$183+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
May 30 — Jun 61
Round-trip
1 adult, Economy
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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 April 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 April 30, 2026.
This Vliegwinkel deal was found by Cheapflights users on 4/27. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Sun 5/246:00 am
ORD
- ANC
1 stop9h 04m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/59:50 pm
ANC
- ORD
Nonstop6h 33m
American Airlines
Mon 6/85:02 pm
ORD
- ANC
Nonstop6h 39m
American Airlines
Deal found 4/27![American Airlines logo]()
$367
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 5/2711:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Wed 6/108:05 pm
ORD
- ANC
1 stop15h 35m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 4/25. 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.
Wed 5/279:30 pm
ANC
- ORD
1 stop12h 31m
Delta
Mon 6/87:01 am
ORD
- ANC
1 stop17h 15m
Delta
Deal found 4/25![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 4/27. 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 5/186:00 am
ANC
- MDW
1 stop8h 56m
Delta
Sun 5/246:23 am
MDW
- ANC
1 stop15h 15m
Delta
Deal found 4/27![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Wed 8/2611:59 pm
ANC
- ORD
Nonstop6h 10m
United Airlines
Sun 8/306:00 am
ORD
- ANC
1 stop11h 05m
United Airlines
Deal found 4/26![United Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 4/27. 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 5/291:55 am
ANC
- ORD
1 stop12h 18m
Delta
Tue 6/97:45 am
ORD
- ANC
2 stops15h 22m
Delta
Deal found 4/27![Delta logo]()
$392
This Delta deal was found by Cheapflights users on 4/26. 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.
Sun 5/246:00 am
ANC
- MDW
2 stops12h 09m
Delta
Sun 5/319:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/26![Delta logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/3011:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Thu 6/1112:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 4/27. 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 5/318:05 pm
ANC
- ORD
1 stop14h 42m
Delta
Wed 6/107:45 am
ORD
- ANC
2 stops15h 22m
Delta
Deal found 4/27![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 4/27. 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 6/11:55 am
ANC
- ORD
1 stop11h 52m
Delta
Sat 6/612:47 pm
ORD
- ANC
1 stop14h 36m
Delta
Deal found 4/27![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 4/27. 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 8/2610:00 pm
ANC
- MDW
1 stop11h 30m
Delta
Sun 8/301:00 pm
MDW
- ANC
1 stop10h 58m
Delta
Deal found 4/27![Delta logo]()
$399
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 April 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 April 30, 2026.
This Delta deal was found by Cheapflights users on 4/26. 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 6/26:00 am
ANC
- ORD
1 stop10h 20m
Delta
Tue 6/96:55 am
ORD
- ANC
1 stop12h 20m
Delta
Deal found 4/26![Delta logo]()
$387
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/307:40 am
ANC
- ORD
1 stop12h 19m
Alaska Airlines
Thu 6/1112:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$403
This Southwest deal was found by Cheapflights users on 4/26. 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.
Wed 8/2611:15 pm
ANC
- MDW
2 stops13h 10m
Southwest
Sun 8/308:10 am
MDW
- ANC
2 stops18h 35m
Southwest
Deal found 4/26![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 4/26. 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 9/21:30 am
ANC
- ORD
1 stop12h 52m
Delta
Mon 9/73:50 pm
ORD
- ANC
1 stop8h 09m
Delta
Deal found 4/26![Delta logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 5/3111:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Tue 6/97:49 pm
ORD
- ANC
1 stop9h 10m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 4/25. 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 7/216:00 am
ANC
- ORD
1 stop14h 38m
Delta
Tue 8/47:45 am
ORD
- ANC
2 stops15h 23m
Delta
Deal found 4/25![Delta logo]()
$404
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 8/296:05 am
ANC
- ORD
1 stop14h 54m
Alaska Airlines
Tue 9/18:00 am
ORD
- ANC
Nonstop6h 44m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 7/166:00 am
ANC
- ORD
1 stop10h 30m
Delta
Mon 8/106:00 pm
ORD
- ANC
1 stop10h 35m
Delta
Deal found 4/29![Delta logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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.
Wed 5/275:29 pm
ANC
- ORD
1 stop9h 51m
Alaska Airlines
Wed 6/37:40 am
ORD
- ANC
1 stop10h 28m
Alaska Airlines
Deal found 4/29![Alaska Airlines logo]()
$419
This Alaska Airlines deal was found by Cheapflights users on 4/26. 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 9/310:26 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Mon 9/78:00 am
ORD
- ANC
Nonstop6h 44m
Alaska Airlines
Deal found 4/26![Alaska Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 4/30. 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 7/85:20 pm
ANC
- MDW
2 stops12h 17m
Delta
Sun 7/129:19 am
MDW
- ANC
1 stop15h 01m
Delta
Deal found 4/30![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 4/27. 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 8/2610:00 pm
ANC
- MDW
1 stop11h 30m
Delta
Sun 8/301:00 pm
MDW
- ANC
2 stops14h 33m
Delta
Deal found 4/27![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 4/25. 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 7/1710:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Mon 7/271:18 pm
MDW
- ANC
2 stops13h 02m
Delta
Deal found 4/25![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 4/28. 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 10/16:10 am
ANC
- MDW
1 stop8h 55m
Delta
Sun 10/49:20 am
MDW
- ANC
1 stop13h 07m
Delta
Deal found 4/28![Delta logo]()
$451
This Delta deal was found by Cheapflights users on 4/29. 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.
Thu 6/2510:30 pm
ANC
- MDW
1 stop11h 11m
Delta
Mon 6/299:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 4/29![Delta logo]()
$451
This Delta deal was found by Cheapflights users on 4/25. 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.
Wed 7/2210:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Mon 7/276:00 am
MDW
- ANC
1 stop15h 48m
Delta
Deal found 4/25![Delta logo]()
$471
This Delta deal was found by Cheapflights users on 4/26. 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 5/265:20 pm
ANC
- MDW
2 stops12h 22m
Delta
Tue 6/29:22 am
MDW
- ANC
2 stops14h 27m
Delta
Deal found 4/26![Delta logo]()
$475
This Delta deal was found by Cheapflights users on 4/30. 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.
Tue 7/281:30 am
ANC
- MDW
2 stops13h 55m
Delta
Sat 8/810:55 am
MDW
- ANC
2 stops13h 05m
Delta
Deal found 4/30![Delta logo]()
$491
Last-minute flights from Anchorage to ChicagoDiscover last-minute flight deals from Anchorage to Chicago. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Anchorage to Chicago. Data last updated April 30, 2026 and is based on user searches.
This Vliegwinkel deal was found by Cheapflights users on 4/27. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1811:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Sun 5/246:00 am
ORD
- ANC
1 stop9h 04m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 4/27. 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 5/186:00 am
ANC
- MDW
1 stop8h 56m
Delta
Sun 5/246:23 am
MDW
- ANC
1 stop15h 15m
Delta
Deal found 4/27![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 4/26. 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.
Sun 5/246:00 am
ANC
- MDW
2 stops12h 09m
Delta
Sun 5/319:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/26![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 4/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:53 pm
ANC
- ORD
Nonstop6h 28m
American Airlines
Tue 6/95:02 pm
ORD
- ANC
Nonstop6h 39m
American Airlines
Deal found 4/25![American Airlines logo]()
$402
This Alaska Airlines deal was found by Cheapflights users on 4/25. 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 5/2711:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Wed 6/108:05 pm
ORD
- ANC
1 stop15h 35m
Alaska Airlines
Deal found 4/25![Alaska Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 4/25. 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.
Wed 5/279:30 pm
ANC
- ORD
1 stop12h 31m
Delta
Mon 6/87:01 am
ORD
- ANC
1 stop17h 15m
Delta
Deal found 4/25![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 4/27. 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 5/278:05 pm
ANC
- ORD
1 stop11h 11m
Delta
Wed 6/1011:30 am
ORD
- ANC
1 stop12h 46m
Delta
Deal found 4/27![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 4/27. 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 5/291:55 am
ANC
- ORD
1 stop12h 18m
Delta
Tue 6/97:45 am
ORD
- ANC
2 stops15h 22m
Delta
Deal found 4/27![Delta logo]()
$392
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/3011:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Thu 6/1112:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$393
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 5/301:10 am
ANC
- ORD
1 stop10h 22m
Alaska Airlines
Thu 6/1112:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 4/29. 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 5/309:59 pm
ANC
- MDW
1 stop12h 20m
Delta
Sat 6/69:22 am
MDW
- ANC
2 stops14h 27m
Delta
Deal found 4/29![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 4/27. 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 5/318:05 pm
ANC
- ORD
1 stop14h 42m
Delta
Wed 6/107:45 am
ORD
- ANC
2 stops15h 22m
Delta
Deal found 4/27![Delta logo]()
$398
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 April 30, 2026.
Search for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Alaska Airlines deal was found by Cheapflights users on 4/27. 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.
Sun 6/711:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 4/27![Alaska Airlines logo]()
$183
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/289:50 pm
ANC
- ORD
Nonstop6h 33m
American Airlines
Deal found 4/27![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 4/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:03 pm
ANC
- ORD
Nonstop6h 22m
American Airlines
Deal found 4/27![American Airlines logo]()
$190
This Delta deal was found by Cheapflights users on 4/27. 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 6/710:30 pm
ANC
- ORD
1 stop14h 56m
Delta
Deal found 4/27![Delta logo]()
$193
This Delta deal was found by Cheapflights users on 4/27. 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 6/710:30 pm
ANC
- MDW
1 stop11h 11m
Delta
Deal found 4/27![Delta logo]()
$193
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:25 pm
ANC
- MDW
2 stops13h 15m
Southwest
Deal found 4/27![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 4/25. 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.
Sun 6/2810:02 pm
ANC
- ORD
1 stop14h 03m
Delta
Deal found 4/25![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 4/27. 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 6/2810:02 pm
ANC
- MDW
1 stop12h 07m
Delta
Deal found 4/27![Delta logo]()
$199
This Delta deal was found by Cheapflights users on 4/28. 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 5/239:30 pm
ANC
- MDW
1 stop12h 12m
Delta
Deal found 4/28![Delta logo]()
$203
This Delta deal was found by Cheapflights users on 4/27. 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.
Tue 8/41:45 am
ANC
- ORD
2 stops14h 12m
Delta
Deal found 4/27![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 4/27. 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 8/1312:30 am
ANC
- MDW
2 stops15h 01m
Delta
Deal found 4/27![Delta logo]()
$204
This Delta deal was found by Cheapflights users on 4/26. 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.
Sun 6/211:30 am
ANC
- ORD
2 stops17h 27m
Delta
Deal found 4/26![Delta logo]()
$210
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 April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $360 (Vliegwinkel) |
One-way from | $183 (Alaska Airlines) |
Popular in | July |
Cheapest in | October |
Average price | $467 |
Good round-trip deal | $574 or less |
Good one-way deal | $304 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 April 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 - ORD
ANCORD
Anchorage
Tue 6/2
6:00 am-7:20 pm
1 stop10h 20m
Chicago O'Hare Intl
Tue 6/9
6:55 am-4:15 pm
1 stop12h 20m
$387
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Wed 9/2
1:30 am-5:22 pm
1 stop12h 52m
Chicago O'Hare Intl
Mon 9/7
3:50 pm-8:59 pm
1 stop8h 09m
$399
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sat 5/30
7:40 am-10:59 pm
1 stop12h 19m
Chicago O'Hare Intl
Thu 6/11
12:59 am-4:41 am
Nonstop6h 42m
$403
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Tue 7/21
6:00 am-11:38 pm
1 stop14h 38m
Chicago O'Hare Intl
Tue 8/4
7:45 am-8:08 pm
2 stops15h 23m
$404
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sun 5/31
11:08 pm-8:25 am
Nonstop6h 17m
Chicago O'Hare Intl
Tue 6/9
7:49 pm-1:59 am
1 stop9h 10m
$409
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sat 8/29
6:05 am-11:59 pm
1 stop14h 54m
Chicago O'Hare Intl
Tue 9/1
8:00 am-11:44 am
Nonstop6h 44m
$419
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 7/16
6:00 am-7:30 pm
1 stop10h 30m
Chicago O'Hare Intl
Mon 8/10
6:00 pm-1:35 am
1 stop10h 35m
$419
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Wed 5/27
5:29 pm-6:20 am
1 stop9h 51m
Chicago O'Hare Intl
Wed 6/3
7:40 am-3:08 pm
1 stop10h 28m
$419
Quickest round-trip
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 9/3
10:26 pm-7:40 am
Nonstop6h 14m
Chicago O'Hare Intl
Mon 9/7
8:00 am-11:44 am
Nonstop6h 44m
$424
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Wed 7/8
5:20 pm-8:37 am
2 stops12h 17m
Chicago Midway
Sun 7/12
9:19 am-9:20 pm
1 stop15h 01m
$424
Showing 1-10 of 35 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 April.
| 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
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.
What is the cheapest month to book a flight from Anchorage to Chicago?
Currently, August is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $158). Flying from Anchorage to Chicago in January is currently the most expensive (average of $408). 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 April 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.
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 April 30, 2026.
The most flights from ANC to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from Anchorage to Chicago?
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 April 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.
Comfort
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
Comfort
7.8
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.0
Food
7.1
Reviews
1 / 20
8.0
ExcellentEugene,Mar 2026
MFR - SEA
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
Hammond
Porter
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Anchorage and Chicago flights
Browse other Anchorage and Chicago flight options. Last updated on April 30, 2026.
Other flights from Anchorage
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Top 5 airlines flying from Anchorage to Chicago
Discover the top 5 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$461 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$314 | Average$546 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$314 | Average$482 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$331 | Average$497 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$440 | FlexibilityNo cancel fee | On-timeN/A |