Cheap flights from Chicago to Washington, D.C. from R2 291

In general, December is the cheapest month to fly from Chicago to Washington, D.C.. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around R5 390. If you aren’t able to travel during the month of December, then book flights to Washington, D.C. from Chicago during January instead. Flights to Washington, D.C. in January, while not as cheap as those in December, still average around R5 868.

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

You are more likely to see cheaper flights to Washington, D.C. from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Washington, D.C. for around R6 178 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Washington, D.C. from Chicago for as low as R4 121 on momondo.

There is only 1 cabin class available to choose from on Chicago to Washington, D.C. 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 53% on your flight if you consider stops on a Chicago to Washington, D.C. flight.

As of November 2026, prices for Chicago to Washington, D.C. flights are approximately 11% cheaper when compared to flights at the same time last year.

Historically, on average around 22% of flights between Chicago and Washington, D.C. have experienced a delay on any given week. The average delay length over the past 12 months has been 133 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the evening have, in the past, seen delays more frequently in comparison.

Tuesday is statistically the day of the week that experiences the fewest delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the fewest delays on this route over the last 12 months, with about 21% of their flights experiencing any sort of delay.

The number of flights available between Chicago and Washington, D.C. is 3 per day as of November 2026. The most frequent departure time is 14:00, with 43% of daily flights leaving at midday.

As of November 2026, 27 flights take off from Chicago and land in Washington, D.C. each week. The most common flight departure day for this route is Mon, with 22% of weekly flights taking off on this day.