$160+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Dec 10 — Dec 171
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 November 10, 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 November 10, 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.
Mon 12/78:26 am -
Nonstop2h 32m
Tue 1/511:22 am -
1 stop6h 06m
Deal found 11/4![American Airlines logo]()
$309
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 12/115:50 pm -
Nonstop2h 39m
Sat 12/124:47 pm -
Nonstop3h 13m
Deal found 11/5![United Airlines logo]()
$320
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 12/72:41 pm -
2 stops7h 39m
Tue 1/55:14 pm -
1 stop5h 00m
Deal found 11/4![Delta logo]()
$324
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.
Thu 12/32:30 pm -
1 stop5h 12m
Mon 12/79:12 am -
1 stop7h 17m
Deal found 11/5![United Airlines logo]()
$344
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 12/45:50 pm -
Nonstop2h 39m
Fri 12/114:47 pm -
Nonstop3h 13m
Deal found 11/6![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.
Mon 11/238:29 am -
1 stop6h 41m
Sat 12/52:00 pm -
1 stop6h 25m
Deal found 11/5![Delta logo]()
$364
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:50 pm -
1 stop5h 09m
Fri 1/16:00 am -
1 stop7h 01m
Deal found 11/5![American Airlines logo]()
$369
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.
Fri 12/45:12 pm -
1 stop5h 40m
Sat 12/512:49 pm -
1 stop6h 12m
Deal found 11/9![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/87:49 am -
1 stop7h 05m
Tue 12/156:18 pm -
1 stop5h 42m
Deal found 11/10![American Airlines logo]()
$375
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:50 pm -
1 stop5h 06m
Fri 12/412:44 pm -
Nonstop3h 16m
Deal found 11/5![American Airlines logo]()
$379
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.
Fri 12/41:34 pm -
2 stops9h 47m
Fri 12/116:00 am -
2 stops11h 17m
Deal found 11/6![Delta logo]()
$380
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/85:30 am -
2 stops8h 35m
Tue 12/1512:06 pm -
1 stop7h 17m
Deal found 11/10![Delta logo]()
$380
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 November 10, 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 November 10, 2026.
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 5/410:35 am -
Nonstop2h 17m
Wed 5/124:48 pm -
Nonstop2h 57m
Deal found 11/5![United Airlines logo]()
$349
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.
Fri 12/46:03 pm -
1 stop5h 18m
Sat 12/54:00 pm -
2 stops8h 56m
Deal found 11/9![Delta logo]()
$374
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.
Tue 5/46:20 am -
1 stop5h 10m
Wed 5/125:20 am -
1 stop8h 15m
Deal found 11/5![Southwest logo]()
$374
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/66:54 pm -
Nonstop2h 48m
Sun 5/97:02 am -
Nonstop3h 17m
Deal found 11/9![American Airlines logo]()
$389
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:30 pm -
1 stop24h 35m
Sun 11/293:37 pm -
1 stop19h 22m
Deal found 11/6![Multiple Airlines logo]()
$613
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 2/2510:50 am -
2 stops11h 29m
Sun 2/286:00 am -
2 stops8h 01m
Deal found 11/7![Delta logo]()
$380
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/46:10 pm -
1 stop4h 45m
Mon 1/113:25 pm -
1 stop6h 25m
Deal found 11/7![Southwest logo]()
$384
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/65:00 am -
1 stop5h 23m
Sun 5/96:30 am -
1 stop5h 17m
Deal found 11/9![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/85:30 am -
2 stops8h 35m
Tue 12/1512:06 pm -
1 stop7h 17m
Deal found 11/10![Delta logo]()
$380
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.
Mon 12/146:03 pm -
1 stop5h 18m
Thu 12/1711:40 am -
1 stop7h 43m
Deal found 11/9![Delta logo]()
$389
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.
Thu 5/69:55 am -
1 stop5h 25m
Sun 5/95:30 am -
2 stops9h 50m
Deal found 11/5![Southwest logo]()
$434
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.
Mon 11/234:40 pm -
1 stop5h 41m
Mon 11/307:35 pm -
1 stop5h 27m
Deal found 11/7![United Airlines logo]()
$453
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 2/119:00 am -
1 stop4h 24m
Mon 2/155:08 am -
1 stop7h 11m
Deal found 11/7![Delta logo]()
$389
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.
Sat 3/206:59 pm -
Nonstop2h 39m
Sat 3/275:45 am -
Nonstop3h 14m
Deal found 11/5![United Airlines logo]()
$468
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.
Mon 12/711:39 am -
2 stops10h 47m
Mon 12/1412:06 pm -
1 stop8h 19m
Deal found 11/9![Delta logo]()
$394
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.
Fri 12/41:15 pm -
2 stops7h 35m
Fri 12/115:10 pm -
2 stops6h 35m
Deal found 11/6![Southwest logo]()
$479
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:29 pm -
1 stop6h 55m
Sat 12/59:38 am -
1 stop5h 50m
Deal found 11/9![United Airlines logo]()
$469
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/126:30 am -
1 stop5h 10m
Mon 2/158:40 am -
2 stops12h 35m
Deal found 11/9![Southwest logo]()
$504
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 3/56:05 am -
1 stop7h 19m
Sat 3/132:00 pm -
2 stops7h 37m
Deal found 11/5![Delta logo]()
$426
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:10 pm -
1 stop4h 45m
Sun 1/35:20 pm -
2 stops7h 20m
Deal found 11/7![Southwest logo]()
$520
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:05 am -
1 stop4h 25m
Fri 11/275:10 pm -
2 stops6h 35m
Deal found 11/9![Southwest logo]()
$536
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.
Thu 5/61:15 pm -
2 stops9h 08m
Sun 5/96:00 am -
1 stop8h 12m
Deal found 11/9![Delta logo]()
$499
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 11/276:18 pm -
Nonstop2h 34m
Sun 11/295:08 pm -
Nonstop2h 55m
Deal found 11/5![United Airlines logo]()
$622
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.
Sat 12/263:40 pm -
1 stop7h 30m
Fri 1/15:15 am -
1 stop4h 45m
Deal found 11/5![Southwest logo]()
$563
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.
Wed 12/165:12 pm -
1 stop5h 21m
Tue 12/294:38 pm -
1 stop17h 11m
Deal found 11/6![Delta logo]()
$513
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.
Sat 12/269:20 pm -
2 stops16h 18m
Fri 1/16:00 am -
1 stop6h 50m
Deal found 11/5![United Airlines logo]()
$633
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.
Sun 12/207:04 am -
1 stop6h 34m
Sat 12/268:00 am -
Nonstop3h 15m
Deal found 11/8![United Airlines logo]()
$633
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.
Sat 3/201:00 pm -
2 stops9h 23m
Sat 3/2711:25 am -
2 stops8h 12m
Deal found 11/8![Delta logo]()
$545
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.
Sun 11/225:29 pm -
1 stop4h 52m
Sat 11/286:00 am -
1 stop6h 45m
Deal found 11/6![United Airlines logo]()
$660
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.
Mon 12/216:10 pm -
1 stop4h 49m
Tue 12/293:38 pm -
2 stops15h 11m
Deal found 11/6![United Airlines logo]()
$678
Last-minute flights from Chicago to MaineDiscover last-minute flight deals from Chicago to Maine. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maine. Data last updated November 10, 2026 and is based on user searches.
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.
Mon 11/238:29 am -
1 stop6h 41m
Sat 12/52:00 pm -
1 stop6h 25m
Deal found 11/5![Delta logo]()
$364
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/254:50 pm -
1 stop5h 06m
Fri 12/412:44 pm -
Nonstop3h 16m
Deal found 11/5![American Airlines logo]()
$379
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.
Thu 12/32:30 pm -
1 stop5h 12m
Mon 12/79:12 am -
1 stop7h 17m
Deal found 11/5![United Airlines logo]()
$344
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 12/45:50 pm -
Nonstop2h 39m
Fri 12/114:47 pm -
Nonstop3h 13m
Deal found 11/6![United Airlines logo]()
$349
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.
Fri 12/45:12 pm -
1 stop5h 40m
Sat 12/512:49 pm -
1 stop6h 12m
Deal found 11/9![Delta logo]()
$369
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.
Fri 12/41:34 pm -
2 stops9h 47m
Fri 12/116:00 am -
2 stops11h 17m
Deal found 11/6![Delta logo]()
$380
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 12/78:26 am -
Nonstop2h 32m
Tue 1/511:22 am -
1 stop6h 06m
Deal found 11/4![American Airlines logo]()
$309
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 12/72:41 pm -
2 stops7h 39m
Tue 1/55:14 pm -
1 stop5h 00m
Deal found 11/4![Delta logo]()
$324
This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/87:49 am -
1 stop7h 05m
Tue 12/156:18 pm -
1 stop5h 42m
Deal found 11/10![American Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/85:30 am -
2 stops8h 35m
Tue 12/1512:06 pm -
1 stop7h 17m
Deal found 11/10![Delta logo]()
$380
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 12/115:50 pm -
Nonstop2h 39m
Sat 12/124:47 pm -
Nonstop3h 13m
Deal found 11/5![United Airlines logo]()
$320
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/244:50 pm -
1 stop5h 09m
Fri 1/16:00 am -
1 stop7h 01m
Deal found 11/5![American Airlines logo]()
$369
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 November 10, 2026.
Search for one-way flight options from Chicago to Maine. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:53 pm -
1 stop4h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$160
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.
Wed 1/1311:20 am -
2 stops10h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$165
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 12/115:50 pm -
Nonstop2h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![United Airlines logo]()
$170
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/117:25 am -
2 stops27h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$171
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:02 pm -
2 stops17h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$171
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/215:58 am -
2 stops34h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$179
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:29 pm -
2 stops33h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$181
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:35 am -
2 stops29h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$182
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.
Tue 12/16:03 pm -
1 stop5h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$185
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.
Sat 12/54:08 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Delta logo]()
$185
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/186:21 pm -
1 stop4h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$187
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:58 am -
2 stops31h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$195
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $309 (American Airlines) |
One-way from | $160 (American Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $449 |
Good round-trip deal | $389 or less |
Good one-way deal | $209 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 November 10, 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
Mon 12/7
2:39 pm-11:20 pm
1 stop7h 41m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$185
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Sat 12/5
2:35 pm-11:33 pm
1 stop7h 58m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$185
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Sun 3/21
9:30 am-4:13 pm
1 stop5h 43m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$185
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Sat 12/5
4:08 pm-11:33 pm
1 stop6h 25m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$185
ChicagoBangor
ORD Chicago O'Hare Intl - BGR Bangor
ORDBGR
Chicago O'Hare Intl
Fri 12/25
9:42 am-3:59 pm
1 stop5h 17m
Bangor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$195
ChicagoBangor
ORD Chicago O'Hare Intl - BGR Bangor
ORDBGR
Chicago O'Hare Intl
Thu 12/24
7:00 am-3:59 pm
1 stop7h 59m
Bangor
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$195
Quickest round-trip
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Fri 12/18
11:59 am-3:31 pm
Nonstop2h 32m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Mon 1/4
7:50 am-4:30 pm
2 stops7h 40m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
ChicagoPortland
MDW Chicago Midway - PWM Portland
MDWPWM
Chicago Midway
Mon 11/23
6:10 pm-11:55 pm
1 stop4h 45m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
ChicagoPortland
ORD Chicago O'Hare Intl - PWM Portland
ORDPWM
Chicago O'Hare Intl
Wed 11/25
5:30 am-1:01 pm
1 stop6h 31m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$205
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-PWM
MDW-PWM
ORD-BGR
ORD-AUG
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-PWM
MDW-PWM
ORD-BGR
ORD-AUG
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 $482). 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 November 10, 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 27% 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 November 10, 2026.
The most flights from CHI to USME are scheduled on a Monday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Chicago to Maine?
Airfare is below average for this route at the moment.
Chicago to Maine flights typically cost between $358 and $505 in December.The cheapest round-trip price found within the last 5 days was $309 on American Airlines (Dec 7-Jan 5).
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 November 10, 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
7.4
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$385 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$234 | Average$410 | FlexibilityNo cancel fee | On-time69% |