$221+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — ANC
Jul 9 — Jul 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 June 9, 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 June 9, 2026.
This Delta deal was found by Cheapflights users on 6/9. 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.
Wed 8/127:25 pm
MDW
- ANC
1 stop8h 34m
Delta
Tue 8/181:32 am
ANC
- MDW
2 stops13h 29m
Delta
Deal found 6/9![Delta logo]()
$400
This Delta deal was found by Cheapflights users on 6/8. 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 7/49:17 am
MDW
- ANC
1 stop14h 59m
Delta
Wed 7/1512:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 6/8. 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 7/49:17 am
MDW
- ANC
2 stops17h 39m
Delta
Sat 7/1112:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$411
This Delta deal was found by Cheapflights users on 6/4. 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 8/131:51 pm
MDW
- ANC
1 stop14h 08m
Delta
Wed 8/1912:39 am
ANC
- MDW
2 stops14h 22m
Delta
Deal found 6/4![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sun 8/3012:20 pm
MDW
- ANC
2 stops13h 25m
Southwest
Wed 9/211:55 pm
ANC
- MDW
2 stops14h 05m
Southwest
Deal found 6/4![Southwest logo]()
$416
This Delta deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/229:30 am
MDW
- ANC
2 stops16h 06m
Delta
Tue 12/299:55 pm
ANC
- MDW
2 stops15h 27m
Delta
Deal found 6/5![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/299:54 am
MDW
- ANC
1 stop11h 47m
Delta
Sat 7/412:35 pm
ANC
- MDW
1 stop17h 02m
Delta
Deal found 6/8![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 6/5. 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.
Sun 6/286:58 pm
MDW
- ANC
1 stop29h 18m
Delta
Wed 7/112:35 pm
ANC
- MDW
1 stop17h 02m
Delta
Deal found 6/5![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/299:54 am
MDW
- ANC
2 stops17h 02m
Delta
Fri 7/310:30 pm
ANC
- MDW
1 stop15h 37m
Delta
Deal found 6/8![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 7/69:17 am
MDW
- ANC
1 stop14h 59m
Delta
Sat 7/1112:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 6/8. 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 7/71:18 pm
MDW
- ANC
2 stops14h 41m
Delta
Wed 7/1512:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 6/8. 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 9/39:59 am
MDW
- FAI
1 stop13h 50m
Delta
Sun 9/610:00 pm
FAI
- MDW
1 stop7h 39m
Delta
Deal found 6/8![Delta logo]()
$470
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 June 9, 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 June 9, 2026.
This Delta deal was found by Cheapflights users on 6/7. 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.
Sat 7/49:17 am
MDW
- ANC
1 stop14h 59m
Delta
Tue 7/1410:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Deal found 6/7![Delta logo]()
$481
This Southwest deal was found by Cheapflights users on 6/4. 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.
Mon 9/711:25 am
MDW
- ANC
2 stops15h 20m
Southwest
Thu 9/1012:55 am
ANC
- MDW
2 stops13h 05m
Southwest
Deal found 6/4![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 6/6. 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 8/39:24 am
MDW
- ANC
1 stop14h 56m
Delta
Fri 8/712:54 pm
ANC
- MDW
1 stop16h 45m
Delta
Deal found 6/6![Delta logo]()
$506
This Delta deal was found by Cheapflights users on 6/6. 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 9/19:59 am
MDW
- FAI
1 stop13h 50m
Delta
Mon 9/710:00 pm
FAI
- MDW
1 stop7h 38m
Delta
Deal found 6/6![Delta logo]()
$531
This Southwest deal was found by Cheapflights users on 6/4. 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.
Sun 8/3012:15 pm
MDW
- ANC
1 stop13h 30m
Southwest
Wed 9/210:25 pm
ANC
- MDW
1 stop10h 25m
Southwest
Deal found 6/4![Southwest logo]()
$595
This Delta deal was found by Cheapflights users on 6/9. 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 8/119:59 am
MDW
- FAI
1 stop13h 50m
Delta
Thu 8/2010:00 pm
FAI
- MDW
1 stop7h 39m
Delta
Deal found 6/9![Delta logo]()
$536
This Delta deal was found by Cheapflights users on 6/8. 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 7/251:18 pm
MDW
- ANC
2 stops14h 41m
Delta
Thu 7/3012:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:54 am
MDW
- ANC
1 stop18h 05m
Delta
Thu 7/3012:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$567
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2711:20 am
MDW
- ANC
1 stop14h 25m
Southwest
Wed 7/110:25 pm
ANC
- MDW
2 stops10h 55m
Southwest
Deal found 6/5![Southwest logo]()
$772
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2711:20 am
MDW
- ANC
1 stop14h 25m
Southwest
Thu 7/211:55 pm
ANC
- MDW
2 stops13h 25m
Southwest
Deal found 6/5![Southwest logo]()
$772
This Delta deal was found by Cheapflights users on 6/4. 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.
Wed 6/249:54 am
MDW
- FAI
1 stop13h 49m
Delta
Thu 7/29:53 pm
FAI
- MDW
1 stop12h 16m
Delta
Deal found 6/4![Delta logo]()
$590
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 7/39:54 am
MDW
- FAI
1 stop13h 49m
Delta
Tue 7/79:59 pm
FAI
- MDW
1 stop12h 10m
Delta
Deal found 6/7![Delta logo]()
$592
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 7/69:54 am
MDW
- FAI
1 stop13h 49m
Delta
Mon 7/132:37 pm
FAI
- MDW
2 stops15h 36m
Delta
Deal found 6/8![Delta logo]()
$609
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 6/159:54 am
MDW
- ANC
1 stop13h 58m
Delta
Fri 6/2610:02 pm
ANC
- MDW
1 stop12h 07m
Delta
Deal found 6/7![Delta logo]()
$639
This Delta deal was found by Cheapflights users on 6/5. 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 6/249:17 am
MDW
- ANC
1 stop14h 59m
Delta
Tue 6/3012:35 am
ANC
- MDW
2 stops14h 43m
Delta
Deal found 6/5![Delta logo]()
$693
This Delta deal was found by Cheapflights users on 6/4. 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.
Fri 6/199:17 am
MDW
- ANC
1 stop14h 59m
Delta
Tue 6/3010:30 pm
ANC
- MDW
1 stop11h 16m
Delta
Deal found 6/4![Delta logo]()
$702
This Delta deal was found by Cheapflights users on 6/8. 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 7/149:54 am
MDW
- FAI
1 stop13h 55m
Delta
Sun 7/192:37 pm
FAI
- MDW
2 stops15h 00m
Delta
Deal found 6/8![Delta logo]()
$704
This Delta deal was found by Cheapflights users on 6/5. 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 9/49:59 am
MDW
- FAI
1 stop13h 50m
Delta
Wed 9/910:05 pm
FAI
- MDW
1 stop12h 06m
Delta
Deal found 6/5![Delta logo]()
$707
This Delta deal was found by Cheapflights users on 6/8. 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 7/59:17 am
MDW
- ANC
1 stop14h 59m
Delta
Wed 7/81:30 am
ANC
- MDW
2 stops13h 48m
Delta
Deal found 6/8![Delta logo]()
$720
This Delta deal was found by Cheapflights users on 6/8. 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 6/279:17 am
MDW
- FAI
2 stops14h 26m
Delta
Thu 7/22:41 pm
FAI
- MDW
2 stops14h 56m
Delta
Deal found 6/8![Delta logo]()
$751
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:05 am
MDW
- JNU
2 stops15h 11m
Delta
Tue 9/17:35 am
JNU
- MDW
2 stops12h 01m
Delta
Deal found 6/8![Delta logo]()
$869
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 8/249:24 am
MDW
- JNU
2 stops11h 52m
Delta
Thu 8/277:35 am
JNU
- MDW
2 stops12h 01m
Delta
Deal found 6/8![Delta logo]()
$1,042
This Delta deal was found by Cheapflights users on 6/7. 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 8/259:24 am
MDW
- JNU
2 stops11h 52m
Delta
Mon 8/317:35 am
JNU
- MDW
2 stops12h 01m
Delta
Deal found 6/7![Delta logo]()
$1,042
This Delta deal was found by Cheapflights users on 6/7. 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 8/279:24 am
MDW
- JNU
2 stops11h 52m
Delta
Sat 9/57:35 am
JNU
- MDW
2 stops12h 01m
Delta
Deal found 6/7![Delta logo]()
$1,126
This Delta deal was found by Cheapflights users on 6/9. 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 8/209:24 am
MDW
- JNU
2 stops11h 52m
Delta
Tue 8/257:35 am
JNU
- MDW
2 stops12h 01m
Delta
Deal found 6/9![Delta logo]()
$1,145
This Delta deal was found by Cheapflights users on 6/7. 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 7/299:19 am
MDW
- JNU
2 stops12h 07m
Delta
Wed 8/57:35 am
JNU
- MDW
2 stops12h 01m
Delta
Deal found 6/7![Delta logo]()
$1,192
Last-minute flights from Midway to AlaskaDiscover last-minute flight deals from Midway to Alaska. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Alaska. Data last updated June 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/5. 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 6/109:17 am
MDW
- ANC
1 stop14h 59m
Delta
Sat 6/136:00 am
ANC
- MDW
1 stop8h 54m
Delta
Deal found 6/5![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 6/5. 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.
Sun 6/286:58 pm
MDW
- ANC
1 stop29h 18m
Delta
Wed 7/112:35 pm
ANC
- MDW
1 stop17h 02m
Delta
Deal found 6/5![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 6/8. 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 6/281:26 pm
MDW
- ANC
1 stop10h 50m
Delta
Fri 7/312:35 pm
ANC
- MDW
1 stop17h 02m
Delta
Deal found 6/8![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/299:54 am
MDW
- ANC
1 stop11h 47m
Delta
Mon 7/612:35 pm
ANC
- MDW
1 stop17h 02m
Delta
Deal found 6/8![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/299:54 am
MDW
- ANC
2 stops17h 02m
Delta
Fri 7/310:30 pm
ANC
- MDW
1 stop15h 37m
Delta
Deal found 6/8![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 6/299:54 am
MDW
- ANC
2 stops17h 02m
Delta
Sun 7/512:35 pm
ANC
- MDW
1 stop17h 02m
Delta
Deal found 6/8![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 6/5. 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 7/39:54 am
MDW
- FAI
2 stops17h 36m
Delta
Wed 7/89:59 pm
FAI
- MDW
1 stop7h 38m
Delta
Deal found 6/5![Delta logo]()
$476
This Delta deal was found by Cheapflights users on 6/8. 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 7/49:17 am
MDW
- ANC
1 stop14h 59m
Delta
Fri 7/1712:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 6/8. 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.
Mon 7/69:17 am
MDW
- ANC
1 stop14h 59m
Delta
Sat 7/1112:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 6/8. 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 7/71:18 pm
MDW
- ANC
2 stops14h 41m
Delta
Mon 7/1312:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 6/8. 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 7/91:18 pm
MDW
- ANC
2 stops14h 41m
Delta
Wed 7/1512:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/8![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 6/5. 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 7/181:18 pm
MDW
- ANC
2 stops14h 41m
Delta
Tue 8/182:22 pm
ANC
- MDW
2 stops15h 17m
Delta
Deal found 6/5![Delta logo]()
$480
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 June 9, 2026.
Search for one-way flight options from Midway to Alaska. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Delta deal was found by Cheapflights users on 6/5. 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 8/81:27 pm
MDW
- ANC
2 stops14h 32m
Delta
Deal found 6/5![Delta logo]()
$221
This Delta deal was found by Cheapflights users on 6/4. 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.
Tue 6/239:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 6/4![Delta logo]()
$235
This Delta deal was found by Cheapflights users on 6/7. 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 7/289:19 am
MDW
- ANC
2 stops14h 41m
Delta
Deal found 6/7![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 6/5. 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 7/249:19 am
MDW
- ANC
1 stop15h 01m
Delta
Deal found 6/5![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 6/8. 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 7/79:19 am
MDW
- ANC
2 stops18h 40m
Delta
Deal found 6/8![Delta logo]()
$253
This Delta deal was found by Cheapflights users on 6/4. 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.
Fri 6/129:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 6/4![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 6/8. 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 8/219:59 am
MDW
- FAI
1 stop13h 50m
Delta
Deal found 6/8![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 6/8. 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 6/191:26 pm
MDW
- ANC
2 stops14h 29m
Delta
Deal found 6/8![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:49 pm
MDW
- ANC
1 stop14h 10m
Delta
Deal found 6/8![Delta logo]()
$272
This Delta deal was found by Cheapflights users on 6/4. 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 6/139:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 6/4![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 6/9. 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 6/279:17 am
MDW
- ANC
2 stops17h 03m
Delta
Deal found 6/9![Delta logo]()
$284
This Delta deal was found by Cheapflights users on 6/4. 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.
Tue 6/309:54 am
MDW
- FAI
1 stop13h 49m
Delta
Deal found 6/4![Delta logo]()
$316
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 June 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $400 (Delta) |
One-way from | $221 (Delta) |
Popular in | June |
Cheapest in | October |
Average price | $588 |
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 June 9, 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
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 7/4
9:17 am-9:16 pm
1 stop14h 59m
Anchorage
Tue 7/14
10:10 pm-1:09 pm
1 stop11h 59m
$481
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Mon 8/3
9:24 am-9:20 pm
1 stop14h 56m
Anchorage
Fri 8/7
12:54 pm-8:39 am
1 stop16h 45m
$506
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Mon 9/7
11:25 am-11:45 pm
2 stops15h 20m
Anchorage
Thu 9/10
12:55 am-5:00 pm
2 stops13h 05m
$528
Quickest round-trip
ChicagoFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Tue 9/1
9:59 am-8:49 pm
1 stop13h 50m
Fairbanks
Mon 9/7
10:00 pm-8:38 am
1 stop7h 38m
$531
ChicagoFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Tue 8/11
9:59 am-8:49 pm
1 stop13h 50m
Fairbanks
Thu 8/20
10:00 pm-8:39 am
1 stop7h 39m
$536
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sat 7/25
1:18 pm-12:59 am
2 stops14h 41m
Anchorage
Thu 7/30
12:44 pm-8:37 am
1 stop16h 53m
$541
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 7/29
9:54 am-12:59 am
1 stop18h 05m
Anchorage
Thu 7/30
12:44 pm-8:37 am
1 stop16h 53m
$567
ChicagoFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Wed 6/24
9:54 am-8:43 pm
1 stop13h 49m
Fairbanks
Thu 7/2
9:53 pm-1:09 pm
1 stop12h 16m
$590
ChicagoFairbanks
MDW - FAI
MDWFAI
Chicago Midway
Fri 7/3
9:54 am-8:43 pm
1 stop13h 49m
Fairbanks
Tue 7/7
9:59 pm-1:09 pm
1 stop12h 10m
$592
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Sun 8/30
12:15 pm-10:45 pm
1 stop13h 30m
Anchorage
Wed 9/2
10:25 pm-11:50 am
1 stop10h 25m
$595
Showing 1-10 of 45 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-SIT
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-SIT
MDW-JNU
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Midway to Alaska. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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
Other flight options
Popular flights