airlines logo]()
$359
Best flights from Maine to ChicagoDiscover carefully curated flight deals from Maine to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
Discover carefully curated flight deals from Maine to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 24, 2026.
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/23:45 pm -
1 stop6h 51m
Sun 12/68:50 am -
1 stop6h 21m
Deal found 9/19![Delta logo]()
$345
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:20 am -
1 stop4h 25m
Tue 10/271:40 pm -
2 stops5h 55m
Deal found 9/21![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:15 am -
1 stop7h 33m
Fri 10/166:10 pm -
Nonstop2h 36m
Deal found 9/19![United Airlines logo]()
$381
This United deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/154:09 pm -
1 stop20h 06m
Tue 11/179:13 am -
1 stop9h 17m
Deal found 9/21![Multiple Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/176:00 am -
1 stop5h 11m
Wed 2/175:00 pm -
1 stop5h 06m
Deal found 9/21![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:30 pm -
1 stop5h 30m
Sat 10/2411:35 am -
2 stops9h 40m
Deal found 9/19![Southwest logo]()
$378
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/245:15 am -
1 stop7h 22m
Wed 1/611:00 am -
Nonstop2h 42m
Deal found 9/23![United Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/106:00 am -
1 stop6h 59m
Tue 11/105:13 pm -
1 stop5h 18m
Deal found 9/23![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/125:10 pm -
2 stops6h 35m
Sat 11/147:45 am -
2 stops6h 00m
Deal found 9/23![Southwest logo]()
$383
This KAYAK deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Mon 10/263:37 pm -
1 stop21h 23m
Thu 10/291:00 pm -
1 stop5h 05m
Deal found 9/22![Multiple Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:27 am -
1 stop5h 03m
Sat 11/1411:18 am -
2 stops11h 13m
Deal found 9/21![Delta logo]()
$378
This Expedia deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/69:00 am -
1 stop11h 03m
Sat 10/109:38 am -
1 stop10h 02m
Deal found 9/21![Multiple Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:15 pm -
1 stop6h 28m
Sat 10/246:20 am -
2 stops8h 42m
Deal found 9/21![Delta logo]()
$378
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 pm -
Nonstop2h 35m
Sat 10/244:10 pm -
Nonstop2h 15m
Deal found 9/20![Southwest logo]()
$417
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 12/318:02 am -
Nonstop3h 18m
Sat 1/26:10 pm -
1 stop4h 49m
Deal found 9/23![United Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:28 pm -
1 stop5h 49m
Tue 10/201:23 pm -
2 stops8h 55m
Deal found 9/19![Delta logo]()
$378
This Southwest deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/1012:45 pm -
1 stop7h 10m
Sun 11/155:05 am -
1 stop4h 25m
Deal found 9/23![Southwest logo]()
$422
This United Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/315:30 am -
1 stop5h 15m
Tue 11/36:04 am -
1 stop7h 23m
Deal found 9/23![United Airlines logo]()
$473
This KAYAK deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Mon 10/264:09 pm -
1 stop20h 51m
Thu 10/298:24 pm -
1 stop13h 42m
Deal found 9/22![Multiple Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/126:00 am -
1 stop6h 59m
Sat 11/1411:27 am -
2 stops11h 52m
Deal found 9/23![Delta logo]()
$378
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:25 am -
1 stop5h 15m
Sun 12/67:50 am -
2 stops7h 40m
Deal found 9/21![Southwest logo]()
$427
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 11/124:03 pm -
2 stops8h 51m
Sat 11/145:30 am -
2 stops8h 46m
Deal found 9/23![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/172:45 pm -
2 stops6h 40m
Sun 3/218:45 am -
1 stop6h 55m
Deal found 9/20![Southwest logo]()
$429
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 1/76:00 am -
2 stops8h 20m
Sun 1/109:50 am -
2 stops11h 11m
Deal found 9/23![Delta logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:43 pm -
Nonstop3h 17m
Sat 10/105:52 pm -
Nonstop2h 47m
Deal found 9/21![United Airlines logo]()
$591
This Delta deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:00 am -
2 stops8h 59m
Fri 12/42:41 pm -
2 stops7h 45m
Deal found 9/19![Delta logo]()
$394
This KAYAK deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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.
Sun 10/257:20 am -
1 stop5h 40m
Thu 10/291:00 pm -
1 stop5h 05m
Deal found 9/22![Multiple Airlines logo]()
$668
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:00 am -
1 stop7h 19m
Mon 11/24:40 pm -
1 stop16h 39m
Deal found 9/21![United Airlines logo]()
$637
This Delta deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:02 pm -
1 stop6h 15m
Sat 10/247:00 am -
1 stop5h 19m
Deal found 9/20![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:00 am -
1 stop6h 59m
Sun 11/226:00 am -
1 stop6h 01m
Deal found 9/21![Delta logo]()
$422
Last-minute flights from Maine to ChicagoDiscover last-minute flight deals from Maine to Chicago. Data last updated September 24, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Chicago. Data last updated September 24, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 10/156:00 am -
Nonstop2h 57m
Tue 10/203:00 pm -
Nonstop2h 43m
Deal found 9/22![United Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:10 pm -
1 stop7h 26m
Mon 10/197:55 am -
1 stop7h 03m
Deal found 9/19![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/156:00 am -
1 stop5h 07m
Mon 10/198:25 am -
Nonstop2h 46m
Deal found 9/23![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
1 stop5h 07m
Thu 10/227:59 pm -
Nonstop2h 44m
Deal found 9/19![American Airlines logo]()
$363
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/155:20 am -
1 stop4h 30m
Tue 10/207:45 am -
Nonstop2h 10m
Deal found 9/21![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:27 pm -
1 stop7h 33m
Sat 10/247:59 pm -
Nonstop2h 44m
Deal found 9/19![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:50 pm -
Nonstop3h 19m
Sat 10/247:13 pm -
Nonstop2h 54m
Deal found 9/20![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:50 pm -
Nonstop3h 19m
Thu 10/297:13 pm -
Nonstop2h 54m
Deal found 9/20![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:45 pm -
Nonstop3h 10m
Sat 10/248:45 am -
Nonstop2h 46m
Deal found 9/19![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:10 pm -
1 stop6h 33m
Wed 10/281:55 pm -
2 stops8h 30m
Deal found 9/21![Delta logo]()
$350
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
Nonstop2h 35m
Tue 10/277:45 am -
Nonstop2h 10m
Deal found 9/21![Southwest logo]()
$353
This American Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:45 pm -
Nonstop3h 10m
Sat 10/311:44 pm -
Nonstop2h 31m
Deal found 9/21![American Airlines logo]()
$344
One-way flights from Maine to ChicagoSearch for one-way flight options from Maine to Chicago. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
Search for one-way flight options from Maine to Chicago. Find affordable one-way fares based on user searches. Data last updated September 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1610:07 am -
2 stops27h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:31 pm -
2 stops22h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$170
This JetBlue deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” 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 10/216:00 am -
1 stop6h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![JetBlue logo]()
$177
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am -
Nonstop2h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$177
This United Airlines deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/204:48 pm -
Nonstop2h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$179
This JetBlue deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am -
1 stop6h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![JetBlue logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:12 pm -
2 stops19h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/175:09 pm -
2 stops20h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1510:46 am -
1 stop30h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 12/212:28 pm -
2 stops33h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/2410:07 am -
2 stops27h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$187
This Delta deal was found by Cheapflights users on 9/22. Clicking the “Pick Dates” 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 11/186:00 am -
1 stop6h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Delta logo]()
$187
Find flight deals from Maine to Chicago
Keep the following information in mind while searching for Maine to Chicago flight deals. Data was last updated September 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $325 (American Airlines) |
One-way from | $129 (Kiwi.com) |
Popular in | July |
Cheapest in | May |
Average price | $383 |
Good round-trip deal | $408 or less |
Good one-way deal | $237 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maine to Chicago 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 7,457,451 searches. Data last updated September 24, 2026.
Use the filters below to find and compare flights from Maine to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 3/20
4:48 pm-6:45 pm
Nonstop2h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$179
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 10/21
1:52 pm-7:20 pm
1 stop6h 28m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Mon 11/23
5:30 am-9:45 am
1 stop5h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 11/18
6:00 am-11:59 am
1 stop6h 59m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Wed 12/16
12:49 pm-6:01 pm
1 stop6h 12m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$187
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sat 10/31
6:25 am-4:41 pm
2 stops11h 16m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Wed 10/14
4:47 pm-11:57 pm
2 stops8h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 11/17
6:27 am-12:51 pm
2 stops7h 24m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Mon 11/23
6:27 am-12:51 pm
2 stops7h 24m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$192
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Tue 3/23
6:00 am-4:25 pm
2 stops11h 25m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$194
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Maine to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Maine with our price prediction graph.
BGR-ORD
PWM-ORD
PWM-MDW
AUG-ORD
RKD-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 Chicago
USME-CHI
BGR-ORD
PWM-ORD
PWM-MDW
AUG-ORD
What is the cheapest month to book a flight from Maine to Chicago?
Currently, May is the cheapest month in which you can book a flight from Maine to Chicago (average of $337). Flying from Maine to Chicago in December is currently the most expensive (average of $428). 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 CHI?
Find hourly flight availability from Maine to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 24, 2026.
When flying from Maine to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 29% versus a flight in the morning.
Weekly flight availability from Maine to Chicago
Explore weekly flight availability from Maine to Chicago. 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 September 24, 2026.
The most flights from USME to CHI are scheduled on a Wednesday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Maine to Chicago?
Airfare is below average for this route at the moment.
Maine to Chicago flights typically cost between $344 and $491 in November.The cheapest round-trip price found within the last 5 days was $344 on American Airlines (Nov 11-Nov 14).
How far ahead should I book a flight from Maine to Chicago?
The best time to book flights from Maine to Chicago 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 day to fly from Maine to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Maine to Chicago. Price data was last updated on September 19, 2026.
Travelers seeking maximum savings on their Maine to Chicago flight should consider departing on Friday at noon when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Maine to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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.
Alternative routes
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Alternative routes for Maine to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 24, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Chicago by cabin class
Find flights from Maine to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maine and Chicago flights
Browse other Maine and Chicago flight options. Last updated on September 24, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Maine to Chicago flights
Consider these flights traveling from Maine to Chicago.
Top 4 airlines flying from Maine to Chicago
Discover the top 4 airlines that operate flights from Maine to Chicago. 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 7,457,451 searches. Data last updated September 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$383 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$239 | Average$388 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$267 | Average$374 | FlexibilityNo cancel fee | On-time63% |