Cheap flights from Alaska to Chicago from $199

The month of October is, on average, the cheapest month to fly to Chicago from Alaska, with most prices found around $158. If you’re not able to fly to Chicago in October, then August is your next best option. Flight prices from Alaska to Chicago during August average around $158.

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $653. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Alaska to Chicago for around $794.

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

You are more likely to see cheaper flights to Chicago from Alaska when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $495 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Alaska for as low as $313 on momondo.

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

United Airlines, Alaska Airlines and Delta are the top three most popular airlines that fly to Chicago from Alaska according to our data. United Airlines is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of May 2026, there are 5 flights per day flying from Alaska to Chicago. The most common time of day flights depart is 8:00PM, with 100% of flights taking off in the evening.

As of May 2026, 35 flights take off from Alaska and land in Chicago each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.