Cheap flights from Chicago to Washington, D.C. from $104

The month of October is, on average, the cheapest month to fly to Washington, D.C. from Chicago, with most prices found around $293. If you’re not able to fly to Washington, D.C. in October, then November is your next best option. Flight prices from Chicago to Washington, D.C. during November average around $327.

On average, the least expensive day to fly to Washington, D.C. from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as $371. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Washington, D.C. for around $558.

In the morning is the cheapest time of day to fly from Chicago to Washington, D.C. when you can find flight prices for as low as $391. Flying to Washington, D.C. in the morning is an ideal time because this is during off-peak travel hours. Try not to purchase tickets at noon because they tend to be around $735. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago Midway to Baltimore/Washington 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 $340 when searching weeks out. 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 $255 on momondo.

There are 4 cabin classes 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 2% on your flight if you consider stops on a Chicago to Washington, D.C. flight.

As of June 2026, prices for Chicago to Washington, D.C. flights are approximately 131% more expensive when compared to flights at the same time last year.

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Washington, D.C. from Chicago according to our data. United Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Washington, D.C.. Keep in mind that there are 5 different airlines that fly to Washington, D.C. on a routine basis, so you have a few additional options to choose from.

Historically, on average around 23% 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 131 minutes.

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

Tuesday is statistically the day of the week which experiences the fewest number of 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 least number of delays on this route over the last 12 months; with about 21% of their flights experiencing any sort of delay.

Atlanta (ATL) was the most common stop: 56% 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 Detroit (DTW) have the shortest average one-way travel time: 3h 56m.

Boston (BOS) has the shortest average layover time for this route: 1h 18m.

The number of flights available between Chicago and Washington, D.C. is 95 per day as of June 2026. The most frequent departure time is 8:00AM, with 47% of daily flights leaving at noon.

As of June 2026, there are 669 flights per week flying from Chicago to Washington, D.C.. The most common day of the week flights depart is Sun, with 20% of flights taking off on this day.