$179+ Cheap flights from Midway (MDW) to Alaska
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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Apr 12 — Apr 191
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Alaska 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 Midway to Alaska
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Cheapest flights from Midway to AlaskaExplore the most affordable flight options available from Midway to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 2026.
Explore the most affordable flight options available from Midway to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 13, 2026.
This Southwest deal was found by Cheapflights users on 3/11. 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.
Sun 6/74:10 pm
MDW
- ANC
1 stop10h 45m
Southwest
Tue 6/912:55 am
ANC
- MDW
1 stop9h 30m
Southwest
Deal found 3/11![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/249:29 am
MDW
- ANC
1 stop12h 17m
Delta
Mon 4/279:15 pm
ANC
- MDW
1 stop13h 17m
Delta
Deal found 3/12![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/36:00 am
MDW
- ANC
2 stops15h 51m
Delta
Fri 4/101:34 am
ANC
- MDW
2 stops14h 06m
Delta
Deal found 3/12![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:46 am
MDW
- ANC
1 stop12h 00m
Delta
Sat 4/259:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/10![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 4/109:30 am
MDW
- ANC
1 stop12h 21m
Delta
Mon 4/139:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/11![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 4/101:10 pm
MDW
- ANC
2 stops14h 19m
Delta
Tue 4/149:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/11![Delta logo]()
$388
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:22 pm
MDW
- ANC
2 stops11h 53m
Delta
Fri 5/159:59 pm
ANC
- MDW
2 stops11h 43m
Delta
Deal found 3/10![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 4/301:24 pm
MDW
- FAI
2 stops14h 16m
Delta
Tue 5/51:45 am
FAI
- MDW
2 stops13h 51m
Delta
Deal found 3/8![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 6/91:00 pm
MDW
- FAI
2 stops14h 06m
Delta
Sun 6/1410:05 pm
FAI
- MDW
2 stops15h 20m
Delta
Deal found 3/9![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/271:00 pm
MDW
- FAI
2 stops14h 06m
Delta
Thu 7/210:05 pm
FAI
- MDW
2 stops15h 20m
Delta
Deal found 3/8![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 6/161:00 pm
MDW
- FAI
2 stops14h 06m
Delta
Tue 6/2310:05 pm
FAI
- MDW
1 stop7h 33m
Delta
Deal found 3/8![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 6/269:20 am
MDW
- FAI
1 stop14h 35m
Delta
Sun 7/510:05 pm
FAI
- MDW
1 stop12h 02m
Delta
Deal found 3/11![Delta logo]()
$585
Best flights from Midway to AlaskaDiscover carefully curated flight deals from Midway to Alaska that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 13, 2026.
Discover carefully curated flight deals from Midway to Alaska that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 13, 2026.
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/229:29 am
MDW
- ANC
1 stop12h 17m
Delta
Sun 4/269:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/10![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:00 am
MDW
- ANC
2 stops15h 51m
Delta
Mon 4/69:15 pm
ANC
- MDW
1 stop13h 09m
Delta
Deal found 3/9![Delta logo]()
$382
This Delta deal was found by Cheapflights users on 3/11. 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 4/239:29 am
MDW
- ANC
1 stop12h 17m
Delta
Mon 4/279:15 pm
ANC
- MDW
1 stop13h 17m
Delta
Deal found 3/11![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 3/8. 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.
Fri 4/249:29 am
MDW
- ANC
1 stop12h 17m
Delta
Mon 4/279:15 pm
ANC
- MDW
2 stops16h 11m
Delta
Deal found 3/8![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 3/11. 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.
Wed 4/89:35 am
MDW
- ANC
2 stops14h 00m
Delta
Wed 4/153:45 pm
ANC
- MDW
2 stops14h 02m
Delta
Deal found 3/11![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/9. 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 5/309:22 am
MDW
- ANC
1 stop13h 59m
Delta
Sun 6/710:00 pm
ANC
- MDW
1 stop11h 30m
Delta
Deal found 3/9![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/9. 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 5/301:22 pm
MDW
- ANC
2 stops14h 34m
Delta
Fri 6/512:05 am
ANC
- MDW
2 stops14h 51m
Delta
Deal found 3/9![Delta logo]()
$401
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:22 pm
MDW
- ANC
2 stops11h 53m
Delta
Sun 5/106:00 am
ANC
- MDW
1 stop8h 56m
Delta
Deal found 3/9![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/11:59 pm
MDW
- ANC
2 stops13h 56m
Delta
Wed 6/109:55 pm
ANC
- MDW
1 stop7h 43m
Delta
Deal found 3/10![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 6/91:00 pm
MDW
- FAI
2 stops14h 06m
Delta
Sun 6/1410:05 pm
FAI
- MDW
1 stop12h 02m
Delta
Deal found 3/9![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 3/11. 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.
Wed 4/89:30 am
MDW
- FAI
2 stops17h 42m
Delta
Tue 4/141:45 am
FAI
- MDW
2 stops13h 51m
Delta
Deal found 3/11![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 4/59:35 am
MDW
- FAI
2 stops17h 37m
Delta
Sat 4/111:30 am
FAI
- MDW
2 stops13h 24m
Delta
Deal found 3/8![Delta logo]()
$706
This Delta deal was found by Cheapflights users on 3/8. 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.
Fri 4/109:35 am
MDW
- FAI
2 stops17h 37m
Delta
Sun 4/121:45 am
FAI
- MDW
2 stops13h 13m
Delta
Deal found 3/8![Delta logo]()
$706
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 4/39:35 am
MDW
- FAI
2 stops17h 37m
Delta
Mon 4/61:30 am
FAI
- MDW
2 stops14h 10m
Delta
Deal found 3/11![Delta logo]()
$726
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 4/161:24 pm
MDW
- FAI
2 stops14h 16m
Delta
Sun 4/191:45 am
FAI
- MDW
2 stops13h 13m
Delta
Deal found 3/8![Delta logo]()
$829
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 7/39:30 am
MDW
- JNU
2 stops11h 37m
Delta
Wed 7/87:05 am
JNU
- MDW
2 stops11h 40m
Delta
Deal found 3/11![Delta logo]()
$875
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:30 am
MDW
- JNU
2 stops11h 37m
Delta
Wed 7/157:05 am
JNU
- MDW
2 stops11h 40m
Delta
Deal found 3/10![Delta logo]()
$1,001
This Delta deal was found by Cheapflights users on 3/11. 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 7/29:30 am
MDW
- JNU
2 stops11h 37m
Delta
Tue 7/77:05 am
JNU
- MDW
2 stops11h 40m
Delta
Deal found 3/11![Delta logo]()
$1,056
This Delta deal was found by Cheapflights users on 3/11. 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 3/269:30 am
MDW
- FAI
2 stops17h 42m
Delta
Sun 3/291:30 am
FAI
- MDW
2 stops13h 24m
Delta
Deal found 3/11![Delta logo]()
$1,329
This Delta deal was found by Cheapflights users on 3/8. 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.
Tue 3/179:35 am
MDW
- FAI
2 stops17h 37m
Delta
Fri 3/201:30 am
FAI
- MDW
2 stops13h 24m
Delta
Deal found 3/8![Delta logo]()
$1,501
This Delta deal was found by Cheapflights users on 3/11. 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.
Sun 6/289:30 am
MDW
- JNU
2 stops11h 37m
Delta
Sat 7/47:05 am
JNU
- MDW
2 stops11h 40m
Delta
Deal found 3/11![Delta logo]()
$1,694
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/19:30 am
MDW
- JNU
2 stops11h 37m
Delta
Sat 7/117:05 am
JNU
- MDW
2 stops11h 40m
Delta
Deal found 3/10![Delta logo]()
$1,698
This Delta deal was found by Cheapflights users on 3/11. 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.
Sat 6/279:30 am
MDW
- JNU
2 stops11h 37m
Delta
Sat 7/47:05 am
JNU
- MDW
2 stops11h 40m
Delta
Deal found 3/11![Delta logo]()
$1,844
Last-minute flights from Midway to AlaskaDiscover last-minute flight deals from Midway to Alaska. Data last updated March 13, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Alaska. Data last updated March 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/36:00 am
MDW
- ANC
2 stops15h 51m
Delta
Fri 4/101:34 am
ANC
- MDW
2 stops14h 06m
Delta
Deal found 3/12![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 4/39:35 am
MDW
- FAI
2 stops17h 37m
Delta
Mon 4/61:30 am
FAI
- MDW
2 stops14h 10m
Delta
Deal found 3/11![Delta logo]()
$726
This Delta deal was found by Cheapflights users on 3/8. 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.
Sun 4/59:35 am
MDW
- FAI
2 stops17h 37m
Delta
Sat 4/111:30 am
FAI
- MDW
2 stops13h 24m
Delta
Deal found 3/8![Delta logo]()
$706
This Delta deal was found by Cheapflights users on 3/11. 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.
Wed 4/89:30 am
MDW
- FAI
2 stops17h 42m
Delta
Tue 4/141:45 am
FAI
- MDW
2 stops13h 51m
Delta
Deal found 3/11![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 4/109:30 am
MDW
- ANC
1 stop12h 21m
Delta
Mon 4/139:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/11![Delta logo]()
$383
This Delta deal was found by Cheapflights users on 3/11. 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.
Fri 4/101:10 pm
MDW
- ANC
2 stops14h 19m
Delta
Tue 4/149:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/11![Delta logo]()
$388
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/109:35 am
MDW
- FAI
2 stops17h 37m
Delta
Sun 4/121:45 am
FAI
- MDW
2 stops13h 13m
Delta
Deal found 3/9![Delta logo]()
$832
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 4/161:24 pm
MDW
- FAI
2 stops14h 16m
Delta
Sun 4/191:45 am
FAI
- MDW
2 stops13h 13m
Delta
Deal found 3/8![Delta logo]()
$829
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:46 am
MDW
- ANC
1 stop12h 00m
Delta
Sat 4/259:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Deal found 3/10![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 4/249:29 am
MDW
- ANC
1 stop12h 17m
Delta
Mon 4/279:15 pm
ANC
- MDW
1 stop13h 17m
Delta
Deal found 3/12![Delta logo]()
$357
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:29 am
MDW
- ANC
1 stop12h 17m
Delta
Fri 5/19:15 pm
ANC
- MDW
1 stop8h 51m
Delta
Deal found 3/10![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 3/8. 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.
Thu 4/301:24 pm
MDW
- FAI
2 stops14h 16m
Delta
Tue 5/51:45 am
FAI
- MDW
2 stops13h 51m
Delta
Deal found 3/8![Delta logo]()
$422
One-way flights from Midway to AlaskaSearch for one-way flight options from Midway to Alaska. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
Search for one-way flight options from Midway to Alaska. Find affordable one-way fares based on user searches. Data last updated March 13, 2026.
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” 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 5/87:13 pm
MDW
- ANC
1 stop8h 18m
Delta
Deal found 3/12![Delta logo]()
$179
This Delta deal was found by Cheapflights users on 3/11. 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 5/71:22 pm
MDW
- ANC
2 stops14h 09m
Delta
Deal found 3/11![Delta logo]()
$190
This Delta deal was found by Cheapflights users on 3/9. 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.
Sun 6/79:30 am
MDW
- ANC
1 stop14h 28m
Delta
Deal found 3/9![Delta logo]()
$195
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/307:20 pm
MDW
- ANC
1 stop26h 31m
Delta
Deal found 3/9![Delta logo]()
$197
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:29 am
MDW
- ANC
1 stop12h 17m
Delta
Deal found 3/9![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 3/11. 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 6/89:30 am
MDW
- ANC
1 stop14h 28m
Delta
Deal found 3/11![Delta logo]()
$205
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:22 am
MDW
- ANC
2 stops14h 27m
Delta
Deal found 3/9![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 3/11. 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 6/112:35 pm
MDW
- ANC
2 stops13h 10m
Southwest
Deal found 3/11![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 3/9. 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.
Tue 4/281:24 pm
MDW
- FAI
2 stops14h 16m
Delta
Deal found 3/9![Delta logo]()
$378
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:15 pm
MDW
- FAI
3 stops38h 27m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$483
This Delta deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:22 pm
MDW
- FAI
2 stops14h 13m
Delta
Deal found 3/10![Delta logo]()
$1,968
Find flight deals from Midway to Alaska
Keep the following information in mind while searching for Midway to Alaska flight deals. Data was last updated March 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $279 (Southwest) |
One-way from | $179 (Delta) |
Popular in | June |
Cheapest in | October |
Average price | $429 |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Alaska 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 March 13, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Alaska that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 4/22
9:29 am-6:46 pm
1 stop12h 17m
Anchorage
Sun 4/26
9:15 pm-8:46 am
1 stop8h 31m
$377
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 4/2
6:00 am-6:51 pm
2 stops15h 51m
Anchorage
Mon 4/6
9:15 pm-1:24 pm
1 stop13h 09m
$382
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 4/23
9:29 am-6:46 pm
1 stop12h 17m
Anchorage
Mon 4/27
9:15 pm-1:32 pm
1 stop13h 17m
$383
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Fri 4/24
9:29 am-6:46 pm
1 stop12h 17m
Anchorage
Mon 4/27
9:15 pm-4:26 pm
2 stops16h 11m
$384
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 4/8
9:35 am-8:35 pm
2 stops14h 00m
Anchorage
Wed 4/15
3:45 pm-8:47 am
2 stops14h 02m
$389
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 5/30
9:22 am-8:21 pm
1 stop13h 59m
Anchorage
Sun 6/7
10:00 pm-12:30 pm
1 stop11h 30m
$389
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 5/30
1:22 pm-12:56 am
2 stops14h 34m
Anchorage
Fri 6/5
12:05 am-5:56 pm
2 stops14h 51m
$401
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 5/7
1:22 pm-10:15 pm
2 stops11h 53m
Anchorage
Sun 5/10
6:00 am-5:56 pm
1 stop8h 56m
$402
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Mon 6/1
1:59 pm-12:55 am
2 stops13h 56m
Anchorage
Wed 6/10
9:55 pm-8:38 am
1 stop7h 43m
$414
ChicagoFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Tue 6/9
1:00 pm-12:06 am
2 stops14h 06m
Fairbanks
Sun 6/14
10:05 pm-1:07 pm
1 stop12h 02m
$541
Showing 1-10 of 34 resultsSorted by cheapest first
Best time to book a flight from Midway to Alaska
Have a flexible travel schedule? Discover the best time to fly to Alaska from Midway with our price prediction graph.
MDW-ANC
MDW-FAI
MDW-JNU
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 Midway Airport to Alaska
MDW-USAK
MDW-ANC
MDW-FAI
MDW-JNU
No data available for this route at this time. Please check back soon.
Related info for your journey
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