$90 Cheap Flights from Washington (IAD) to Chicago (MDW)

View $90 flight on Tue, May 19, 2026Opens in a new window

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

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Washington to Chicago (IAD-MDW)

Prices were available within the past 7 days and start at $90 for one-way flights and $160 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sun, May 24 - Thu, May 28
IAD
Washington
MDW
Chicago
$160 Roundtrip, found 16 hours ago
$160
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, May 24 from Washington to Chicago, returning Thu, May 28, priced at $160 found 16 hours ago
Frontier Airlines
Wed, May 27 - Sat, May 30
IAD
Washington
MDW
Chicago
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 27 from Washington to Chicago, returning Sat, May 30, priced at $180 found 1 hour ago
Frontier Airlines
Wed, Jun 3 - Wed, Jun 10
IAD
Washington
MDW
Chicago
$185 Roundtrip, just found
$185
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Jun 3 from Washington to Chicago, returning Wed, Jun 10, priced at $185 just found
Frontier Airlines
Tue, May 12 - Tue, May 19
IAD
Washington
MDW
Chicago
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 12 from Washington to Chicago, returning Tue, May 19, priced at $189 found 5 days ago
Frontier Airlines
Sun, May 24 - Sat, Aug 1
IAD
Washington
MDW
Chicago
$189 Roundtrip, found 16 hours ago
$189
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sun, May 24 from Washington to Chicago, returning Sat, Aug 1, priced at $189 found 16 hours ago
Frontier Airlines
Tue, Jul 7 - Wed, Jul 8
IAD
Washington
MDW
Chicago
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Washington to Chicago, returning Wed, Jul 8, priced at $190 found 2 days ago
Delta
Wed, May 27 - Mon, Jun 1
IAD
Washington
MDW
Chicago
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 27 from Washington to Chicago, returning Mon, Jun 1, priced at $194 found 1 day ago
Delta
Tue, Jun 16 - Tue, Jun 23
IAD
Washington
MDW
Chicago
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 16 from Washington to Chicago, returning Tue, Jun 23, priced at $197 found 1 day ago
Delta
Tue, Jun 30 - Tue, Jul 7
IAD
Washington
MDW
Chicago
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Delta flight, departing Tue, Jun 30 from Washington to Chicago, returning Tue, Jul 7, priced at $199 just found
Southwest Airlines
Wed, May 27 - Sat, May 30
IAD
Washington
MDW
Chicago
$299 Roundtrip, found 1 hour ago
$299
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, May 27 from Washington to Chicago, returning Sat, May 30, priced at $299 found 1 hour ago

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. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $195
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $195

Frequently asked questions

How much does a flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights and cheap return flights from $160 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights usually range from $126 to $614, and return flights typically cost between $353 and $1268. 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from IAD to MDW 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter IAD to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
Frontier Airlines is one of the cheapest airlines offering connecting flights from Washington Dulles Intl. (IAD) to Midway Intl. (MDW), with round-trip tickets starting from around $154. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago (MDW-Midway Intl.) typically departs at around 5:00 AM, operated by Southwest Airlines. This is a seasonal service active in June and July, allowing you to start your day early in Chicago. 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Washington, DC (IAD) to Chicago, IL (MDW) are in the morning, from 6am to 9am. About 45% of passengers prefer this time window. Many major carriers, including Delta Airlines and United Airlines, offer flights during this window. This timing works well because it allows you to arrive in Chicago with plenty of time to explore the city.
How long does it take to fly from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
Flights from IAD to MDW with one stop typically take around 7 hours, 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the IAD to MDW route with Delta Air Lines.
How do I earn miles on a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway 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 Chicago from Washington Dulles Intl. (IAD)?
When traveling from Washington Dulles Intl. (IAD) to Chicago, you can fly into O'Hare Intl. (ORD) and Midway Intl. (MDW). Some flights may connect through major hubs like Charlotte-Douglas Intl. (CLT), DuBois Regional (DUJ), LNS (LNS) before reaching Chicago. 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago 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 Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Washington, DC (IAD-Washington Dulles Intl.) to Chicago, IL (MDW-Midway 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
Washington Dulles Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$160
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 May. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $90 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

*Flight schedules are subject to change.

*Available to One Key members.

 

Explore a world of travel with Expedia