$262+ Cheap flights from Chicago (CHI) to Anchorage (ANC)
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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ANC
Nov 19 — Nov 261
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Anchorage 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.Cheapflights Tip: The best prices from Chicago to Anchorage are usually found in February or September, booked 33 days in advance, depart on a Thursday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Anchorage
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Cheapest flights from Chicago to AnchorageExplore the most affordable flight options available from Chicago to Anchorage. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
Explore the most affordable flight options available from Chicago to Anchorage. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2026.
This SmartFares deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop10h 38m
Thu 12/102:53 pm -
1 stop11h 44m
Deal found 10/19![Alaska Airlines logo]()
$498
This Alaska Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:00 am -
1 stop19h 17m
Thu 12/102:53 pm -
1 stop11h 44m
Deal found 10/16![Alaska Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:39 pm -
1 stop11h 14m
Mon 12/1410:05 pm -
1 stop15h 45m
Deal found 10/16![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:55 pm -
1 stop22h 31m
Thu 12/104:03 pm -
1 stop18h 27m
Deal found 10/16![Delta logo]()
$527
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/253:47 pm -
2 stops12h 52m
Mon 11/306:06 am -
1 stop14h 53m
Deal found 10/19![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:41 pm -
2 stops15h 04m
Mon 12/710:05 pm -
1 stop7h 50m
Deal found 10/15![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 12/36:40 am -
1 stop11h 24m
Wed 12/91:15 am -
2 stops15h 30m
Deal found 10/19![Delta logo]()
$530
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1112:39 pm -
1 stop11h 14m
Mon 12/144:03 pm -
2 stops13h 52m
Deal found 10/15![Delta logo]()
$530
This Expedia deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:20 am -
2 stops13h 06m
Thu 11/198:00 am -
2 stops12h 49m
Deal found 10/18![Alaska Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:39 am -
2 stops17h 06m
Tue 12/154:03 pm -
2 stops12h 56m
Deal found 10/16![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 12/310:24 am -
2 stops16h 04m
Thu 12/104:03 pm -
2 stops13h 52m
Deal found 10/19![Delta logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:08 pm -
2 stops26h 30m
Tue 12/152:53 pm -
1 stop22h 38m
Deal found 10/19![Alaska Airlines logo]()
$537
Best flights from Chicago to AnchorageDiscover carefully curated flight deals from Chicago to Anchorage that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
Discover carefully curated flight deals from Chicago to Anchorage that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 20, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:08 pm -
2 stops26h 30m
Tue 12/152:53 pm -
1 stop22h 38m
Deal found 10/18![Alaska Airlines logo]()
$537
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2612:50 pm -
1 stop15h 55m
Tue 3/301:30 am -
1 stop9h 01m
Deal found 10/18![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 1/143:35 pm -
Nonstop6h 54m
Mon 1/188:31 pm -
Nonstop6h 28m
Deal found 10/19![United Airlines logo]()
$583
This Alaska Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 1/108:00 am -
2 stops15h 30m
Sun 1/102:28 am -
1 stop18h 31m
Deal found 10/19![Alaska Airlines logo]()
$542
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:37 am -
2 stops16h 51m
Sat 12/54:03 pm -
2 stops14h 34m
Deal found 10/17![Delta logo]()
$555
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/254:20 pm -
1 stop9h 36m
Mon 11/308:43 pm -
Nonstop6h 16m
Deal found 10/19![United Airlines logo]()
$593
This Alaska Airlines deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/32:13 pm -
2 stops13h 38m
Sat 12/52:53 pm -
1 stop11h 44m
Deal found 10/17![Alaska Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:58 pm -
1 stop13h 26m
Mon 11/236:06 am -
1 stop14h 53m
Deal found 10/17![Delta logo]()
$561
This United Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 4/173:00 pm -
1 stop10h 39m
Sat 4/248:44 pm -
Nonstop6h 18m
Deal found 10/19![United Airlines logo]()
$619
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/17![Delta logo]()
$568
This Alaska Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/107:00 am -
1 stop17h 45m
Wed 11/116:45 am -
1 stop14h 14m
Deal found 10/19![Alaska Airlines logo]()
$593
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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.
Sun 11/153:35 pm -
Nonstop7h 04m
Sun 11/2211:59 pm -
1 stop10h 30m
Deal found 10/18![United Airlines logo]()
$619
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/410:12 am -
1 stop13h 47m
Wed 11/1110:08 pm -
1 stop7h 42m
Deal found 10/17![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:27 pm -
1 stop11h 32m
Wed 10/2810:09 pm -
1 stop7h 35m
Deal found 10/17![Delta logo]()
$601
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:12 am -
2 stops13h 29m
Sat 11/77:45 pm -
1 stop13h 09m
Deal found 10/15![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:29 am -
2 stops14h 12m
Sat 11/1410:08 pm -
1 stop10h 42m
Deal found 10/17![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/29:37 am -
2 stops16h 51m
Tue 12/152:21 pm -
2 stops15h 34m
Deal found 10/18![Delta logo]()
$641
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 12/1612:39 pm -
1 stop11h 14m
Wed 12/237:45 pm -
1 stop15h 56m
Deal found 10/19![Delta logo]()
$663
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/171:31 pm -
2 stops15h 08m
Tue 11/242:21 pm -
2 stops15h 29m
Deal found 10/19![Delta logo]()
$693
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:30 pm -
2 stops13h 54m
Fri 11/2710:08 pm -
2 stops15h 10m
Deal found 10/17![Delta logo]()
$694
Last-minute flights from Chicago to AnchorageDiscover last-minute flight deals from Chicago to Anchorage. Data last updated October 20, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Anchorage. Data last updated October 20, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/223:49 pm -
1 stop10h 50m
Thu 11/198:00 am -
1 stop12h 59m
Deal found 10/14![Alaska Airlines logo]()
$561
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1112:30 pm -
1 stop11h 28m
Wed 11/184:04 pm -
2 stops14h 42m
Deal found 10/17![Delta logo]()
$568
This Priceline deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/167:00 am -
2 stops16h 55m
Mon 11/233:55 pm -
2 stops11h 01m
Deal found 10/17![Alaska Airlines logo]()
$535
This Expedia deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:20 am -
2 stops13h 06m
Thu 11/198:00 am -
2 stops12h 49m
Deal found 10/18![Alaska Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/1712:30 pm -
2 stops16h 09m
Thu 11/192:21 pm -
2 stops15h 29m
Deal found 10/18![Delta logo]()
$535
This Alaska Airlines deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:54 pm -
1 stop9h 55m
Fri 11/276:00 am -
1 stop14h 59m
Deal found 10/19![Alaska Airlines logo]()
$563
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/212:44 pm -
2 stops13h 55m
Thu 11/261:15 am -
1 stop9h 22m
Deal found 10/19![Delta logo]()
$568
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:58 pm -
1 stop13h 26m
Fri 11/276:06 am -
1 stop14h 53m
Deal found 10/19![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:44 pm -
2 stops13h 55m
Mon 11/3010:08 pm -
2 stops15h 09m
Deal found 10/17![Delta logo]()
$565
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/241:31 pm -
2 stops15h 08m
Tue 12/110:05 pm -
1 stop7h 50m
Deal found 10/18![Delta logo]()
$566
This Travelocity deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:19 pm -
1 stop9h 40m
Mon 11/303:45 pm -
1 stop11h 11m
Deal found 10/19![Alaska Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” 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 11/253:47 pm -
2 stops12h 52m
Mon 11/306:06 am -
1 stop14h 53m
Deal found 10/19![Delta logo]()
$528
One-way flights from Chicago to AnchorageSearch for one-way flight options from Chicago to Anchorage. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
Search for one-way flight options from Chicago to Anchorage. Find affordable one-way fares based on user searches. Data last updated October 20, 2026.
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/812:40 pm -
1 stop16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$262
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/812:30 pm -
2 stops16h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$268
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:40 am -
1 stop11h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$282
This Delta deal was found by Cheapflights users on 10/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:39 pm -
2 stops13h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/95:55 pm -
1 stop10h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:35 pm -
Nonstop7h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:35 am -
1 stop9h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$315
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/89:29 am -
2 stops14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 10/244:05 pm -
Nonstop6h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![United Airlines logo]()
$334
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 10/246:04 am -
1 stop15h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Delta logo]()
$343
This Alaska Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/182:08 pm -
2 stops23h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Alaska Airlines logo]()
$348
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 10/247:35 am -
2 stops16h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Delta logo]()
$349
Find flight deals from Chicago to Anchorage
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Anchorage (ANC). 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 October 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $498 (SmartFares) |
One-way from | $262 (Delta) |
Popular in | July |
Cheapest in | February |
Average price | $571 |
Good round-trip deal | $503 or less |
Good one-way deal | $252 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Anchorage that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 20, 2026.
Use the filters below to find and compare flights from Chicago to Anchorage that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Fri 1/8
12:30 pm-1:45 am
2 stops16h 15m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$268
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sun 11/22
6:40 am-3:04 pm
1 stop11h 24m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$282
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Sat 12/12
12:39 pm-11:28 pm
2 stops13h 49m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$288
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Mon 11/9
5:55 pm-1:39 am
1 stop10h 44m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$300
Quickest round-trip
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Fri 12/18
3:30 pm-7:23 pm
Nonstop6h 53m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$306
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Sun 11/8
6:35 am-1:28 pm
1 stop9h 53m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$315
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Sun 11/8
9:29 am-8:59 pm
2 stops14h 30m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$326
ChicagoAnchorage
ORD Chicago O'Hare Intl - ANC Anchorage
ORDANC
Chicago O'Hare Intl
Fri 12/18
2:08 pm-11:02 am
2 stops23h 54m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$348
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Sat 10/24
9:29 am-8:59 pm
2 stops14h 30m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$349
ChicagoAnchorage
MDW Chicago Midway - ANC Anchorage
MDWANC
Chicago Midway
Mon 11/9
9:30 am-8:58 pm
2 stops14h 28m
Anchorage
Wed 12/31
12:00 am-4:00 am
Nonstop0h 00m
$351
Showing 1-10 of 37 resultsSorted by cheapest first
Compare providers for flights from Chicago to Anchorage
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 Chicago to Anchorage in October.
| 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 Chicago-Anchorage flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Anchorage flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Anchorage flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Anchorage 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 Chicago-Anchorage 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 Chicago to Anchorage
Have a flexible travel schedule? Discover the best time to fly to Anchorage from Chicago with our price prediction graph.
CHI-ANC
ORD-ANC
MDW-ANC
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Anchorage
CHI-ANC
ORD-ANC
MDW-ANC
What is the cheapest month to book a flight from Chicago to Anchorage?
Currently, February is the cheapest month in which you can book a flight from Chicago to Anchorage (average of $358). Flying from Chicago to Anchorage in July is currently the most expensive (average of $593). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to ANC?
Find hourly flight availability from Chicago to Anchorage. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 41% on flights from Chicago to Anchorage by exploring options for tickets in the afternoon.
Weekly flight availability from Chicago to Anchorage
Explore weekly flight availability from Chicago to Anchorage. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 20, 2026.
The most flights from CHI to ANC are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
How much does it cost to fly round-trip from Chicago to Anchorage?
Airfare is typical for this route at the moment.
Chicago to Anchorage flights typically cost between $471 and $695 in December.The cheapest round-trip price found within the last 5 days was $498 on Alaska Airlines (Dec 3-Dec 10).
What’s the top layover airport for flights from Chicago to Anchorage?
Share of 1-stop round-trip flights from Chicago to Anchorage chosen by Cheapflights users in the past 12 months, using the same layover each way.
Seattle (SEA) – chosen by Cheapflights users on 67% of 1-stop itineraries from Chicago to Anchorage on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Anchorage?
Average round-trip fare for 1-stop flights from Chicago to Anchorage, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Seattle (SEA) is the most affordable 1-stop option, with an average round-trip price of $562.
What’s the fastest layover option from Chicago to Anchorage?
Shortest average travel time for 1-stop one-way flights from Chicago to Anchorage, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 10h 00m.
Which airport typically offers the quickest layover for flights from Chicago to Anchorage?
Average layover duration for 1-stop one-way flights from Chicago to Anchorage, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 1h 43m.
How far ahead should I book a flight from Chicago to Anchorage?
Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Anchorage. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to Anchorage?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Anchorage. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Chicago to Anchorage flight should consider departing on Friday at noon when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The best insider tips for Chicago to Anchorage 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 Chicago to Anchorage trip
Our travel experts
Reviews of airlines servicing Anchorage
Get insights into the airlines that provide service to Anchorage. 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 Anchorage. Reviews last updated October 20, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines,Delta, andUnited Airlines from Chicago to Anchorage to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Boarding
8.1
Crew
8.5
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentGeorgana,Dec 2025
ORD - PDX
Related info for your journey
Find useful and relevant information for your journey from Chicago to Anchorage. 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 Anchorage?
Book flights to Anchorage if you plan to visit one of these locationsSeward
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Top 4 airlines flying from Chicago to Anchorage
Discover the top 4 airlines that operate flights from Chicago to Anchorage. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$213 | Average$446 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$500 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$373 | Average$509 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$373 | Average$512 | FlexibilityNo cancel fee | On-time69% |