Cheap Flights from Washington (DCA) to Chicago (PWK)

Popular airlines from Ronald Reagan Washington National Airport (DCA) to Chicago, IL (PWK-Chicago Executive)

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Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $397
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $397
Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $423
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $423
Flights from Washington (DCA) to Chicago (PWK)
Origin airport
Ronald Reagan Washington National
Destination airport
Chicago Executive
Distance
613 mi

Washington to Chicago Flights

The cheapest times to fly from Washington to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Washington to Chicago are during the month of . You can find some of the cheapest flights from Washington to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Washington to Chicago

Sunday is one of the best days to book for cheap flights from Washington to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Washington to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Washington to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Washington to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Washington to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK) cost?
Grab a cheap one-way flight or cheap return flight from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK)?
Traveling in can help you save, as it's the cheapest month for flights between DCA and PWK. You'll usually find the lowest prices during off-peak months.
What is the cheapest airline that flies from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK)?
To find the cheapest airline flying from DCA to PWK, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK)?
There aren't any daily direct flights available from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from DCA to PWK?
Usually you'll find the widest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can change based on the season, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK)?
Opt for a flight from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK) that takes off before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Ronald Reagan Washington National Airport (DCA)?
Catch a direct flight from Ronald Reagan Washington National Airport (DCA) to Chicago and arrive at O'Hare Intl. Airport (ORD). An alternative point of entry into the city is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK) last-minute?
Waiting until right before your break to book a flight from DCA to PWK often results in higher prices. While you may find some last-minute offers, they aren't always guaranteed. Keep your travel plans flexible to maximize your chances of getting a bargain.
Is it cheaper to book a DCA to PWK flight and hotel package?
You can save money by booking a DCA to PWK flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. Once you've selected your preferred accommodations and flights, consider adding extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Ronald Reagan Washington National Airport (DCA) to Chicago Executive Airport (PWK)?
If you reserved your DCA to PWK flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the fare type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

*Flight schedules are subject to change.

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