$55 Cheap Flights from Chicago (MDW) to Washington (IAD)

View $55 flight on Sat, Nov 15, 2025Opens in a new window

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

Cheap Flights from Chicago to Washington (MDW-IAD)

Prices were available within the past 7 days and start at $55 for one-way flights and $110 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Nov 15 - Wed, Nov 19
MDW
Chicago
IAD
Washington
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Chicago to Washington, returning Wed, Nov 19, priced at $110 found 1 day ago
Frontier Airlines
Sat, Nov 15 - Mon, Nov 17
MDW
Chicago
IAD
Washington
$120 Roundtrip, found 23 hours ago
$120
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Chicago to Washington, returning Mon, Nov 17, priced at $120 found 23 hours ago
Frontier Airlines
Fri, Nov 14 - Mon, Nov 17
MDW
Chicago
IAD
Washington
$128 Roundtrip, found 7 hours ago
$128
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Chicago to Washington, returning Mon, Nov 17, priced at $128 found 7 hours ago
Frontier Airlines
Fri, Feb 27 - Mon, Mar 2
MDW
Chicago
IAD
Washington
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 27 from Chicago to Washington, returning Mon, Mar 2, priced at $134 found 1 day ago
Frontier Airlines
Mon, Nov 17 - Thu, Nov 20
MDW
Chicago
IAD
Washington
$140 Roundtrip, found 2 days ago
$140
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 17 from Chicago to Washington, returning Thu, Nov 20, priced at $140 found 2 days ago
Frontier Airlines
Fri, Nov 14 - Sun, Nov 16
MDW
Chicago
IAD
Washington
$146 Roundtrip, found 1 hour ago
$146
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Chicago to Washington, returning Sun, Nov 16, priced at $146 found 1 hour ago
Frontier Airlines
Fri, Dec 5 - Sun, Dec 7
MDW
Chicago
IAD
Washington
$148 Roundtrip, found 22 hours ago
$148
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Chicago to Washington, returning Sun, Dec 7, priced at $148 found 22 hours ago
Frontier Airlines
Mon, Nov 10 - Thu, Nov 13
MDW
Chicago
IAD
Washington
$160 Roundtrip, found 18 hours ago
$160
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Chicago to Washington, returning Thu, Nov 13, priced at $160 found 18 hours ago
Southwest Airlines
Thu, Jan 15 - Sun, Jan 18
MDW
Chicago
IAD
Washington
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Chicago to Washington, returning Sun, Jan 18, priced at $211 found 1 day ago
Delta
Thu, Dec 18 - Thu, Dec 25
MDW
Chicago
IAD
Washington
$288 Roundtrip, just found
$288
Roundtrip
just found
Select Delta flight, departing Thu, Dec 18 from Chicago to Washington, returning Thu, Dec 25, priced at $288 just found

Find the cheapest month to fly from Chicago (MDW) to Washington (IAD)

February is typically the cheapest month to fly

From $110 - $668 per traveler.

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 $423
DCA
Ronald Reagan Washington National
Closest
Average driving time to city center8 min
Flights from $423

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD) cost?
Lock in a cheap one-way flight from $55 or cheap return flight from $110 from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD)?
November is the least expensive month to fly from MDW to IAD. Traveling during an off-peak travel window is often the key to finding a great deal.
Which airlines fly direct from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD)?
You can't take a direct flight from Chicago, IL (MDW-Midway Intl.) to Washington Dulles Intl. Airport (IAD). However, you can seamlessly travel to Washington without any layovers by departing from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD)?
To find the cheapest airline flying from MDW to IAD, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD)?
Direct flights from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to IAD?
You'll generally find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD)?
To avoid possible delays on the Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD) route, aim to fly before 3 PM. Departures after this time are 22% more likely to be canceled.**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 Washington from Midway Intl. Airport (MDW)?
If you're traveling on a direct flight from Midway Intl. Airport (MDW) to Washington, you can land at either Ronald Reagan Washington National Airport (DCA) or Baltimore Washington Intl. Thurgood Marshall Airport (BWI).
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD) last-minute?
Last-minute bookings from MDW to IAD are typically more expensive. To secure the lowest prices, start looking for flights as early as possible. That being said, if you're flexible with your travel dates, it's possible to land a cheap ticket right before you leave.
Is it cheaper to book a MDW to IAD flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to IAD flight and hotel package with Expedia could result in significant savings. Better still, having it all in one place will take the stress out of planning your trip. Just pick your flights and select from our wide range of hotels, then customize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD)?
Typically, you can cancel or reschedule your MDW to IAD flight. However, there may be additional fees, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you need further details, go to our Customer Service portal.

Travel information

Origin airport
Midway Intl.
Destination airport
Washington Dulles Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$110
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 November. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $55 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

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*Available to One Key members.