Cheap flights from Anchorage to Historic Route 66

View AU$246 flight on Sat, 6 Sep. 2025Opens in a new window

Popular airlines from Anchorage to Historic Route 66

  • Delta

    Delta

  • American Airlines

    American Airlines

  • Alaska Airlines

    Alaska Airlines

  • United

    United

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Cheap Flights from Anchorage (ANC) to Historic Route 66 (CHI)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Alaska Airlines
Sat, 6 Sep. - Sun, 21 Sep.
ANC
Anchorage
ORD
Chicago
AU$507 Return, found 1 day ago
AU$507
Return
found 1 day ago
Select Alaska Airlines flight, departing Sat, 6 Sep. from Anchorage to Chicago, returning Sun, 21 Sep., priced at AU$507 found 1 day ago
Alaska Airlines
Sat, 6 Sep. - Sun, 21 Sep.
ANC
Anchorage
ORD
Chicago
AU$508 Return, found 1 day ago
AU$508
Return
found 1 day ago
Select Alaska Airlines flight, departing Sat, 6 Sep. from Anchorage to Chicago, returning Sun, 21 Sep., priced at AU$508 found 1 day ago
Hawaiian Airlines
Wed, 27 Aug. - Sat, 13 Sep.
ANC
Anchorage
ORD
Chicago
AU$514 Return, found 5 days ago
AU$514
Return
found 5 days ago
Select Hawaiian Airlines flight, departing Wed, 27 Aug. from Anchorage to Chicago, returning Sat, 13 Sep., priced at AU$514 found 5 days ago
Hawaiian Airlines
Wed, 27 Aug. - Mon, 15 Sep.
ANC
Anchorage
ORD
Chicago
AU$521 Return, found 5 days ago
AU$521
Return
found 5 days ago
Select Hawaiian Airlines flight, departing Wed, 27 Aug. from Anchorage to Chicago, returning Mon, 15 Sep., priced at AU$521 found 5 days ago
Delta
Sat, 6 Sep. - Sun, 21 Sep.
ANC
Anchorage
ORD
Chicago
AU$522 Return, found 1 day ago
AU$522
Return
found 1 day ago
Select Delta flight, departing Sat, 6 Sep. from Anchorage to Chicago, returning Sun, 21 Sep., priced at AU$522 found 1 day ago
Delta
Sat, 6 Sep. - Sun, 21 Sep.
ANC
Anchorage
ORD
Chicago
AU$523 Return, found 1 day ago
AU$523
Return
found 1 day ago
Select Delta flight, departing Sat, 6 Sep. from Anchorage to Chicago, returning Sun, 21 Sep., priced at AU$523 found 1 day ago

Find the cheapest month to fly from Anchorage (ANC) to Chicago (ORD)

April is typically the cheapest month to fly

From AU$490 - AU$968 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.