$210+ 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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Jul 23 — Jul 301
Round-trip
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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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 June 23, 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 June 23, 2026.
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 10/131:30 pm
ORD
- ANC
1 stop12h 13m
United Airlines
Sat 10/178:59 pm
ANC
- ORD
Nonstop6h 11m
United Airlines
Deal found 6/22![United Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 10/127:30 am
ORD
- ANC
2 stops18h 06m
Delta
Mon 10/199:55 pm
ANC
- ORD
1 stop7h 48m
Delta
Deal found 6/22![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 10/1012:30 pm
MDW
- ANC
2 stops24h 46m
Delta
Thu 10/159:55 pm
ANC
- MDW
1 stop7h 54m
Delta
Deal found 6/22![Delta logo]()
$398
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/217:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Sun 8/3010:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Thu 8/68:20 pm
ORD
- ANC
1 stop9h 20m
Alaska Airlines
Wed 8/1212:57 am
ANC
- ORD
2 stops15h 00m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/146:05 am
MDW
- ANC
1 stop15h 55m
Delta
Wed 8/1912:39 am
ANC
- MDW
2 stops14h 22m
Delta
Deal found 6/19![Delta logo]()
$400
This Priceline deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am
ORD
- ANC
2 stops17h 47m
Alaska Airlines
Tue 11/312:25 am
ANC
- ORD
2 stops15h 35m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:30 am
MDW
- ANC
2 stops15h 15m
Southwest
Mon 8/3110:25 pm
ANC
- MDW
2 stops12h 10m
Southwest
Deal found 6/20![Southwest logo]()
$403
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/112:00 pm
ORD
- ANC
2 stops12h 55m
Delta
Tue 8/181:32 am
ANC
- ORD
2 stops13h 47m
Delta
Deal found 6/22![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:00 pm
MDW
- ANC
2 stops15h 45m
Delta
Sat 10/108:30 pm
ANC
- MDW
2 stops13h 03m
Delta
Deal found 6/19![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/411:22 am
ORD
- ANC
1 stop12h 58m
Delta
Tue 8/111:32 am
ANC
- ORD
1 stop8h 51m
Delta
Deal found 6/19![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/197:25 pm
MDW
- ANC
1 stop8h 34m
Delta
Mon 8/3110:10 pm
ANC
- MDW
1 stop12h 00m
Delta
Deal found 6/20![Delta logo]()
$406
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 June 23, 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 June 23, 2026.
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/108:55 am
ORD
- ANC
2 stops11h 19m
Delta
Thu 9/171:32 am
ANC
- ORD
2 stops13h 47m
Delta
Deal found 6/18![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” 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.
Tue 8/256:45 am
ORD
- KTN
1 stop15h 48m
American Airlines
Thu 9/311:53 am
KTN
- ORD
1 stop7h 14m
American Airlines
Deal found 6/23![American Airlines logo]()
$434
This Alaska Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 10/246:00 am
ORD
- FAI
1 stop17h 37m
Alaska Airlines
Tue 10/275:35 am
FAI
- ORD
1 stop15h 24m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$475
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 10/104:05 pm
ORD
- ANC
Nonstop6h 52m
United Airlines
Mon 10/1211:45 pm
ANC
- ORD
1 stop9h 51m
United Airlines
Deal found 6/19![United Airlines logo]()
$486
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:10 pm
MDW
- ANC
1 stop11h 35m
Southwest
Wed 9/210:25 pm
ANC
- MDW
1 stop14h 45m
Southwest
Deal found 6/22![Southwest logo]()
$523
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/208:28 am
ORD
- ANC
2 stops14h 44m
Delta
Fri 8/286:15 am
ANC
- ORD
2 stops12h 15m
Delta
Deal found 6/18![Delta logo]()
$405
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/122:00 pm
ORD
- ANC
2 stops12h 55m
Delta
Wed 8/191:32 am
ANC
- ORD
2 stops13h 47m
Delta
Deal found 6/20![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Thu 9/36:45 am
ORD
- KTN
1 stop11h 14m
American Airlines
Fri 9/119:18 am
KTN
- ORD
1 stop9h 52m
American Airlines
Deal found 6/20![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 10/99:30 am
MDW
- ANC
2 stops14h 33m
Delta
Mon 10/125:15 pm
ANC
- MDW
2 stops12h 34m
Delta
Deal found 6/20![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Wed 8/266:45 am
ORD
- KTN
1 stop15h 48m
American Airlines
Sat 8/2911:53 am
KTN
- ORD
1 stop15h 12m
American Airlines
Deal found 6/19![American Airlines logo]()
$447
This Alaska Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/1212:59 am
ORD
- FAI
1 stop13h 22m
Alaska Airlines
Sat 8/221:28 am
FAI
- ORD
2 stops19h 31m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$507
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/213:35 pm
ORD
- FAI
Nonstop6h 41m
United Airlines
Sat 8/221:00 am
FAI
- ORD
1 stop9h 30m
United Airlines
Deal found 6/20![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/212:00 pm
ORD
- ANC
2 stops12h 55m
Delta
Sun 8/3010:10 pm
ANC
- ORD
2 stops15h 07m
Delta
Deal found 6/22![Delta logo]()
$418
This Alaska Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/286:00 am
ORD
- FAI
2 stops17h 40m
Alaska Airlines
Tue 9/17:09 am
FAI
- ORD
2 stops13h 50m
Alaska Airlines
Deal found 6/18![Alaska Airlines logo]()
$512
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Tue 8/256:45 am
ORD
- KTN
1 stop11h 14m
American Airlines
Mon 8/319:18 am
KTN
- ORD
1 stop9h 49m
American Airlines
Deal found 6/18![American Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/81:00 pm
MDW
- ANC
2 stops15h 45m
Delta
Sun 10/115:15 pm
ANC
- MDW
2 stops12h 30m
Delta
Deal found 6/19![Delta logo]()
$425
This Alaska Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/2812:59 am
ORD
- JNU
3 stops19h 41m
Alaska Airlines
Wed 8/57:36 am
JNU
- ORD
1 stop20h 04m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/811:22 am
ORD
- ANC
1 stop12h 58m
Delta
Fri 8/211:32 am
ANC
- ORD
1 stop18h 57m
Delta
Deal found 6/21![Delta logo]()
$431
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Sun 8/912:59 am
ORD
- JNU
3 stops19h 41m
Alaska Airlines
Tue 8/117:35 am
JNU
- ORD
2 stops25h 28m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$522
This Alaska Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Thu 8/277:20 am
ORD
- JNU
3 stops13h 36m
Alaska Airlines
Sat 9/57:03 am
JNU
- ORD
1 stop13h 56m
Alaska Airlines
Deal found 6/20![Alaska Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/121:25 pm
MDW
- ANC
2 stops14h 34m
Delta
Wed 8/1912:39 am
ANC
- MDW
2 stops14h 22m
Delta
Deal found 6/20![Delta logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 8/56:00 am
ORD
- FAI
2 stops21h 55m
Alaska Airlines
Sun 8/92:25 pm
FAI
- ORD
1 stop15h 10m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$532
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/41:00 pm
ORD
- ANC
1 stop10h 07m
Delta
Tue 7/146:00 am
ANC
- ORD
1 stop14h 38m
Delta
Deal found 6/21![Delta logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/156:00 am
ORD
- JNU
3 stops27h 44m
Alaska Airlines
Tue 9/229:48 am
JNU
- ORD
3 stops17h 32m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$534
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/1512:50 pm
ORD
- JNU
1 stop8h 26m
Delta
Sat 9/267:34 am
JNU
- ORD
1 stop13h 23m
Delta
Deal found 6/21![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Wed 8/267:00 am
ORD
- KTN
2 stops10h 59m
American Airlines
Mon 8/319:18 am
KTN
- ORD
1 stop17h 47m
American Airlines
Deal found 6/18![American Airlines logo]()
$722
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/1012:54 pm
ORD
- JNU
1 stop8h 22m
Delta
Tue 8/117:35 am
JNU
- ORD
1 stop12h 54m
Delta
Deal found 6/22![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 8/111:51 pm
MDW
- ANC
1 stop14h 08m
Delta
Sun 8/1610:10 pm
ANC
- MDW
1 stop12h 00m
Delta
Deal found 6/22![Delta logo]()
$451
This Alaska Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/292:18 pm
ORD
- KTN
2 stops32h 15m
Alaska Airlines
Thu 10/15:45 pm
KTN
- ORD
3 stops33h 35m
Alaska Airlines
Deal found 6/19![Alaska Airlines logo]()
$616
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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
Wed 9/27:35 am
JNU
- MDW
2 stops22h 04m
Delta
Deal found 6/18![Delta logo]()
$459
Last-minute flights from Chicago to AlaskaDiscover last-minute flight deals from Chicago to Alaska. Data last updated June 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Alaska. Data last updated June 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/411:15 am
ORD
- ANC
1 stop13h 01m
Delta
Sat 7/116:00 am
ANC
- ORD
1 stop14h 38m
Delta
Deal found 6/18![Delta logo]()
$444
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/64:10 pm
ORD
- ANC
Nonstop6h 44m
United Airlines
Tue 7/1411:59 pm
ANC
- ORD
Nonstop6h 20m
United Airlines
Deal found 6/22![United Airlines logo]()
$424
This Expedia deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Tue 7/712:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Wed 7/159:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$436
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/88:20 pm
ORD
- ANC
1 stop15h 20m
Alaska Airlines
Tue 7/1411:15 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/91:49 pm
MDW
- ANC
1 stop14h 10m
Delta
Fri 7/1712:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/22![Delta logo]()
$444
This Alaska Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Sun 7/1212:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Wed 7/229:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$411
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/141:18 pm
MDW
- ANC
2 stops14h 41m
Delta
Fri 7/2412:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/20![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/141:00 pm
ORD
- ANC
1 stop13h 58m
Delta
Tue 7/2112:44 pm
ANC
- ORD
1 stop16h 46m
Delta
Deal found 6/21![Delta logo]()
$431
This Alaska Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/1412:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Wed 7/229:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 6/21![Alaska Airlines logo]()
$441
This Delta deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/185:55 pm
ORD
- ANC
1 stop19h 26m
Delta
Tue 7/2112:44 pm
ANC
- ORD
1 stop16h 46m
Delta
Deal found 6/21![Delta logo]()
$406
This Alaska Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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.
Mon 7/2712:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Sun 8/29:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/276:55 am
ORD
- JNU
1 stop14h 31m
Delta
Wed 8/57:35 am
JNU
- ORD
1 stop12h 54m
Delta
Deal found 6/22![Delta logo]()
$444
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 June 23, 2026.
Search for one-way flight options from Chicago to Alaska. Find affordable one-way fares based on user searches. Data last updated June 23, 2026.
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 7/185:55 pm
ORD
- ANC
1 stop19h 26m
Delta
Deal found 6/22![Delta logo]()
$210
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 7/126:55 am
ORD
- ANC
1 stop30h 26m
Delta
Deal found 6/19![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/167:48 am
ORD
- ANC
2 stops15h 24m
Delta
Deal found 6/19![Delta logo]()
$221
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Tue 9/227:17 am
ORD
- FAI
1 stop10h 52m
American Airlines
Deal found 6/21![American Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 6/22![Alaska Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Tue 8/256:45 am
ORD
- FAI
1 stop19h 09m
American Airlines
Deal found 6/20![American Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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.
Thu 9/104:53 pm
ORD
- ANC
Nonstop6h 56m
American Airlines
Deal found 6/21![American Airlines logo]()
$225
This United Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 6/294:10 pm
ORD
- ANC
Nonstop6h 44m
United Airlines
Deal found 6/22![United Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/174:05 pm
ORD
- ANC
Nonstop6h 54m
United Airlines
Deal found 6/19![United Airlines logo]()
$233
This United Airlines deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 9/223:35 pm
ORD
- FAI
Nonstop6h 41m
United Airlines
Deal found 6/21![United Airlines logo]()
$233
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” 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 stop13h 58m
Delta
Deal found 6/22![Delta logo]()
$235
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Fri 8/216:01 pm
ORD
- FAI
1 stop10h 47m
American Airlines
Deal found 6/20![American Airlines logo]()
$235
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 June 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $396 (United Airlines) |
One-way from | $210 (Delta) |
Popular in | July |
Cheapest in | October |
Average price | $565 |
Good round-trip deal | $444 or less |
Good one-way deal | $268 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 June 23, 2026.
Use the filters below to find and compare flights from Chicago to Alaska that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Thu 9/10
8:55 am-5:14 pm
2 stops11h 19m
Anchorage
Thu 9/17
1:32 am-6:19 pm
2 stops13h 47m
$405
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Thu 8/20
8:28 am-8:12 pm
2 stops14h 44m
Anchorage
Fri 8/28
6:15 am-9:30 pm
2 stops12h 15m
$405
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Wed 8/12
2:00 pm-11:55 pm
2 stops12h 55m
Anchorage
Wed 8/19
1:32 am-6:19 pm
2 stops13h 47m
$405
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Fri 10/9
9:30 am-9:03 pm
2 stops14h 33m
Anchorage
Mon 10/12
5:15 pm-8:49 am
2 stops12h 34m
$405
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Fri 8/21
2:00 pm-11:55 pm
2 stops12h 55m
Anchorage
Sun 8/30
10:10 pm-4:17 pm
2 stops15h 07m
$418
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Thu 10/8
1:00 pm-1:45 am
2 stops15h 45m
Anchorage
Sun 10/11
5:15 pm-8:45 am
2 stops12h 30m
$425
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sat 8/8
11:22 am-9:20 pm
1 stop12h 58m
Anchorage
Fri 8/21
1:32 am-11:29 pm
1 stop18h 57m
$431
ChicagoKetchikan
ORD - KTN
ORDKTN
Chicago O'Hare Intl
Tue 8/25
6:45 am-7:33 pm
1 stop15h 48m
Ketchikan
Thu 9/3
11:53 am-10:07 pm
1 stop7h 14m
$434
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 8/12
1:25 pm-12:59 am
2 stops14h 34m
Anchorage
Wed 8/19
12:39 am-6:01 pm
2 stops14h 22m
$443
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sat 7/4
1:00 pm-8:07 pm
1 stop10h 07m
Anchorage
Tue 7/14
6:00 am-11:38 pm
1 stop14h 38m
$444
Showing 1-10 of 60 resultsSorted by cheapest first
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
ORD-FAI
MDW-ANC
MDW-FAI
ORD-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
ORD-FAI
MDW-ANC
MDW-FAI
What is the cheapest month to book a flight from Chicago to Alaska?
Currently, September is the cheapest month in which you can book a flight from Chicago to Alaska (average of $68). Flying from Chicago to Alaska in February is currently the most expensive (average of $352). 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 June 23, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 40% on flights from Chicago to Alaska by exploring options for tickets in the evening.
Weekly flight availability from Chicago to Alaska
Explore weekly flight availability from Chicago to Alaska. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 23, 2026.
The most flights from CHI to USAK are scheduled on a Tuesday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago to Alaska?
How far ahead should I book a flight from Chicago to Alaska?
The price you pay for your flight from Chicago to Alaska may vary depending on when you book. For the best chance of a lower fare, look to book 86 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago to Alaska?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Alaska. Price data was last updated on June 20, 2026.
Travelers seeking maximum savings on their Chicago to Alaska flight should consider departing on Friday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 June 23, 2026.
See what other customers who have flown with Alaska Airlines,Delta, andUnited 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.
Entertainment
7.0
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Entertainment
7.0
Crew
8.5
Boarding
8.1
Food
7.0
Comfort
7.8
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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.
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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 June 23, 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 June 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$387 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$209 | Average$473 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$318 | Average$663 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$543 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$592 | FlexibilityNo cancel fee | On-time75% |