Cheap flights from Seattle to Chicago from $99

The month of February is, on average, the cheapest month to fly to Chicago from Seattle, with most prices found around $217. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Seattle to Chicago during January average around $267.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $388. 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 Seattle to Chicago for around $484.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Seattle to Chicago during this time can be as low as $292. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $438.

Fly from Seattle/Tacoma Intl to Chicago Midway for the best Seattle/Tacoma Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Seattle when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $301 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Seattle for as low as $258 on momondo.

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

You could potentially save up to 10% on your flight if you consider stops on a Seattle to Chicago flight.

As of March 2026, prices for Seattle to Chicago flights are approximately 41% more expensive when compared to flights at the same time last year.

United Airlines, Southwest, and Delta are the most popular carriers operating from Seattle/Tacoma Intl to Chicago

Alaska Airlines, Delta and American Airlines are the top three most popular airlines that fly to Chicago from Seattle according to our data. Alaska Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

37 flights are operational daily from Seattle to Chicago as of March 2026. The most popular departure time for this route is 7:00AM, with 56% of flights per day taking off at noon.

As of March 2026, 262 flights take off from Seattle and land in Chicago each week. The most common flight departure day for this route is Mon, with 16% of weekly flights taking off on this day.