Cheap flights from District of Columbia to Chicago from $99

The month of October is, on average, the cheapest month to fly to Chicago from District of Columbia, 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 District of Columbia 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 District of Columbia 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 District of Columbia 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 District of Columbia - Chicago flight prices

You are more likely to see cheaper flights to Chicago from District of Columbia 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 District of Columbia for as low as $230 on momondo.

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

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from District of Columbia 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.

The number of flights available between District of Columbia and Chicago is 86 per day as of June 2026. The most frequent departure time is 10:00AM, with 49% of daily flights leaving at noon.

The number of flights available between District of Columbia and Chicago is 607 per week as of June 2026. The most frequent departure day is Wed, with 17% of weekly flights leaving on this day.