$100+ Cheap flights from Maine to Chicago (CHI)
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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — CHI
Sep 9 — Sep 161
Round-trip
1 adult, Economy
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Find cheap flights from Maine to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Maine to ChicagoExplore the most affordable flight options available from Maine to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 2026.
Explore the most affordable flight options available from Maine to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 10, 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 9/38:20 pm -
Nonstop2h 45m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$166
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 9/195:30 am -
1 stop5h 00m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/9![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 10/2111:28 am -
1 stop10h 00m
Fri 10/239:33 pm -
1 stop12h 19m
Deal found 8/7![Frontier logo]()
$176
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.
Wed 9/91:20 pm -
2 stops6h 45m
Thu 9/105:45 am -
Nonstop2h 15m
Deal found 8/9![Southwest logo]()
$181
This Super.com deal was found by Cheapflights users on 8/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/5![Frontier logo]()
$182
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.
Tue 10/62:50 pm -
1 stop7h 30m
Wed 10/74:45 pm -
1 stop4h 55m
Deal found 8/10![Southwest logo]()
$185
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm -
1 stop8h 23m
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/7![Frontier logo]()
$186
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.
Fri 9/46:40 pm -
Nonstop2h 45m
Thu 9/105:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$188
This Trip.com deal was found by Cheapflights users on 8/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:54 pm -
1 stop6h 29m
Sat 9/263:50 pm -
1 stop18h 08m
Deal found 8/5![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 8/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:15 am -
1 stop15h 40m
Tue 10/209:33 pm -
1 stop12h 19m
Deal found 8/5![Frontier logo]()
$192
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:15 am -
1 stop15h 40m
Mon 10/199:33 pm -
1 stop12h 19m
Deal found 8/9![Frontier logo]()
$196
This CheapOair deal was found by Cheapflights users on 8/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm -
1 stop8h 23m
Sat 9/128:24 pm -
Nonstop2h 45m
Deal found 8/5![Multiple Airlines logo]()
$197
Best flights from Maine to ChicagoDiscover carefully curated flight deals from Maine to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
Discover carefully curated flight deals from Maine to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 10, 2026.
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:30 am -
Nonstop2h 35m
Wed 9/96:40 am -
Nonstop2h 15m
Deal found 8/6![Southwest logo]()
$231
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:45 pm -
1 stop9h 23m
Wed 9/238:24 pm -
Nonstop2h 45m
Deal found 8/6![JetBlue logo]()
$234
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 pm -
Nonstop2h 59m
Sun 9/137:35 am -
Nonstop2h 33m
Deal found 8/9![Delta logo]()
$241
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:31 pm -
Nonstop2h 59m
Sun 9/66:24 pm -
Nonstop2h 35m
Deal found 8/9![United Airlines logo]()
$250
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1010:19 am -
1 stop24h 21m
Mon 10/1210:39 am -
1 stop22h 30m
Deal found 8/8![Multiple Airlines logo]()
$339
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:00 pm -
Nonstop3h 01m
Sat 9/263:00 pm -
1 stop7h 39m
Deal found 8/6![JetBlue logo]()
$234
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:05 am -
Nonstop2h 59m
Fri 9/119:40 pm -
Nonstop2h 30m
Deal found 8/9![United Airlines logo]()
$250
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.
Sat 9/125:30 am -
1 stop5h 00m
Sun 9/136:00 am -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$251
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/56:00 am -
2 stops11h 51m
Sun 9/65:30 am -
2 stops9h 31m
Deal found 8/5![Delta logo]()
$265
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.
Wed 8/267:30 am -
Nonstop2h 35m
Wed 8/2612:50 pm -
Nonstop2h 20m
Deal found 8/7![Southwest logo]()
$255
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.
Fri 9/43:30 pm -
Nonstop2h 52m
Thu 9/1012:52 pm -
Nonstop2h 35m
Deal found 8/10![United Airlines logo]()
$255
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/241:40 pm -
Nonstop3h 00m
Wed 12/25:46 pm -
Nonstop2h 28m
Deal found 8/9![JetBlue logo]()
$255
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:30 am -
Nonstop2h 35m
Tue 8/256:40 am -
Nonstop2h 15m
Deal found 8/6![Southwest logo]()
$255
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/182:45 pm -
1 stop9h 23m
Mon 9/218:24 pm -
Nonstop2h 45m
Deal found 8/9![JetBlue logo]()
$258
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 12/267:50 pm -
Nonstop2h 54m
Thu 12/3112:20 pm -
Nonstop2h 31m
Deal found 8/5![Delta logo]()
$292
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:05 am -
Nonstop2h 59m
Sat 8/299:40 pm -
Nonstop2h 31m
Deal found 8/9![United Airlines logo]()
$286
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 9/17:30 am -
Nonstop2h 35m
Tue 9/86:00 pm -
Nonstop2h 25m
Deal found 8/9![Southwest logo]()
$261
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:01 am -
1 stop4h 50m
Thu 9/103:00 pm -
1 stop7h 39m
Deal found 8/5![JetBlue logo]()
$265
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:12 pm -
1 stop21h 04m
Sat 10/249:33 pm -
2 stops20h 07m
Deal found 8/10![Multiple Airlines logo]()
$365
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 9/15:20 am -
2 stops12h 31m
Tue 9/152:29 pm -
1 stop7h 51m
Deal found 8/7![Delta logo]()
$310
This Southwest deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:40 am -
Nonstop2h 30m
Mon 9/146:10 pm -
Nonstop2h 25m
Deal found 8/5![Southwest logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 9/96:53 pm -
1 stop6h 35m
Mon 9/2111:00 am -
Nonstop2h 34m
Deal found 8/5![United Airlines logo]()
$299
This Delta deal was found by Cheapflights users on 8/5. 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 9/91:59 pm -
1 stop7h 32m
Wed 9/1611:17 am -
2 stops11h 11m
Deal found 8/5![Delta logo]()
$314
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:50 pm -
1 stop5h 10m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/6![Southwest logo]()
$265
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:20 pm -
Nonstop3h 06m
Sun 9/68:20 pm -
Nonstop2h 56m
Deal found 8/7![JetBlue logo]()
$311
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 10/224:47 pm -
2 stops8h 05m
Sat 10/246:10 am -
1 stop6h 41m
Deal found 8/7![Delta logo]()
$314
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:50 am -
1 stop6h 00m
Thu 9/35:45 am -
Nonstop2h 15m
Deal found 8/7![Southwest logo]()
$265
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am -
Nonstop2h 57m
Tue 9/2212:16 pm -
1 stop5h 13m
Deal found 8/9![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:28 am -
2 stops10h 51m
Mon 11/26:04 am -
1 stop5h 58m
Deal found 8/5![Delta logo]()
$314
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
2 stops17h 44m
Sat 10/249:38 am -
1 stop8h 12m
Deal found 8/7![Multiple Airlines logo]()
$474
Last-minute flights from Maine to ChicagoDiscover last-minute flight deals from Maine to Chicago. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Chicago. Data last updated August 10, 2026 and is based on user searches.
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.
Mon 8/319:36 am -
1 stop11h 23m
Sat 9/57:44 pm -
1 stop12h 25m
Deal found 8/9![Frontier logo]()
$176
This Super.com deal was found by Cheapflights users on 8/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:45 pm -
1 stop8h 23m
Wed 9/93:50 pm -
1 stop17h 32m
Deal found 8/5![Frontier logo]()
$182
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 9/38:20 pm -
Nonstop2h 45m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$166
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.
Fri 9/46:40 pm -
Nonstop2h 45m
Thu 9/105:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$188
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.
Fri 9/45:50 pm -
1 stop5h 10m
Mon 9/75:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$198
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm -
1 stop8h 23m
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/7![Frontier logo]()
$186
This CheapOair deal was found by Cheapflights users on 8/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:45 pm -
1 stop8h 23m
Sat 9/128:24 pm -
Nonstop2h 45m
Deal found 8/5![Multiple Airlines logo]()
$197
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.
Wed 9/91:20 pm -
2 stops6h 45m
Thu 9/105:45 am -
Nonstop2h 15m
Deal found 8/9![Southwest logo]()
$181
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:54 pm -
1 stop6h 29m
Sat 9/123:50 pm -
1 stop18h 08m
Deal found 8/6![Frontier logo]()
$196
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 9/195:30 am -
1 stop5h 00m
Mon 9/215:45 am -
Nonstop2h 15m
Deal found 8/10![Southwest logo]()
$175
This Trip.com deal was found by Cheapflights users on 8/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:54 pm -
1 stop6h 29m
Sat 9/263:50 pm -
1 stop18h 08m
Deal found 8/5![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 8/5. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2212:52 pm -
1 stop6h 31m
Sat 9/263:50 pm -
1 stop18h 08m
Deal found 8/5![Frontier logo]()
$192
One-way flights from Maine to ChicagoSearch for one-way flight options from Maine to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
Search for one-way flight options from Maine to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Frontier deal was found by Cheapflights users on 8/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:35 pm -
1 stop10h 18m
Deal found 8/5![Frontier logo]()
$100
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/111:17 am -
1 stop12h 42m
Deal found 8/7![Frontier logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 8/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am -
Nonstop2h 48m
Deal found 8/5![JetBlue logo]()
$102
This Super.com deal was found by Cheapflights users on 8/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:45 pm -
1 stop11h 02m
Deal found 8/5![Frontier logo]()
$103
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:36 am -
1 stop12h 23m
Deal found 8/9![Frontier logo]()
$103
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.
Fri 11/612:35 pm -
1 stop10h 18m
Deal found 8/9![Frontier logo]()
$104
This Delta deal was found by Cheapflights users on 8/5. 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 9/94:05 pm -
Nonstop2h 56m
Deal found 8/5![Delta logo]()
$104
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.
Fri 9/258:20 pm -
Nonstop2h 40m
Deal found 8/9![Southwest logo]()
$105
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:43 pm -
1 stop6h 15m
Deal found 8/6![JetBlue logo]()
$108
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:00 pm -
Nonstop3h 22m
Deal found 8/9![JetBlue logo]()
$112
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:45 pm -
1 stop8h 14m
Deal found 8/9![Frontier logo]()
$113
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 9/1510:05 am -
Nonstop2h 30m
Deal found 8/7![Southwest logo]()
$114
Find flight deals from Maine to Chicago
Keep the following information in mind while searching for Maine to Chicago flight deals. Data was last updated August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $166 (Southwest) |
One-way from | $100 (Frontier) |
Popular in | July |
Cheapest in | September |
Average price | $340 |
Good round-trip deal | $366 or less |
Good one-way deal | $236 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maine to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 10, 2026.
Use the filters below to find and compare flights from Maine to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Wed 9/2
7:30 am-9:05 am
Nonstop2h 35m
Chicago Midway
Wed 9/9
6:40 am-9:55 am
Nonstop2h 15m
$231
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 9/19
2:45 pm-11:08 pm
1 stop9h 23m
Chicago O'Hare Intl
Wed 9/23
8:24 pm-12:09 am
Nonstop2h 45m
$234
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 9/19
5:00 pm-7:01 pm
Nonstop3h 01m
Chicago O'Hare Intl
Sat 9/26
3:00 pm-11:39 pm
1 stop7h 39m
$234
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Sat 9/12
6:00 pm-7:59 pm
Nonstop2h 59m
Chicago O'Hare Intl
Sun 9/13
7:35 am-11:08 am
Nonstop2h 33m
$241
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 9/4
8:31 pm-10:30 pm
Nonstop2h 59m
Chicago O'Hare Intl
Sun 9/6
6:24 pm-9:59 pm
Nonstop2h 35m
$250
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 9/4
7:05 am-9:04 am
Nonstop2h 59m
Chicago O'Hare Intl
Fri 9/11
9:40 pm-1:10 am
Nonstop2h 30m
$250
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Sat 9/12
5:30 am-9:30 am
1 stop5h 00m
Chicago Midway
Sun 9/13
6:00 am-9:15 am
Nonstop2h 15m
$251
BostonChicago
BOS Boston Logan Intl - MDW Chicago Midway
BOSMDW
Boston Logan Intl
Wed 8/26
7:30 am-9:05 am
Nonstop2h 35m
Chicago Midway
Wed 8/26
12:50 pm-4:10 pm
Nonstop2h 20m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Fri 9/4
3:30 pm-5:22 pm
Nonstop2h 52m
Chicago O'Hare Intl
Thu 9/10
12:52 pm-4:27 pm
Nonstop2h 35m
$255
BostonChicago
BOS Boston Logan Intl - ORD Chicago O'Hare Intl
BOSORD
Boston Logan Intl
Tue 11/24
1:40 pm-3:40 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 12/2
5:46 pm-9:14 pm
Nonstop2h 28m
$255
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Maine to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Maine with our price prediction graph.
BOS-MDW
BOS-RFD
BOS-ORD
PWM-ORD
BGR-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Maine to Chicago
USME-CHI
BOS-MDW
BOS-RFD
BOS-ORD
PWM-ORD
What is the cheapest month to book a flight from Maine to Chicago?
Currently, September is the cheapest month in which you can book a flight from Maine to Chicago (average of $322). Flying from Maine to Chicago in December is currently the most expensive (average of $430). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ME to CHI?
Find hourly flight availability from Maine to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 10, 2026.
When flying from Maine to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 29% versus a flight in the morning.
Weekly flight availability from Maine to Chicago
Explore weekly flight availability from Maine to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 10, 2026.
The most flights from USME to CHI are scheduled on a Friday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Maine to Chicago?
Airfare is below average for this route at the moment.
Maine to Chicago flights typically cost between $269 and $401 in September.The cheapest round-trip price found within the last 5 days was $245 on American Airlines (Sep 5-Sep 6).
How far ahead should I book a flight from Maine to Chicago?
The best time to book flights from Maine to Chicago is 82 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Related info for your journey
Find useful and relevant information for your journey from Maine to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Maine to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Chicago by cabin class
Find flights from Maine to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Maine and Chicago flights
Browse other Maine and Chicago flight options. Last updated on August 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Maine to Chicago flights
Consider these flights traveling from Maine to Chicago.
Top 4 airlines flying from Maine to Chicago
Discover the top 4 airlines that operate flights from Maine to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$209 | Average$363 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$405 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$234 | Average$346 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$378 | FlexibilityNo cancel fee | On-time63% |