$155+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Dec 9 — Dec 161
Round-trip
1 adult, Economy
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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 November 9, 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 November 9, 2026.
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/44:47 pm -
Nonstop3h 13m
Tue 12/811:59 am -
Nonstop2h 39m
Deal found 11/7![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/2512:59 pm -
1 stop5h 45m
Sat 1/99:56 am -
2 stops10h 14m
Deal found 11/5![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/254:28 pm -
Nonstop3h 12m
Tue 1/511:00 am -
Nonstop2h 44m
Deal found 11/5![United Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Mon 12/712:44 pm -
Nonstop3h 16m
Thu 12/108:30 am -
Nonstop2h 32m
Deal found 11/4![American Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/134:53 pm -
2 stops8h 03m
Wed 12/1611:39 am -
2 stops10h 54m
Deal found 11/5![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/44:02 pm -
1 stop6h 22m
Sun 12/68:30 am -
Nonstop2h 32m
Deal found 11/7![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/304:32 pm -
1 stop8h 00m
Tue 1/56:45 am -
1 stop4h 43m
Deal found 11/8![American Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/207:08 pm -
1 stop5h 53m
Tue 1/511:00 am -
Nonstop2h 44m
Deal found 11/5![United Airlines logo]()
$361
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/175:08 pm -
Nonstop2h 57m
Tue 12/811:59 am -
Nonstop2h 39m
Deal found 11/5![United Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/107:00 am -
1 stop5h 47m
Sun 12/135:29 pm -
1 stop4h 55m
Deal found 11/4![United Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/256:00 am -
1 stop6h 13m
Mon 1/410:05 am -
1 stop5h 29m
Deal found 11/8![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/43:25 pm -
1 stop7h 05m
Mon 12/76:00 am -
1 stop5h 10m
Deal found 11/8![Southwest logo]()
$369
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 November 9, 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 November 9, 2026.
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/26:00 am -
2 stops11h 17m
Wed 12/95:02 pm -
2 stops6h 19m
Deal found 11/4![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 2/194:40 pm -
Nonstop3h 18m
Sat 2/275:45 pm -
Nonstop2h 31m
Deal found 11/6![United Airlines logo]()
$349
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/133:25 pm -
1 stop6h 25m
Sun 1/176:35 am -
1 stop4h 40m
Deal found 11/6![Southwest logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/312:27 pm -
1 stop5h 57m
Sun 12/68:53 am -
1 stop6h 01m
Deal found 11/4![American Airlines logo]()
$389
This Priceline deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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.
Sat 11/2112:01 pm -
1 stop5h 39m
Wed 11/2511:00 am -
1 stop7h 30m
Deal found 11/5![Multiple Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/136:12 am -
1 stop5h 23m
Wed 12/162:41 pm -
2 stops7h 39m
Deal found 11/5![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/139:51 am -
Nonstop3h 09m
Tue 12/1511:59 am -
Nonstop2h 39m
Deal found 11/5![United Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/2512:59 pm -
1 stop5h 45m
Tue 1/56:00 am -
2 stops9h 34m
Deal found 11/5![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/2510:25 am -
1 stop5h 15m
Tue 1/58:50 am -
1 stop4h 55m
Deal found 11/5![Southwest logo]()
$405
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/259:48 am -
1 stop8h 06m
Sat 1/26:10 pm -
1 stop4h 49m
Deal found 11/8![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/134:53 pm -
2 stops8h 03m
Tue 12/159:59 am -
2 stops12h 34m
Deal found 11/5![Delta logo]()
$354
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/193:25 pm -
2 stops8h 20m
Thu 1/71:30 pm -
2 stops7h 20m
Deal found 11/8![Southwest logo]()
$419
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/312:09 pm -
1 stop8h 06m
Wed 1/66:00 pm -
1 stop4h 59m
Deal found 11/8![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/238:49 am -
1 stop6h 05m
Fri 11/275:29 pm -
1 stop4h 52m
Deal found 11/8![United Airlines logo]()
$409
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/43:25 pm -
1 stop7h 05m
Sun 12/67:30 am -
1 stop4h 35m
Deal found 11/8![Southwest logo]()
$424
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/1212:47 pm -
1 stop6h 13m
Sat 1/165:10 pm -
1 stop5h 16m
Deal found 11/6![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/195:08 pm -
Nonstop2h 57m
Mon 11/2310:50 am -
Nonstop2h 26m
Deal found 11/6![United Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/411:26 am -
2 stops30h 20m
Sun 1/108:30 pm -
1 stop12h 47m
Deal found 11/6![Multiple Airlines logo]()
$552
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2212:50 pm -
1 stop6h 47m
Thu 3/259:30 am -
1 stop5h 43m
Deal found 11/8![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/1912:45 pm -
1 stop7h 10m
Mon 11/236:10 pm -
1 stop4h 45m
Deal found 11/6![Southwest logo]()
$449
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/25:19 pm -
1 stop5h 54m
Fri 12/41:34 pm -
2 stops9h 47m
Deal found 11/7![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/144:25 pm -
Nonstop3h 19m
Sat 1/1611:07 am -
Nonstop2h 44m
Deal found 11/6![United Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/26:00 am -
2 stops11h 16m
Fri 12/45:12 pm -
1 stop5h 40m
Deal found 11/7![Delta logo]()
$374
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/252:09 pm -
1 stop8h 06m
Tue 1/53:01 pm -
2 stops7h 58m
Deal found 11/5![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/313:19 pm -
1 stop6h 56m
Mon 1/45:45 pm -
1 stop4h 41m
Deal found 11/5![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:52 pm -
1 stop6h 21m
Mon 12/1411:35 am -
2 stops10h 51m
Deal found 11/7![Delta logo]()
$394
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/105:10 am -
2 stops12h 56m
Mon 12/142:41 pm -
2 stops7h 45m
Deal found 11/7![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/313:19 pm -
1 stop6h 56m
Tue 1/52:40 pm -
1 stop7h 46m
Deal found 11/8![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/313:19 pm -
1 stop6h 56m
Wed 1/61:45 pm -
2 stops8h 41m
Deal found 11/8![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:00 am -
2 stops11h 39m
Fri 11/274:13 pm -
1 stop6h 18m
Deal found 11/8![Delta logo]()
$414
Last-minute flights from Maine to ChicagoDiscover last-minute flight deals from Maine to Chicago. Data last updated November 9, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Chicago. Data last updated November 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/175:08 pm -
Nonstop2h 57m
Tue 12/811:59 am -
Nonstop2h 39m
Deal found 11/5![United Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/44:47 pm -
Nonstop3h 13m
Tue 12/811:59 am -
Nonstop2h 39m
Deal found 11/7![United Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/44:02 pm -
1 stop6h 22m
Sun 12/68:30 am -
Nonstop2h 32m
Deal found 11/7![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/43:25 pm -
1 stop7h 05m
Mon 12/76:00 am -
1 stop5h 10m
Deal found 11/8![Southwest logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates ” 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.
Mon 12/712:44 pm -
Nonstop3h 16m
Thu 12/108:30 am -
Nonstop2h 32m
Deal found 11/4![American Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/107:00 am -
1 stop5h 47m
Sun 12/135:29 pm -
1 stop4h 55m
Deal found 11/4![United Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/134:53 pm -
2 stops8h 03m
Tue 12/159:59 am -
2 stops12h 34m
Deal found 11/5![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/207:08 pm -
1 stop5h 53m
Tue 1/511:00 am -
Nonstop2h 44m
Deal found 11/5![United Airlines logo]()
$361
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/2512:59 pm -
1 stop5h 45m
Sat 1/99:56 am -
2 stops10h 14m
Deal found 11/5![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/254:28 pm -
Nonstop3h 12m
Tue 1/511:00 am -
Nonstop2h 44m
Deal found 11/5![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/256:00 am -
1 stop6h 13m
Mon 1/410:05 am -
1 stop5h 29m
Deal found 11/8![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/304:32 pm -
1 stop8h 00m
Tue 1/56:45 am -
1 stop4h 43m
Deal found 11/8![American Airlines logo]()
$361
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 November 9, 2026.
Search for one-way flight options from Maine to Chicago. Find affordable one-way fares based on user searches. Data last updated November 9, 2026.
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/195:00 am -
1 stop6h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![American Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 1/115:00 pm -
3 stops32h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Multiple Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:17 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$160
This Delta deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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 12/176:12 am -
1 stop7h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/1712:49 pm -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/111:40 am -
2 stops7h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 11/1810:07 am -
2 stops30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Multiple Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/223:06 pm -
1 stop7h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![American Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/226:27 am -
1 stop5h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$205
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/2211:10 am -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 1/155:00 pm -
3 stops32h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/2212:35 pm -
Nonstop3h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![American Airlines logo]()
$215
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 November 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $349 (United Airlines) |
One-way from | $155 (American Airlines) |
Popular in | July |
Cheapest in | May |
Average price | $420 |
Good round-trip deal | $420 or less |
Good one-way deal | $220 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 November 9, 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
Tue 1/19
6:17 am-3:53 pm
2 stops10h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$160
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sun 1/10
3:10 pm-9:52 pm
1 stop7h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Sun 12/20
5:35 am-11:19 am
1 stop6h 44m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Fri 12/25
6:00 am-11:13 am
1 stop6h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 12/3
12:49 pm-6:01 pm
1 stop6h 12m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Thu 12/17
12:49 pm-6:01 pm
1 stop6h 12m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Sun 12/6
6:00 am-12:04 pm
1 stop7h 04m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - MDW Chicago Midway
PWMMDW
Portland
Fri 12/25
12:59 pm-5:44 pm
1 stop5h 45m
Chicago Midway
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$185
PortlandChicago
PWM Portland - ORD Chicago O'Hare Intl
PWMORD
Portland
Thu 12/17
6:00 am-4:43 pm
2 stops11h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$190
BangorChicago
BGR Bangor - ORD Chicago O'Hare Intl
BGRORD
Bangor
Wed 11/18
10:07 am-3:37 pm
2 stops30h 30m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$204
Showing 1-10 of 59 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.
PWM-ORD
PWM-MDW
BGR-ORD
AUG-ORD
BGR-MDW
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
PWM-ORD
PWM-MDW
BGR-ORD
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 $339). Flying from Maine to Chicago in December is currently the most expensive (average of $453). 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 November 9, 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 30% 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 November 9, 2026.
The most flights from USME to CHI are scheduled on a Friday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 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 $373 and $500 in December.The cheapest round-trip price found within the last 5 days was $349 on United Airlines (Dec 4-Dec 8).
How far ahead should I book a flight from Maine to Chicago?
The best time to book flights from Maine to Chicago is 82 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 November 7, 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
Merrillville
Lansing
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 November 9, 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 November 9, 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 November 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$385 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$238 | Average$440 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$267 | Average$403 | FlexibilityNo cancel fee | On-time63% |