$186+ 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 7/13. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Jul 13 — Jul 201
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 June 13, 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 June 13, 2026.
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/10![Alaska Airlines logo]()
$373
This lol.travel deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/59:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Sun 7/1212:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$376
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/2710:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Tue 9/12:22 pm
ORD
- ANC
1 stop9h 29m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$383
This Alaska Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Sun 8/307:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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
Sun 8/301:59 pm
ORD
- ANC
1 stop10h 21m
Delta
Deal found 6/9![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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
Sun 8/301:27 pm
MDW
- ANC
1 stop10h 53m
Delta
Deal found 6/10![Delta logo]()
$393
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/241:29 am
ANC
- ORD
1 stop19h 30m
Alaska Airlines
Sat 8/297:20 am
ORD
- ANC
Nonstop6h 52m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/36:00 am
ANC
- ORD
2 stops11h 30m
Delta
Mon 9/76:00 am
ORD
- ANC
1 stop8h 39m
Delta
Deal found 6/10![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/256:00 am
ANC
- MDW
1 stop9h 01m
Delta
Sat 8/299:24 am
MDW
- ANC
2 stops14h 36m
Delta
Deal found 6/10![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/59:57 pm
ANC
- ORD
Nonstop6h 22m
American Airlines
Sun 7/125:00 pm
ORD
- ANC
Nonstop6h 52m
American Airlines
Deal found 6/10![American Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/912:55 am
ANC
- MDW
2 stops13h 05m
Southwest
Sun 9/1312:20 pm
MDW
- ANC
2 stops14h 25m
Southwest
Deal found 6/11![Southwest logo]()
$403
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 11/118:00 am
ANC
- ORD
1 stop12h 57m
Alaska Airlines
Sun 11/159:31 am
ORD
- ANC
1 stop9h 54m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$406
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 June 13, 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 June 13, 2026.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/96:10 am
ANC
- MDW
1 stop8h 55m
Delta
Mon 9/149:49 am
MDW
- ANC
1 stop14h 11m
Delta
Deal found 6/10![Delta logo]()
$393
This United Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/98:00 pm
ANC
- ORD
Nonstop6h 18m
United Airlines
Sun 7/125:00 am
ORD
- ANC
1 stop9h 10m
United Airlines
Deal found 6/12![United Airlines logo]()
$409
This Alaska Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:08 pm
ANC
- ORD
1 stop19h 30m
Alaska Airlines
Thu 7/912:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 6/11![Alaska Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/1011:55 pm
ANC
- MDW
1 stop10h 40m
Southwest
Tue 8/1810:30 am
MDW
- ANC
2 stops15h 15m
Southwest
Deal found 6/9![Southwest logo]()
$473
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ANC
- MDW
1 stop9h 01m
Delta
Sun 8/301:27 pm
MDW
- ANC
1 stop10h 53m
Delta
Deal found 6/13![Delta logo]()
$393
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/36:00 am
ANC
- ORD
2 stops11h 30m
Delta
Mon 9/76:00 am
ORD
- ANC
1 stop8h 39m
Delta
Deal found 6/10![Delta logo]()
$398
This Alaska Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Sat 7/1112:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:20 pm
ANC
- ORD
1 stop14h 49m
Delta
Tue 9/111:22 am
ORD
- ANC
2 stops15h 02m
Delta
Deal found 6/13![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 9/310:10 pm
ANC
- MDW
2 stops11h 29m
Delta
Mon 9/79:24 am
MDW
- ANC
1 stop14h 56m
Delta
Deal found 6/10![Delta logo]()
$398
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:15 pm
ANC
- ORD
2 stops15h 14m
Delta
Sun 9/136:00 pm
ORD
- ANC
1 stop10h 35m
Delta
Deal found 6/11![Delta logo]()
$436
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/261:30 am
ANC
- ORD
1 stop12h 15m
Delta
Fri 7/311:30 am
ORD
- ANC
1 stop12h 46m
Delta
Deal found 6/8![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/301:30 am
ANC
- ORD
1 stop12h 15m
Delta
Sat 7/45:55 pm
ORD
- ANC
1 stop9h 01m
Delta
Deal found 6/13![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/262:10 pm
ANC
- MDW
2 stops15h 27m
Delta
Fri 7/39:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 6/8![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Sat 8/89:24 am
MDW
- ANC
1 stop14h 56m
Delta
Deal found 6/12![Delta logo]()
$528
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/2812:35 am
ANC
- MDW
2 stops14h 43m
Delta
Sat 8/81:27 pm
MDW
- ANC
2 stops14h 32m
Delta
Deal found 6/9![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Mon 7/201:49 pm
MDW
- ANC
1 stop14h 10m
Delta
Deal found 6/13![Delta logo]()
$623
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/510:02 pm
ANC
- MDW
1 stop12h 07m
Delta
Mon 7/139:19 am
MDW
- ANC
1 stop15h 01m
Delta
Deal found 6/12![Delta logo]()
$629
Last-minute flights from Anchorage to ChicagoDiscover last-minute flight deals from Anchorage to Chicago. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Anchorage to Chicago. Data last updated June 13, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 6/266:00 am
ANC
- ORD
1 stop14h 39m
Delta
Fri 7/31:00 pm
ORD
- ANC
1 stop13h 56m
Delta
Deal found 6/10![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 6/262:10 pm
ANC
- MDW
2 stops15h 27m
Delta
Fri 7/39:54 am
MDW
- ANC
2 stops17h 02m
Delta
Deal found 6/8![Delta logo]()
$497
This United Airlines deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/111:59 pm
ANC
- ORD
Nonstop6h 20m
United Airlines
Sat 7/49:04 am
ORD
- ANC
Nonstop6h 52m
United Airlines
Deal found 6/13![United Airlines logo]()
$424
This Alaska Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/111:15 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Sun 7/56:00 am
ORD
- ANC
1 stop19h 22m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$429
This flugladen.de deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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.
Sat 7/43:50 pm
ANC
- ORD
1 stop18h 31m
Alaska Airlines
Sun 7/126:00 am
ORD
- ANC
1 stop20h 08m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/43:50 pm
ANC
- ORD
1 stop28h 46m
Alaska Airlines
Tue 7/78:20 pm
ORD
- ANC
1 stop16h 16m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$423
This lol.travel deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/59:24 pm
ANC
- ORD
Nonstop6h 16m
Alaska Airlines
Sun 7/1212:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 6/12![Alaska Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/59:57 pm
ANC
- ORD
Nonstop6h 22m
American Airlines
Sun 7/125:00 pm
ORD
- ANC
Nonstop6h 52m
American Airlines
Deal found 6/10![American Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/98:00 pm
ANC
- ORD
Nonstop6h 18m
United Airlines
Sun 7/125:00 am
ORD
- ANC
1 stop9h 10m
United Airlines
Deal found 6/10![United Airlines logo]()
$409
This Priceline deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/96:02 pm
ANC
- ORD
1 stop9h 18m
Alaska Airlines
Sun 7/126:00 am
ORD
- ANC
1 stop22h 37m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 6/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:30 am
ANC
- ORD
1 stop12h 13m
Delta
Sat 8/86:00 pm
ORD
- ANC
1 stop9h 59m
Delta
Deal found 6/13![Delta logo]()
$431
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2910:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Sat 8/81:51 pm
MDW
- ANC
1 stop14h 08m
Delta
Deal found 6/11![Delta logo]()
$488
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 June 13, 2026.
Search for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/139:57 pm
ANC
- ORD
Nonstop6h 22m
American Airlines
Deal found 6/10![American Airlines logo]()
$186
This Trip.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Tue 8/2512:39 am
ANC
- ORD
1 stop17h 51m
Delta
Deal found 6/10![Delta logo]()
$189
This Trip.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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.
Wed 8/2610:30 pm
ANC
- MDW
1 stop11h 09m
Delta
Deal found 6/10![Delta logo]()
$189
This Trip.com deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:30 pm
ANC
- ORD
1 stop14h 47m
Delta
Deal found 6/9![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/2410:30 pm
ANC
- ORD
1 stop11h 38m
Delta
Deal found 6/10![Delta logo]()
$196
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/1312:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/9![Delta logo]()
$196
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/59:57 pm
ANC
- ORD
Nonstop6h 22m
American Airlines
Deal found 6/12![American Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1311:55 pm
ANC
- MDW
2 stops10h 55m
Southwest
Deal found 6/11![Southwest logo]()
$201
This Alaska Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 8/2410:28 pm
ANC
- ORD
Nonstop6h 12m
Alaska Airlines
Deal found 6/10![Alaska Airlines logo]()
$206
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” 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 7/121:30 am
ANC
- ORD
2 stops14h 27m
Delta
Deal found 6/10![Delta logo]()
$207
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:44 pm
ANC
- ORD
1 stop16h 46m
Delta
Deal found 6/11![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/712:44 pm
ANC
- MDW
1 stop16h 53m
Delta
Deal found 6/9![Delta logo]()
$209
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 June 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $373 (American Airlines) |
One-way from | $186 (American Airlines) |
Popular in | July |
Cheapest in | October |
Average price | $489 |
Good round-trip deal | $610 or less |
Good one-way deal | $301 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 June 13, 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 - MDW
ANCMDW
Anchorage
Wed 9/9
6:10 am-6:05 pm
1 stop8h 55m
Chicago Midway
Mon 9/14
9:49 am-9:00 pm
1 stop14h 11m
$393
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Thu 8/27
6:00 am-6:01 pm
1 stop9h 01m
Chicago Midway
Sun 8/30
1:27 pm-9:20 pm
1 stop10h 53m
$393
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 9/3
6:00 am-8:30 pm
2 stops11h 30m
Chicago O'Hare Intl
Mon 9/7
6:00 am-11:39 am
1 stop8h 39m
$398
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 8/27
8:20 pm-2:09 pm
1 stop14h 49m
Chicago O'Hare Intl
Tue 9/1
11:22 am-11:24 pm
2 stops15h 02m
$398
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Thu 9/3
10:10 pm-12:39 pm
2 stops11h 29m
Chicago Midway
Mon 9/7
9:24 am-9:20 pm
1 stop14h 56m
$398
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 7/9
8:00 pm-5:18 am
Nonstop6h 18m
Chicago O'Hare Intl
Sun 7/12
5:00 am-11:10 am
1 stop9h 10m
$409
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 7/2
7:08 pm-5:38 pm
1 stop19h 30m
Chicago O'Hare Intl
Thu 7/9
12:59 am-4:41 am
Nonstop6h 42m
$429
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Fri 9/11
5:15 pm-11:29 am
2 stops15h 14m
Chicago O'Hare Intl
Sun 9/13
6:00 pm-1:35 am
1 stop10h 35m
$436
Quickest round-trip
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 7/9
9:24 pm-6:40 am
Nonstop6h 16m
Chicago O'Hare Intl
Sat 7/11
12:59 am-4:41 am
Nonstop6h 42m
$439
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Fri 6/26
1:30 am-4:45 pm
1 stop12h 15m
Chicago O'Hare Intl
Fri 7/3
11:30 am-9:16 pm
1 stop12h 46m
$444
Showing 1-10 of 36 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 June.
| 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, 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 June 13, 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 June 13, 2026.
The most flights from ANC to CHI are scheduled on a Saturday (11 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Anchorage to Chicago?
How far ahead should I book a flight from Anchorage to Chicago?
Booking 75 days in advance of your planned departure date is, on average, the best time to get cheap flights from Anchorage to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
The best insider tips for Anchorage to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Anchorage to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 13, 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.
Food
7.1
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
Food
7.1
Boarding
8.1
Comfort
7.8
Entertainment
7.0
Crew
8.5
Overall
7.9
Reviews
1 / 20
4.0
OkayAnonymous,Jun 2026
SEA - RNO
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
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Anchorage and Chicago flights
Browse other Anchorage and Chicago flight options. Last updated on June 13, 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 June 13, 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 2,558,603 searches. Data last updated June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$314 | Average$503 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$472 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$331 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$337 | Average$480 | FlexibilityNo cancel fee | On-timeN/A |