Cheap flights from Chicago to Anchorage

One-way fares from $254 · CHI → ANC · prices found by travellers in the last 48 hours

Compare all dates Anchorage → Chicago
Cheapest fare
$254

Alaska Airlines · Tue, Nov 10

Cheapest month
November

from $254

Direct flights
Not recently

Usually 1+ stop

Quickest trip
8h 30m

4,590 km

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Cheapest month to fly from Chicago to Anchorage

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $254

Cheapest dates in November 2026

The lowest fares we've seen for each day, cheapest first.

Alaska Airlines
Depart14:07 Tue, Nov 10ORD → ANC 8h 40m · 1 stop
$254one way, per person
View deal
Alaska Airlines
Depart14:07 Fri, Nov 6ORD → ANC 8h 40m · 1 stop
$285one way, per person
View deal
American Airlines
Depart11:00 Wed, Nov 25ORD → ANC 9h 58m · 1 stop
$295one way, per person
View deal
Alaska Airlines
Depart18:35 Wed, Nov 4ORD → ANC 8h 55m · 1 stop
$306one way, per person
View deal
Alaska Airlines
Depart18:35 Mon, Nov 9ORD → ANC 8h 55m · 1 stop
$306one way, per person
View deal
Alaska Airlines
Depart07:00 Wed, Nov 18ORD → ANC 8h 36m · 1 stop
$308one way, per person
View deal
Alaska Airlines
Depart09:30 Fri, Nov 13ORD → ANC 8h 30m · 1 stop
$346one way, per person
View deal
See every date in November 2026 →

Plan the rest of your trip to Anchorage

Where to stay, what to do and getting around, from our travel partners.

Where to stay

Hotels in AnchorageCompare places to stay on Booking.com Find hotels →

Things to do

Things to do in AnchorageTours, attractions and day trips on Klook Explore →

Getting around

Airport transfer in AnchoragePre-book a driver to meet you at arrivals, with Kiwitaxi Book a transfer → Car hire in AnchorageCompare rental cars from major brands on EconomyBookings Compare cars →

About flights from Chicago to Anchorage

Chicago (CHI) and Anchorage (ANC) are about 4,590 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 8h 30m. Over the next few months, one-way fares start from $254, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Chicago to Anchorage?

The cheapest one-way fare we've seen recently is $254 with Alaska Airlines, departing Tuesday, November 10, 2026.

What is the cheapest month to fly from Chicago to Anchorage?

November 2026 currently has the lowest fares, from $254 one way.

Are there direct flights from Chicago to Anchorage?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Chicago to Anchorage?

The quickest journey we've seen takes about 8h 30m. Chicago and Anchorage are around 4,590 km apart.

Which airlines fly from Chicago to Anchorage?

Recent fares on this route were with Alaska Airlines and American Airlines.

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