$92+ Cheap flights from Chicago (CHI) to Maine
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PWM
Sep 11 — Sep 181
Round-trip
1 adult, Economy
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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 August 12, 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 August 12, 2026.
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:45 am -
Nonstop2h 15m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/10![Southwest logo]()
$166
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Thu 9/38:45 pm -
Nonstop2h 36m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/11![Multiple Airlines logo]()
$171
This Jetabroad deal was found by Cheapflights users on 8/10. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:24 pm -
Nonstop2h 34m
Tue 10/136:55 am -
Nonstop2h 51m
Deal found 8/10![JetBlue logo]()
$174
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/111:30 am -
1 stop7h 11m
Wed 9/24:16 pm -
Nonstop3h 04m
Deal found 8/11![Delta logo]()
$175
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/315:45 am -
Nonstop2h 15m
Wed 9/28:30 am -
1 stop6h 00m
Deal found 8/11![Southwest logo]()
$175
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$176
This Frontier deal was found by Cheapflights users on 8/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Thu 9/1011:17 am -
1 stop12h 42m
Deal found 8/9![Frontier logo]()
$177
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/18:50 am -
2 stops7h 15m
Wed 9/27:15 pm -
Nonstop2h 35m
Deal found 8/11![Southwest logo]()
$180
This Vliegwinkel deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 pm -
Nonstop2h 36m
Mon 9/75:01 am -
1 stop4h 50m
Deal found 8/11![JetBlue logo]()
$181
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$182
This Super.com deal was found by Cheapflights users on 8/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:24 pm -
Nonstop2h 45m
Sat 9/265:00 pm -
Nonstop3h 01m
Deal found 8/10![JetBlue logo]()
$184
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/115:45 am -
Nonstop2h 15m
Tue 9/157:15 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$184
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 August 12, 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 August 12, 2026.
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/177:35 am -
Nonstop2h 33m
Tue 9/222:00 pm -
1 stop7h 31m
Deal found 8/11![Delta logo]()
$175
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/116:00 am -
1 stop4h 17m
Wed 9/167:05 am -
Nonstop2h 58m
Deal found 8/11![United Airlines logo]()
$197
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:10 pm -
Nonstop2h 25m
Tue 9/222:45 pm -
1 stop7h 05m
Deal found 8/10![Southwest logo]()
$206
This JetBlue deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:24 pm -
Nonstop2h 45m
Mon 10/56:19 am -
1 stop8h 28m
Deal found 8/11![JetBlue logo]()
$213
This American Airlines deal was found by Cheapflights users on 8/6. 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.
Tue 10/138:40 am -
1 stop6h 18m
Sat 10/174:54 pm -
1 stop7h 50m
Deal found 8/6![American Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:59 pm -
Nonstop2h 35m
Mon 9/78:35 pm -
1 stop4h 53m
Deal found 8/10![United Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/149:10 am -
Nonstop2h 20m
Sat 10/177:40 am -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 8/8. 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.
Wed 8/267:30 pm -
Nonstop2h 30m
Sun 9/612:25 pm -
Nonstop2h 54m
Deal found 8/8![Delta logo]()
$250
This JetBlue deal was found by Cheapflights users on 8/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:20 pm -
Nonstop2h 31m
Sun 9/68:10 am -
Nonstop2h 56m
Deal found 8/8![JetBlue logo]()
$250
This Expedia deal was found by Cheapflights users on 8/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:38 am -
1 stop10h 02m
Wed 9/167:14 am -
2 stops16h 54m
Deal found 8/10![Multiple Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 10/176:10 am -
Nonstop2h 24m
Sat 10/245:45 am -
1 stop4h 52m
Deal found 8/7![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:40 am -
Nonstop2h 15m
Sat 9/267:05 am -
Nonstop2h 35m
Deal found 8/10![Southwest logo]()
$247
This JetBlue deal was found by Cheapflights users on 8/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:38 am -
Nonstop2h 28m
Sun 10/255:35 am -
1 stop9h 04m
Deal found 8/8![JetBlue logo]()
$258
This Southwest deal was found by Cheapflights users on 8/8. 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.
Wed 10/214:45 pm -
1 stop4h 55m
Sat 10/243:10 pm -
2 stops7h 30m
Deal found 8/8![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 8/7. 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 9/259:24 pm -
Nonstop2h 30m
Sun 10/47:01 am -
Nonstop2h 59m
Deal found 8/7![United Airlines logo]()
$255
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Tue 9/16:24 pm -
Nonstop2h 35m
Fri 9/410:38 am -
Nonstop2h 51m
Deal found 8/7![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/6. 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 10/68:36 am -
1 stop7h 11m
Tue 10/131:52 pm -
1 stop5h 28m
Deal found 8/6![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/115:45 am -
Nonstop2h 15m
Sun 9/135:30 am -
1 stop5h 25m
Deal found 8/11![Southwest logo]()
$259
This United Airlines deal was found by Cheapflights users on 8/8. 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.
Thu 10/16:10 am -
Nonstop2h 23m
Fri 10/26:43 pm -
Nonstop2h 57m
Deal found 8/8![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/6. 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 10/63:40 pm -
1 stop6h 55m
Mon 10/124:47 pm -
1 stop4h 43m
Deal found 8/6![Delta logo]()
$309
This Southwest deal was found by Cheapflights users on 8/9. 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.
Tue 9/81:00 pm -
2 stops8h 15m
Sat 9/125:50 am -
2 stops8h 15m
Deal found 8/9![Southwest logo]()
$261
This United Airlines deal was found by Cheapflights users on 8/7. 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 9/213:35 pm -
Nonstop2h 44m
Thu 9/248:31 pm -
Nonstop2h 58m
Deal found 8/7![United Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/6. 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 10/78:29 am -
2 stops7h 18m
Mon 10/124:47 pm -
1 stop4h 43m
Deal found 8/6![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/7. 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.
Tue 9/12:00 pm -
2 stops7h 10m
Fri 9/46:40 pm -
Nonstop2h 45m
Deal found 8/7![Southwest logo]()
$270
This Delta deal was found by Cheapflights users on 8/7. 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.
Tue 9/297:05 am -
2 stops8h 44m
Tue 10/61:52 pm -
1 stop6h 28m
Deal found 8/7![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 8/8. 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 10/3012:45 pm -
Nonstop2h 20m
Mon 11/24:20 pm -
Nonstop2h 45m
Deal found 8/8![Southwest logo]()
$270
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sat 11/710:50 am -
Nonstop2h 26m
Mon 11/95:08 pm -
Nonstop2h 57m
Deal found 8/7![United Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 8/7. 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 1/286:00 am -
2 stops9h 59m
Mon 2/112:50 pm -
2 stops10h 20m
Deal found 8/7![Delta logo]()
$319
This Priceline deal was found by Cheapflights users on 8/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:01 am -
1 stop6h 27m
Tue 9/811:21 am -
1 stop9h 04m
Deal found 8/7![Multiple Airlines logo]()
$522
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/35:45 am -
Nonstop2h 15m
Wed 9/98:15 am -
2 stops6h 15m
Deal found 8/11![Southwest logo]()
$270
Last-minute flights from Chicago to MaineDiscover last-minute flight deals from Chicago to Maine. Data last updated August 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Maine. Data last updated August 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/313:19 pm -
Nonstop2h 40m
Wed 9/21:00 pm -
1 stop7h 12m
Deal found 8/11![Delta logo]()
$175
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 8/315:45 am -
Nonstop2h 15m
Wed 9/28:30 am -
1 stop6h 00m
Deal found 8/11![Southwest logo]()
$175
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/18:50 am -
2 stops7h 15m
Wed 9/27:15 pm -
Nonstop2h 35m
Deal found 8/11![Southwest logo]()
$180
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$176
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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.
Thu 9/38:45 pm -
Nonstop2h 36m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/11![Multiple Airlines logo]()
$171
This Vliegwinkel deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:45 pm -
Nonstop2h 36m
Mon 9/75:01 am -
1 stop4h 50m
Deal found 8/11![JetBlue logo]()
$181
This Frontier deal was found by Cheapflights users on 8/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Thu 9/1011:17 am -
1 stop12h 42m
Deal found 8/9![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 8/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Sun 9/612:45 pm -
1 stop8h 19m
Deal found 8/7![Frontier logo]()
$182
This Southwest deal was found by Cheapflights users on 8/9. 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.
Thu 9/105:45 am -
Nonstop2h 15m
Mon 9/146:40 pm -
Nonstop2h 45m
Deal found 8/9![Southwest logo]()
$166
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/107:55 pm -
1 stop11h 05m
Thu 9/178:20 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/115:45 am -
Nonstop2h 15m
Tue 9/157:15 pm -
Nonstop2h 40m
Deal found 8/11![Southwest logo]()
$184
This Super.com deal was found by Cheapflights users on 8/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/188:24 pm -
Nonstop2h 45m
Sat 9/265:00 pm -
Nonstop3h 01m
Deal found 8/10![JetBlue logo]()
$184
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 August 12, 2026.
Search for one-way flight options from Chicago to Maine. Find affordable one-way fares based on user searches. Data last updated August 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 10/27:11 am -
1 stop25h 18m
Deal found 8/11![Multiple Airlines logo]()
$92
This Super.com deal was found by Cheapflights users on 8/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/10![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 8/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3110:30 am -
1 stop6h 20m
Deal found 8/10![Southwest logo]()
$93
This Frontier deal was found by Cheapflights users on 8/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/139:33 pm -
1 stop12h 19m
Deal found 8/10![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/199:33 pm -
1 stop12h 19m
Deal found 8/6![Frontier logo]()
$95
This Trip.com deal was found by Cheapflights users on 8/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:50 pm -
1 stop17h 32m
Deal found 8/10![Frontier logo]()
$97
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/12:00 pm -
2 stops7h 10m
Deal found 8/11![Southwest logo]()
$98
This United Airlines deal was found by Cheapflights users on 8/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:50 pm -
Nonstop2h 33m
Deal found 8/10![United Airlines logo]()
$101
This Super.com deal was found by Cheapflights users on 8/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/184:49 pm -
1 stop14h 31m
Deal found 8/7![Frontier logo]()
$101
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” 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 9/115:45 am -
Nonstop2h 15m
Deal found 8/11![Southwest logo]()
$101
This Super.com deal was found by Cheapflights users on 8/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:05 am -
1 stop6h 22m
Deal found 8/7![JetBlue logo]()
$102
This Southwest deal was found by Cheapflights users on 8/9. 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.
Sat 10/244:10 pm -
Nonstop2h 10m
Deal found 8/9![Southwest logo]()
$102
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 August 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Southwest) |
One-way from | $92 (Kiwi.com) |
Popular in | July |
Cheapest in | May |
Average price | $377 |
Good round-trip deal | $323 or less |
Good one-way deal | $177 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 2,558,603 searches. Data last updated August 12, 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
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 9/17
7:35 am-11:08 am
Nonstop2h 33m
Boston Logan Intl
Tue 9/22
2:00 pm-8:31 pm
1 stop7h 31m
$175
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Fri 9/11
6:00 am-11:17 am
1 stop4h 17m
Boston Logan Intl
Wed 9/16
7:05 am-9:03 am
Nonstop2h 58m
$197
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Sat 9/19
3:10 pm-6:35 pm
Nonstop2h 25m
Boston Logan Intl
Tue 9/22
2:45 pm-8:50 pm
1 stop7h 05m
$206
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 9/5
7:59 pm-11:34 pm
Nonstop2h 35m
Boston Logan Intl
Mon 9/7
8:35 pm-12:28 am
1 stop4h 53m
$212
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Thu 10/1
8:24 pm-12:09 am
Nonstop2h 45m
Boston Logan Intl
Mon 10/5
6:19 am-1:47 pm
1 stop8h 28m
$213
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 10/14
9:10 am-12:30 pm
Nonstop2h 20m
Boston Logan Intl
Sat 10/17
7:40 am-9:15 am
Nonstop2h 35m
$227
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Sat 10/17
6:10 am-9:34 am
Nonstop2h 24m
Boston Logan Intl
Sat 10/24
5:45 am-9:37 am
1 stop4h 52m
$237
Quickest round-trip
ChicagoBoston
MDW Chicago Midway - BOS Boston Logan Intl
MDWBOS
Chicago Midway
Wed 9/23
6:40 am-9:55 am
Nonstop2h 15m
Boston Logan Intl
Sat 9/26
7:05 am-8:40 am
Nonstop2h 35m
$247
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Wed 8/26
7:30 pm-11:00 pm
Nonstop2h 30m
Boston Logan Intl
Sun 9/6
12:25 pm-2:19 pm
Nonstop2h 54m
$250
ChicagoBoston
ORD Chicago O'Hare Intl - BOS Boston Logan Intl
ORDBOS
Chicago O'Hare Intl
Mon 8/24
8:20 pm-11:51 pm
Nonstop2h 31m
Boston Logan Intl
Sun 9/6
8:10 am-10:06 am
Nonstop2h 56m
$250
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-BOS
MDW-BOS
ORD-BGR
ORD-AUG
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-BOS
MDW-BOS
ORD-BGR
ORD-AUG
What is the cheapest month to book a flight from Chicago to Maine?
Currently, March is the cheapest month in which you can book a flight from Chicago to Maine (average of $317). Flying from Chicago to Maine in December is currently the most expensive (average of $438). 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 August 12, 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 afternoon, which can drop the price by up to 16% versus a flight at noon.
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 August 12, 2026.
The most flights from CHI to USME are scheduled on a Monday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 $308 and $491 in September.The cheapest round-trip price found within the last 5 days was $279 on Delta (Sep 22-Sep 30).
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 46 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. Sunday mornings 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 August 12, 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.
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Comfort
8.0
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 August 12, 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 2,558,603 searches. Data last updated August 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$229 | Average$383 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$230 | Average$391 | FlexibilityNo cancel fee | On-time69% |