$171+ Cheap flights from Chicago (CHI) 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.
CHI — ANC
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Chicago 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 Chicago to Alaska
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Cheapest flights from Chicago to AlaskaExplore the most affordable flight options available from Chicago to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Chicago to Alaska. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:59 am
ORD
- ANC
Nonstop6h 45m
Alaska Airlines
Mon 7/1311:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/47:20 am
ORD
- ANC
1 stop13h 06m
Alaska Airlines
Thu 7/911:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:00 am
ORD
- ANC
1 stop30h 46m
Alaska Airlines
Sun 5/2411:23 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$353
This Delta deal was found by Cheapflights users on 2/9. 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 7/412:15 pm
ORD
- ANC
1 stop11h 44m
Delta
Mon 7/131:59 am
ANC
- ORD
1 stop8h 31m
Delta
Deal found 2/9![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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 8/189:30 am
MDW
- ANC
1 stop14h 28m
Delta
Thu 8/2710:00 pm
ANC
- MDW
1 stop11h 30m
Delta
Deal found 2/9![Delta logo]()
$359
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:20 am
ORD
- ANC
Nonstop6h 48m
Alaska Airlines
Sun 5/1711:23 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:09 pm
ORD
- ANC
1 stop9h 38m
Alaska Airlines
Fri 4/101:47 am
ANC
- ORD
1 stop25h 52m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$362
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/127:46 pm
ORD
- ANC
1 stop30h 44m
Alaska Airlines
Mon 6/159:05 am
ANC
- ORD
1 stop16h 55m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 2/9. 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 7/47:15 am
ORD
- ANC
2 stops15h 52m
Delta
Wed 7/812:55 am
ANC
- ORD
1 stop13h 35m
Delta
Deal found 2/9![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 2/9. 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 8/181:00 pm
MDW
- ANC
2 stops14h 33m
Delta
Tue 8/256:10 am
ANC
- MDW
1 stop8h 55m
Delta
Deal found 2/9![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 2/9. 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 8/276:00 pm
ORD
- ANC
1 stop10h 35m
Delta
Thu 9/35:15 pm
ANC
- ORD
2 stops13h 09m
Delta
Deal found 2/9![Delta logo]()
$366
This Delta deal was found by Cheapflights users on 2/8. 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 3/199:30 am
MDW
- ANC
1 stop12h 21m
Delta
Thu 3/263:40 pm
ANC
- MDW
2 stops14h 10m
Delta
Deal found 2/8![Delta logo]()
$366
Best flights from Chicago to AlaskaDiscover carefully curated flight deals from Chicago to Alaska that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Chicago to Alaska that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/24:10 pm
ORD
- ANC
Nonstop6h 45m
United Airlines
Mon 4/69:04 pm
ANC
- ORD
Nonstop6h 16m
United Airlines
Deal found 2/9![United Airlines logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:40 pm
ORD
- ANC
1 stop16h 07m
Alaska Airlines
Tue 6/2311:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 2/11![Alaska Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 2/9. 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 7/72:00 pm
MDW
- ANC
1 stop13h 33m
Delta
Fri 7/1012:49 pm
ANC
- MDW
1 stop16h 49m
Delta
Deal found 2/9![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:07 pm
ORD
- KTN
1 stop18h 46m
American Airlines
Sat 8/157:23 pm
KTN
- ORD
1 stop8h 17m
American Airlines
Deal found 2/11![American Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:10 pm
ORD
- ANC
Nonstop6h 45m
United Airlines
Sat 4/119:04 pm
ANC
- ORD
Nonstop6h 16m
United Airlines
Deal found 2/9![United Airlines logo]()
$339
This Alaska Airlines deal was found by Cheapflights users on 2/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/33:22 pm
ORD
- ANC
1 stop9h 13m
Alaska Airlines
Tue 4/712:10 pm
ANC
- ORD
1 stop8h 49m
Alaska Airlines
Deal found 2/8![Alaska Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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 4/19:30 am
MDW
- ANC
1 stop12h 21m
Delta
Tue 4/79:15 pm
ANC
- MDW
1 stop13h 10m
Delta
Deal found 2/9![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:10 pm
ORD
- ANC
Nonstop6h 45m
United Airlines
Mon 4/1311:47 pm
ANC
- ORD
1 stop8h 36m
United Airlines
Deal found 2/9![United Airlines logo]()
$349
This Alaska Airlines deal was found by Cheapflights users on 2/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:20 am
ORD
- ANC
Nonstop6h 48m
Alaska Airlines
Wed 6/1011:10 am
ANC
- ORD
2 stops14h 50m
Alaska Airlines
Deal found 2/8![Alaska Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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 4/169:31 am
MDW
- ANC
1 stop12h 15m
Delta
Mon 4/209:15 pm
ANC
- MDW
1 stop8h 36m
Delta
Deal found 2/9![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/12:35 pm
ORD
- ANC
1 stop11h 10m
United Airlines
Tue 4/711:47 pm
ANC
- ORD
1 stop10h 25m
United Airlines
Deal found 2/9![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 2/8. 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 3/289:30 am
MDW
- ANC
1 stop12h 21m
Delta
Sat 4/49:15 pm
ANC
- MDW
1 stop13h 10m
Delta
Deal found 2/8![Delta logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:09 pm
ORD
- ANC
2 stops24h 01m
Alaska Airlines
Sat 4/1110:48 am
ANC
- ORD
1 stop16h 51m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 2/8. 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 3/199:30 am
MDW
- ANC
1 stop12h 21m
Delta
Thu 3/269:15 pm
ANC
- MDW
1 stop8h 35m
Delta
Deal found 2/8![Delta logo]()
$359
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/42:09 pm
ORD
- FAI
2 stops27h 37m
Alaska Airlines
Sat 4/117:57 am
FAI
- ORD
2 stops19h 42m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 2/8. 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 5/273:55 pm
ORD
- ANC
1 stop11h 38m
Delta
Wed 6/108:30 pm
ANC
- ORD
2 stops13h 09m
Delta
Deal found 2/8![Delta logo]()
$366
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:00 am
ORD
- FAI
1 stop19h 35m
Alaska Airlines
Sat 4/113:53 pm
FAI
- ORD
1 stop11h 46m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 2/10. 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 7/44:20 pm
ORD
- ANC
1 stop10h 11m
Delta
Mon 7/1312:55 am
ANC
- ORD
1 stop10h 05m
Delta
Deal found 2/10![Delta logo]()
$369
This Expedia deal was found by Cheapflights users on 2/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
ORD
- FAI
1 stop9h 58m
Alaska Airlines
Sun 5/310:30 pm
FAI
- ORD
2 stops22h 29m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 2/9. 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 7/102:55 pm
ORD
- ANC
1 stop12h 01m
Delta
Mon 7/2012:55 am
ANC
- ORD
1 stop10h 05m
Delta
Deal found 2/9![Delta logo]()
$369
This Expedia deal was found by Cheapflights users on 2/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/27:24 pm
ORD
- FAI
1 stop9h 20m
Alaska Airlines
Mon 4/610:29 pm
FAI
- ORD
2 stops22h 30m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 2/9. 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 4/29:30 am
MDW
- ANC
1 stop12h 21m
Delta
Mon 4/69:15 pm
ANC
- MDW
1 stop8h 35m
Delta
Deal found 2/9![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 2/10. 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 7/299:20 am
MDW
- ANC
1 stop18h 13m
Delta
Fri 8/712:49 pm
ANC
- MDW
1 stop16h 49m
Delta
Deal found 2/10![Delta logo]()
$369
This Delta deal was found by Cheapflights users on 2/10. 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 7/259:20 am
MDW
- ANC
1 stop18h 13m
Delta
Fri 8/712:49 pm
ANC
- MDW
1 stop16h 49m
Delta
Deal found 2/10![Delta logo]()
$369
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:24 pm
ORD
- JNU
2 stops29h 04m
Alaska Airlines
Sat 4/117:24 am
JNU
- ORD
2 stops20h 15m
Alaska Airlines
Deal found 2/11![Alaska Airlines logo]()
$449
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
ORD
- JNU
1 stop29h 44m
Alaska Airlines
Sat 5/168:49 pm
JNU
- ORD
1 stop8h 51m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 2/9. 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 3/76:30 am
ORD
- FAI
2 stops43h 41m
Delta
Tue 3/101:30 am
FAI
- ORD
1 stop19h 21m
Delta
Deal found 2/9![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 2/9. 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 5/112:46 pm
ORD
- FAI
1 stop14h 54m
Delta
Sat 5/21:45 am
FAI
- ORD
1 stop11h 54m
Delta
Deal found 2/9![Delta logo]()
$398
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:00 am
ORD
- JNU
1 stop18h 27m
Alaska Airlines
Thu 4/307:24 am
JNU
- ORD
2 stops13h 35m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$491
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/135:29 pm
ORD
- JNU
2 stops31h 05m
Alaska Airlines
Tue 3/179:50 am
JNU
- ORD
3 stops17h 49m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$512
Last-minute flights from Chicago to AlaskaDiscover last-minute flight deals from Chicago to Alaska. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Alaska. Data last updated February 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 2/9. 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 3/86:15 am
ORD
- ANC
1 stop15h 36m
Delta
Sat 3/141:34 am
ANC
- ORD
1 stop8h 51m
Delta
Deal found 2/9![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 2/9. 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 3/97:20 am
ORD
- ANC
2 stops16h 14m
Delta
Sat 3/141:34 am
ANC
- ORD
1 stop8h 51m
Delta
Deal found 2/9![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/1012:15 pm
ORD
- ANC
2 stops15h 13m
Delta
Mon 3/161:34 am
ANC
- ORD
2 stops15h 15m
Delta
Deal found 2/10![Delta logo]()
$381
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/102:01 pm
ORD
- ANC
1 stop11h 49m
United Airlines
Tue 3/179:10 pm
ANC
- ORD
Nonstop6h 07m
United Airlines
Deal found 2/10![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 3/102:05 pm
MDW
- ANC
2 stops13h 23m
Delta
Tue 3/179:15 pm
ANC
- MDW
1 stop13h 10m
Delta
Deal found 2/10![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 2/8. 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 3/199:30 am
MDW
- ANC
1 stop12h 21m
Delta
Thu 3/269:15 pm
ANC
- MDW
1 stop8h 35m
Delta
Deal found 2/8![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 2/10. 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.
Sun 3/226:15 am
ORD
- ANC
1 stop15h 36m
Delta
Thu 3/261:34 am
ANC
- ORD
1 stop8h 51m
Delta
Deal found 2/10![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/242:45 pm
ORD
- ANC
1 stop11h 05m
United Airlines
Fri 3/279:10 pm
ANC
- ORD
Nonstop6h 07m
United Airlines
Deal found 2/9![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:30 am
MDW
- ANC
1 stop12h 21m
Delta
Sun 3/293:40 pm
ANC
- MDW
2 stops14h 10m
Delta
Deal found 2/11![Delta logo]()
$376
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/274:10 pm
ORD
- ANC
Nonstop6h 51m
United Airlines
Mon 3/309:04 pm
ANC
- ORD
Nonstop6h 16m
United Airlines
Deal found 2/9![United Airlines logo]()
$339
This Delta deal was found by Cheapflights users on 2/9. 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 3/276:15 am
ORD
- ANC
1 stop15h 36m
Delta
Mon 3/309:15 pm
ANC
- ORD
2 stops13h 02m
Delta
Deal found 2/9![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/284:10 pm
ORD
- ANC
Nonstop6h 51m
United Airlines
Sat 4/49:04 pm
ANC
- ORD
Nonstop6h 16m
United Airlines
Deal found 2/8![United Airlines logo]()
$375
One-way flights from Chicago to AlaskaSearch for one-way flight options from Chicago to Alaska. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Chicago to Alaska. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:59 am
ORD
- ANC
Nonstop6h 45m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$171
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:10 pm
ORD
- ANC
Nonstop6h 45m
United Airlines
Deal found 2/11![United Airlines logo]()
$176
This Delta deal was found by Cheapflights users on 2/9. 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 5/87:10 am
ORD
- ANC
1 stop12h 02m
Delta
Deal found 2/9![Delta logo]()
$180
This Delta deal was found by Cheapflights users on 2/11. 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 6/72:55 pm
ORD
- ANC
1 stop12h 01m
Delta
Deal found 2/11![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 2/10. 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 7/276:45 pm
MDW
- ANC
1 stop8h 48m
Delta
Deal found 2/10![Delta logo]()
$185
This Delta deal was found by Cheapflights users on 2/9. 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 4/77:20 am
ORD
- ANC
2 stops16h 15m
Delta
Deal found 2/9![Delta logo]()
$186
This Alaska Airlines deal was found by Cheapflights users on 2/11. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:50 am
ORD
- ANC
2 stops16h 53m
Alaska Airlines
Deal found 2/11![Alaska Airlines logo]()
$187
This Alaska Airlines deal was found by Cheapflights users on 2/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:20 am
ORD
- ANC
1 stop21h 26m
Alaska Airlines
Deal found 2/9![Alaska Airlines logo]()
$189
This Alaska Airlines deal was found by Cheapflights users on 2/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:00 am
ORD
- ANC
1 stop30h 46m
Alaska Airlines
Deal found 2/10![Alaska Airlines logo]()
$190
This Delta deal was found by Cheapflights users on 2/10. 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 7/271:35 pm
ORD
- ANC
2 stops13h 58m
Delta
Deal found 2/10![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 2/10. 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 3/232:05 pm
MDW
- ANC
2 stops13h 24m
Delta
Deal found 2/10![Delta logo]()
$191
This Delta deal was found by Cheapflights users on 2/11. 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 5/108:05 pm
ORD
- ANC
1 stop25h 43m
Delta
Deal found 2/11![Delta logo]()
$193
Find flight deals from Chicago to Alaska
Keep the following information in mind while searching for Chicago to Alaska flight deals. Data was last updated February 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $339 (Alaska Airlines) |
One-way from | $171 (Alaska Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $488 |
Good round-trip deal | $403 or less |
Good one-way deal | $259 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 February 12, 2026.
Use the filters below to find and compare flights from Chicago to Alaska that are best for you.
Fly from
Chicago
Fly to
Alaska
Route
Depart
Return
Price
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Thu 4/2
4:10 pm-7:55 pm
Nonstop6h 45m
Anchorage
Mon 4/6
9:04 pm-6:20 am
Nonstop6h 16m
$339
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sat 4/4
4:10 pm-7:55 pm
Nonstop6h 45m
Anchorage
Sat 4/11
9:04 pm-6:20 am
Nonstop6h 16m
$339
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Tue 6/16
7:40 pm-8:47 am
1 stop16h 07m
Anchorage
Tue 6/23
11:24 pm-8:40 am
Nonstop6h 16m
$349
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Mon 4/6
4:10 pm-7:55 pm
Nonstop6h 45m
Anchorage
Mon 4/13
11:47 pm-11:23 am
1 stop8h 36m
$349
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Tue 7/7
2:00 pm-12:33 am
1 stop13h 33m
Anchorage
Fri 7/10
12:49 pm-8:38 am
1 stop16h 49m
$359
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Fri 4/3
3:22 pm-9:35 pm
1 stop9h 13m
Anchorage
Tue 4/7
12:10 pm-11:59 pm
1 stop8h 49m
$359
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 4/1
9:30 am-6:51 pm
1 stop12h 21m
Anchorage
Tue 4/7
9:15 pm-1:25 pm
1 stop13h 10m
$359
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Wed 5/27
8:20 am-12:08 pm
Nonstop6h 48m
Anchorage
Wed 6/10
11:10 am-5:00 am
2 stops14h 50m
$359
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 4/16
9:31 am-6:46 pm
1 stop12h 15m
Anchorage
Mon 4/20
9:15 pm-8:51 am
1 stop8h 36m
$359
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Wed 4/1
2:35 pm-10:45 pm
1 stop11h 10m
Anchorage
Tue 4/7
11:47 pm-1:12 pm
1 stop10h 25m
$359
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Alaska
Have a flexible travel schedule? Discover the best time to fly to Alaska from Chicago with our price prediction graph.
ORD-ANC
MDW-ANC
ORD-JNU
ORD-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 to Alaska
CHI-USAK
ORD-ANC
MDW-ANC
ORD-JNU
ORD-FAI
What is the cheapest month to book a flight from Chicago to Alaska?
Currently, May is the cheapest month in which you can book a flight from Chicago to Alaska (average of $198). Flying from Chicago to Alaska in July is currently the most expensive (average of $407). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to AK?
Find hourly flight availability from Chicago to Alaska. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 36% on flights from Chicago to Alaska by exploring options for tickets at noon.
Reviews of airlines servicing Alaska
Get insights into the airlines that provide service to Alaska. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Alaska. Reviews last updated February 12, 2026.
See what other customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from Chicago to Alaska have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.1
Crew
8.5
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.1
Crew
8.5
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.1
Crew
8.5
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.1
Crew
8.5
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.1
Crew
8.5
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Food
7.1
Crew
8.5
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Related info for your journey
Find useful and relevant information for your journey from Chicago 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.
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Alternative routes for Chicago to Alaska
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Alaska by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Alaska by cabin class
Find flights from Chicago to Alaska, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Alaska flights
Browse other Chicago and Alaska flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Alaska flights
Consider these flights traveling from Chicago to Alaska.
Top 5 airlines flying from Chicago to Alaska
Discover the top 5 airlines that operate flights from Chicago to Alaska. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$187 | Average$512 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$198 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$318 | Average$705 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$574 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$345 | Average$648 | FlexibilityNo cancel fee | On-time75% |