$68+ Cheap flights from Maine to Midway (MDW)
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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MDW
Mar 10 — Mar 171
1 adult, Economy
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Find cheap flights from Maine to Midway 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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Maine to Midway
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Cheapest flights from Maine to MidwayExplore the most affordable flight options available from Maine to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.
Explore the most affordable flight options available from Maine to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 8, 2026.
This Southwest deal was found by Cheapflights users on 2/7. 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 2/285:15 am
BOS
- MDW
Nonstop2h 45m
Southwest
Sat 2/2810:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 2/6. 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 3/45:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/6![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 2/7. 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 2/282:10 pm
BOS
- MDW
1 stop6h 15m
Southwest
Mon 3/26:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 2/5. 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.
Mon 3/93:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 3/106:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/5![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 2/7. 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 2/285:00 am
BOS
- MDW
2 stops9h 30m
Southwest
Tue 3/32:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 2/7![Southwest logo]()
$140
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:55 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 4/137:00 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/4![Southwest logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:50 pm
BOS
- MDW
1 stop21h 06m
Multiple Airlines
Thu 2/265:16 pm
MDW
- BOS
1 stop6h 57m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$145
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Tue 2/245:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/4![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 2/6. 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 2/275:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Sun 3/16:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/6![Southwest logo]()
$147
This Priceline deal was found by Cheapflights users on 2/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BOS
- MDW
1 stop11h 16m
Frontier
Mon 3/22:19 pm
MDW
- BOS
1 stop9h 54m
Frontier
Deal found 2/4![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:50 pm
BOS
- MDW
1 stop21h 06m
Multiple Airlines
Mon 3/22:19 pm
MDW
- BOS
2 stops25h 26m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 2/7. 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 2/235:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 2/2810:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$150
Best flights from Maine to MidwayDiscover carefully curated flight deals from Maine to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 8, 2026.
Discover carefully curated flight deals from Maine to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 8, 2026.
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/206:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Tue 3/246:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/4![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:31 am
PWM
- MDW
1 stop7h 28m
Delta
Tue 3/31:29 pm
MDW
- PWM
2 stops8h 37m
Delta
Deal found 2/4![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Mon 3/22:40 pm
MDW
- BOS
1 stop6h 30m
Southwest
Deal found 2/4![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 2/5. 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.
Mon 3/25:20 pm
BOS
- MDW
1 stop6h 10m
Southwest
Wed 3/42:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 2/5![Southwest logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Sun 4/127:53 pm
BGR
- MDW
1 stop25h 16m
Multiple Airlines
Thu 4/169:14 am
MDW
- BGR
1 stop8h 59m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 2/7. 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 3/233:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Wed 3/2511:15 am
MDW
- BOS
1 stop10h 45m
Southwest
Deal found 2/7![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 2/7. 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 3/2411:25 am
BOS
- MDW
Nonstop2h 50m
Southwest
Tue 3/318:15 am
MDW
- BOS
1 stop5h 20m
Southwest
Deal found 2/7![Southwest logo]()
$167
This Delta deal was found by Cheapflights users on 2/5. 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 2/266:00 am
PWM
- MDW
2 stops7h 46m
Delta
Mon 3/21:29 pm
MDW
- PWM
2 stops8h 51m
Delta
Deal found 2/5![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 2/7. 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.
Thu 2/195:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 2/286:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/4. 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.
Sat 3/72:35 pm
PWM
- MDW
2 stops8h 56m
Delta
Mon 3/91:10 pm
MDW
- PWM
2 stops9h 12m
Delta
Deal found 2/4![Delta logo]()
$259
This Southwest deal was found by Cheapflights users on 2/5. 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 4/910:40 am
BOS
- MDW
Nonstop2h 40m
Southwest
Sun 4/127:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/5![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 2/7. 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 3/146:35 pm
BOS
- MDW
Nonstop2h 55m
Southwest
Sat 3/216:25 pm
MDW
- BOS
1 stop4h 40m
Southwest
Deal found 2/7![Southwest logo]()
$190
This Delta deal was found by Cheapflights users on 2/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:46 pm
PWM
- MDW
1 stop6h 12m
Delta
Sat 4/189:27 am
MDW
- PWM
1 stop5h 30m
Delta
Deal found 2/7![Delta logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:54 pm
BGR
- MDW
2 stops25h 13m
Multiple Airlines
Thu 3/57:30 am
MDW
- BGR
1 stop10h 43m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$370
This Southwest deal was found by Cheapflights users on 2/5. 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 2/265:20 am
BOS
- MDW
2 stops13h 00m
Southwest
Sun 3/19:20 pm
MDW
- BOS
1 stop10h 00m
Southwest
Deal found 2/5![Southwest logo]()
$193
This Delta deal was found by Cheapflights users on 2/6. 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 4/76:03 am
PWM
- MDW
2 stops7h 26m
Delta
Sun 4/129:35 am
MDW
- PWM
1 stop5h 31m
Delta
Deal found 2/6![Delta logo]()
$289
This KAYAK deal was found by Cheapflights users on 2/5. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Tue 4/712:45 pm
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/5![Southwest logo]()
$196
This Delta deal was found by Cheapflights users on 2/5. 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 2/205:06 am
BGR
- MDW
2 stops8h 40m
Delta
Tue 2/249:50 am
MDW
- BGR
2 stops12h 35m
Delta
Deal found 2/5![Delta logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 3/57:53 pm
BGR
- MDW
1 stop18h 15m
Multiple Airlines
Thu 3/129:10 am
MDW
- BGR
1 stop9h 03m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$452
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
Tue 3/39:50 am
MDW
- PWM
1 stop4h 05m
Southwest
Deal found 2/4![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 2/7. 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 3/232:50 pm
PWM
- MDW
1 stop6h 25m
Southwest
Wed 3/259:20 am
MDW
- PWM
1 stop5h 35m
Southwest
Deal found 2/7![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 2/6. 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 5/135:15 am
BGR
- MDW
2 stops12h 02m
Delta
Mon 5/181:22 pm
MDW
- BGR
2 stops9h 11m
Delta
Deal found 2/6![Delta logo]()
$399
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/71:10 pm
PWM
- MDW
1 stop8h 00m
Southwest
Mon 3/910:35 am
MDW
- PWM
1 stop5h 10m
Southwest
Deal found 2/4![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 2/6. 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.
Sat 4/116:00 am
BGR
- MDW
2 stops7h 29m
Delta
Wed 4/1512:53 pm
MDW
- BGR
2 stops9h 38m
Delta
Deal found 2/6![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:30 pm
PWM
- MDW
2 stops7h 35m
Southwest
Tue 3/39:50 am
MDW
- PWM
1 stop4h 05m
Southwest
Deal found 2/4![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 2/5. 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 2/245:06 am
BGR
- MDW
2 stops8h 59m
Delta
Thu 2/2610:49 am
MDW
- BGR
2 stops11h 36m
Delta
Deal found 2/5![Delta logo]()
$451
This Delta deal was found by Cheapflights users on 2/6. 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.
Mon 3/25:06 am
BGR
- MDW
2 stops8h 40m
Delta
Thu 3/51:29 pm
MDW
- BGR
2 stops8h 56m
Delta
Deal found 2/6![Delta logo]()
$469
Last-minute flights from Maine to MidwayDiscover last-minute flight deals from Maine to Midway. Data last updated February 8, 2026 and is based on user searches.
Discover last-minute flight deals from Maine to Midway. Data last updated February 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Tue 2/245:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/4![Southwest logo]()
$146
This Southwest deal was found by Cheapflights users on 2/7. 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 2/235:20 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 2/2810:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:50 pm
BOS
- MDW
1 stop21h 06m
Multiple Airlines
Thu 2/265:16 pm
MDW
- BOS
1 stop6h 57m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:50 pm
BOS
- MDW
1 stop21h 06m
Multiple Airlines
Mon 3/22:19 pm
MDW
- BOS
2 stops25h 26m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$149
This Priceline deal was found by Cheapflights users on 2/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
BOS
- MDW
1 stop11h 16m
Frontier
Mon 3/22:19 pm
MDW
- BOS
1 stop9h 54m
Frontier
Deal found 2/4![Frontier logo]()
$148
This Southwest deal was found by Cheapflights users on 2/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:50 pm
PWM
- MDW
1 stop6h 55m
Southwest
Tue 3/39:50 am
MDW
- PWM
1 stop4h 05m
Southwest
Deal found 2/4![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 2/6. 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 2/275:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Sun 3/16:05 am
MDW
- BOS
Nonstop2h 20m
Southwest
Deal found 2/6![Southwest logo]()
$147
This Southwest deal was found by Cheapflights users on 2/7. 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 2/285:15 am
BOS
- MDW
Nonstop2h 45m
Southwest
Sat 2/2810:15 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$132
This Southwest deal was found by Cheapflights users on 2/7. 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 2/285:55 am
BOS
- MDW
1 stop9h 35m
Southwest
Mon 3/26:35 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/7![Southwest logo]()
$134
This Southwest deal was found by Cheapflights users on 2/6. 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 3/45:30 am
BOS
- MDW
Nonstop2h 50m
Southwest
Sat 3/77:40 am
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/6![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 2/5. 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.
Mon 3/93:10 pm
BOS
- MDW
Nonstop2h 45m
Southwest
Tue 3/106:10 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/5![Southwest logo]()
$137
This Southwest deal was found by Cheapflights users on 2/6. 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 3/276:25 pm
BOS
- MDW
Nonstop3h 00m
Southwest
Fri 4/33:30 pm
MDW
- BOS
Nonstop2h 15m
Southwest
Deal found 2/6![Southwest logo]()
$142
One-way flights from Maine to MidwaySearch for one-way flight options from Maine to Midway. Find affordable one-way fares based on user searches. Data last updated February 8, 2026.
Search for one-way flight options from Maine to Midway. Find affordable one-way fares based on user searches. Data last updated February 8, 2026.
This Southwest deal was found by Cheapflights users on 2/5. 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.
Wed 2/252:40 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Deal found 2/5![Southwest logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 2/5. 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.
Wed 2/255:50 pm
BOS
- MDW
1 stop21h 06m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$71
This Southwest deal was found by Cheapflights users on 2/7. 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 3/146:35 pm
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/7![Southwest logo]()
$74
This Southwest deal was found by Cheapflights users on 2/7. 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 2/289:00 am
BOS
- MDW
1 stop5h 20m
Southwest
Deal found 2/7![Southwest logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/266:00 am
BOS
- MDW
1 stop11h 16m
Frontier
Deal found 2/5![Frontier logo]()
$77
This Southwest deal was found by Cheapflights users on 2/5. 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.
Sun 2/225:00 am
BOS
- MDW
Nonstop2h 55m
Southwest
Deal found 2/5![Southwest logo]()
$79
This Frontier deal was found by Cheapflights users on 2/7. 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 4/812:42 pm
BOS
- MDW
1 stop8h 25m
Frontier
Deal found 2/7![Frontier logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 2/245:27 am
BOS
- MDW
2 stops14h 40m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$81
This Frontier deal was found by Cheapflights users on 2/7. 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 3/1111:51 am
BOS
- MDW
1 stop11h 28m
Frontier
Deal found 2/7![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 2/5. 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 3/912:35 pm
BOS
- MDW
1 stop8h 12m
Frontier
Deal found 2/5![Frontier logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 2/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:01 am
BOS
- MDW
1 stop8h 40m
Multiple Airlines
Deal found 2/6![Multiple Airlines logo]()
$88
This Delta deal was found by Cheapflights users on 2/6. 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 4/812:51 pm
PWM
- MDW
1 stop6h 03m
Delta
Deal found 2/6![Delta logo]()
$115
Find flight deals from Maine to Midway
Keep the following information in mind while searching for Maine to Midway flight deals. Data was last updated February 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $132 (Southwest) |
One-way from | $68 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $333 |
Good round-trip deal | $482 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Maine to Midway 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 February 8, 2026.
Use the filters below to find and compare flights from Maine to Chicago Midway Airport that are best for you.
Fly from
Maine
Fly to
Midway
Route
Depart
Return
Price
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 3/20
6:25 pm-8:25 pm
Nonstop3h 00m
Chicago Midway
Tue 3/24
6:10 pm-9:25 pm
Nonstop2h 15m
$137
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Wed 2/25
5:30 am-7:20 am
Nonstop2h 50m
Chicago Midway
Mon 3/2
2:40 pm-10:10 pm
1 stop6h 30m
$147
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 3/2
5:20 pm-10:30 pm
1 stop6h 10m
Chicago Midway
Wed 3/4
2:00 pm-5:10 pm
Nonstop2h 10m
$147
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 3/23
3:10 pm-4:55 pm
Nonstop2h 45m
Chicago Midway
Wed 3/25
11:15 am-11:00 pm
1 stop10h 45m
$153
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Tue 3/24
11:25 am-1:15 pm
Nonstop2h 50m
Chicago Midway
Tue 3/31
8:15 am-2:35 pm
1 stop5h 20m
$167
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 2/19
5:20 am-7:10 am
Nonstop2h 50m
Chicago Midway
Sat 2/28
6:10 pm-9:25 pm
Nonstop2h 15m
$177
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 4/9
10:40 am-12:20 pm
Nonstop2h 40m
Chicago Midway
Sun 4/12
7:40 am-10:55 am
Nonstop2h 15m
$187
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Sat 3/14
6:35 pm-8:30 pm
Nonstop2h 55m
Chicago Midway
Sat 3/21
6:25 pm-12:05 am
1 stop4h 40m
$190
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Thu 2/26
5:20 am-5:20 pm
2 stops13h 00m
Chicago Midway
Sun 3/1
9:20 pm-8:20 am
1 stop10h 00m
$193
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 4/6
6:25 pm-8:25 pm
Nonstop3h 00m
Chicago Midway
Tue 4/7
12:45 pm-4:05 pm
Nonstop2h 20m
$196
Showing 1-10 of 56 results
Best time to book a flight from Maine to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from Maine with our price prediction graph.
BOS-MDW
PWM-MDW
BGR-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Maine to Chicago Midway Airport
USME-MDW
BOS-MDW
PWM-MDW
BGR-MDW
What is the cheapest time of day to fly from ME to MDW?
Find hourly flight availability from Maine to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 8, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 10% on flights from Maine to Chicago Midway Airport by exploring options for tickets in the morning.
Related info for your journey
Find useful and relevant information for your journey from Maine to Midway. 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 Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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
Complete your trip
Flights by cabin class
Midway flight routes
Other flight options
Popular flights
Top destinations
Alternative routes for Maine to Midway
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Midway by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Maine to Midway by cabin class
Find flights from Maine to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 8, 2026.
Maine and Midway flights
Browse other Maine and Midway flight options. Last updated on February 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Maine to Midway flights
Consider these flights traveling from Maine to Midway.
Top 2 airlines flying from Maine to Midway
Discover the top 2 airlines that operate flights from Maine to Midway. 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 February 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$246 | Average$397 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$262 | Average$329 | FlexibilityNo cancel fee | On-timeN/A |