$187+ Cheap flights from Alaska 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
May 10 — May 171
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Alaska to ChicagoExplore the most affordable flight options available from Alaska to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 10, 2026.
Explore the most affordable flight options available from Alaska to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 10, 2026.
This United Airlines deal was found by Cheapflights users on 4/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:45 pm
ANC
- ORD
Nonstop6h 17m
United Airlines
Thu 5/74:20 pm
ORD
- ANC
Nonstop6h 46m
United Airlines
Deal found 4/9![United Airlines logo]()
$377
This Trip.com deal was found by Cheapflights users on 4/9. 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.
Thu 4/305:25 pm
ANC
- ORD
1 stop10h 15m
Alaska Airlines
Wed 5/68:48 pm
ORD
- ANC
1 stop18h 15m
Alaska Airlines
Deal found 4/9![Alaska Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 4/10. 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 6/46:00 am
ANC
- ORD
1 stop10h 20m
Delta
Mon 6/88:52 am
ORD
- ANC
1 stop15h 24m
Delta
Deal found 4/10![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 4/9. 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 5/116:00 am
ANC
- MDW
1 stop8h 56m
Delta
Fri 5/229:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/9![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 4/8. 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.
Sat 5/26:00 am
ANC
- ORD
2 stops12h 18m
Delta
Tue 5/512:46 pm
ORD
- ANC
1 stop14h 39m
Delta
Deal found 4/8![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/8. 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.
Sat 5/29:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Tue 5/51:24 pm
MDW
- ANC
2 stops14h 01m
Delta
Deal found 4/8![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/9. 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 4/303:45 pm
ANC
- MDW
2 stops14h 02m
Delta
Wed 5/69:29 am
MDW
- ANC
2 stops14h 17m
Delta
Deal found 4/9![Delta logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:21 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Thu 8/279:05 am
ORD
- ANC
Nonstop6h 50m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$409
This Kiwi.com deal was found by Cheapflights users on 4/10. 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 Kiwi.com 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
Sun 6/1412:59 am
ORD
- ANC
Nonstop6h 42m
Alaska Airlines
Deal found 4/10![Alaska Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 4/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:53 pm
ANC
- ORD
Nonstop6h 28m
American Airlines
Mon 6/85:02 pm
ORD
- ANC
Nonstop6h 45m
American Airlines
Deal found 4/8![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/2311:30 am
ANC
- ORD
1 stop9h 27m
Delta
Wed 5/2712:47 pm
ORD
- ANC
1 stop12h 28m
Delta
Deal found 4/7![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Sat 5/2310:25 pm
ANC
- MDW
1 stop9h 15m
Southwest
Thu 5/2811:40 am
MDW
- ANC
1 stop12h 35m
Southwest
Deal found 4/7![Southwest logo]()
$417
Best flights from Alaska to ChicagoDiscover carefully curated flight deals from Alaska to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
Discover carefully curated flight deals from Alaska to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2026.
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/66:00 am
ANC
- ORD
1 stop14h 55m
Delta
Mon 6/88:21 pm
ORD
- ANC
1 stop8h 02m
Delta
Deal found 4/5![Delta logo]()
$397
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Sat 5/2310:25 pm
ANC
- ORD
1 stop13h 35m
Southwest
Thu 5/288:00 am
ORD
- ANC
2 stops16h 15m
Southwest
Deal found 4/7![Southwest logo]()
$422
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 6/37:00 am
FAI
- ORD
2 stops13h 59m
Alaska Airlines
Tue 6/912:59 am
ORD
- FAI
1 stop26h 45m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/229:59 pm
ANC
- ORD
2 stops15h 30m
Delta
Wed 5/277:12 am
ORD
- ANC
1 stop12h 11m
Delta
Deal found 4/5![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/221:55 am
ANC
- MDW
2 stops13h 01m
Delta
Thu 5/289:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/5![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/1512:35 am
ANC
- ORD
2 stops13h 16m
Delta
Tue 5/199:25 am
ORD
- ANC
2 stops15h 50m
Delta
Deal found 4/6![Delta logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 8/288:00 am
FAI
- ORD
1 stop12h 59m
Alaska Airlines
Tue 9/19:05 am
ORD
- FAI
1 stop17h 54m
Alaska Airlines
Deal found 4/5![Alaska Airlines logo]()
$545
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/229:30 pm
ANC
- MDW
1 stop12h 12m
Delta
Wed 5/279:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/7![Delta logo]()
$417
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/116:00 am
ANC
- ORD
1 stop10h 31m
Delta
Mon 6/1511:30 am
ORD
- ANC
1 stop12h 46m
Delta
Deal found 4/5![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/151:35 am
ANC
- ORD
1 stop8h 55m
Delta
Wed 6/2411:30 am
ORD
- ANC
1 stop12h 46m
Delta
Deal found 4/5![Delta logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 9/11:46 pm
SIT
- ORD
1 stop13h 36m
Alaska Airlines
Wed 9/29:00 am
ORD
- SIT
2 stops12h 36m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$660
This Delta deal was found by Cheapflights users on 4/9. 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 8/1712:30 am
ANC
- ORD
1 stop14h 31m
Delta
Sat 8/223:50 pm
ORD
- ANC
1 stop8h 09m
Delta
Deal found 4/9![Delta logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:20 am
SIT
- ORD
2 stops21h 47m
Alaska Airlines
Sun 9/66:00 am
ORD
- SIT
1 stop9h 50m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$666
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/1110:30 pm
ANC
- MDW
1 stop11h 06m
Delta
Mon 6/157:16 pm
MDW
- ANC
1 stop9h 07m
Delta
Deal found 4/5![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/166:00 am
ANC
- MDW
1 stop9h 18m
Delta
Wed 6/249:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 4/5![Delta logo]()
$429
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/1610:30 pm
ANC
- MDW
1 stop11h 06m
Delta
Thu 6/251:49 pm
MDW
- ANC
1 stop14h 34m
Delta
Deal found 4/5![Delta logo]()
$429
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:29 pm
OTZ
- ORD
2 stops26h 30m
Alaska Airlines
Tue 5/58:48 pm
ORD
- OTZ
2 stops23h 56m
Alaska Airlines
Deal found 4/8![Alaska Airlines logo]()
$778
This Delta deal was found by Cheapflights users on 4/9. 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 6/15:20 pm
ANC
- ORD
2 stops14h 09m
Delta
Thu 6/46:20 pm
ORD
- ANC
1 stop9h 35m
Delta
Deal found 4/9![Delta logo]()
$435
This Alaska Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/2811:26 am
OTZ
- ORD
2 stops16h 14m
Alaska Airlines
Wed 4/295:52 pm
ORD
- OTZ
2 stops26h 52m
Alaska Airlines
Deal found 4/6![Alaska Airlines logo]()
$778
This Delta deal was found by Cheapflights users on 4/9. 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.
Sun 5/101:55 am
ANC
- MDW
2 stops13h 38m
Delta
Fri 5/229:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/9![Delta logo]()
$435
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/271:45 am
FAI
- ORD
1 stop11h 54m
Delta
Fri 5/16:00 pm
ORD
- FAI
1 stop9h 40m
Delta
Deal found 4/7![Delta logo]()
$438
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/176:00 am
ANC
- MDW
1 stop8h 56m
Delta
Sun 5/249:22 am
MDW
- ANC
2 stops14h 27m
Delta
Deal found 4/6![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/71:30 am
ANC
- MDW
2 stops14h 03m
Delta
Sat 5/91:59 pm
MDW
- ANC
1 stop13h 32m
Delta
Deal found 4/7![Delta logo]()
$455
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/1210:30 pm
ANC
- MDW
1 stop11h 06m
Delta
Sun 6/149:17 am
MDW
- ANC
1 stop14h 59m
Delta
Deal found 4/5![Delta logo]()
$456
This Delta deal was found by Cheapflights users on 4/10. 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 7/2910:10 pm
ANC
- MDW
1 stop11h 59m
Delta
Sat 8/89:49 am
MDW
- ANC
1 stop14h 11m
Delta
Deal found 4/10![Delta logo]()
$456
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/159:53 pm
FAI
- MDW
2 stops15h 23m
Delta
Sat 6/271:16 pm
MDW
- FAI
2 stops14h 14m
Delta
Deal found 4/7![Delta logo]()
$544
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/159:53 pm
FAI
- MDW
1 stop12h 16m
Delta
Fri 6/269:54 am
MDW
- FAI
1 stop13h 49m
Delta
Deal found 4/7![Delta logo]()
$552
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 7/302:41 pm
FAI
- MDW
2 stops14h 56m
Delta
Wed 8/59:49 am
MDW
- FAI
1 stop14h 00m
Delta
Deal found 4/7![Delta logo]()
$611
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/201:45 am
FAI
- MDW
2 stops13h 51m
Delta
Sat 4/259:27 am
MDW
- FAI
2 stops18h 13m
Delta
Deal found 4/6![Delta logo]()
$665
This Delta deal was found by Cheapflights users on 4/10. 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 4/241:45 am
FAI
- MDW
2 stops13h 51m
Delta
Wed 4/291:24 pm
MDW
- FAI
2 stops14h 16m
Delta
Deal found 4/10![Delta logo]()
$665
Last-minute flights from Alaska to ChicagoDiscover last-minute flight deals from Alaska to Chicago. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Alaska to Chicago. Data last updated April 10, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 4/9. 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.
Thu 4/305:25 pm
ANC
- ORD
1 stop10h 15m
Alaska Airlines
Wed 5/68:48 pm
ORD
- ANC
1 stop18h 15m
Alaska Airlines
Deal found 4/9![Alaska Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 4/9. 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 4/303:45 pm
ANC
- MDW
2 stops14h 02m
Delta
Wed 5/69:29 am
MDW
- ANC
2 stops14h 17m
Delta
Deal found 4/9![Delta logo]()
$407
This Alaska Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/11:49 am
ANC
- ORD
1 stop10h 07m
Alaska Airlines
Sat 5/28:48 pm
ORD
- ANC
1 stop17h 23m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 4/8. 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.
Sat 5/26:00 am
ANC
- ORD
2 stops12h 18m
Delta
Tue 5/512:46 pm
ORD
- ANC
1 stop14h 39m
Delta
Deal found 4/8![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 4/8. 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.
Sat 5/29:15 pm
ANC
- MDW
1 stop8h 31m
Delta
Tue 5/51:24 pm
MDW
- ANC
2 stops14h 01m
Delta
Deal found 4/8![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 4/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/48:45 pm
ANC
- ORD
Nonstop6h 17m
United Airlines
Thu 5/74:20 pm
ORD
- ANC
Nonstop6h 46m
United Airlines
Deal found 4/9![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 4/9. 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 5/116:00 am
ANC
- MDW
1 stop8h 56m
Delta
Fri 5/229:22 am
MDW
- ANC
1 stop13h 54m
Delta
Deal found 4/9![Delta logo]()
$397
This Delta deal was found by Cheapflights users on 4/10. 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 5/1512:35 am
ANC
- ORD
2 stops13h 16m
Delta
Tue 5/199:25 am
ORD
- ANC
2 stops15h 50m
Delta
Deal found 4/10![Delta logo]()
$407
This Expedia deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:24 pm
ANC
- ORD
2 stops25h 31m
Alaska Airlines
Thu 5/282:10 pm
ORD
- ANC
2 stops22h 41m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/2311:30 am
ANC
- ORD
1 stop9h 27m
Delta
Wed 5/2712:47 pm
ORD
- ANC
1 stop12h 28m
Delta
Deal found 4/7![Delta logo]()
$417
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Sat 5/2310:25 pm
ANC
- MDW
1 stop9h 15m
Southwest
Thu 5/2811:40 am
MDW
- ANC
1 stop12h 35m
Southwest
Deal found 4/7![Southwest logo]()
$417
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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
Sat 6/205:00 pm
ORD
- ANC
2 stops11h 55m
Delta
Deal found 4/5![Delta logo]()
$418
One-way flights from Alaska to ChicagoSearch for one-way flight options from Alaska to Chicago. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
Search for one-way flight options from Alaska to Chicago. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/811:08 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 4/9![Alaska Airlines logo]()
$187
This Alaska Airlines deal was found by Cheapflights users on 4/8. 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 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 4/8![Alaska Airlines logo]()
$188
This Delta deal was found by Cheapflights users on 4/9. 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.
Fri 5/229:30 pm
ANC
- MDW
1 stop12h 12m
Delta
Deal found 4/9![Delta logo]()
$198
This American Airlines deal was found by Cheapflights users on 4/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/249:53 pm
ANC
- ORD
Nonstop6h 28m
American Airlines
Deal found 4/8![American Airlines logo]()
$199
This Alaska Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/51:30 am
ANC
- ORD
2 stops19h 29m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$203
This Southwest deal was found by Cheapflights users on 4/9. 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.
Fri 5/2210:25 pm
ANC
- MDW
2 stops13h 15m
Southwest
Deal found 4/9![Southwest logo]()
$203
This Alaska Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/1711:21 pm
ANC
- ORD
Nonstop6h 14m
Alaska Airlines
Deal found 4/7![Alaska Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 stop11h 34m
Delta
Deal found 4/6![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/710:02 pm
ANC
- MDW
1 stop7h 35m
Delta
Deal found 4/7![Delta logo]()
$208
This Delta deal was found by Cheapflights users on 4/10. 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.
Sat 5/239:59 pm
ANC
- ORD
2 stops15h 30m
Delta
Deal found 4/10![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 4/10. 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.
Sat 5/301:40 am
FAI
- ORD
1 stop9h 05m
Delta
Deal found 4/10![Delta logo]()
$209
This United Airlines deal was found by Cheapflights users on 4/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/611:40 pm
ANC
- ORD
1 stop9h 02m
United Airlines
Deal found 4/8![United Airlines logo]()
$214
Find flight deals from Alaska to Chicago
Keep the following information in mind while searching for Alaska to Chicago flight deals. Data was last updated April 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $377 (United Airlines) |
One-way from | $187 (Kiwi.com) |
Popular in | July |
Cheapest in | October |
Average price | $413 |
Good round-trip deal | $520 or less |
Good one-way deal | $279 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Alaska 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 10, 2026.
Use the filters below to find and compare flights from Alaska to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sat 6/6
6:00 am-11:55 pm
1 stop14h 55m
Chicago O'Hare Intl
Mon 6/8
8:21 pm-1:23 am
1 stop8h 02m
$397
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Fri 5/22
9:59 pm-4:29 pm
2 stops15h 30m
Chicago O'Hare Intl
Wed 5/27
7:12 am-4:23 pm
1 stop12h 11m
$402
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Fri 5/22
1:55 am-5:56 pm
2 stops13h 01m
Chicago Midway
Thu 5/28
9:22 am-8:16 pm
1 stop13h 54m
$402
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Fri 5/15
12:35 am-4:51 pm
2 stops13h 16m
Chicago O'Hare Intl
Tue 5/19
9:25 am-10:15 pm
2 stops15h 50m
$407
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Fri 5/22
9:30 pm-12:42 pm
1 stop12h 12m
Chicago Midway
Wed 5/27
9:22 am-8:16 pm
1 stop13h 54m
$417
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sat 5/23
10:25 pm-3:00 pm
1 stop13h 35m
Chicago O'Hare Intl
Thu 5/28
8:00 am-9:15 pm
2 stops16h 15m
$422
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Thu 6/11
6:00 am-7:31 pm
1 stop10h 31m
Chicago O'Hare Intl
Mon 6/15
11:30 am-9:16 pm
1 stop12h 46m
$429
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Mon 6/15
1:35 am-1:30 pm
1 stop8h 55m
Chicago O'Hare Intl
Wed 6/24
11:30 am-9:16 pm
1 stop12h 46m
$429
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Mon 8/17
12:30 am-6:01 pm
1 stop14h 31m
Chicago O'Hare Intl
Sat 8/22
3:50 pm-8:59 pm
1 stop8h 09m
$429
Quickest round-trip
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Thu 6/11
10:30 pm-12:36 pm
1 stop11h 06m
Chicago Midway
Mon 6/15
7:16 pm-1:23 am
1 stop9h 07m
$429
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Alaska to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Alaska with our price prediction graph.
ANC-ORD
ANC-MDW
FAI-ORD
SIT-ORD
OTZ-ORD
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 Alaska to Chicago
USAK-CHI
ANC-ORD
ANC-MDW
FAI-ORD
SIT-ORD
What is the cheapest month to book a flight from Alaska to Chicago?
Currently, June is the cheapest month in which you can book a flight from Alaska to Chicago (average of $204). Flying from Alaska to Chicago in January is currently the most expensive (average of $697). 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 AK to CHI?
Find hourly flight availability from Alaska 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 10, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Alaska to Chicago as you normally would.
Weekly flight availability from Alaska to Chicago
Explore weekly flight availability from Alaska 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 10, 2026.
The most flights from USAK to CHI are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Alaska to Chicago?
Related info for your journey
Find useful and relevant information for your journey from Alaska 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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
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Alternative routes for Alaska to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Alaska to Chicago by cabin class
Find flights from Alaska to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Alaska and Chicago flights
Browse other Alaska and Chicago flight options. Last updated on April 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Alaska to Chicago flights
Consider these flights traveling from Alaska to Chicago.
Top 5 airlines flying from Alaska to Chicago
Discover the top 5 airlines that operate flights from Alaska 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$461 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$262 | Average$474 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$314 | Average$482 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$337 | Average$489 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$517 | FlexibilityNo cancel fee | On-time71% |