$251+ Cheap flights from Anchorage (ANC) 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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Oct 16 — Oct 231
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 Anchorage to ChicagoExplore the most affordable flight options available from Anchorage to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
Explore the most affordable flight options available from Anchorage to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2026.
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 10/218:59 pm -
Nonstop6h 11m
Tue 10/273:35 pm -
Nonstop7h 04m
Deal found 9/15![United Airlines logo]()
$503
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 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
Tue 10/273:35 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 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.
Wed 12/26:15 am -
1 stop14h 47m
Fri 2/267:00 am -
1 stop12h 18m
Deal found 9/13![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 10/1210:09 pm -
1 stop7h 35m
Tue 10/2012:27 pm -
1 stop11h 32m
Deal found 9/11![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.
Thu 10/228:59 pm -
Nonstop6h 11m
Wed 10/282:30 pm -
1 stop11h 26m
Deal found 9/15![United Airlines logo]()
$524
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 9/11. 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 12/226:00 am -
1 stop14h 59m
Wed 12/307:00 am -
2 stops19h 18m
Deal found 9/11![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.
Thu 11/1910:06 pm -
1 stop7h 44m
Sun 11/221:31 pm -
2 stops15h 08m
Deal found 9/15![Delta logo]()
$528
Best flights from Anchorage to ChicagoDiscover carefully curated flight deals from Anchorage to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 2026.
Discover carefully curated flight deals from Anchorage to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 16, 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 10/212:30 pm -
1 stop11h 13m
Deal found 9/14![United Airlines logo]()
$513
This Delta deal was found by Cheapflights users on 9/13. 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 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.
Thu 11/198:43 pm -
Nonstop6h 16m
Sun 11/221:30 pm -
1 stop12h 26m
Deal found 9/15![United Airlines logo]()
$533
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 Delta deal was found by Cheapflights users on 9/11. 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.
Mon 10/1210:09 pm -
1 stop7h 35m
Tue 10/2012:27 pm -
1 stop11h 32m
Deal found 9/11![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.
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 9/15. 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 -
2 stops12h 53m
Sun 12/65:55 pm -
1 stop10h 50m
Deal found 9/15![Delta logo]()
$528
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 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.
Thu 11/196:15 am -
2 stops12h 18m
Sun 11/226:40 am -
1 stop9h 46m
Deal found 9/15![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 11/254:04 pm -
2 stops16h 21m
Fri 11/2711:05 am -
1 stop12h 51m
Deal found 9/12![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 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.
Thu 11/1910:06 pm -
1 stop7h 44m
Sun 11/221:31 pm -
2 stops15h 08m
Deal found 9/15![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 10/124:05 pm -
2 stops13h 48m
Tue 10/206:20 am -
2 stops11h 49m
Deal found 9/11![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 9/11. 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 12/225:12 pm -
2 stops21h 12m
Wed 12/309:30 am -
2 stops18h 02m
Deal found 9/11![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 10/1411:29 am -
1 stop9h 05m
Wed 11/46:35 am -
1 stop11h 34m
Deal found 9/15![Delta logo]()
$541
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 10/96:30 am -
1 stop14h 04m
Sun 11/18:29 am -
2 stops15h 30m
Deal found 9/11![Delta logo]()
$546
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 12/215:12 pm -
2 stops21h 12m
Mon 12/289:30 am -
2 stops18h 02m
Deal found 9/11![Delta logo]()
$563
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 9/14. 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
Last-minute flights from Anchorage to ChicagoDiscover last-minute flight deals from Anchorage to Chicago. Data last updated September 16, 2026 and is based on user searches.
Discover last-minute flight deals from Anchorage to Chicago. Data last updated September 16, 2026 and is based on user searches.
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.
Sat 10/108:59 pm -
Nonstop6h 11m
Sat 10/174:05 pm -
Nonstop6h 52m
Deal found 9/12![United Airlines logo]()
$539
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.
Sat 10/104:05 pm -
2 stops13h 39m
Sat 10/171:27 pm -
2 stops14h 08m
Deal found 9/12![Delta logo]()
$551
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.
Mon 10/126:30 am -
1 stop14h 04m
Mon 10/196:35 am -
1 stop11h 34m
Deal found 9/12![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 10/1210:09 pm -
1 stop7h 35m
Tue 10/2012:27 pm -
1 stop11h 32m
Deal found 9/11![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 9/11. 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.
Mon 10/1210:09 pm -
1 stop7h 44m
Tue 10/206:20 am -
2 stops11h 49m
Deal found 9/11![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.
Tue 10/131:40 am -
1 stop12h 13m
Wed 10/2112:50 pm -
1 stop14h 45m
Deal found 9/15![Delta logo]()
$541
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 11/43:56 pm -
1 stop10h 00m
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.
Thu 10/152:24 pm -
2 stops15h 20m
Fri 10/161:27 pm -
2 stops14h 08m
Deal found 9/14![Delta logo]()
$563
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 10/218:59 pm -
Nonstop6h 11m
Tue 10/273:35 pm -
Nonstop7h 04m
Deal found 9/15![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 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 Anchorage to ChicagoSearch for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
Search for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated September 16, 2026.
This Alaska Airlines deal was found by Cheapflights users on 9/11. 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 10/127:02 am -
1 stop13h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![Alaska Airlines logo]()
$251
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.
Thu 10/151:40 am -
2 stops19h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$255
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 10/248:59 pm -
Nonstop6h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![United Airlines logo]()
$259
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.
Fri 12/111:15 am -
1 stop19h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$261
This Delta deal was found by Cheapflights users on 9/11. 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 11/110:09 pm -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![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 American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:55 pm -
Nonstop6h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![American 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 9/11. 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 11/510:09 pm -
2 stops33h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/11![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 Anchorage to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Anchorage (ANC) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $483 (United Airlines) |
One-way from | $241 (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 Anchorage 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 16, 2026.
Use the filters below to find and compare flights from Anchorage 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 11/16
10:06 pm-9:04 am
1 stop7h 58m
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 - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Tue 12/15
1:15 am-12:02 am
1 stop19h 47m
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 12/11
1:15 am-12:02 am
1 stop19h 47m
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 11/18
1:15 am-4:47 pm
1 stop12h 32m
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
Sat 10/17
1:40 am-11:34 pm
1 stop18h 54m
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
Sat 12/12
1:15 am-4:50 pm
1 stop12h 35m
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
1:40 am-11:54 pm
1 stop19h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Sat 10/24
10:09 pm-8:44 am
1 stop7h 35m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
Showing 1-10 of 40 resultsSorted by cheapest first
Compare providers for flights from Anchorage to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Anchorage to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Anchorage-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Anchorage-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Anchorage-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Anchorage-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Anchorage-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Anchorage to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Anchorage with our price prediction graph.
ANC-CHI
ANC-ORD
ANC-MDW
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 Anchorage to Chicago
ANC-CHI
ANC-ORD
ANC-MDW
What is the cheapest month to book a flight from Anchorage to Chicago?
Currently, February is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $358). Flying from Anchorage 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 ANC to CHI?
Find hourly flight availability from Anchorage 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 16, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Anchorage to Chicago as you normally would.
Weekly flight availability from Anchorage to Chicago
Explore weekly flight availability from Anchorage 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 16, 2026.
The most flights from ANC 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 Anchorage to Chicago?
Airfare is typical for this route at the moment.
Anchorage to Chicago flights typically cost between $397 and $487 in March.The cheapest round-trip price found within the last 5 days was $483 on United Airlines (Mar 10-Mar 24).
How far ahead should I book a flight from Anchorage to Chicago?
Booking 75 days in advance of your planned departure date is, on average, the best time to get cheap flights from Anchorage to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
The best insider tips for Anchorage to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Anchorage to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 16, 2026.
Get a feel of what it's like to fly with Alaska Airlines,Delta, andUnited Airlines from Anchorage to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Comfort
7.8
Crew
8.5
Entertainment
7.0
Food
7.0
Boarding
8.1
Overall
7.9
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Related info for your journey
Find useful and relevant information for your journey from Anchorage 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
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Top 4 airlines flying from Anchorage to Chicago
Discover the top 4 airlines that operate flights from Anchorage 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 16, 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 |