Cheap flights from Anchorage to Chicago

One-way fares from $282 · ANC → CHI · prices found by travellers in the last 48 hours

Compare all dates Chicago → Anchorage
Cheapest fare
$282

Alaska Airlines · Fri, Nov 13

Cheapest month
November

from $282

Direct flights
Not recently

Usually 1+ stop

Quickest trip
7h 30m

4,590 km

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Cheapest month to fly from Anchorage to Chicago

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

  1. November 2026 Cheapest $282
  2. March 2027 $391

Cheapest dates in November 2026

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

Alaska Airlines
Depart17:28 Fri, Nov 13ANC → ORD 7h 30m · 1 stop
$282one way, per person
View deal
American Airlines
Depart20:14 Thu, Nov 12ANC → ORD 9h 14m · 1 stop
$293one way, per person
View deal
Alaska Airlines
Depart12:04 Mon, Nov 9ANC → ORD 7h 40m · 1 stop
$304one way, per person
View deal
See every date in November 2026 →

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About flights from Anchorage to Chicago

Anchorage (ANC) and Chicago (CHI) 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 7h 30m. Over the next few months, one-way fares start from $282, 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 Anchorage to Chicago?

The cheapest one-way fare we've seen recently is $282 with Alaska Airlines, departing Friday, November 13, 2026. Over the coming months, the lowest fare in each month ranges from $282 to $391.

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

November 2026 currently has the lowest fares, from $282 one way.

Are there direct flights from Anchorage to Chicago?

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

How long is the flight from Anchorage to Chicago?

The quickest journey we've seen takes about 7h 30m. Anchorage and Chicago are around 4,590 km apart.

Which airlines fly from Anchorage to Chicago?

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

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