$96 Cheap Flights from Chicago (MDW) to Washington (IAD)

View $96 flight on Wed, May 20, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Washington Dulles Intl. Airport (IAD)

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Cheap Flights from Chicago to Washington (MDW-IAD)

Prices were available within the past 7 days and start at $96 for one-way flights and $170 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, May 12 - Wed, May 20
MDW
Chicago
IAD
Washington
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 12 from Chicago to Washington, returning Wed, May 20, priced at $170 found 2 days ago
Frontier Airlines
Sat, May 16 - Wed, May 20
MDW
Chicago
IAD
Washington
$180 Roundtrip, found 7 hours ago
$180
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, May 16 from Chicago to Washington, returning Wed, May 20, priced at $180 found 7 hours ago
Frontier Airlines
Tue, May 5 - Wed, May 20
MDW
Chicago
IAD
Washington
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Chicago to Washington, returning Wed, May 20, priced at $181 found 2 days ago
Frontier Airlines
Tue, May 19 - Sat, May 23
MDW
Chicago
IAD
Washington
$185 Roundtrip, found 13 hours ago
$185
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Tue, May 19 from Chicago to Washington, returning Sat, May 23, priced at $185 found 13 hours ago
Frontier Airlines
Wed, Jul 15 - Tue, Jul 21
MDW
Chicago
IAD
Washington
$190 Roundtrip, found 9 hours ago
$190
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Jul 15 from Chicago to Washington, returning Tue, Jul 21, priced at $190 found 9 hours ago
Frontier Airlines
Wed, May 6 - Wed, May 20
MDW
Chicago
IAD
Washington
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 6 from Chicago to Washington, returning Wed, May 20, priced at $191 found 1 day ago
Delta
Wed, May 27 - Sat, May 30
MDW
Chicago
IAD
Washington
$194 Roundtrip, found 14 hours ago
$194
Roundtrip
found 14 hours ago
Select Delta flight, departing Wed, May 27 from Chicago to Washington, returning Sat, May 30, priced at $194 found 14 hours ago
Frontier Airlines
Sat, May 23 - Fri, May 29
MDW
Chicago
IAD
Washington
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 23 from Chicago to Washington, returning Fri, May 29, priced at $195 found 5 days ago
Delta
Tue, Jun 2 - Wed, Jun 3
MDW
Chicago
IAD
Washington
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Jun 2 from Chicago to Washington, returning Wed, Jun 3, priced at $197 found 7 hours ago
Southwest Airlines
Sun, May 24 - Fri, May 29
MDW
Chicago
IAD
Washington
$309 Roundtrip, found 19 hours ago
$309
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Sun, May 24 from Chicago to Washington, returning Fri, May 29, priced at $309 found 19 hours ago

Alternative airports near Washington

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

Select flight to Ronald Reagan Washington National DCA. Closest option available. Average driving time to city center is 8 minutes. Flights from $443
DCA
Ronald Reagan Washington National
Closest
Average driving time to city center8 min
Flights from $443

Frequently asked questions

How much does a flight from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) cost?
You can find cheap one-way flights and cheap return flights from $170 Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) with Expedia. One-way flights generally range between $221 and $641, and roundtrip flights usually range from $287 to $1328. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
The cheapest month to fly from MDW to IAD is May when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
Enter MDW to IAD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
To find a cheap flight from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
The earliest flight from Chicago (MDW) to Washington, DC (IAD) usually leaves at around 5:00 AM, operated by Southwest Airlines. This seasonal service is active in December, making it a convenient option for early travelers. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
The most popular departure times for flights from Midway Intl. (MDW) to Washington Dulles Intl. (IAD) are in the late morning, from 9am to 12pm. About 37% of passengers prefer this time window. Southwest Airlines and Delta Airlines offer flights during this period. Many travelers like this timing because it allows for a relaxed morning before heading off to their destination.
How long does it take to fly from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
A flight from MDW to IAD with a layover takes around 5 hours, with the route covering approximately 576 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
First class seats are offered on the MDW to IAD route with Delta Air Lines.
How do I earn miles on a Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) flight with Expedia?
It's easy to earn miles on a Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Washington from Midway Intl. (MDW)?
When traveling from Midway Intl. (MDW) to Washington, you can fly into Ronald Reagan Washington National (DCA) and Washington Dulles Intl. (IAD). Some flights may connect through major hubs like Birmingham Intl. (BHM), Hartsfield-Jackson Atlanta Intl. (ATL), Lambert-St. Louis Intl. (STL) before reaching Washington. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) at the last minute?
Typically, booking a last minute flight from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) flight and hotel package?
Securing a Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) Fairfax County Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.)?
If you booked your Chicago, IL (MDW-Midway Intl.) to Washington, DC (IAD-Washington Dulles Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Midway Intl.
Destination airport
Washington Dulles Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$170
Distance
575 mi

Book with confidence

Chicago to Washington Flights

The cheapest times to fly from Chicago to Washington

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 Chicago to Washington are during the month of May. You can find some of the cheapest flights from Chicago to Washington with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Washington

Sunday is one of the best days to book for cheap flights from Chicago to Washington: 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 Chicago to Washington

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 Chicago to Washington in 2026. You can also book with separate airlines for your outbound and return journeys, from $96 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 Chicago to Washington 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 Chicago to Washington 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.

 

Chicago to Washington Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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