Cheap flights from Washington, D.C. to Chicago from $99

The month of October is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $217. If you’re not able to fly to Chicago in October, then August is your next best option. Flight prices from Washington, D.C. to Chicago during August average around $221.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $397. 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. to Chicago for around $529.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Washington, D.C. to Chicago during this time can be as low as $399. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $442.

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

You are more likely to see cheaper flights to Chicago from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $383 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. for as low as $230 on momondo.

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

No. A direct flight is the cheapest option for a flight between Washington, D.C. to Chicago.

As of June 2026, prices for Washington, D.C. to Chicago flights are approximately 126% more expensive when compared to flights at the same time last year.

United Airlines, Southwest, and Delta are the most popular carriers operating from Washington, D.C. to Chicago

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Atlanta (ATL) was the most common stop: 71% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $142.

Flights connecting via New York (JFK) have the shortest average one-way travel time: 4h 57m.

New York (JFK) has the shortest average layover time for this route: 2h 01m.

As of June 2026, there are 108 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 10:00AM, with 49% of flights taking off at noon.

As of June 2026, 756 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Tue, with 19% of weekly flights taking off on this day.