$212+ 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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Sep 16 — Sep 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 August 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 August 17, 2026.
This SmartFares deal was found by Cheapflights users on 8/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop12h 04m
Mon 10/512:24 pm -
1 stop8h 35m
Deal found 8/14![Alaska Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:53 pm -
Nonstop6h 56m
Thu 9/249:54 pm -
Nonstop6h 31m
Deal found 8/13![American Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:53 pm -
Nonstop6h 56m
Wed 9/309:54 pm -
Nonstop6h 31m
Deal found 8/14![American Airlines logo]()
$427
This eDestinos deal was found by Cheapflights users on 8/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:00 am -
2 stops12h 24m
Tue 10/61:59 am -
2 stops13h 54m
Deal found 8/16![Alaska Airlines logo]()
$432
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:30 pm -
1 stop12h 13m
Mon 10/58:59 pm -
Nonstop6h 11m
Deal found 8/15![United Airlines logo]()
$433
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:53 pm -
Nonstop6h 56m
Mon 10/58:22 pm -
1 stop10h 38m
Deal found 8/14![American Airlines logo]()
$434
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop16h 38m
Sun 9/202:28 am -
1 stop18h 31m
Deal found 8/13![Alaska Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 10/2110:01 am -
1 stop13h 58m
Mon 10/2610:09 pm -
1 stop15h 38m
Deal found 8/12![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 10/219:29 am -
2 stops14h 30m
Sun 10/2510:09 pm -
1 stop15h 38m
Deal found 8/12![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/12. 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 10/231:27 pm -
2 stops14h 08m
Sat 10/2411:34 am -
2 stops18h 10m
Deal found 8/12![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/289:59 am -
1 stop14h 01m
Mon 10/510:10 pm -
2 stops11h 37m
Deal found 8/13![Delta logo]()
$450
This Delta deal was found by Cheapflights users on 8/15. 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.
Tue 10/2012:27 pm -
1 stop11h 32m
Sun 10/2510:09 pm -
1 stop7h 35m
Deal found 8/15![Delta logo]()
$453
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 August 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 August 17, 2026.
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:00 am -
1 stop12h 13m
Mon 9/288:59 pm -
Nonstop6h 11m
Deal found 8/16![United Airlines logo]()
$433
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:16 pm -
1 stop9h 23m
Mon 10/191:59 am -
1 stop13h 21m
Deal found 8/15![Alaska Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 8/13. 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 10/225:30 pm -
1 stop10h 05m
Mon 10/261:40 am -
1 stop8h 49m
Deal found 8/13![Delta logo]()
$443
This American Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 9/2010:00 am -
1 stop12h 33m
Sat 9/269:18 am -
1 stop17h 47m
Deal found 8/12![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 8/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:17 am -
2 stops18h 42m
Tue 9/2211:23 am -
2 stops15h 42m
Deal found 8/16![Multiple Airlines logo]()
$732
This Delta deal was found by Cheapflights users on 8/13. 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 10/2312:50 pm -
1 stop10h 51m
Mon 10/2610:09 pm -
1 stop7h 44m
Deal found 8/13![Delta logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:00 am -
1 stop9h 18m
Mon 9/286:17 pm -
1 stop9h 03m
Deal found 8/15![Alaska Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 8/13. 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 9/207:00 am -
1 stop9h 23m
Mon 9/286:12 am -
1 stop14h 45m
Deal found 8/13![Delta logo]()
$443
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 9/113:35 pm -
Nonstop6h 41m
Sun 9/208:22 pm -
Nonstop5h 58m
Deal found 8/13![United Airlines logo]()
$531
This Delta deal was found by Cheapflights users on 8/15. 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.
Mon 10/196:35 am -
1 stop11h 34m
Mon 10/266:30 am -
1 stop14h 04m
Deal found 8/15![Delta logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 8/277:20 am -
3 stops13h 36m
Sat 9/55:17 pm -
1 stop11h 23m
Deal found 8/14![Alaska Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 8/15. 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.
Tue 10/2010:01 am -
1 stop13h 58m
Tue 10/2710:09 pm -
1 stop10h 38m
Deal found 8/15![Delta logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 8/13. 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.
Sun 9/276:00 am -
1 stop17h 55m
Sun 10/45:36 am -
1 stop15h 23m
Deal found 8/13![Alaska Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 8/13. 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 11/312:27 pm -
1 stop11h 32m
Tue 11/1010:06 pm -
1 stop7h 44m
Deal found 8/13![Delta logo]()
$443
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:35 pm -
Nonstop6h 41m
Sat 9/198:22 pm -
Nonstop5h 58m
Deal found 8/15![United Airlines logo]()
$630
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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.
Wed 10/289:00 am -
1 stop19h 37m
Sun 11/112:13 pm -
1 stop14h 27m
Deal found 8/14![Alaska Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 8/13. 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.
Sat 10/2412:27 pm -
1 stop11h 32m
Mon 10/2610:09 pm -
1 stop7h 35m
Deal found 8/13![Delta logo]()
$443
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:00 am -
2 stops15h 59m
Mon 10/511:17 am -
2 stops15h 48m
Deal found 8/14![Multiple Airlines logo]()
$743
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/155:55 pm -
1 stop11h 43m
Mon 1/185:00 am -
2 stops15h 59m
Deal found 8/15![Alaska Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 8/14. 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 9/282:00 pm -
1 stop10h 00m
Mon 10/510:10 pm -
1 stop7h 34m
Deal found 8/14![Delta logo]()
$443
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:00 am -
2 stops15h 46m
Mon 9/211:51 pm -
2 stops13h 29m
Deal found 8/15![Alaska Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 10/2112:27 pm -
1 stop11h 32m
Tue 10/2710:09 pm -
1 stop7h 35m
Deal found 8/15![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/142:05 pm -
2 stops13h 22m
Mon 9/2111:51 am -
1 stop9h 06m
Deal found 8/13![Delta logo]()
$448
This Alaska Airlines deal was found by Cheapflights users on 8/15. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:00 am -
2 stops15h 40m
Sat 9/191:51 pm -
2 stops13h 29m
Deal found 8/15![Alaska Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 8/14. 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 10/12:05 pm -
2 stops13h 22m
Mon 10/51:40 am -
1 stop8h 49m
Deal found 8/14![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/13. 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 10/239:29 am -
2 stops14h 30m
Mon 10/2610:09 pm -
1 stop7h 35m
Deal found 8/13![Delta logo]()
$448
This Alaska Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 10/16:00 am -
1 stop19h 46m
Thu 10/812:04 pm -
2 stops22h 21m
Deal found 8/16![Alaska Airlines logo]()
$623
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/274:53 pm -
1 stop18h 32m
Sun 10/43:00 pm -
2 stops17h 05m
Deal found 8/13![Multiple Airlines logo]()
$1,111
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 10/2112:27 pm -
2 stops15h 08m
Mon 10/2610:09 pm -
1 stop10h 38m
Deal found 8/15![Delta logo]()
$448
This Delta deal was found by Cheapflights users on 8/14. 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 9/287:00 am -
1 stop9h 23m
Mon 10/510:10 pm -
2 stops15h 22m
Deal found 8/14![Delta logo]()
$450
Last-minute flights from Chicago to AlaskaDiscover last-minute flight deals from Chicago to Alaska. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Alaska. Data last updated August 17, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:53 pm -
Nonstop6h 56m
Thu 9/249:54 pm -
Nonstop6h 31m
Deal found 8/13![American Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/144:53 pm -
Nonstop6h 56m
Mon 9/218:20 pm -
1 stop10h 48m
Deal found 8/13![American Airlines logo]()
$433
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop16h 38m
Sun 9/202:28 am -
1 stop18h 31m
Deal found 8/13![Alaska Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 8/14. 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 9/141:19 pm -
2 stops14h 26m
Mon 9/2110:10 pm -
1 stop12h 10m
Deal found 8/14![Delta logo]()
$448
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:53 pm -
Nonstop6h 56m
Wed 9/309:54 pm -
Nonstop6h 31m
Deal found 8/14![American Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 8/15. 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.
Wed 9/239:59 am -
1 stop10h 15m
Sat 9/2610:10 pm -
1 stop7h 38m
Deal found 8/15![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 8/14. 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 9/249:29 am -
2 stops14h 31m
Mon 9/282:28 pm -
2 stops15h 20m
Deal found 8/14![Delta logo]()
$455
This SmartFares deal was found by Cheapflights users on 8/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am -
1 stop12h 04m
Mon 10/512:24 pm -
1 stop8h 35m
Deal found 8/14![Alaska Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:53 pm -
Nonstop6h 56m
Mon 10/58:22 pm -
1 stop10h 38m
Deal found 8/14![American Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 8/14. 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 9/282:00 pm -
1 stop10h 00m
Mon 10/510:10 pm -
1 stop7h 34m
Deal found 8/14![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 8/14. 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 9/287:00 am -
1 stop14h 16m
Mon 10/57:23 am -
1 stop13h 34m
Deal found 8/14![Delta logo]()
$464
This eDestinos deal was found by Cheapflights users on 8/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/308:00 am -
2 stops12h 24m
Tue 10/61:59 am -
2 stops13h 54m
Deal found 8/16![Alaska Airlines logo]()
$432
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 August 17, 2026.
Search for one-way flight options from Chicago to Alaska. Find affordable one-way fares based on user searches. Data last updated August 17, 2026.
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:53 pm -
Nonstop6h 56m
Deal found 8/17![American Airlines logo]()
$212
This United Airlines deal was found by Cheapflights users on 8/13. 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.
Mon 9/144:05 pm -
Nonstop6h 54m
Deal found 8/13![United Airlines logo]()
$213
This Alaska Airlines deal was found by Cheapflights users on 8/14. 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 10/157:16 pm -
1 stop20h 15m
Deal found 8/14![Alaska Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 8/14. 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 10/1510:01 am -
1 stop13h 58m
Deal found 8/14![Delta logo]()
$222
This Delta deal was found by Cheapflights users on 8/13. 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.
Mon 9/142:05 pm -
2 stops13h 22m
Deal found 8/13![Delta logo]()
$228
This Delta deal was found by Cheapflights users on 8/12. 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 9/262:00 pm -
2 stops13h 27m
Deal found 8/12![Delta logo]()
$228
This American Airlines deal was found by Cheapflights users on 8/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:53 pm -
Nonstop6h 56m
Deal found 8/13![American Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 8/17. 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 9/187:00 am -
1 stop12h 27m
Deal found 8/17![Delta logo]()
$232
This Delta deal was found by Cheapflights users on 8/16. 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 9/309:59 am -
1 stop14h 01m
Deal found 8/16![Delta logo]()
$232
This Delta deal was found by Cheapflights users on 8/13. 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 9/137:05 am -
2 stops20h 22m
Deal found 8/13![Delta logo]()
$233
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Wed 9/94:26 pm -
1 stop10h 33m
Deal found 8/12![United Airlines logo]()
$240
This Delta deal was found by Cheapflights users on 8/14. 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.
Wed 9/97:13 pm -
1 stop8h 47m
Deal found 8/14![Delta logo]()
$240
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 August 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $422 (SmartFares) |
One-way from | $212 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $500 |
Good round-trip deal | $406 or less |
Good one-way deal | $235 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 August 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
Thu 9/17
5:00 am-2:13 pm
1 stop12h 13m
Anchorage
Mon 9/28
8:59 pm-6:10 am
Nonstop6h 11m
$433
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Thu 10/15
7:16 pm-1:39 am
1 stop9h 23m
Anchorage
Mon 10/19
1:59 am-6:20 pm
1 stop13h 21m
$443
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Thu 10/22
5:30 pm-12:35 am
1 stop10h 05m
Anchorage
Mon 10/26
1:40 am-1:29 pm
1 stop8h 49m
$443
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Fri 10/23
12:50 pm-8:41 pm
1 stop10h 51m
Anchorage
Mon 10/26
10:09 pm-8:53 am
1 stop7h 44m
$443
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Tue 9/15
8:00 am-2:18 pm
1 stop9h 18m
Anchorage
Mon 9/28
6:17 pm-6:20 am
1 stop9h 03m
$443
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sun 9/20
7:00 am-1:23 pm
1 stop9h 23m
Anchorage
Mon 9/28
6:12 am-11:57 pm
1 stop14h 45m
$443
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Mon 10/19
6:35 am-3:09 pm
1 stop11h 34m
Anchorage
Mon 10/26
6:30 am-11:34 pm
1 stop14h 04m
$443
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Tue 10/20
10:01 am-8:59 pm
1 stop13h 58m
Anchorage
Tue 10/27
10:09 pm-11:47 am
1 stop10h 38m
$443
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Tue 11/3
12:27 pm-8:59 pm
1 stop11h 32m
Anchorage
Tue 11/10
10:06 pm-8:50 am
1 stop7h 44m
$443
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Sat 10/24
12:27 pm-8:59 pm
1 stop11h 32m
Anchorage
Mon 10/26
10:09 pm-8:44 am
1 stop7h 35m
$443
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-KTN
ORD-SIT
ORD-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-KTN
ORD-SIT
ORD-FAI
What is the cheapest month to book a flight from Chicago to Alaska?
Currently, October is the cheapest month in which you can book a flight from Chicago to Alaska (average of $428). Flying from Chicago to Alaska in March is currently the most expensive (average of $632). 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 August 17, 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 August 17, 2026.
The most flights from CHI to USAK are scheduled on a Sunday (11 on average). You will have fewer flight options on Wednesday, 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?
Airfare is typical for this route at the moment.
Chicago to Alaska flights typically cost between $404 and $623 in September.The cheapest round-trip price found within the last 5 days was $422 on Alaska Airlines (Sep 28-Oct 5).
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 August 15, 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 August 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.
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.0
Crew
8.5
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Comfort
7.8
Food
7.0
Overall
7.9
Boarding
8.1
Entertainment
7.0
Crew
8.5
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 August 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 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$213 | Average$493 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$318 | Average$666 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$338 | Average$576 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$348 | Average$531 | FlexibilityNo cancel fee | On-time71% |