Cheap flights from Washington, D.C. to Chicago from $89

The month of September is, on average, the cheapest month to fly to Chicago from Washington, D.C., with most prices found around $203. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Washington, D.C. to Chicago during August average around $224.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $386. 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 Washington, D.C. to Chicago for around $514.

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 $380. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $423.

Fly from Baltimore/Washington to Chicago O'Hare Intl 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 $353 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 $199 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.

You could potentially save up to 2% on your flight if you consider stops on a Washington, D.C. to Chicago flight.

As of April 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, Delta, and Southwest 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 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 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: 63% of momondo users choosing 1-stop flights on this route connected there.

Flights via New York (JFK) offer the lowest average round-trip price of $152.

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

Orlando (MCO) has the shortest average layover time for this route: 1h 43m.

As of April 2026, there are 86 flights per day flying from Washington, D.C. to Chicago. The most common time of day flights depart is 5:00PM, with 40% of flights taking off at noon.

As of April 2026, 605 flights take off from Washington, D.C. and land in Chicago each week. The most common flight departure day for this route is Wed, with 21% of weekly flights taking off on this day.