Cheap flights from Chicago to District of Columbia from $105

In general, October is the cheapest month to fly from Chicago to District of Columbia. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $292. If you don’t want to visit District of Columbia in October, then you should wait until November to fly from Chicago, when ticket prices are also cheap, with an average price of $328.

The cheapest day to depart on your flight to District of Columbia is on a Friday when prices can be found for as low as $382. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $581.

Flying to District of Columbia from Chicago in the morning is the least expensive time of day to depart. momondo users have found prices as low as $398 when looking at flights departing in the morning. Flights to District of Columbia are more costly at noon, with an average ticket price of $786. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

Fly from Chicago Midway to Baltimore/Washington for the best Chicago - District of Columbia flight prices

You are more likely to see cheaper flights to District of Columbia from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to District of Columbia for around $339 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to District of Columbia from Chicago for as low as $255 on momondo.

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

Delta, United Airlines, and Southwest are the most popular carriers operating from Chicago to District of Columbia

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to District of Columbia from Chicago according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to District of Columbia. Keep in mind that there are 5 different airlines that fly to District of Columbia on a routine basis, so you have a few additional options to choose from.

As of June 2026, 81 flights take off from Chicago and land in District of Columbia each day. The most common flight departure time for this route is 6:00PM, with 45% of daily flights taking off at noon.

572 flights are operational weekly from Chicago to District of Columbia as of June 2026. The most popular departure day for this route is Wed, with 19% of flights per week taking off on this day.