$251+ Cheap flights from Alaska to Chicago (CHI)
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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Oct 18 — Oct 251
Round-trip
1 adult, Economy
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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 Alaska to ChicagoExplore the most affordable flight options available from Alaska to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2026.
Explore the most affordable flight options available from Alaska to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:59 pm -
Nonstop6h 11m
Tue 10/273:35 pm -
Nonstop7h 04m
Deal found 9/16![United Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/228:59 pm -
Nonstop6h 11m
Wed 10/283:35 pm -
Nonstop7h 04m
Deal found 9/15![United Airlines logo]()
$514
This Trip.com deal was found by Cheapflights users on 9/13. 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.
Thu 12/105:00 am -
1 stop8h 31m
Thu 12/178:59 pm -
1 stop15h 55m
Deal found 9/13![Alaska Airlines logo]()
$516
This Delta deal was found by Cheapflights users on 9/16. 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 10/1611:29 am -
1 stop9h 05m
Tue 10/207:20 am -
2 stops16h 21m
Deal found 9/16![Delta logo]()
$517
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/182:29 am -
1 stop11h 21m
Mon 10/267:16 pm -
1 stop19h 05m
Deal found 9/15![Alaska Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/148:59 pm -
Nonstop6h 11m
Wed 11/43:35 pm -
Nonstop7h 04m
Deal found 9/15![United Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 9/13. 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 12/11:15 am -
1 stop19h 47m
Sun 2/287:00 am -
1 stop18h 36m
Deal found 9/13![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 9/15. 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 10/1910:09 pm -
1 stop10h 38m
Mon 10/2610:12 am -
1 stop13h 47m
Deal found 9/15![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 9/13. 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 12/410:07 pm -
1 stop7h 57m
Tue 3/212:40 pm -
1 stop26h 35m
Deal found 9/13![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/201:40 am -
1 stop8h 50m
Tue 10/2712:30 pm -
2 stops11h 11m
Deal found 9/16![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 11/1910:06 pm -
1 stop7h 44m
Sun 11/229:30 am -
2 stops16h 54m
Deal found 9/16![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/17. 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.
Tue 11/31:50 am -
1 stop18h 44m
Sun 11/87:29 am -
2 stops20h 16m
Deal found 9/17![Delta logo]()
$529
Best flights from Alaska to ChicagoDiscover carefully curated flight deals from Alaska to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 18, 2026.
Discover carefully curated flight deals from Alaska to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/12. 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.
Mon 11/211:59 pm -
1 stop10h 16m
Mon 11/93:35 pm -
Nonstop7h 04m
Deal found 9/12![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 9/13. 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 12/41:15 am -
1 stop12h 35m
Wed 12/912:58 pm -
1 stop15h 47m
Deal found 9/13![Delta logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 10/311:43 pm -
2 stops32h 16m
Tue 11/33:59 pm -
2 stops22h 16m
Deal found 9/13![Alaska Airlines logo]()
$592
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/164:06 pm -
1 stop17h 20m
Thu 10/2212:55 pm -
1 stop15h 42m
Deal found 9/15![American Airlines logo]()
$592
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:59 pm -
Nonstop6h 11m
Wed 10/212:30 pm -
1 stop11h 13m
Deal found 9/14![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 9/14. 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.
Tue 10/131:40 am -
1 stop12h 13m
Wed 10/2112:50 pm -
1 stop14h 45m
Deal found 9/14![Delta logo]()
$523
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/148:59 pm -
Nonstop6h 11m
Wed 11/43:35 pm -
Nonstop7h 04m
Deal found 9/15![United Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 9/13. 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 12/510:07 pm -
1 stop7h 48m
Wed 12/910:24 am -
1 stop13h 30m
Deal found 9/13![Delta logo]()
$523
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/295:30 am -
1 stop13h 40m
Fri 10/24:53 pm -
1 stop10h 00m
Deal found 9/15![American Airlines logo]()
$609
This Alaska Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 2/225:50 am -
1 stop15h 09m
Wed 2/245:55 pm -
1 stop9h 23m
Deal found 9/16![Alaska Airlines logo]()
$610
This Delta deal was found by Cheapflights users on 9/14. 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 10/152:24 pm -
2 stops15h 29m
Fri 10/165:30 pm -
1 stop10h 05m
Deal found 9/14![Delta logo]()
$528
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 10/168:59 pm -
Nonstop6h 11m
Tue 10/201:30 pm -
1 stop12h 13m
Deal found 9/16![United Airlines logo]()
$531
This Delta deal was found by Cheapflights users on 9/13. 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 12/106:15 am -
1 stop14h 47m
Thu 12/172:04 pm -
2 stops14h 41m
Deal found 9/13![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/12. 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 11/2510:06 pm -
2 stops17h 08m
Fri 11/276:40 am -
1 stop9h 46m
Deal found 9/12![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/16. 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.
Thu 11/196:15 am -
2 stops12h 32m
Sun 11/226:40 am -
1 stop11h 24m
Deal found 9/16![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/15. 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 10/1910:09 pm -
1 stop10h 38m
Mon 10/261:27 pm -
2 stops14h 08m
Deal found 9/15![Delta logo]()
$528
This Alaska Airlines deal was found by Cheapflights users on 9/14. 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 10/209:40 am -
2 stops26h 13m
Sat 10/249:00 am -
2 stops35h 09m
Deal found 9/14![Alaska Airlines logo]()
$899
This Delta deal was found by Cheapflights users on 9/15. 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 11/2510:06 pm -
1 stop9h 19m
Sun 12/61:41 pm -
2 stops15h 04m
Deal found 9/15![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/17. 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 11/41:50 am -
1 stop8h 40m
Sun 11/87:29 am -
2 stops20h 16m
Deal found 9/17![Delta logo]()
$529
This Delta deal was found by Cheapflights users on 9/13. 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 11/192:21 pm -
2 stops15h 29m
Sun 11/229:30 am -
2 stops16h 54m
Deal found 9/13![Delta logo]()
$533
This Alaska Airlines deal was found by Cheapflights users on 9/13. 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 9/2811:34 am -
2 stops27h 27m
Fri 10/21:03 pm -
2 stops31h 45m
Deal found 9/13![Alaska Airlines logo]()
$1,041
This Delta deal was found by Cheapflights users on 9/16. 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 10/164:05 pm -
2 stops13h 39m
Tue 10/2010:12 am -
2 stops13h 29m
Deal found 9/16![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 9/15. 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 10/146:30 am -
1 stop14h 04m
Wed 11/42:03 pm -
2 stops13h 32m
Deal found 9/15![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 9/17. 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 11/41:50 am -
1 stop8h 40m
Mon 11/97:45 am -
2 stops19h 57m
Deal found 9/17![Delta logo]()
$560
This Delta deal was found by Cheapflights users on 9/17. 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.
Tue 11/31:50 am -
2 stops16h 42m
Mon 11/93:47 pm -
2 stops11h 55m
Deal found 9/17![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 9/17. 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 11/410:09 pm -
1 stop7h 35m
Sun 11/89:29 am -
2 stops14h 30m
Deal found 9/17![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 10/104:05 pm -
2 stops14h 27m
Tue 10/139:29 am -
2 stops14h 12m
Deal found 9/14![Delta logo]()
$569
This Delta deal was found by Cheapflights users on 9/13. 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 9/2910:10 pm -
1 stop12h 10m
Sat 10/39:59 am -
1 stop14h 01m
Deal found 9/13![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 9/14. 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.
Sat 10/104:05 pm -
2 stops13h 39m
Mon 10/1210:12 am -
1 stop13h 47m
Deal found 9/14![Delta logo]()
$646
This Delta deal was found by Cheapflights users on 9/15. 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 9/292:30 pm -
2 stops15h 37m
Fri 10/21:19 pm -
2 stops14h 11m
Deal found 9/15![Delta logo]()
$711
Last-minute flights from Alaska to ChicagoDiscover last-minute flight deals from Alaska to Chicago. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Alaska to Chicago. Data last updated September 18, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/148:59 pm -
Nonstop6h 11m
Wed 11/43:35 pm -
Nonstop7h 04m
Deal found 9/15![United Airlines logo]()
$521
This Delta deal was found by Cheapflights users on 9/15. 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 10/1410:09 pm -
2 stops15h 05m
Wed 10/219:29 am -
2 stops14h 30m
Deal found 9/15![Delta logo]()
$551
This Delta deal was found by Cheapflights users on 9/14. 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 10/152:24 pm -
2 stops15h 20m
Fri 10/161:27 pm -
2 stops14h 08m
Deal found 9/14![Delta logo]()
$563
This Delta deal was found by Cheapflights users on 9/16. 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 10/1611:29 am -
1 stop9h 05m
Tue 10/207:20 am -
2 stops16h 21m
Deal found 9/16![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 9/16. 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 10/164:05 pm -
2 stops13h 39m
Tue 10/2012:27 pm -
1 stop11h 32m
Deal found 9/16![Delta logo]()
$528
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/182:29 am -
1 stop11h 21m
Mon 10/267:16 pm -
1 stop19h 05m
Deal found 9/15![Alaska Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 9/15. 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 10/1910:09 pm -
1 stop10h 38m
Mon 10/2610:12 am -
1 stop13h 47m
Deal found 9/15![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/201:40 am -
1 stop8h 50m
Tue 10/2712:30 pm -
2 stops11h 11m
Deal found 9/16![Delta logo]()
$528
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/218:59 pm -
Nonstop6h 11m
Tue 10/273:35 pm -
Nonstop7h 04m
Deal found 9/16![United Airlines logo]()
$503
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/2111:45 pm -
1 stop9h 51m
Wed 10/281:30 pm -
1 stop12h 26m
Deal found 9/15![United Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/228:59 pm -
Nonstop6h 11m
Wed 10/283:35 pm -
Nonstop7h 04m
Deal found 9/15![United Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 9/15. 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 10/281:40 am -
2 stops12h 07m
Mon 11/212:27 pm -
1 stop11h 32m
Deal found 9/15![Delta logo]()
$558
One-way flights from Alaska to ChicagoSearch for one-way flight options from Alaska to Chicago. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
Search for one-way flight options from Alaska to Chicago. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:59 pm -
Nonstop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$251
This Delta deal was found by Cheapflights users on 9/17. 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.
Mon 11/161:15 am -
2 stops19h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$255
This Delta deal was found by Cheapflights users on 9/17. 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 11/121:15 am -
1 stop19h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$261
This Delta deal was found by Cheapflights users on 9/13. 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 11/110:09 pm -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$261
This Delta deal was found by Cheapflights users on 9/15. 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 12/152:21 pm -
2 stops24h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 9/17. 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.
Sat 11/142:21 pm -
2 stops17h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 9/13. 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 10/134:05 pm -
2 stops14h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/128:59 pm -
Nonstop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![United Airlines logo]()
$269
This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:43 pm -
Nonstop6h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![United Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 9/14. 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 10/1410:09 pm -
2 stops19h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Delta logo]()
$272
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 10/184:05 pm -
2 stops25h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$273
This Delta deal was found by Cheapflights users on 9/15. 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 10/121:40 am -
2 stops19h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$274
Find flight deals from Alaska to Chicago
Keep the following information in mind while searching for Alaska to Chicago flight deals. Data was last updated September 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $503 (United Airlines) |
One-way from | $251 (United Airlines) |
Popular in | November |
Cheapest in | February |
Average price | $412 |
Good round-trip deal | $557 or less |
Good one-way deal | $287 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Alaska to Chicago 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 September 18, 2026.
Use the filters below to find and compare flights from Alaska to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Wed 10/14
8:59 pm-6:10 am
Nonstop6h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$251
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Mon 11/9
10:02 am-11:59 pm
1 stop10h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Wed 12/16
10:07 pm-4:43 pm
1 stop15h 36m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Wed 11/11
1:48 am-11:59 pm
1 stop19h 11m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Fri 10/16
11:29 am-11:34 pm
1 stop9h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Tue 3/9
11:41 am-11:59 pm
1 stop9h 18m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Wed 10/14
1:40 am-1:30 pm
1 stop8h 50m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Sun 11/1
10:09 pm-8:44 am
1 stop7h 35m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Fri 1/15
9:55 pm-8:49 am
1 stop7h 54m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Mon 3/15
1:30 am-9:53 pm
2 stops17h 23m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Alaska to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Alaska with our price prediction graph.
ANC-ORD
ANC-MDW
FAI-ORD
OME-ORD
OTZ-ORD
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 Alaska to Chicago
USAK-CHI
ANC-ORD
ANC-MDW
FAI-ORD
OME-ORD
What is the cheapest month to book a flight from Alaska to Chicago?
Currently, February is the cheapest month in which you can book a flight from Alaska to Chicago (average of $358). Flying from Alaska to Chicago in January is currently the most expensive (average of $734). 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 AK to CHI?
Find hourly flight availability from Alaska to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 18, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Alaska to Chicago as you normally would.
Weekly flight availability from Alaska to Chicago
Explore weekly flight availability from Alaska to Chicago. 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 September 18, 2026.
The most flights from USAK to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).
How much does it cost to fly round-trip from Alaska to Chicago?
Airfare is above average for this route at the moment.
Alaska to Chicago flights typically cost between $397 and $487 in October.The cheapest round-trip price found within the last 5 days was $503 on United Airlines (Oct 21-Oct 27).
How far ahead should I book a flight from Alaska to Chicago?
To ensure you get the cheapest price possible for a flight from Alaska to Chicago, you should look to book at least 75 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Related info for your journey
Find useful and relevant information for your journey from Alaska to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Alaska to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 18, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Alaska to Chicago by cabin class
Find flights from Alaska to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Alaska and Chicago flights
Browse other Alaska and Chicago flight options. Last updated on September 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Alaska to Chicago flights
Consider these flights traveling from Alaska to Chicago.
Top 4 airlines flying from Alaska to Chicago
Discover the top 4 airlines that operate flights from Alaska to Chicago. 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 September 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$532 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$318 | Average$560 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$331 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$489 | FlexibilityNo cancel fee | On-timeN/A |