$180+ Cheap flights from Anchorage (ANC) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Aug 28 — Sep 41
Round-trip
1 adult, Economy
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Find cheap flights from Anchorage to Chicago with Cheapflights
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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 July 29, 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 July 29, 2026.
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:56 pm
ANC
- ORD
Nonstop6h 29m
American Airlines
Wed 9/24:57 pm
ORD
- ANC
Nonstop6h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/310:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Mon 9/77:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/38:00 pm
ANC
- ORD
Nonstop6h 12m
United Airlines
Sun 9/64:05 pm
ORD
- ANC
Nonstop6h 54m
United Airlines
Deal found 7/23![United Airlines logo]()
$397
This flugladen.de deal was found by Cheapflights users on 7/26. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:09 pm
ANC
- ORD
1 stop27h 50m
Alaska Airlines
Wed 9/27:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:56 pm
ANC
- ORD
Nonstop6h 29m
American Airlines
Sat 9/124:53 pm
ORD
- ANC
Nonstop6h 56m
American Airlines
Deal found 7/26![American Airlines logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/2610:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Mon 8/316:00 am
ORD
- ANC
1 stop12h 05m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$403
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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
ANC
- ORD
Nonstop6h 11m
United Airlines
Sun 10/253:35 pm
ORD
- ANC
Nonstop7h 04m
United Airlines
Deal found 7/24![United Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ANC
- ORD
1 stop10h 30m
American Airlines
Sun 9/64:57 pm
ORD
- ANC
Nonstop6h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:00 pm
ANC
- ORD
Nonstop6h 12m
United Airlines
Sat 9/128:50 am
ORD
- ANC
1 stop13h 12m
United Airlines
Deal found 7/27![United Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Mon 9/79:56 pm
ANC
- ORD
Nonstop6h 29m
American Airlines
Mon 9/147:09 am
ORD
- ANC
1 stop15h 04m
American Airlines
Deal found 7/24![American Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 7/26. 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 8/276:00 am
ANC
- MDW
1 stop9h 01m
Delta
Wed 9/27:25 pm
MDW
- ANC
1 stop8h 34m
Delta
Deal found 7/26![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 7/26. 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.
Tue 9/226:00 am
ANC
- MDW
1 stop9h 19m
Delta
Tue 9/299:59 am
MDW
- ANC
1 stop10h 15m
Delta
Deal found 7/26![Delta logo]()
$421
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 July 29, 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 July 29, 2026.
This Alaska Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 9/310:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Mon 9/77:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 7/27. 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 8/2610:30 pm
ANC
- ORD
1 stop14h 47m
Delta
Mon 8/316:44 pm
ORD
- ANC
1 stop9h 15m
Delta
Deal found 7/27![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:55 pm
ANC
- MDW
2 stops14h 05m
Southwest
Wed 9/210:30 am
MDW
- ANC
2 stops15h 15m
Southwest
Deal found 7/26![Southwest logo]()
$466
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Mon 8/317:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 7/27. 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 9/311:01 am
ANC
- ORD
1 stop9h 28m
Delta
Mon 9/76:00 am
ORD
- ANC
1 stop8h 39m
Delta
Deal found 7/27![Delta logo]()
$413
This Alaska Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 9/296:07 am
ANC
- ORD
1 stop14h 52m
Alaska Airlines
Wed 10/147:00 am
ORD
- ANC
1 stop10h 45m
Alaska Airlines
Deal found 7/23![Alaska Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 7/26. 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 8/3112:39 am
ANC
- ORD
1 stop14h 40m
Delta
Sun 9/612:54 pm
ORD
- ANC
1 stop10h 18m
Delta
Deal found 7/26![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 7/27. 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 9/410:10 pm
ANC
- MDW
1 stop14h 47m
Delta
Sat 9/126:05 am
MDW
- ANC
1 stop15h 45m
Delta
Deal found 7/27![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 7/26. 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.
Tue 9/16:00 am
ANC
- MDW
1 stop9h 01m
Delta
Sun 9/66:05 am
MDW
- ANC
1 stop15h 55m
Delta
Deal found 7/26![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 7/26. 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 8/2711:01 am
ANC
- ORD
1 stop9h 28m
Delta
Wed 9/212:29 pm
ORD
- ANC
2 stops14h 26m
Delta
Deal found 7/26![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 7/26. 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 8/276:00 am
ANC
- MDW
1 stop9h 01m
Delta
Wed 9/29:24 am
MDW
- ANC
2 stops14h 36m
Delta
Deal found 7/26![Delta logo]()
$418
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/2310:10 pm
ANC
- ORD
1 stop7h 20m
Delta
Sun 9/277:00 am
ORD
- ANC
1 stop16h 15m
Delta
Deal found 7/24![Delta logo]()
$423
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/710:10 pm
ANC
- MDW
1 stop12h 10m
Delta
Mon 9/142:00 pm
MDW
- ANC
2 stops13h 27m
Delta
Deal found 7/24![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/242:28 pm
ANC
- MDW
2 stops15h 20m
Delta
Sun 9/279:29 am
MDW
- ANC
2 stops14h 31m
Delta
Deal found 7/24![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 7/27. 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 8/2110:10 pm
ANC
- MDW
1 stop12h 00m
Delta
Mon 8/241:25 pm
MDW
- ANC
1 stop10h 55m
Delta
Deal found 7/27![Delta logo]()
$472
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/246:00 am
ANC
- MDW
1 stop9h 01m
Delta
Mon 8/311:51 pm
MDW
- ANC
1 stop10h 09m
Delta
Deal found 7/24![Delta logo]()
$498
This Delta deal was found by Cheapflights users on 7/25. 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 8/1810:30 pm
ANC
- MDW
1 stop11h 09m
Delta
Tue 8/251:25 pm
MDW
- ANC
1 stop10h 55m
Delta
Deal found 7/25![Delta logo]()
$538
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/2110:05 pm
ANC
- MDW
1 stop10h 43m
Delta
Sun 10/259:59 am
MDW
- ANC
1 stop13h 56m
Delta
Deal found 7/24![Delta logo]()
$543
Last-minute flights from Anchorage to ChicagoDiscover last-minute flight deals from Anchorage to Chicago. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Anchorage to Chicago. Data last updated July 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 7/26. 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 8/1410:10 pm
ANC
- MDW
1 stop12h 00m
Delta
Sun 8/231:25 pm
MDW
- ANC
1 stop10h 55m
Delta
Deal found 7/26![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 7/25. 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 8/1810:30 pm
ANC
- ORD
1 stop14h 47m
Delta
Tue 8/256:45 pm
ORD
- ANC
1 stop9h 14m
Delta
Deal found 7/25![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 7/27. 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 8/201:32 am
ANC
- ORD
1 stop8h 51m
Delta
Mon 8/242:00 pm
ORD
- ANC
1 stop12h 24m
Delta
Deal found 7/27![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 7/27. 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 8/2110:10 pm
ANC
- MDW
1 stop12h 00m
Delta
Mon 8/241:25 pm
MDW
- ANC
1 stop10h 55m
Delta
Deal found 7/27![Delta logo]()
$472
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/239:20 pm
ANC
- ORD
Nonstop6h 12m
United Airlines
Sun 8/304:05 pm
ORD
- ANC
Nonstop6h 54m
United Airlines
Deal found 7/23![United Airlines logo]()
$401
This Alaska Airlines deal was found by Cheapflights users on 7/25. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Mon 8/317:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/25![Alaska Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 7/27. 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 8/2610:30 pm
ANC
- ORD
1 stop14h 47m
Delta
Mon 8/316:44 pm
ORD
- ANC
1 stop9h 15m
Delta
Deal found 7/27![Delta logo]()
$413
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:56 pm
ANC
- ORD
Nonstop6h 29m
American Airlines
Wed 9/24:57 pm
ORD
- ANC
Nonstop6h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$392
This flugladen.de deal was found by Cheapflights users on 7/26. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:09 pm
ANC
- ORD
1 stop27h 50m
Alaska Airlines
Wed 9/27:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 7/26. 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 8/276:00 am
ANC
- MDW
1 stop9h 01m
Delta
Wed 9/27:25 pm
MDW
- ANC
1 stop8h 34m
Delta
Deal found 7/26![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 7/28. 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 8/276:00 am
ANC
- MDW
1 stop9h 01m
Delta
Thu 9/37:25 pm
MDW
- ANC
1 stop8h 34m
Delta
Deal found 7/28![Delta logo]()
$433
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:55 pm
ANC
- MDW
2 stops14h 05m
Southwest
Wed 9/210:30 am
MDW
- ANC
2 stops15h 15m
Southwest
Deal found 7/26![Southwest logo]()
$466
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 July 29, 2026.
Search for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This SmartFares deal was found by Cheapflights users on 7/26. 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.
Tue 8/2511:01 am
ANC
- ORD
1 stop9h 28m
Delta
Deal found 7/26![Delta logo]()
$180
This Alaska Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/2610:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$196
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/410:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Deal found 7/27![Alaska Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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.
Mon 9/79:56 pm
ANC
- ORD
Nonstop6h 29m
American Airlines
Deal found 7/23![American Airlines logo]()
$201
This Delta deal was found by Cheapflights users on 7/27. 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 8/278:15 am
ANC
- ORD
1 stop12h 14m
Delta
Deal found 7/27![Delta logo]()
$206
This Southwest deal was found by Cheapflights users on 7/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:25 pm
ANC
- MDW
1 stop10h 25m
Southwest
Deal found 7/25![Southwest logo]()
$206
This Trip.com deal was found by Cheapflights users on 7/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/223:47 pm
ANC
- ORD
1 stop18h 35m
Alaska Airlines
Deal found 7/26![Alaska Airlines logo]()
$207
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:06 pm
ANC
- ORD
Nonstop6h 19m
American Airlines
Deal found 7/26![American Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 7/27. 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 9/2511:51 am
ANC
- ORD
1 stop9h 06m
Delta
Deal found 7/27![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:55 pm
ANC
- MDW
1 stop11h 15m
Southwest
Deal found 7/24![Southwest logo]()
$210
This Alaska Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/241:59 am
ANC
- ORD
2 stops14h 22m
Alaska Airlines
Deal found 7/24![Alaska Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 7/27. 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 11/1310:06 pm
ANC
- MDW
1 stop10h 44m
Delta
Deal found 7/27![Delta logo]()
$211
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 July 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $392 (American Airlines) |
One-way from | $180 (SmartFares) |
Popular in | July |
Cheapest in | October |
Average price | $539 |
Good round-trip deal | $535 or less |
Good one-way deal | $300 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 2,558,603 searches. Data last updated July 29, 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
Quickest round-trip
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 9/3
10:28 pm-7:40 am
Nonstop6h 12m
Chicago O'Hare Intl
Mon 9/7
7:20 am-11:12 am
Nonstop6h 52m
$393
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Wed 8/26
10:28 pm-7:40 am
Nonstop6h 12m
Chicago O'Hare Intl
Mon 8/31
7:20 am-11:12 am
Nonstop6h 52m
$393
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Wed 8/26
10:30 pm-4:17 pm
1 stop14h 47m
Chicago O'Hare Intl
Mon 8/31
6:44 pm-12:59 am
1 stop9h 15m
$413
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 9/3
11:01 am-11:29 pm
1 stop9h 28m
Chicago O'Hare Intl
Mon 9/7
6:00 am-11:39 am
1 stop8h 39m
$413
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Tue 9/29
6:07 am-11:59 pm
1 stop14h 52m
Chicago O'Hare Intl
Wed 10/14
7:00 am-2:45 pm
1 stop10h 45m
$413
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Mon 8/31
12:39 am-6:19 pm
1 stop14h 40m
Chicago O'Hare Intl
Sun 9/6
12:54 pm-8:12 pm
1 stop10h 18m
$413
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Fri 9/4
10:10 pm-3:57 pm
1 stop14h 47m
Chicago Midway
Sat 9/12
6:05 am-6:50 pm
1 stop15h 45m
$413
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Tue 9/1
6:00 am-6:01 pm
1 stop9h 01m
Chicago Midway
Sun 9/6
6:05 am-7:00 pm
1 stop15h 55m
$413
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 8/27
11:01 am-11:29 pm
1 stop9h 28m
Chicago O'Hare Intl
Wed 9/2
12:29 pm-11:55 pm
2 stops14h 26m
$418
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Thu 8/27
6:00 am-6:01 pm
1 stop9h 01m
Chicago Midway
Wed 9/2
9:24 am-9:00 pm
2 stops14h 36m
$418
Showing 1-10 of 39 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 July.
| 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 July 29, 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 July 29, 2026.
The most flights from ANC to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (5 on average).
How far ahead should I book a flight from Anchorage to Chicago?
Booking 73 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 July 29, 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.
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
Reviews
1 / 20
10.0
ExcellentMarty,Jun 2024
ANC - DEN
Crew
8.5
Boarding
8.1
Food
7.0
Overall
7.9
Comfort
7.8
Entertainment
7.0
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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Other flights to Chicago
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Anchorage and Chicago flights
Browse other Anchorage and Chicago flight options. Last updated on July 29, 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 July 29, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 2,558,603 searches. Data last updated July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$204 | Average$515 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$314 | Average$538 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$331 | Average$424 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$480 | FlexibilityNo cancel fee | On-timeN/A |