$156+ Cheap flights from Chicago (CHI) to Maine
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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Oct 26 — Nov 21
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Maine 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 Chicago to MaineExplore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
Explore the most affordable flight options available from Chicago to Maine. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2026.
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:36 pm -
Nonstop2h 44m
Sat 10/316:37 am -
Nonstop3h 17m
Deal found 9/22![American Airlines logo]()
$311
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:13 pm -
Nonstop2h 54m
Sat 10/2412:57 pm -
1 stop8h 05m
Deal found 9/22![American Airlines logo]()
$335
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.
Wed 10/287:00 am -
2 stops8h 22m
Sat 10/314:10 pm -
1 stop6h 33m
Deal found 9/23![Delta logo]()
$336
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:45 am -
Nonstop2h 46m
Tue 10/275:45 pm -
Nonstop3h 10m
Deal found 9/22![American Airlines logo]()
$344
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:59 pm -
Nonstop2h 44m
Sat 10/315:45 pm -
Nonstop3h 10m
Deal found 9/22![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/217:13 pm -
Nonstop2h 54m
Sat 10/2412:57 pm -
1 stop8h 05m
Deal found 9/25![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.
Sat 10/1711:09 am -
2 stops8h 59m
Sat 10/242:00 pm -
1 stop6h 20m
Deal found 9/21![Delta logo]()
$350
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.
Sat 10/176:10 pm -
Nonstop2h 36m
Tue 10/207:58 am -
Nonstop3h 02m
Deal found 9/22![United Airlines logo]()
$353
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:45 am -
Nonstop2h 10m
Tue 10/276:00 pm -
Nonstop2h 35m
Deal found 9/22![Southwest logo]()
$353
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:52 pm -
1 stop6h 52m
Sat 11/712:40 pm -
Nonstop3h 10m
Deal found 9/22![American Airlines logo]()
$354
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 10/201:23 pm -
2 stops9h 02m
Sat 10/244:51 pm -
2 stops8h 06m
Deal found 9/23![Delta logo]()
$355
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.
Fri 10/165:50 pm -
1 stop5h 09m
Wed 10/215:10 pm -
1 stop7h 26m
Deal found 9/23![American Airlines logo]()
$359
Best flights from Chicago to MaineDiscover carefully curated flight deals from Chicago to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
Discover carefully curated flight deals from Chicago to Maine that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 26, 2026.
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/287:00 am -
2 stops7h 30m
Sat 10/314:10 pm -
1 stop6h 33m
Deal found 9/24![Delta logo]()
$336
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:40 pm -
Nonstop2h 15m
Tue 10/276:00 pm -
Nonstop2h 35m
Deal found 9/22![Southwest logo]()
$371
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.
Wed 10/149:38 am -
1 stop8h 27m
Mon 10/193:37 pm -
1 stop18h 10m
Deal found 9/22![Multiple Airlines logo]()
$412
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 11/79:50 pm -
2 stops11h 29m
Wed 11/1111:00 am -
1 stop6h 21m
Deal found 9/21![United Airlines logo]()
$651
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 11/111:30 pm -
2 stops8h 55m
Sat 11/143:45 pm -
2 stops9h 09m
Deal found 9/22![Delta logo]()
$342
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 11/125:30 am -
2 stops9h 50m
Mon 11/165:00 pm -
1 stop6h 18m
Deal found 9/21![Delta logo]()
$364
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:00 pm -
1 stop5h 05m
Wed 11/47:20 am -
1 stop5h 40m
Deal found 9/21![Multiple Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/217:00 am -
2 stops7h 30m
Sat 10/244:10 pm -
1 stop6h 33m
Deal found 9/25![Delta logo]()
$364
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.
Wed 10/149:38 am -
1 stop8h 27m
Tue 10/207:20 am -
1 stop12h 54m
Deal found 9/22![Multiple Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/187:50 pm -
Nonstop2h 15m
Sat 10/245:35 am -
1 stop6h 05m
Deal found 9/24![Southwest logo]()
$477
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 10/289:29 am -
1 stop5h 33m
Wed 11/412:42 pm -
1 stop6h 18m
Deal found 9/22![Delta logo]()
$373
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.
Wed 10/149:38 am -
1 stop8h 27m
Sun 10/1811:06 am -
1 stop22h 41m
Deal found 9/22![Multiple Airlines logo]()
$425
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.
Wed 9/306:50 pm -
Nonstop2h 20m
Sat 10/35:35 am -
2 stops9h 20m
Deal found 9/21![Southwest logo]()
$482
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/79:29 am -
1 stop5h 33m
Wed 11/1112:45 pm -
1 stop6h 19m
Deal found 9/25![Delta logo]()
$373
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:24 pm -
1 stop13h 17m
Mon 11/23:37 pm -
1 stop21h 23m
Deal found 9/21![Multiple Airlines logo]()
$427
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 11/116:00 am -
1 stop6h 01m
Wed 11/186:00 am -
1 stop6h 59m
Deal found 9/22![Delta logo]()
$373
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:24 pm -
1 stop14h 42m
Tue 11/34:09 pm -
1 stop20h 51m
Deal found 9/21![Multiple Airlines logo]()
$427
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:10 pm -
Nonstop2h 15m
Tue 10/206:00 pm -
Nonstop2h 35m
Deal found 9/22![Southwest logo]()
$522
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/288:29 am -
2 stops7h 18m
Sat 10/316:01 am -
1 stop7h 12m
Deal found 9/25![Delta logo]()
$378
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:24 pm -
1 stop17h 03m
Sun 11/111:06 am -
1 stop25h 54m
Deal found 9/21![Multiple Airlines logo]()
$440
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.
Tue 11/247:10 am -
1 stop4h 35m
Mon 11/305:20 pm -
1 stop6h 55m
Deal found 9/21![Southwest logo]()
$546
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.
Sat 10/102:00 pm -
1 stop6h 08m
Wed 10/144:10 pm -
1 stop6h 33m
Deal found 9/22![Delta logo]()
$384
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/261:00 pm -
1 stop21h 06m
Mon 11/212:01 pm -
1 stop24h 59m
Deal found 9/21![Multiple Airlines logo]()
$457
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/62:10 pm -
2 stops7h 30m
Fri 10/96:30 am -
Nonstop2h 35m
Deal found 9/22![Southwest logo]()
$554
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 12/113:59 pm -
1 stop6h 53m
Mon 12/144:53 pm -
2 stops7h 59m
Deal found 9/24![Delta logo]()
$396
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.
Tue 10/138:04 pm -
1 stop14h 02m
Mon 10/194:09 pm -
1 stop28h 05m
Deal found 9/22![Multiple Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/228:29 am -
2 stops7h 18m
Mon 10/264:47 pm -
1 stop4h 43m
Deal found 9/24![Delta logo]()
$396
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.
Wed 10/148:04 pm -
1 stop14h 02m
Mon 10/194:09 pm -
1 stop28h 05m
Deal found 9/22![Multiple Airlines logo]()
$472
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 10/206:20 am -
2 stops8h 42m
Fri 10/2311:55 am -
1 stop8h 43m
Deal found 9/23![Delta logo]()
$396
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.
Mon 11/26:59 am -
1 stop5h 19m
Tue 11/103:08 pm -
1 stop21h 07m
Deal found 9/21![Multiple Airlines logo]()
$489
Last-minute flights from Chicago to MaineDiscover last-minute flight deals from Chicago to Maine. Data last updated September 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maine. Data last updated September 26, 2026 and is based on user searches.
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.
Fri 10/165:50 pm -
1 stop5h 09m
Wed 10/215:10 pm -
1 stop7h 26m
Deal found 9/23![American Airlines logo]()
$359
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:13 pm -
Nonstop2h 54m
Sat 10/2412:57 pm -
1 stop8h 05m
Deal found 9/22![American Airlines logo]()
$335
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:59 pm -
Nonstop2h 44m
Sat 10/315:45 pm -
Nonstop3h 10m
Deal found 9/22![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.
Sat 10/1711:09 am -
2 stops8h 59m
Sat 10/242:00 pm -
1 stop6h 20m
Deal found 9/21![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/176:10 pm -
Nonstop2h 36m
Tue 10/206:00 am -
Nonstop2h 57m
Deal found 9/25![United Airlines logo]()
$353
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:45 am -
Nonstop2h 10m
Tue 10/276:00 pm -
Nonstop2h 35m
Deal found 9/22![Southwest logo]()
$353
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 10/201:23 pm -
2 stops9h 02m
Sat 10/244:51 pm -
2 stops8h 06m
Deal found 9/23![Delta logo]()
$355
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/217:13 pm -
Nonstop2h 54m
Sat 10/2412:57 pm -
1 stop8h 05m
Deal found 9/25![American Airlines logo]()
$349
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:45 am -
Nonstop2h 46m
Tue 10/275:45 pm -
Nonstop3h 10m
Deal found 9/22![American Airlines logo]()
$344
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/242:52 pm -
1 stop6h 52m
Sat 11/712:40 pm -
Nonstop3h 10m
Deal found 9/22![American Airlines logo]()
$354
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:36 pm -
Nonstop2h 44m
Sat 10/316:37 am -
Nonstop3h 17m
Deal found 9/22![American Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/285:27 am -
2 stops9h 55m
Sat 10/314:10 pm -
1 stop6h 33m
Deal found 9/25![Delta logo]()
$336
One-way flights from Chicago to MaineSearch for one-way flight options from Chicago to Maine. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
Search for one-way flight options from Chicago to Maine. Find affordable one-way fares based on user searches. Data last updated September 26, 2026.
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 10/208:04 am -
2 stops32h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$156
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 11/255:58 pm -
1 stop5h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![American Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 11/68:00 am -
2 stops32h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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 10/206:00 am -
2 stops26h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/277:15 am -
2 stops25h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$174
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.
Mon 10/267:44 pm -
2 stops36h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$175
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:25 am -
Nonstop2h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![American Airlines logo]()
$177
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.
Mon 10/196:40 pm -
Nonstop2h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” 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 10/277:15 am -
3 stops33h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Multiple Airlines logo]()
$178
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.
Sat 10/246:00 am -
2 stops34h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$178
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.
Wed 11/256:18 pm -
Nonstop2h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” 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.
Thu 11/510:26 am -
2 stops26h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/24![Multiple Airlines logo]()
$181
Find flight deals from Chicago to Maine
Keep the following information in mind while searching for Chicago to Maine flight deals. Data was last updated September 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $311 (American Airlines) |
One-way from | $156 (Kiwi.com) |
Popular in | November |
Cheapest in | May |
Average price | $348 |
Good round-trip deal | $369 or less |
Good one-way deal | $198 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Maine 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 26, 2026.
Use the filters below to find and compare flights from Chicago to Maine that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 10/29
10:50 am-2:16 pm
Nonstop2h 26m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
Quickest round-trip
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Thu 10/29
6:40 pm-9:55 pm
Nonstop2h 15m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 10/21
7:00 am-11:57 am
1 stop3h 57m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Thu 10/29
6:00 am-1:12 pm
1 stop6h 12m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 10/28
5:55 am-1:26 pm
1 stop6h 31m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Tue 11/10
5:50 pm-11:21 pm
1 stop4h 31m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 10/24
8:29 am-4:02 pm
1 stop6h 33m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Mon 11/23
9:30 am-4:10 pm
1 stop5h 40m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Wed 11/18
6:00 am-1:01 pm
1 stop6h 01m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Mon 10/26
6:04 am-1:02 pm
1 stop5h 58m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Maine
Have a flexible travel schedule? Discover the best time to fly to Maine from Chicago with our price prediction graph.
ORD-BGR
MDW-PWM
ORD-AUG
ORD-RKD
ORD-PWM
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 Chicago to Maine
CHI-USME
ORD-BGR
MDW-PWM
ORD-AUG
ORD-RKD
What is the cheapest month to book a flight from Chicago to Maine?
Currently, April is the cheapest month in which you can book a flight from Chicago to Maine (average of $334). Flying from Chicago to Maine in December is currently the most expensive (average of $463). 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 CHI to ME?
Find hourly flight availability from Chicago to Maine. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 26, 2026.
When flying from Chicago to Maine, 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 28% versus a flight in the morning.
Weekly flight availability from Chicago to Maine
Explore weekly flight availability from Chicago to Maine. 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 26, 2026.
The most flights from CHI to USME are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (10 on average).
How much does it cost to fly round-trip from Chicago to Maine?
Airfare is typical for this route at the moment.
Chicago to Maine flights typically cost between $343 and $498 in October.The cheapest round-trip price found within the last 5 days was $344 on American Airlines (Oct 24-Oct 27).
How far ahead should I book a flight from Chicago to Maine?
The price you pay for your flight from Chicago to Maine may vary depending on when you book. For the best chance of a lower fare, look to book 55 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Maine?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Maine. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Chicago to Maine flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Maine
Get insights into the airlines that provide service to Maine. 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 Maine. Reviews last updated September 26, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Maine by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
10.0
ExcellentEdward,Sep 2026
MCO - BWI
Related info for your journey
Find useful and relevant information for your journey from Chicago to Maine. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Maine
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Maine by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Maine by cabin class
Find flights from Chicago to Maine, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Maine flights
Browse other Chicago and Maine flight options. Last updated on September 26, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Maine flights
Consider these flights traveling from Chicago to Maine.
Top 2 airlines flying from Chicago to Maine
Discover the top 2 airlines that operate flights from Chicago to Maine. 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 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$382 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$406 | FlexibilityNo cancel fee | On-time69% |