$69 Cheap Flights from Washington (IAD) to Chicago (MDW)

View $69 flight on Sun, Dec 7, 2025Opens in a new window

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

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Cheap Flights from Washington to Chicago (IAD-MDW)

Prices were available within the past 7 days and start at $69 for one-way flights and $120 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Jan 22 - Thu, Jan 29
IAD
Washington
MDW
Chicago
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Washington to Chicago, returning Thu, Jan 29, priced at $120 found 2 days ago
Frontier Airlines
Fri, Dec 5 - Mon, Dec 8
IAD
Washington
MDW
Chicago
$124 Roundtrip, found 9 hours ago
$124
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Washington to Chicago, returning Mon, Dec 8, priced at $124 found 9 hours ago
Frontier Airlines
Fri, Nov 14 - Tue, Nov 18
IAD
Washington
MDW
Chicago
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Washington to Chicago, returning Tue, Nov 18, priced at $128 found 1 day ago
Frontier Airlines
Thu, Feb 19 - Sun, Feb 22
IAD
Washington
MDW
Chicago
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Washington to Chicago, returning Sun, Feb 22, priced at $134 found 2 days ago
Frontier Airlines
Fri, Jan 9 - Mon, Jan 12
IAD
Washington
MDW
Chicago
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Washington to Chicago, returning Mon, Jan 12, priced at $137 found 2 days ago
Frontier Airlines
Fri, Dec 5 - Sun, Dec 7
IAD
Washington
MDW
Chicago
$142 Roundtrip, found 9 hours ago
$142
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Fri, Dec 5 from Washington to Chicago, returning Sun, Dec 7, priced at $142 found 9 hours ago
Frontier Airlines
Mon, Nov 10 - Thu, Nov 13
IAD
Washington
MDW
Chicago
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Nov 10 from Washington to Chicago, returning Thu, Nov 13, priced at $143 found 3 days ago
Frontier Airlines
Fri, Jan 30 - Sun, Feb 1
IAD
Washington
MDW
Chicago
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jan 30 from Washington to Chicago, returning Sun, Feb 1, priced at $148 found 2 days ago
Delta
Thu, Dec 4 - Mon, Dec 8
IAD
Washington
MDW
Chicago
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Dec 4 from Washington to Chicago, returning Mon, Dec 8, priced at $194 found 5 days ago
Southwest Airlines
Mon, Dec 8 - Thu, Dec 11
IAD
Washington
MDW
Chicago
$319 Roundtrip, just found
$319
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Dec 8 from Washington to Chicago, returning Thu, Dec 11, priced at $319 just found

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

February is typically the cheapest month to fly

From $110 - $608 per traveler.

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. Average driving time to city center is 23 minutes. Flights from $386
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $386

Frequently asked questions

How much does a flight from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $69 or cheap return flight from $120 from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
January is the most affordable month to fly from IAD to MDW. Traveling during an off-peak travel window is often the key to better flight prices.
Which airlines fly direct from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
You can't fly nonstop from Washington, DC (IAD-Washington Dulles Intl.) to Midway Intl. Airport (MDW). However, you can arrive in Chicago without any layovers by departing from Ronald Reagan Washington National Airport (DCA).
What is the cheapest airline that flies from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from IAD to MDW, 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 fares upfront.
How many flights per day from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
There are no daily direct flights available from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way in no time at all.
What day of the week has the most flights from IAD to MDW?
Generally you'll find the most flight options available on a Friday. Tuesdays are often the quietest.* But this can change depending on the season, carrier 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 Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW) route, fly before 3 PM. Later departures 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 Chicago from Washington Dulles Intl. Airport (IAD)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Washington Dulles Intl. Airport (IAD). Browse the options and find affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW) last-minute?
Holding off until just before your departure to book a flight from IAD to MDW generally means paying more. While you may come across some last-minute offers, they aren't always guaranteed. Keep your travel plans flexible to boost your chances of getting a bargain.
Is it cheaper to book an IAD to MDW flight and hotel package?
You'll typically save money by securing an IAD to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've selected your ideal accommodations and flights, consider adding extras such as activities, tours and car rentals.
Can I cancel or change the date of my flight from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
If you booked your IAD to MDW flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you want more information.

Travel information

Origin airport
Washington Dulles Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$110
Distance
575 mi

Book with confidence

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 January. 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 2025. You can also book with separate airlines for your outbound and return journeys, from $69 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.

 

Washington to Chicago Flights

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*Available to One Key members.