$94 Cheap Flights from Washington (IAD) to Chicago (MDW)

View $94 flight on Wed, Aug 6, 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 $94 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Sep 3 - Thu, Sep 4
IAD
Washington
MDW
Chicago
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Washington to Chicago, returning Thu, Sep 4, priced at $177 found 5 days ago
Frontier Airlines
Tue, Aug 5 - Sat, Aug 9
IAD
Washington
MDW
Chicago
$188 Roundtrip, just found
$188
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Aug 5 from Washington to Chicago, returning Sat, Aug 9, priced at $188 just found
Southwest Airlines
Tue, Sep 9 - Fri, Sep 12
IAD
Washington
MDW
Chicago
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Washington to Chicago, returning Fri, Sep 12, priced at $193 found 4 days ago
Delta
Mon, Sep 29 - Sat, Oct 4
IAD
Washington
MDW
Chicago
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Sep 29 from Washington to Chicago, returning Sat, Oct 4, priced at $197 found 4 days ago
Southwest Airlines
Tue, Sep 9 - Fri, Sep 12
IAD
Washington
MDW
Chicago
$198 Roundtrip, found 4 days ago
$198
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Sep 9 from Washington to Chicago, returning Fri, Sep 12, priced at $198 found 4 days ago
Delta
Sun, Oct 12 - Fri, Oct 31
IAD
Washington
MDW
Chicago
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Oct 12 from Washington to Chicago, returning Fri, Oct 31, priced at $201 found 6 days ago
Delta
Sun, Sep 7 - Wed, Sep 10
IAD
Washington
MDW
Chicago
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, Sep 7 from Washington to Chicago, returning Wed, Sep 10, priced at $201 found 4 days ago
Delta
Tue, Sep 9 - Fri, Sep 12
IAD
Washington
MDW
Chicago
$203 Roundtrip, found 4 days ago
$203
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 9 from Washington to Chicago, returning Fri, Sep 12, priced at $203 found 4 days ago
Frontier Airlines
Tue, Sep 9 - Fri, Sep 12
IAD
Washington
MDW
Chicago
$204 Roundtrip, found 4 days ago
$204
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 9 from Washington to Chicago, returning Fri, Sep 12, priced at $204 found 4 days ago
Delta
Sat, Nov 1 - Mon, Nov 3
IAD
Washington
MDW
Chicago
$207 Roundtrip, found 4 days ago
$207
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Nov 1 from Washington to Chicago, returning Mon, Nov 3, priced at $207 found 4 days ago

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.

Graph displaying average flight prices per month

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 $302
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $302
Flights from Washington (IAD) to Chicago (MDW)
Origin airport
Washington Dulles Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$176
Distance
575 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 September. 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 $94 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 Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from IAD to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from IAD to MDW?
The cheapest flights from IAD to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 IAD to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from IAD to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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Chicago nearby Airports

Chicago

Washington to O'Hare Intl.
$207.98
*Available to One Key members.