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

View $94 flight on Sat, Aug 9, 2025Opens 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 $94 for one-way flights and $183 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Aug 19 - Wed, Aug 27
MDW
Chicago
IAD
Washington
$183 Roundtrip, found 1 hour ago
$183
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Aug 19 from Chicago to Washington, returning Wed, Aug 27, priced at $183 found 1 hour ago
Frontier Airlines
Sat, Oct 25 - Sat, Nov 1
MDW
Chicago
IAD
Washington
$188 Roundtrip, found 5 hours ago
$188
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to Washington, returning Sat, Nov 1, priced at $188 found 5 hours ago
Frontier Airlines
Thu, Aug 7 - Sat, Aug 9
MDW
Chicago
IAD
Washington
$193 Roundtrip, just found
$193
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Aug 7 from Chicago to Washington, returning Sat, Aug 9, priced at $193 just found
Frontier Airlines
Sat, Oct 25 - Thu, Oct 30
MDW
Chicago
IAD
Washington
$198 Roundtrip, found 5 hours ago
$198
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Chicago to Washington, returning Thu, Oct 30, priced at $198 found 5 hours ago
Frontier Airlines
Sun, Aug 31 - Sun, Sep 7
MDW
Chicago
IAD
Washington
$203 Roundtrip, just found
$203
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Aug 31 from Chicago to Washington, returning Sun, Sep 7, priced at $203 just found
Frontier Airlines
Thu, Oct 30 - Sun, Nov 2
MDW
Chicago
IAD
Washington
$208 Roundtrip, found 5 hours ago
$208
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Oct 30 from Chicago to Washington, returning Sun, Nov 2, priced at $208 found 5 hours ago
Delta
Sat, Aug 30 - Mon, Sep 1
MDW
Chicago
IAD
Washington
$223 Roundtrip, found 2 hours ago
$223
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Aug 30 from Chicago to Washington, returning Mon, Sep 1, priced at $223 found 2 hours ago
Frontier Airlines
Mon, Aug 18 - Wed, Aug 27
MDW
Chicago
IAD
Washington
$223 Roundtrip, found 1 hour ago
$223
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Aug 18 from Chicago to Washington, returning Wed, Aug 27, priced at $223 found 1 hour ago
Delta
Tue, Sep 2 - Sat, Sep 6
MDW
Chicago
IAD
Washington
$227 Roundtrip, found 8 hours ago
$227
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Sep 2 from Chicago to Washington, returning Sat, Sep 6, priced at $227 found 8 hours ago
Southwest Airlines
Sat, Aug 30 - Mon, Sep 1
MDW
Chicago
IAD
Washington
$233 Roundtrip, found 2 hours ago
$233
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Chicago to Washington, returning Mon, Sep 1, priced at $233 found 2 hours ago

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.

Graph displaying average flight prices per month

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. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $306
DCA
Ronald Reagan Washington National
CheapestClosest
Average driving time to city center8 min
Flights from $306
Flights from Chicago (MDW) to Washington (IAD)
Origin airport
Midway Intl.
Destination airport
Washington Dulles Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$177
Distance
575 mi

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 August. 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 $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 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.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Washington Dulles Intl. Airport (IAD) cost?
Discover the latest flight deals from MDW to IAD 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 MDW to IAD?
The cheapest flights from MDW to IAD 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 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 MDW to IAD?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from MDW to IAD. Sort your results by "Price (lowest to highest)" to snap up a great deal.
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.

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*Available to One Key members.