Cheap flights from Chicago to Alaska from $221

If you don’t want to visit Alaska in February, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $429.

The cheapest day to depart from Chicago to Alaska is on a Thursday. Travelers who choose to depart for Alaska on a Thursday will often find tickets for as low as $473. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Alaska for around $610.

Our data shows that the cheapest Chicago to Alaska flights are usually those with departure times in the afternoon. Our users have found flights to Alaska in the afternoon for as low as $495. At noon is when there is more demand to fly to Alaska, so prices are often more expensive at around $868 per ticket.

Fly from Chicago O'Hare Intl to Anchorage for the best Chicago - Alaska flight prices

You are more likely to see cheaper flights to Alaska from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Alaska for around $474 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Alaska from Chicago for as low as $440 on momondo.

There are 4 cabin classes available to choose from on Chicago to Alaska flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

United Airlines, Delta, and Alaska Airlines are the most popular carriers operating from Chicago to Alaska

Alaska Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to Alaska from Chicago according to our data. Alaska Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Alaska. Keep in mind that there are 4 different airlines that fly to Alaska on a routine basis, so you have a few additional options to choose from.

As of September 2026, 4 flights take off from Chicago and land in Alaska each day. The most common flight departure time for this route is 4:00PM, with 100% of daily flights taking off in the afternoon.

As of September 2026, there are 32 flights per week flying from Chicago to Alaska. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.