$201+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Jun 6 — Jun 131
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 May 7, 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 May 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Tue 9/110:26 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$398
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:57 pm
ORD
- ANC
Nonstop6h 51m
American Airlines
Tue 9/89:55 pm
ANC
- ORD
Nonstop6h 25m
American Airlines
Deal found 5/5![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Sun 5/319:53 pm
ANC
- ORD
Nonstop6h 28m
American Airlines
Deal found 5/4![American Airlines logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/67:49 pm
ORD
- ANC
1 stop18h 20m
Alaska Airlines
Sun 6/711:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$403
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:49 pm
ORD
- ANC
1 stop17h 02m
Alaska Airlines
Thu 6/411:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/295:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Sun 6/79:50 pm
ANC
- ORD
Nonstop6h 33m
American Airlines
Deal found 5/2![American Airlines logo]()
$408
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:20 pm
ORD
- ANC
1 stop9h 20m
Alaska Airlines
Mon 8/1711:21 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:20 am
ORD
- ANC
1 stop16h 18m
Alaska Airlines
Wed 9/210:26 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$410
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:49 pm
ORD
- ANC
1 stop25h 33m
Alaska Airlines
Fri 6/129:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$412
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:20 am
ORD
- ANC
1 stop29h 42m
Alaska Airlines
Wed 7/19:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 5/4. 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 8/111:52 pm
MDW
- ANC
1 stop14h 07m
Delta
Wed 8/1212:54 pm
ANC
- MDW
1 stop16h 46m
Delta
Deal found 5/4![Delta logo]()
$413
This Expedia deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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.
Sat 8/812:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Sun 8/1612:57 am
ANC
- ORD
2 stops15h 00m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$414
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 May 7, 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 May 7, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:59 pm
ORD
- ANC
1 stop20h 26m
Alaska Airlines
Mon 8/2410:26 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3012:47 pm
ORD
- ANC
1 stop12h 43m
Delta
Sat 6/61:30 am
ANC
- ORD
1 stop9h 00m
Delta
Deal found 5/6![Delta logo]()
$419
This American Airlines deal was found by Cheapflights users on 5/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/216:55 am
ORD
- KTN
1 stop9h 11m
American Airlines
Mon 5/259:20 am
KTN
- ORD
1 stop17h 52m
American Airlines
Deal found 5/6![American Airlines logo]()
$778
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 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 42m
Alaska Airlines
Wed 9/21:35 am
ANC
- ORD
1 stop19h 06m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 5/4. 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.
Sun 5/319:25 am
ORD
- ANC
1 stop13h 51m
Delta
Thu 7/306:00 am
ANC
- ORD
1 stop14h 38m
Delta
Deal found 5/4![Delta logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:40 am
ORD
- ANC
1 stop13h 42m
Alaska Airlines
Mon 6/11:09 pm
ANC
- ORD
1 stop14h 11m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/249:54 am
MDW
- ANC
1 stop18h 01m
Delta
Tue 7/712:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 5/6![Delta logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:00 am
ORD
- ANC
2 stops14h 51m
Alaska Airlines
Tue 9/86:15 pm
ANC
- ORD
1 stop9h 07m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 7/72:02 pm
ORD
- ANC
2 stops11h 24m
Delta
Wed 7/156:00 am
ANC
- ORD
1 stop14h 38m
Delta
Deal found 5/3![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 5/5. 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 5/2912:30 pm
ORD
- ANC
2 stops15h 20m
Delta
Sat 6/612:35 am
ANC
- ORD
1 stop15h 23m
Delta
Deal found 5/5![Delta logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 8/157:20 am
ORD
- ANC
2 stops14h 17m
Alaska Airlines
Wed 8/196:05 am
ANC
- ORD
1 stop14h 54m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/241:26 pm
MDW
- ANC
2 stops14h 29m
Delta
Wed 7/16:00 am
ANC
- MDW
1 stop9h 18m
Delta
Deal found 5/2![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 8/98:48 am
ORD
- ANC
1 stop15h 08m
Delta
Sun 8/161:32 am
ANC
- ORD
2 stops13h 47m
Delta
Deal found 5/3![Delta logo]()
$426
This Delta deal was found by Cheapflights users on 5/5. 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.
Mon 6/297:01 am
ORD
- ANC
2 stops14h 40m
Delta
Fri 7/108:15 am
ANC
- ORD
2 stops10h 33m
Delta
Deal found 5/5![Delta logo]()
$431
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:49 pm
ORD
- SIT
2 stops25h 40m
Alaska Airlines
Tue 6/97:00 am
SIT
- ORD
1 stop9h 03m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 5/5. 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 6/241:26 pm
MDW
- ANC
2 stops14h 29m
Delta
Wed 7/112:35 am
ANC
- MDW
2 stops12h 05m
Delta
Deal found 5/5![Delta logo]()
$431
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:20 am
ORD
- FAI
1 stop20h 35m
Alaska Airlines
Sat 7/1812:39 am
FAI
- ORD
1 stop25h 21m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 stops14h 41m
Delta
Wed 7/156:00 am
ANC
- MDW
1 stop9h 18m
Delta
Deal found 5/3![Delta logo]()
$456
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2712:59 am
ORD
- JNU
3 stops19h 41m
Alaska Airlines
Tue 8/115:03 am
JNU
- ORD
2 stops15h 33m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/165:55 pm
ORD
- FAI
1 stop9h 40m
Delta
Mon 7/201:35 am
FAI
- ORD
1 stop12h 08m
Delta
Deal found 5/5![Delta logo]()
$470
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2612:59 am
ORD
- JNU
3 stops19h 41m
Alaska Airlines
Wed 8/127:00 am
JNU
- ORD
2 stops13h 36m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$587
This Delta deal was found by Cheapflights users on 5/6. 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.
Fri 6/126:55 am
ORD
- FAI
1 stop9h 40m
Delta
Mon 6/221:35 am
FAI
- ORD
2 stops14h 23m
Delta
Deal found 5/6![Delta logo]()
$476
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/1212:59 am
ORD
- FAI
1 stop26h 45m
Alaska Airlines
Thu 6/1812:39 am
FAI
- ORD
1 stop25h 21m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 7/226:55 am
ORD
- JNU
1 stop14h 26m
Delta
Thu 7/307:20 am
JNU
- ORD
1 stop13h 18m
Delta
Deal found 5/2![Delta logo]()
$480
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 8/58:48 pm
JNU
- ORD
2 stops19h 09m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$592
This Delta deal was found by Cheapflights users on 5/4. 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 6/41:22 pm
MDW
- ANC
2 stops14h 09m
Delta
Thu 6/1110:02 pm
ANC
- MDW
1 stop7h 35m
Delta
Deal found 5/4![Delta logo]()
$486
This Alaska Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 6/196:00 am
ORD
- FAI
2 stops21h 55m
Alaska Airlines
Fri 6/2612:39 am
FAI
- ORD
1 stop25h 21m
Alaska Airlines
Deal found 5/3![Alaska Airlines logo]()
$596
This Delta deal was found by Cheapflights users on 5/5. 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.
Mon 6/19:22 am
MDW
- ANC
2 stops14h 27m
Delta
Fri 6/59:30 pm
ANC
- MDW
1 stop12h 12m
Delta
Deal found 5/5![Delta logo]()
$488
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:52 pm
ORD
- SIT
1 stop7h 50m
Alaska Airlines
Sun 6/142:08 pm
SIT
- ORD
2 stops11h 52m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$603
This Delta deal was found by Cheapflights users on 5/6. 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 6/309:54 am
MDW
- FAI
1 stop13h 49m
Delta
Sun 7/129:59 pm
FAI
- MDW
1 stop17h 19m
Delta
Deal found 5/6![Delta logo]()
$503
Last-minute flights from Chicago to AlaskaDiscover last-minute flight deals from Chicago to Alaska. Data last updated May 7, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Alaska. Data last updated May 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Sun 5/319:53 pm
ANC
- ORD
Nonstop6h 28m
American Airlines
Deal found 5/4![American Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Tue 6/29:53 pm
ANC
- ORD
Nonstop6h 28m
American Airlines
Deal found 5/5![American Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:49 pm
ORD
- ANC
1 stop17h 02m
Alaska Airlines
Thu 6/411:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 5/295:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Sun 6/79:50 pm
ANC
- ORD
Nonstop6h 33m
American Airlines
Deal found 5/2![American Airlines logo]()
$408
This American Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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.
Sat 5/305:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Sat 6/69:50 pm
ANC
- ORD
Nonstop6h 33m
American Airlines
Deal found 5/2![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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.
Sat 5/305:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Sun 6/711:42 pm
ANC
- ORD
1 stop10h 01m
American Airlines
Deal found 5/3![American Airlines logo]()
$418
This Alaska Airlines deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/67:49 pm
ORD
- ANC
1 stop18h 20m
Alaska Airlines
Sun 6/711:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 5/2![Alaska Airlines logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:49 pm
ORD
- ANC
1 stop25h 33m
Alaska Airlines
Fri 6/129:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$412
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:40 am
ORD
- ANC
1 stop16h 00m
Alaska Airlines
Tue 6/1611:21 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:20 am
ORD
- ANC
1 stop29h 42m
Alaska Airlines
Wed 7/19:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 5/5. 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 6/241:00 pm
ORD
- ANC
1 stop13h 56m
Delta
Wed 7/112:35 am
ANC
- ORD
1 stop15h 23m
Delta
Deal found 5/5![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 5/5. 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 6/241:49 pm
MDW
- ANC
1 stop14h 06m
Delta
Wed 7/110:30 pm
ANC
- MDW
1 stop11h 16m
Delta
Deal found 5/5![Delta logo]()
$419
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 May 7, 2026.
Search for one-way flight options from Chicago to Alaska. Find affordable one-way fares based on user searches. Data last updated May 7, 2026.
This American Airlines deal was found by Cheapflights users on 5/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/124:57 pm
ORD
- ANC
Nonstop6h 51m
American Airlines
Deal found 5/6![American Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 5/6. 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 6/231:00 pm
ORD
- ANC
1 stop10h 07m
Delta
Deal found 5/6![Delta logo]()
$210
This Delta deal was found by Cheapflights users on 5/4. 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 6/237:16 pm
MDW
- ANC
1 stop8h 39m
Delta
Deal found 5/4![Delta logo]()
$210
This Delta deal was found by Cheapflights users on 5/6. 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 7/285:18 pm
ORD
- ANC
2 stops11h 36m
Delta
Deal found 5/6![Delta logo]()
$216
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” 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 stops12h 24m
Delta
Deal found 5/3![Delta logo]()
$216
This Delta deal was found by Cheapflights users on 5/5. 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 6/268:21 pm
ORD
- ANC
1 stop25h 20m
Delta
Deal found 5/5![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 5/4. 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 5/2812:47 pm
ORD
- FAI
1 stop14h 48m
Delta
Deal found 5/4![Delta logo]()
$219
This Delta deal was found by Cheapflights users on 5/6. 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.
Sun 6/217:37 pm
ORD
- ANC
1 stop30h 43m
Delta
Deal found 5/6![Delta logo]()
$220
This Alaska Airlines deal was found by Cheapflights users on 5/6. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:05 am
ORD
- ANC
Nonstop6h 48m
Alaska Airlines
Deal found 5/6![Alaska Airlines logo]()
$221
This Alaska Airlines deal was found by Cheapflights users on 5/5. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:40 am
ORD
- ANC
1 stop12h 42m
Alaska Airlines
Deal found 5/5![Alaska Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 5/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:15 pm
ORD
- JNU
1 stop13h 29m
American Airlines
Deal found 5/6![American Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 5/2. Clicking the “Pick Dates” 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 6/78:36 am
ORD
- ANC
1 stop15h 16m
Delta
Deal found 5/2![Delta logo]()
$239
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 May 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $399 (American Airlines) |
One-way from | $201 (American Airlines) |
Popular in | June |
Cheapest in | October |
Average price | $494 |
Good round-trip deal | $473 or less |
Good one-way deal | $205 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 May 7, 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
Fri 8/14
7:59 pm-1:25 pm
1 stop20h 26m
Anchorage
Mon 8/24
10:26 pm-7:40 am
Nonstop6h 14m
$409
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sat 8/8
12:59 am-4:41 am
Nonstop6h 42m
Anchorage
Wed 9/2
1:35 am-11:41 pm
1 stop19h 06m
$409
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sat 5/30
12:47 pm-10:30 pm
1 stop12h 43m
Anchorage
Sat 6/6
1:30 am-1:30 pm
1 stop9h 00m
$419
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sun 5/31
9:25 am-8:16 pm
1 stop13h 51m
Anchorage
Thu 7/30
6:00 am-11:38 pm
1 stop14h 38m
$419
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Fri 5/29
7:40 am-6:22 pm
1 stop13h 42m
Anchorage
Mon 6/1
1:09 pm-6:20 am
1 stop14h 11m
$419
ChicagoAnchorage
MDW - ANC
MDWANC
Chicago Midway
Wed 6/24
9:54 am-12:55 am
1 stop18h 01m
Anchorage
Tue 7/7
12:44 pm-8:37 am
1 stop16h 53m
$419
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Thu 8/27
9:00 am-8:51 pm
2 stops14h 51m
Anchorage
Tue 9/8
6:15 pm-6:22 am
1 stop9h 07m
$424
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Tue 7/7
2:02 pm-10:26 pm
2 stops11h 24m
Anchorage
Wed 7/15
6:00 am-11:38 pm
1 stop14h 38m
$424
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Fri 5/29
12:30 pm-12:50 am
2 stops15h 20m
Anchorage
Sat 6/6
12:35 am-6:58 pm
1 stop15h 23m
$424
ChicagoAnchorage
ORD - ANC
ORDANC
Chicago O'Hare Intl
Sat 8/15
7:20 am-6:37 pm
2 stops14h 17m
Anchorage
Wed 8/19
6:05 am-11:59 pm
1 stop14h 54m
$424
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
MDW-ANC
ORD-FAI
ORD-JNU
ORD-SIT
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-FAI
ORD-JNU
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 47 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 $160). 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 May 7, 2026.
Unlike in the afternoon, when flights are generally more expensive, you can save up to 29% on flights from Chicago to Alaska by exploring options for tickets at noon.
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 May 7, 2026.
The most flights from CHI to USAK are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Chicago to Alaska?
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 May 7, 2026.
See what other customers who have flown with Alaska Airlines,Delta, andHawaiian 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.
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Food
7.1
Crew
8.5
Comfort
7.8
Boarding
8.1
Overall
7.9
Entertainment
7.0
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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 May 7, 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 May 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$178 | Average$463 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$187 | Average$512 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$318 | Average$693 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$551 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$683 | FlexibilityNo cancel fee | On-time75% |