$262+ Cheap flights from Chicago (CHI) to Alaska
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Nov 16 — Nov 231
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 October 17, 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 October 17, 2026.
This lol.travel deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:00 am -
1 stop14h 48m
Wed 11/183:51 pm -
2 stops10h 49m
Deal found 10/12![Alaska Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/46:40 am -
1 stop19h 48m
Sun 12/131:15 am -
1 stop12h 35m
Deal found 10/16![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1310:34 am -
1 stop13h 24m
Mon 11/1610:08 pm -
1 stop7h 42m
Deal found 10/14![Delta logo]()
$523
This flugladen.de deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/43:19 pm -
1 stop9h 58m
Tue 12/88:05 am -
1 stop12h 54m
Deal found 10/12![Alaska Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/612:58 pm -
1 stop27h 28m
Sun 12/131:15 am -
1 stop19h 42m
Deal found 10/16![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/211:39 am -
2 stops17h 06m
Mon 12/141:15 am -
1 stop9h 15m
Deal found 10/16![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:55 pm -
1 stop10h 44m
Thu 11/262:21 pm -
2 stops18h 42m
Deal found 10/12![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/12![Delta logo]()
$530
This Alaska Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/22:08 pm -
2 stops26h 30m
Thu 12/35:18 pm -
1 stop18h 03m
Deal found 10/16![Alaska Airlines logo]()
$533
This Alaska Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/22:08 pm -
2 stops26h 30m
Tue 12/152:53 pm -
1 stop22h 38m
Deal found 10/17![Alaska Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/2312:58 pm -
1 stop13h 26m
Fri 11/276:06 am -
1 stop14h 53m
Deal found 10/16![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 12/712:39 pm -
1 stop11h 14m
Sun 12/1310:05 pm -
1 stop10h 54m
Deal found 10/16![Delta logo]()
$543
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 October 17, 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 October 17, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/88:00 am -
1 stop16h 39m
Thu 3/185:00 am -
1 stop15h 59m
Deal found 10/12![Alaska Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:49 am -
2 stops17h 04m
Mon 12/141:15 am -
1 stop12h 35m
Deal found 10/12![Delta logo]()
$528
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:35 pm -
1 stop11h 24m
Mon 12/78:45 pm -
Nonstop6h 14m
Deal found 10/12![United Airlines logo]()
$606
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 12/276:54 am -
1 stop12h 54m
Sat 1/25:35 pm -
1 stop16h 00m
Deal found 10/15![American Airlines logo]()
$751
This Alaska Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/236:00 am -
1 stop10h 27m
Mon 11/3012:11 pm -
2 stops14h 45m
Deal found 10/14![Alaska Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/12![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 3/2612:50 pm -
1 stop15h 55m
Tue 3/301:30 am -
1 stop9h 01m
Deal found 10/15![Delta logo]()
$543
This Alaska Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/22:08 pm -
2 stops26h 30m
Tue 12/152:53 pm -
2 stops25h 07m
Deal found 10/17![Alaska Airlines logo]()
$545
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 2/42:24 pm -
1 stop11h 51m
Sun 2/78:31 pm -
Nonstop6h 28m
Deal found 10/13![United Airlines logo]()
$606
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 2/28:00 am -
2 stops15h 30m
Fri 2/124:00 pm -
1 stop18h 09m
Deal found 10/13![Alaska Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/39:37 am -
2 stops16h 51m
Sat 12/54:03 pm -
2 stops14h 34m
Deal found 10/17![Delta logo]()
$555
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:35 pm -
Nonstop7h 04m
Sat 10/318:54 pm -
Nonstop6h 16m
Deal found 10/12![United Airlines logo]()
$622
This Alaska Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/69:00 am -
1 stop17h 21m
Sat 12/122:53 pm -
1 stop11h 44m
Deal found 10/17![Alaska Airlines logo]()
$563
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/1112:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/17![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/1312:30 pm -
2 stops16h 09m
Fri 11/204:04 pm -
2 stops13h 46m
Deal found 10/13![Delta logo]()
$585
This Alaska Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/229:01 am -
1 stop17h 10m
Thu 12/317:03 am -
2 stops19h 37m
Deal found 10/14![Alaska Airlines logo]()
$608
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 10/2912:27 pm -
1 stop11h 32m
Mon 11/210:09 pm -
1 stop7h 35m
Deal found 10/17![Delta logo]()
$599
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 12/236:57 pm -
1 stop9h 51m
Wed 12/305:10 am -
2 stops11h 51m
Deal found 10/13![Alaska Airlines logo]()
$608
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 12/116:20 am -
2 stops11h 44m
Sun 12/275:12 pm -
2 stops15h 41m
Deal found 10/17![Delta logo]()
$603
This Priceline deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:29 pm -
1 stop12h 06m
Sat 12/125:00 am -
2 stops11h 10m
Deal found 10/12![Alaska Airlines logo]()
$608
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 10/219:29 am -
2 stops14h 30m
Mon 10/264:05 pm -
2 stops13h 39m
Deal found 10/16![Delta logo]()
$611
This Alaska Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/276:00 am -
1 stop10h 27m
Sun 11/296:47 pm -
1 stop26h 12m
Deal found 10/16![Alaska Airlines logo]()
$624
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:27 pm -
2 stops11h 14m
Mon 11/24:05 pm -
2 stops13h 39m
Deal found 10/12![Delta logo]()
$611
This Alaska Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/66:35 pm -
1 stop10h 15m
Mon 11/912:13 pm -
1 stop8h 46m
Deal found 10/16![Alaska Airlines logo]()
$630
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 10/299:29 am -
2 stops14h 12m
Sat 11/1410:08 pm -
1 stop10h 42m
Deal found 10/17![Delta logo]()
$619
This Alaska Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 1/42:08 pm -
2 stops24h 09m
Sun 1/105:07 am -
2 stops15h 52m
Deal found 10/17![Alaska Airlines logo]()
$633
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/1012:58 pm -
1 stop14h 39m
Mon 11/161:42 am -
2 stops11h 59m
Deal found 10/13![Delta logo]()
$623
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:29 am -
2 stops14h 12m
Mon 11/210:09 pm -
1 stop7h 35m
Deal found 10/12![Delta logo]()
$647
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/2212:27 pm -
1 stop11h 32m
Sat 10/317:45 pm -
1 stop13h 02m
Deal found 10/13![Delta logo]()
$662
This Alaska Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/316:00 am -
3 stops41h 02m
Tue 1/127:16 am -
2 stops28h 05m
Deal found 10/14![Alaska Airlines logo]()
$841
Last-minute flights from Chicago to AlaskaDiscover last-minute flight deals from Chicago to Alaska. Data last updated October 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Alaska. Data last updated October 17, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/223:49 pm -
1 stop10h 50m
Thu 11/198:00 am -
1 stop12h 59m
Deal found 10/14![Alaska Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” 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 11/1112:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/17![Delta logo]()
$568
This American Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:54 pm -
1 stop11h 43m
Wed 11/186:33 pm -
1 stop14h 53m
Deal found 10/12![American Airlines logo]()
$574
This lol.travel deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:00 am -
1 stop14h 48m
Wed 11/183:51 pm -
2 stops10h 49m
Deal found 10/12![Alaska Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/12![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1212:38 pm -
2 stops16h 01m
Wed 11/184:04 pm -
2 stops14h 00m
Deal found 10/12![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/1212:30 pm -
1 stop11h 28m
Thu 11/192:21 pm -
2 stops15h 29m
Deal found 10/13![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1310:34 am -
1 stop13h 24m
Mon 11/1610:08 pm -
1 stop7h 42m
Deal found 10/14![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/1312:38 pm -
2 stops13h 46m
Mon 11/1610:08 pm -
1 stop13h 47m
Deal found 10/14![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/219:59 am -
1 stop13h 59m
Thu 11/261:15 am -
1 stop9h 22m
Deal found 10/16![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:55 pm -
1 stop10h 44m
Wed 11/251:15 am -
1 stop12h 32m
Deal found 10/12![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” 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 11/2312:58 pm -
1 stop13h 26m
Fri 11/276:06 am -
1 stop14h 53m
Deal found 10/16![Delta logo]()
$543
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 October 17, 2026.
Search for one-way flight options from Chicago to Alaska. Find affordable one-way fares based on user searches. Data last updated October 17, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/127:00 am -
1 stop19h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Alaska Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 1/812:30 pm -
2 stops16h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/115:20 pm -
1 stop30h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Delta logo]()
$270
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/135:55 pm -
1 stop10h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$272
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/167:00 am -
2 stops16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Alaska Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 3/296:59 pm -
2 stops20h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/31:41 pm -
2 stops15h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$278
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/138:40 pm -
1 stop27h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$280
This Alaska Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/147:00 am -
1 stop14h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Alaska Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 1/105:15 pm -
2 stops26h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Delta logo]()
$283
This American Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” 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 2/211:00 am -
1 stop16h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![American Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/273:35 pm -
Nonstop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![United Airlines logo]()
$291
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 October 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $507 (Expedia) |
One-way from | $262 (Alaska Airlines) |
Popular in | November |
Cheapest in | February |
Average price | $571 |
Good round-trip deal | $503 or less |
Good one-way deal | $292 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 7,457,451 searches. Data last updated October 17, 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 Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Fri 11/13
8:29 am-11:24 pm
2 stops17h 55m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$268
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Fri 1/8
12:30 pm-1:45 am
2 stops16h 15m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$268
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sun 11/15
6:40 am-11:24 pm
1 stop19h 44m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$282
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sun 11/22
6:40 am-3:04 pm
1 stop11h 24m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$282
ChicagoJuneau
ORD Chicago O'Hare Intl - JNU Juneau Intl
ORDJNU
Chicago O'Hare Intl
Tue 2/2
11:00 am-12:28 am
1 stop16h 28m
Juneau Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$287
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sat 11/14
2:44 pm-1:39 am
2 stops13h 55m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$288
Quickest round-trip
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Wed 1/20
3:35 pm-7:34 pm
Nonstop6h 59m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$293
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Mon 11/9
5:55 pm-1:39 am
1 stop10h 44m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$300
ChicagoFairbanks
ORD Chicago O'Hare Intl - FAI Fairbanks
ORDFAI
Chicago O'Hare Intl
Sat 11/14
12:00 pm-12:37 am
1 stop15h 37m
Fairbanks
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$302
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sun 11/8
3:35 pm-7:39 pm
Nonstop7h 04m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$306
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-JNU
ORD-FAI
MDW-FAI
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, February is the cheapest month in which you can book a flight from Chicago to Alaska (average of $426). Flying from Chicago to Alaska in March is currently the most expensive (average of $650). 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 October 17, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 39% 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 October 17, 2026.
The most flights from CHI to USAK are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, 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?
Airfare is typical for this route at the moment.
Chicago to Alaska flights typically cost between $463 and $700 in April.The cheapest round-trip price found within the last 5 days was $507 on Alaska Airlines (Apr 5-Apr 13).
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 October 10, 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 October 17, 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.
Overall
7.9
Food
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Overall
7.9
Food
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Overall
7.9
Food
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Overall
7.9
Food
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Overall
7.9
Food
7.0
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
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 October 17, 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 4 airlines flying from Chicago to Alaska
Discover the top 4 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 7,457,451 searches. Data last updated October 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$213 | Average$495 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$578 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$369 | Average$658 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$373 | Average$537 | FlexibilityNo cancel fee | On-time71% |