$174+ 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 6/29. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — CHI
Apr 7 — Apr 141
Round-trip
1 adult, Economy
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Find cheap flights from Anchorage to Chicago with Cheapflights
1. Tell us where you want to go
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 March 8, 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 March 8, 2026.
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/288:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Mon 5/41:15 pm
ORD
- ANC
Nonstop6h 46m
United Airlines
Deal found 3/3![United Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/18:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Wed 4/82:35 pm
ORD
- ANC
1 stop11h 10m
United Airlines
Deal found 3/3![United Airlines logo]()
$359
This Orbitz deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1311:23 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Thu 5/288:20 am
ORD
- ANC
Nonstop6h 48m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$363
This United Airlines deal was found by Cheapflights users on 3/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:49 pm
ANC
- ORD
1 stop10h 26m
United Airlines
Mon 5/44:20 pm
ORD
- ANC
Nonstop6h 46m
United Airlines
Deal found 3/6![United Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/58:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Fri 4/104:03 pm
ORD
- ANC
Nonstop6h 45m
United Airlines
Deal found 3/3![United Airlines logo]()
$369
This Trip.com deal was found by Cheapflights users on 3/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:21 am
ANC
- ORD
1 stop18h 18m
Multiple Airlines
Sun 4/56:00 am
ORD
- ANC
1 stop9h 41m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 3/7. 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 5/86:00 am
ANC
- ORD
1 stop14h 59m
Alaska Airlines
Thu 5/288:20 am
ORD
- ANC
Nonstop6h 48m
Alaska Airlines
Deal found 3/7![Alaska Airlines logo]()
$373
This Expedia deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
Tue 4/288:00 am
ANC
- ORD
1 stop8h 52m
Alaska Airlines
Mon 5/48:50 am
ORD
- ANC
2 stops18h 52m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$374
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 3/3110:48 am
ANC
- ORD
1 stop10h 11m
Alaska Airlines
Wed 4/18:00 am
ORD
- ANC
1 stop18h 35m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 3/6. 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.
Thu 5/76:00 am
ANC
- MDW
1 stop8h 56m
Delta
Wed 5/139:23 am
MDW
- ANC
1 stop14h 26m
Delta
Deal found 3/6![Delta logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:15 am
ANC
- ORD
1 stop13h 44m
Alaska Airlines
Sun 9/139:30 am
ORD
- ANC
Nonstop6h 48m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$379
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/251:30 am
ANC
- ORD
2 stops15h 22m
Alaska Airlines
Sat 5/26:00 am
ORD
- ANC
1 stop10h 11m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$382
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 March 8, 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 March 8, 2026.
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/18:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Wed 4/82:35 pm
ORD
- ANC
1 stop11h 10m
United Airlines
Deal found 3/3![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 3/6. 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.
Thu 5/76:00 am
ANC
- MDW
1 stop8h 56m
Delta
Wed 5/139:23 am
MDW
- ANC
1 stop14h 26m
Delta
Deal found 3/6![Delta logo]()
$377
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/251:30 am
ANC
- ORD
2 stops15h 22m
Alaska Airlines
Sat 5/26:00 am
ORD
- ANC
1 stop10h 11m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$382
This Delta deal was found by Cheapflights users on 3/6. 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 5/13:45 pm
ANC
- MDW
2 stops14h 21m
Delta
Mon 5/49:29 am
MDW
- ANC
1 stop12h 17m
Delta
Deal found 3/6![Delta logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/1911:23 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Sat 5/239:00 am
ORD
- ANC
2 stops17h 40m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 3/7. 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.
Tue 4/281:41 pm
ANC
- MDW
2 stops16h 06m
Delta
Mon 5/111:59 pm
MDW
- ANC
1 stop13h 32m
Delta
Deal found 3/7![Delta logo]()
$382
This Alaska Airlines deal was found by Cheapflights users on 3/6. 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 6/244:00 pm
ANC
- ORD
1 stop28h 39m
Alaska Airlines
Sat 6/2712:59 am
ORD
- ANC
Nonstop6h 45m
Alaska Airlines
Deal found 3/6![Alaska Airlines logo]()
$383
This Alaska Airlines deal was found by Cheapflights users on 3/5. 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.
Sat 5/1612:07 pm
ANC
- ORD
1 stop22h 07m
Alaska Airlines
Tue 5/199:00 am
ORD
- ANC
2 stops17h 40m
Alaska Airlines
Deal found 3/5![Alaska Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 3/6. 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.
Wed 4/81:34 am
ANC
- ORD
2 stops15h 15m
Delta
Mon 4/135:15 am
ORD
- ANC
2 stops16h 31m
Delta
Deal found 3/6![Delta logo]()
$387
This Delta deal was found by Cheapflights users on 3/7. 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 6/59:59 pm
ANC
- ORD
1 stop7h 37m
Delta
Mon 6/86:00 pm
ORD
- ANC
1 stop10h 35m
Delta
Deal found 3/7![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/231:55 am
ANC
- ORD
1 stop8h 50m
Delta
Sun 6/216:00 am
ORD
- ANC
1 stop16h 30m
Delta
Deal found 3/3![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/2311:59 pm
ANC
- ORD
1 stop8h 53m
Delta
Tue 6/2310:35 am
ORD
- ANC
1 stop13h 23m
Delta
Deal found 3/3![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/5. 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 6/810:00 pm
ANC
- MDW
1 stop11h 30m
Delta
Fri 6/122:00 pm
MDW
- ANC
1 stop13h 33m
Delta
Deal found 3/5![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/249:35 pm
ANC
- MDW
1 stop17h 58m
Delta
Tue 6/236:45 pm
MDW
- ANC
1 stop8h 48m
Delta
Deal found 3/3![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/189:15 pm
ANC
- MDW
1 stop13h 17m
Delta
Sat 4/256:00 am
MDW
- ANC
1 stop15h 49m
Delta
Deal found 3/4![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 5/259:59 pm
ANC
- MDW
1 stop7h 43m
Delta
Tue 6/236:45 pm
MDW
- ANC
1 stop8h 48m
Delta
Deal found 3/3![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/16:15 am
ANC
- ORD
1 stop14h 37m
Delta
Wed 4/85:30 am
ORD
- ANC
2 stops16h 21m
Delta
Deal found 3/3![Delta logo]()
$394
Last-minute flights from Anchorage to ChicagoDiscover last-minute flight deals from Anchorage to Chicago. Data last updated March 8, 2026 and is based on user searches.
Discover last-minute flight deals from Anchorage to Chicago. Data last updated March 8, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 3/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/309:21 am
ANC
- ORD
1 stop18h 18m
Multiple Airlines
Sun 4/56:00 am
ORD
- ANC
1 stop9h 41m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$370
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 3/3110:48 am
ANC
- ORD
1 stop10h 11m
Alaska Airlines
Wed 4/18:00 am
ORD
- ANC
1 stop18h 35m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/18:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Wed 4/82:35 pm
ORD
- ANC
1 stop11h 10m
United Airlines
Deal found 3/3![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/16:15 am
ANC
- ORD
1 stop14h 37m
Delta
Thu 4/3012:46 pm
ORD
- ANC
1 stop14h 39m
Delta
Deal found 3/3![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/58:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Sat 4/114:03 pm
ORD
- ANC
Nonstop6h 45m
United Airlines
Deal found 3/4![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/79:15 pm
ANC
- MDW
1 stop8h 35m
Delta
Mon 4/139:29 am
MDW
- ANC
1 stop12h 17m
Delta
Deal found 3/4![Delta logo]()
$377
This Delta deal was found by Cheapflights users on 3/6. 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 4/109:15 pm
ANC
- ORD
2 stops16h 03m
Delta
Mon 4/135:15 am
ORD
- ANC
2 stops16h 31m
Delta
Deal found 3/6![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/188:30 pm
ANC
- ORD
1 stop10h 09m
American Airlines
Sat 4/256:57 am
ORD
- ANC
1 stop14h 53m
American Airlines
Deal found 3/4![American Airlines logo]()
$388
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 4/251:30 am
ANC
- ORD
2 stops15h 22m
Alaska Airlines
Sat 5/26:00 am
ORD
- ANC
1 stop10h 11m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 4/288:50 pm
ANC
- ORD
Nonstop6h 15m
United Airlines
Mon 5/41:15 pm
ORD
- ANC
Nonstop6h 46m
United Airlines
Deal found 3/3![United Airlines logo]()
$349
This Expedia deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
Tue 4/288:00 am
ANC
- ORD
1 stop8h 52m
Alaska Airlines
Mon 5/48:50 am
ORD
- ANC
2 stops18h 52m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 3/5. 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 4/283:45 pm
ANC
- MDW
2 stops14h 02m
Delta
Mon 5/46:00 am
MDW
- ANC
2 stops15h 46m
Delta
Deal found 3/5![Delta logo]()
$387
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 March 8, 2026.
Search for one-way flight options from Anchorage to Chicago. Find affordable one-way fares based on user searches. Data last updated March 8, 2026.
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 6/299:24 pm
ANC
- ORD
Nonstop6h 18m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$174
This United Airlines deal was found by Cheapflights users on 3/7. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:45 pm
ANC
- ORD
Nonstop6h 17m
United Airlines
Deal found 3/7![United Airlines logo]()
$178
This Trip.com deal was found by Cheapflights users on 3/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:00 am
ANC
- ORD
1 stop8h 52m
Alaska Airlines
Deal found 3/8![Alaska Airlines logo]()
$183
This Alaska Airlines deal was found by Cheapflights users on 3/5. 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.
Sun 6/711:23 pm
ANC
- ORD
Nonstop6h 17m
Alaska Airlines
Deal found 3/5![Alaska Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:05 am
ANC
- ORD
1 stop11h 54m
Alaska Airlines
Deal found 3/8![Alaska Airlines logo]()
$186
This Alaska Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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 5/48:00 am
ANC
- ORD
1 stop19h 40m
Alaska Airlines
Deal found 3/4![Alaska Airlines logo]()
$188
This Delta deal was found by Cheapflights users on 3/7. 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 3/309:15 pm
ANC
- MDW
1 stop8h 35m
Delta
Deal found 3/7![Delta logo]()
$188
This Alaska Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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 6/309:05 am
ANC
- ORD
2 stops16h 57m
Alaska Airlines
Deal found 3/3![Alaska Airlines logo]()
$189
This Delta deal was found by Cheapflights users on 3/5. 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 6/612:30 am
ANC
- ORD
1 stop14h 31m
Delta
Deal found 3/5![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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
- MDW
1 stop7h 43m
Delta
Deal found 3/4![Delta logo]()
$194
This Delta deal was found by Cheapflights users on 3/6. 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.
Sat 4/49:15 pm
ANC
- ORD
1 stop21h 11m
Delta
Deal found 3/6![Delta logo]()
$195
This Delta deal was found by Cheapflights users on 3/8. 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 4/103:40 pm
ANC
- ORD
1 stop29h 12m
Delta
Deal found 3/8![Delta logo]()
$196
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 March 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $349 (United Airlines) |
One-way from | $174 (Alaska Airlines) |
Popular in | April |
Cheapest in | October |
Average price | $429 |
Good round-trip deal | $428 or less |
Good one-way deal | $223 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 March 8, 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
Wed 4/1
8:50 pm-6:05 am
Nonstop6h 15m
Chicago O'Hare Intl
Wed 4/8
2:35 pm-10:45 pm
1 stop11h 10m
$359
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Thu 5/7
6:00 am-5:56 pm
1 stop8h 56m
Chicago Midway
Wed 5/13
9:23 am-8:49 pm
1 stop14h 26m
$377
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sat 4/25
1:30 am-7:52 pm
2 stops15h 22m
Chicago O'Hare Intl
Sat 5/2
6:00 am-1:11 pm
1 stop10h 11m
$382
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Fri 5/1
3:45 pm-9:06 am
2 stops14h 21m
Chicago Midway
Mon 5/4
9:29 am-6:46 pm
1 stop12h 17m
$382
AnchorageChicago
ANC - MDW
ANCMDW
Anchorage
Tue 4/28
1:41 pm-8:47 am
2 stops16h 06m
Chicago Midway
Mon 5/11
1:59 pm-12:31 am
1 stop13h 32m
$382
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Tue 5/19
11:23 pm-8:40 am
Nonstop6h 17m
Chicago O'Hare Intl
Sat 5/23
9:00 am-11:40 pm
2 stops17h 40m
$383
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Wed 6/24
4:00 pm-11:39 pm
1 stop28h 39m
Chicago O'Hare Intl
Sat 6/27
12:59 am-4:44 am
Nonstop6h 45m
$383
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Sat 5/16
12:07 pm-1:14 pm
1 stop22h 07m
Chicago O'Hare Intl
Tue 5/19
9:00 am-11:40 pm
2 stops17h 40m
$386
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Wed 4/8
1:34 am-7:49 pm
2 stops15h 15m
Chicago O'Hare Intl
Mon 4/13
5:15 am-6:46 pm
2 stops16h 31m
$387
AnchorageChicago
ANC - ORD
ANCORD
Anchorage
Fri 6/5
9:59 pm-8:36 am
1 stop7h 37m
Chicago O'Hare Intl
Mon 6/8
6:00 pm-1:35 am
1 stop10h 35m
$389
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 March.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | 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, May is the cheapest month in which you can book a flight from Anchorage to Chicago (average of $187). Flying from Anchorage 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.
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 March 8, 2026.
The most flights from ANC 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).
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 March 8, 2026.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and Hawaiian Airlines from Anchorage to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Food
7.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Food
7.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Food
7.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
Boarding
8.1
Food
7.1
Crew
8.5
Comfort
7.8
Entertainment
7.0
Overall
8.0
Reviews
1 / 20
10.0
Excellentrobert,Feb 2026
LAS - SAN
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 locationsLansing
Merrillville
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Benton Harbor
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Anchorage and Chicago flights
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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 March 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$158 | Average$461 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$187 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$471 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$490 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$338 | Average$513 | FlexibilityNo cancel fee | On-time71% |