$261+ 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Nov 29 — Dec 61
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 October 30, 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 October 30, 2026.
This SmartFares deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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.
Wed 12/92:26 am -
2 stops13h 34m
Thu 12/176:00 am -
1 stop11h 14m
Deal found 10/26![Alaska Airlines logo]()
$495
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/312:24 pm -
1 stop8h 35m
Mon 12/76:47 pm -
1 stop10h 26m
Deal found 10/27![Alaska Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/310:05 pm -
1 stop7h 50m
Mon 12/712:39 pm -
1 stop11h 14m
Deal found 10/27![Delta logo]()
$523
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/310:05 pm -
1 stop7h 59m
Mon 12/77:05 am -
2 stops16h 48m
Deal found 10/27![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/91:15 am -
2 stops12h 35m
Thu 12/179:37 am -
2 stops16h 51m
Deal found 10/26![Delta logo]()
$533
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/276:06 am -
1 stop14h 53m
Thu 12/36:40 am -
1 stop11h 24m
Deal found 10/29![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 54m
Wed 12/910:24 am -
1 stop13h 29m
Deal found 10/25![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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
Fri 12/181:34 pm -
2 stops14h 25m
Deal found 10/27![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/112:21 pm -
2 stops15h 34m
Fri 12/181:02 pm -
2 stops14h 57m
Deal found 10/27![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 stop9h 22m
Fri 11/276:40 am -
1 stop11h 24m
Deal found 10/28![Delta logo]()
$561
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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
Thu 11/266:00 am -
2 stops14h 56m
Deal found 10/27![Delta logo]()
$566
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/226:07 am -
1 stop14h 52m
Sun 1/36:00 am -
1 stop13h 17m
Deal found 10/28![Delta logo]()
$573
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 October 30, 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 October 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/225:00 am -
1 stop15h 59m
Tue 3/95:55 pm -
1 stop11h 16m
Deal found 10/30![Alaska Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/16:05 am -
1 stop14h 52m
Tue 12/812:58 pm -
1 stop13h 30m
Deal found 10/25![Delta logo]()
$523
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 2/209:10 am -
1 stop9h 20m
Fri 2/263:42 pm -
Nonstop7h 11m
Deal found 10/29![United Airlines logo]()
$619
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/310:05 pm -
1 stop10h 54m
Tue 12/812:39 pm -
1 stop11h 14m
Deal found 10/25![Delta logo]()
$523
This Alaska Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 2/177:15 am -
1 stop9h 40m
Wed 3/36:00 am -
2 stops14h 22m
Deal found 10/26![Alaska Airlines logo]()
$528
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/110:05 pm -
1 stop7h 50m
Tue 12/89:37 am -
2 stops16h 51m
Deal found 10/25![Delta logo]()
$528
This Alaska Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 2/42:58 am -
1 stop12h 01m
Sat 2/68:00 am -
1 stop13h 45m
Deal found 10/29![Alaska Airlines logo]()
$563
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 4/168:44 pm -
Nonstop6h 18m
Mon 4/194:00 pm -
Nonstop6h 40m
Deal found 10/26![United Airlines logo]()
$634
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 12/102:21 pm -
2 stops15h 34m
Thu 12/1710:24 am -
1 stop13h 29m
Deal found 10/26![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/236:07 am -
1 stop14h 52m
Sun 1/36:00 am -
1 stop9h 51m
Deal found 10/27![Delta logo]()
$543
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 4/165:15 pm -
2 stops12h 28m
Mon 4/191:35 pm -
2 stops15h 10m
Deal found 10/26![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 4/165:15 pm -
2 stops12h 30m
Mon 4/191:00 pm -
2 stops15h 45m
Deal found 10/26![Delta logo]()
$553
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 12/221:50 pm -
2 stops16h 29m
Sun 1/36:00 am -
1 stop9h 51m
Deal found 10/25![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 2/225:15 pm -
2 stops12h 43m
Tue 3/99:50 am -
2 stops15h 46m
Deal found 10/28![Delta logo]()
$586
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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
Mon 11/3010:34 am -
1 stop13h 24m
Deal found 10/29![Delta logo]()
$591
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 stop15h 31m
Mon 11/3010:34 am -
1 stop13h 24m
Deal found 10/29![Delta logo]()
$606
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/91:15 am -
1 stop12h 32m
Sat 11/1410:32 am -
1 stop10h 50m
Deal found 10/26![Delta logo]()
$642
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 11/147:51 pm -
1 stop11h 33m
Wed 11/1812:30 pm -
1 stop11h 28m
Deal found 10/30![Delta logo]()
$642
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/217:40 pm -
1 stop10h 33m
Wed 12/306:00 am -
1 stop15h 25m
Deal found 10/28![Delta logo]()
$653
This Delta deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” 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 12/239:50 pm -
1 stop10h 11m
Wed 1/69:56 am -
1 stop11h 40m
Deal found 10/30![Delta logo]()
$699
Last-minute flights from Anchorage to ChicagoDiscover last-minute flight deals from Anchorage to Chicago. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Anchorage to Chicago. Data last updated October 30, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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.
Wed 11/45:47 am -
1 stop15h 12m
Sun 11/87:00 am -
1 stop18h 46m
Deal found 10/28![Alaska Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 11/44:05 pm -
2 stops12h 36m
Sun 11/86:20 am -
2 stops11h 49m
Deal found 10/28![Delta logo]()
$652
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/55:47 am -
1 stop15h 12m
Mon 11/96:35 pm -
1 stop19h 31m
Deal found 10/27![Alaska Airlines logo]()
$694
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 stops15h 23m
Mon 11/92:03 pm -
2 stops14h 36m
Deal found 10/27![Delta logo]()
$721
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/1110:08 pm -
1 stop7h 42m
Tue 11/1710:34 am -
1 stop13h 24m
Deal found 10/26![Delta logo]()
$599
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1110:08 pm -
1 stop7h 42m
Sun 11/1510:34 am -
1 stop13h 24m
Deal found 10/27![Delta logo]()
$642
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:15 am -
2 stops12h 24m
Wed 11/181:31 pm -
2 stops12h 53m
Deal found 10/27![Delta logo]()
$609
This Delta deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” 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 11/184:04 pm -
2 stops14h 42m
Sun 11/2210:34 am -
1 stop13h 24m
Deal found 10/26![Delta logo]()
$619
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/2011:44 am -
2 stops18h 06m
Mon 11/3010:34 am -
1 stop13h 24m
Deal found 10/29![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/217:51 pm -
1 stop11h 33m
Mon 11/3010:34 am -
1 stop13h 24m
Deal found 10/29![Delta logo]()
$606
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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
Mon 11/3010:34 am -
1 stop13h 24m
Deal found 10/29![Delta logo]()
$591
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/302:21 pm -
2 stops15h 34m
Mon 12/712:39 pm -
1 stop11h 14m
Deal found 10/27![Delta logo]()
$588
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 October 30, 2026.
Search for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Priceline deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 12/142:56 am -
1 stop11h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Alaska Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/310:05 pm -
1 stop15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$261
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 12/154:03 pm -
2 stops14h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$266
This Alaska Airlines deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/410:10 am -
1 stop10h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Alaska Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 stop15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$281
This United Airlines deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 1/48:30 pm -
Nonstop6h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 stop9h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 10/27. Clicking the “Pick Dates” 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 11/1110:08 pm -
1 stop10h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Delta logo]()
$299
This Delta deal was found by Cheapflights users on 10/28. Clicking the “Pick Dates” 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 12/196:07 am -
1 stop14h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Delta logo]()
$301
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/201:15 am -
1 stop12h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/217:51 pm -
1 stop11h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$314
This Delta deal was found by Cheapflights users on 10/29. Clicking the “Pick Dates” 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 11/204:04 pm -
2 stops13h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Delta logo]()
$319
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $495 (SmartFares) |
One-way from | $261 (Priceline) |
Popular in | November |
Cheapest in | February |
Average price | $498 |
Good round-trip deal | $616 or less |
Good one-way deal | $328 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 October 30, 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
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
$261
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Tue 12/8
10:05 pm-4:50 pm
1 stop15h 45m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Wed 12/9
10:05 pm-8:55 am
1 stop7h 50m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Thu 12/3
10:05 pm-4:50 pm
1 stop15h 45m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$261
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Tue 12/1
6:05 am-9:56 pm
2 stops12h 51m
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
Tue 12/15
4:03 pm-9:04 am
2 stops14h 01m
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 12/7
1:15 am-6:06 pm
2 stops13h 51m
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 12/15
4:03 pm-8:55 am
2 stops13h 52m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$266
AnchorageChicago
ANC Anchorage - ORD Chicago O'Hare Intl
ANCORD
Anchorage
Fri 12/4
10:10 am-11:59 pm
1 stop10h 49m
Chicago O'Hare Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$281
AnchorageChicago
ANC Anchorage - MDW Chicago Midway
ANCMDW
Anchorage
Sat 12/5
1:15 am-6:01 pm
2 stops13h 46m
Chicago Midway
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$286
Showing 1-10 of 41 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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 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 October 30, 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.
How far ahead should I book a flight from Anchorage to Chicago?
Booking 71 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 October 30, 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.
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Boarding
8.1
Food
7.0
Overall
7.9
Entertainment
7.0
Comfort
7.8
Crew
8.5
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
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Anchorage and Chicago flights
Browse other Anchorage and Chicago flight options. Last updated on October 30, 2026.
Other flights from Anchorage
Browse through other flights departing from Anchorage. Flights are based on user searches made on Cheapflights and were last updated on October 30, 2026.
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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 October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$533 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$331 | Average$489 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$489 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$339 | Average$617 | FlexibilityNo cancel fee | On-time69% |