￥19,660 Cheap Flights from Washington (IAD) to Chicago (MDW)

View ￥19,660 flight on Wed, Mar 4, 2026Opens 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 ￥19,660 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

February is typically the cheapest month to fly

From ￥17,143 - ￥94,638 per traveler.
Flights from Washington (IAD) to Chicago (MDW)
Origin airport
Washington Dulles Intl.
Destination airport
Midway Intl.
Distance
921 km

Washington to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Washington to will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at Expedia.com, we’ll pair you up with IAD to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Washington for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Frequently asked questions

How much is a flight from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW)?
Start packing your bags, because round-trip flights from Dulles Intl. Airport to Midway Intl. Airport (MDW) start from . That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to score the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Washington Dulles Intl. Airport (IAD) to Midway Airport?
Every air carrier has its own set of terms and conditions. If you decide to cancel your vacation, head to our Customer Service Portal.
How do I find cheap flights from IAD to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Washington Dulles Intl. Airport (IAD) to MDW flights, you'll see a "no change fees" filter for you to select.
How many hours is the flight from Dulles Intl. Airport to Midway Intl. Airport (MDW)?
The flight time from IAD to Midway Airport is only about 3 hours and 27 minutes, so don't get too settled. There's a good chance the next time you glance out the window you'll be cruising over Chicago.
How far is the flight from Washington Dulles Intl. Airport (IAD) to Midway Airport?
With a flight distance of 930 kilometers, it's just a hop from Washington Dulles Intl. Airport (IAD) to Midway Intl. Airport (MDW). It might be a quick journey, but it's still worth bringing along a good book to read.
Which airlines fly direct from Washington Dulles Intl. Airport (IAD) to MDW?
You won't find any airlines operating directly between Dulles Intl. Airport and Midway Intl. Airport (MDW), so be prepared to make at least one stop on your journey. A layover, whether short or long, can be a nice way to break up a trip!
Are Washington Dulles Intl. Airport (IAD) to Midway Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from Washington Dulles Intl. Airport (IAD) to Chicago Airport last minute could be your ticket to a cheap deal. However, it might cost you a whole lot more! If you'd prefer not to take any chances, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia all the time.

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