$266+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Dec 11 — Dec 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Alaska to Chicago 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Alaska to Chicago
Cheapest
Best
Last-minute
One-way
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 November 11, 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 November 11, 2026.
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/231:20 am -
1 stop19h 39m
Fri 12/259:59 am -
1 stop11h 56m
Deal found 11/10![Delta logo]()
$533
This Trip.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/287:00 am -
1 stop19h 40m
Wed 1/66:47 pm -
1 stop21h 27m
Deal found 11/9![Alaska Airlines logo]()
$534
This Priceline deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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.
Mon 12/282:50 am -
1 stop18h 09m
Thu 1/78:00 am -
2 stops15h 55m
Deal found 11/9![Alaska Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/295:40 am -
2 stops15h 22m
Thu 1/71:45 pm -
2 stops15h 03m
Deal found 11/9![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/205:40 am -
1 stop12h 59m
Thu 12/242:27 pm -
1 stop9h 23m
Deal found 11/10![Delta logo]()
$553
This Priceline deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/61:37 am -
1 stop8h 33m
Sun 12/136:00 am -
2 stops21h 47m
Deal found 11/6![Alaska Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:05 pm -
1 stop10h 54m
Sun 12/139:37 am -
2 stops14h 16m
Deal found 11/6![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/205:40 am -
2 stops28h 06m
Fri 12/257:00 am -
2 stops14h 55m
Deal found 11/10![Delta logo]()
$565
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/81:15 am -
1 stop9h 15m
Mon 12/145:55 pm -
1 stop10h 50m
Deal found 11/10![Delta logo]()
$571
This Priceline deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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.
Fri 12/112:26 am -
1 stop18h 33m
Sun 12/208:59 pm -
1 stop17h 03m
Deal found 11/11![Alaska Airlines logo]()
$573
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/235:40 am -
1 stop24h 39m
Fri 12/256:00 am -
1 stop17h 50m
Deal found 11/10![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/910:05 pm -
1 stop7h 50m
Mon 12/1410:24 am -
2 stops16h 04m
Deal found 11/10![Delta logo]()
$576
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 November 11, 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 November 11, 2026.
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 2/29:45 pm -
1 stop8h 13m
Tue 2/99:56 am -
1 stop11h 40m
Deal found 11/11![Delta logo]()
$533
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 2/179:05 am -
2 stops11h 54m
Wed 3/39:30 am -
1 stop12h 47m
Deal found 11/10![Alaska Airlines logo]()
$538
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 2/28:37 pm -
Nonstop6h 28m
Tue 2/93:35 pm -
Nonstop6h 59m
Deal found 11/11![United Airlines logo]()
$593
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 1/209:45 pm -
1 stop16h 08m
Tue 1/265:40 pm -
1 stop27h 56m
Deal found 11/8![Delta logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/49:05 am -
2 stops11h 54m
Mon 2/82:11 pm -
2 stops13h 19m
Deal found 11/6![Alaska Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 2/156:05 am -
1 stop14h 50m
Thu 2/181:29 pm -
2 stops15h 16m
Deal found 11/10![Delta logo]()
$538
This United Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 2/19:00 am -
1 stop9h 33m
Thu 2/43:35 pm -
Nonstop6h 54m
Deal found 11/10![United Airlines logo]()
$603
This Alaska Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 2/512:45 am -
2 stops15h 53m
Sun 2/148:00 am -
1 stop14h 10m
Deal found 11/7![Alaska Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 2/152:23 pm -
2 stops15h 37m
Thu 2/1812:42 pm -
1 stop9h 03m
Deal found 11/10![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 2/19:45 pm -
1 stop11h 19m
Thu 2/49:38 am -
2 stops11h 58m
Deal found 11/10![Delta logo]()
$538
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 2/57:30 am -
1 stop13h 29m
Tue 2/98:00 am -
1 stop10h 01m
Deal found 11/10![Alaska Airlines logo]()
$614
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 1/249:45 pm -
1 stop14h 11m
Tue 1/266:00 am -
1 stop10h 28m
Deal found 11/8![Delta logo]()
$553
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 4/155:50 am -
1 stop15h 09m
Mon 4/195:55 pm -
2 stops20h 32m
Deal found 11/10![Alaska Airlines logo]()
$618
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:05 pm -
1 stop10h 54m
Sun 12/139:37 am -
2 stops14h 16m
Deal found 11/6![Delta logo]()
$558
This Alaska Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 2/12:12 am -
1 stop18h 47m
Sat 2/68:00 am -
2 stops13h 15m
Deal found 11/11![Alaska Airlines logo]()
$618
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 1/239:45 pm -
1 stop11h 19m
Tue 1/269:38 am -
2 stops16h 12m
Deal found 11/8![Delta logo]()
$558
This Alaska Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 12/65:45 am -
1 stop9h 04m
Sat 12/125:46 pm -
1 stop9h 35m
Deal found 11/8![Alaska Airlines logo]()
$640
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/410:05 pm -
1 stop10h 47m
Fri 12/116:40 am -
1 stop11h 24m
Deal found 11/6![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/104:03 pm -
2 stops13h 52m
Thu 12/1712:39 pm -
1 stop11h 14m
Deal found 11/11![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/221:15 am -
1 stop12h 32m
Fri 11/276:40 am -
1 stop11h 24m
Deal found 11/8![Delta logo]()
$609
This Gotogate deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/266:32 pm -
1 stop8h 08m
Mon 1/48:59 pm -
2 stops27h 31m
Deal found 11/9![Alaska Airlines logo]()
$880
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/14:03 pm -
2 stops12h 56m
Mon 12/712:34 pm -
1 stop11h 19m
Deal found 11/9![Delta logo]()
$614
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/101:42 am -
2 stops15h 33m
Fri 12/182:04 pm -
2 stops13h 40m
Deal found 11/10![Delta logo]()
$625
This Alaska Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/912:39 pm -
2 stops26h 10m
Wed 12/163:19 pm -
2 stops31h 20m
Deal found 11/10![Alaska Airlines logo]()
$926
This Booking.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/267:17 am -
2 stops19h 23m
Sun 1/38:59 pm -
2 stops27h 33m
Deal found 11/9![Alaska Airlines logo]()
$935
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 11/2210:08 pm -
1 stop10h 42m
Thu 11/2611:05 am -
1 stop9h 51m
Deal found 11/9![Delta logo]()
$652
This Alaska Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/237:17 am -
2 stops19h 39m
Fri 11/276:00 am -
2 stops18h 32m
Deal found 11/8![Alaska Airlines logo]()
$996
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” 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 11/232:21 pm -
2 stops15h 29m
Fri 11/2711:05 am -
1 stop12h 53m
Deal found 11/8![Delta logo]()
$741
Last-minute flights from Alaska to ChicagoDiscover last-minute flight deals from Alaska to Chicago. Data last updated November 11, 2026 and is based on user searches.
Discover last-minute flight deals from Alaska to Chicago. Data last updated November 11, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/61:37 am -
1 stop8h 33m
Sun 12/136:00 am -
2 stops21h 47m
Deal found 11/6![Alaska Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:05 pm -
1 stop10h 54m
Sun 12/139:37 am -
2 stops14h 16m
Deal found 11/6![Delta logo]()
$558
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/81:15 am -
1 stop9h 15m
Mon 12/145:55 pm -
1 stop10h 50m
Deal found 11/10![Delta logo]()
$571
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/910:05 pm -
1 stop7h 50m
Mon 12/1410:24 am -
2 stops16h 04m
Deal found 11/10![Delta logo]()
$576
This Priceline deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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.
Fri 12/112:26 am -
1 stop18h 33m
Sun 12/208:59 pm -
1 stop17h 03m
Deal found 11/11![Alaska Airlines logo]()
$573
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/205:40 am -
1 stop12h 59m
Thu 12/242:27 pm -
1 stop9h 23m
Deal found 11/10![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/205:40 am -
2 stops28h 06m
Fri 12/257:00 am -
2 stops14h 55m
Deal found 11/10![Delta logo]()
$565
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/231:20 am -
1 stop19h 39m
Fri 12/259:59 am -
1 stop11h 56m
Deal found 11/10![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 12/235:40 am -
1 stop24h 39m
Fri 12/256:00 am -
1 stop17h 50m
Deal found 11/10![Delta logo]()
$574
This Trip.com deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/287:00 am -
1 stop19h 40m
Wed 1/66:47 pm -
1 stop21h 27m
Deal found 11/9![Alaska Airlines logo]()
$534
This Priceline deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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.
Mon 12/282:50 am -
1 stop18h 09m
Thu 1/78:00 am -
2 stops15h 55m
Deal found 11/9![Alaska Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/295:40 am -
2 stops15h 22m
Thu 1/71:45 pm -
2 stops15h 03m
Deal found 11/9![Delta logo]()
$543
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 November 11, 2026.
Search for one-way flight options from Alaska to Chicago. Find affordable one-way fares based on user searches. Data last updated November 11, 2026.
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/141:15 am -
1 stop9h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 1/149:45 pm -
1 stop8h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Delta logo]()
$266
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/141:15 am -
2 stops13h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$271
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/206:07 am -
1 stop14h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/205:40 am -
1 stop8h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Delta logo]()
$286
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:05 am -
2 stops12h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 1/159:45 pm -
2 stops12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” 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 12/298:30 pm -
Nonstop6h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/164:03 pm -
1 stop18h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” 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 11/2310:08 pm -
1 stop15h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Delta logo]()
$304
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 11/2510:08 pm -
2 stops15h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” 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 12/215:12 pm -
2 stops16h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Delta logo]()
$315
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 November 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $512 (Expedia) |
One-way from | $266 (Delta) |
Popular in | December |
Cheapest in | February |
Average price | $592 |
Good round-trip deal | $608 or less |
Good one-way deal | $248 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 November 11, 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
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Mon 12/14
6:05 am-11:57 pm
1 stop14h 52m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Thu 12/10
7:05 am-11:59 pm
1 stop13h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Mon 12/14
1:15 am-1:30 pm
1 stop9h 15m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Tue 1/19
9:45 pm-12:04 pm
1 stop11h 19m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Thu 1/14
9:45 pm-8:58 am
1 stop8h 13m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Tue 1/19
9:45 pm-3:53 pm
2 stops15h 08m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$271
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Wed 12/16
4:03 pm-8:55 am
2 stops13h 52m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$271
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Tue 12/15
2:21 pm-8:55 am
2 stops15h 34m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$271
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Fri 1/15
9:45 pm-8:58 am
1 stop8h 13m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$286
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Wed 12/2
2:56 am-11:59 pm
1 stop18h 03m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$304
Showing 1-10 of 53 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-MDW
ANC-ORD
FAI-ORD
JNU-ORD
BET-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-MDW
ANC-ORD
FAI-ORD
JNU-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 November 11, 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 November 11, 2026.
The most flights from USAK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Alaska to Chicago?
Airfare is below average for this route at the moment.
Alaska to Chicago flights typically cost between $548 and $598 in February.The cheapest round-trip price found within the last 5 days was $512 on Alaska Airlines (Feb 1-Feb 9).
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 70 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
Merrillville
Lansing
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 November 11, 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 November 11, 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 November 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$535 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$331 | Average$489 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$339 | Average$611 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$357 | Average$498 | FlexibilityNo cancel fee | On-timeN/A |