Cheap flights from Washington, D.C. Reagan-National Airport to Chicago from $116

The month of February is, on average, the cheapest month to fly to Chicago from Washington, D.C. Reagan-National Airport, with most prices found around $325. If you’re not able to fly to Chicago in February, then December is your next best option. Flight prices from Washington, D.C. Reagan-National Airport to Chicago during December average around $340.

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $419. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Washington, D.C. Reagan-National Airport to Chicago for around $534.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. Reagan-National Airport to Chicago during this time can be as low as $436. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $472.

Fly from Washington, D.C. Reagan-National to Chicago Midway for the best Washington, D.C. Reagan-National - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Washington, D.C. Reagan-National Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $375 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Washington, D.C. Reagan-National Airport for as low as $275 on momondo.

There are 4 cabin classes available to choose from on Washington, D.C. Reagan-National Airport 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 2% on your flight if you consider stops on a Washington, D.C. Reagan-National Airport to Chicago flight.

As of November 2026, prices for Washington, D.C. Reagan-National Airport to Chicago flights are approximately 68% more expensive when compared to flights at the same time last year.

Frontier, American Airlines, and United Airlines are the most popular carriers operating from Washington, D.C. Reagan-National to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Washington, D.C. Reagan-National Airport according to our data. United Airlines is the first choice among our users, with 50% 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 November 2026, there are 43 flights per day flying from Washington, D.C. Reagan-National Airport to Chicago. The most common time of day flights depart is 3:00PM, with 45% of flights taking off at noon.

As of November 2026, 302 flights take off from Washington, D.C. Reagan-National Airport and land in Chicago each week. The most common flight departure day for this route is Sun, with 20% of weekly flights taking off on this day.