IAD - MDW

$78 Find Cheap Flights from Washington Dulles Airport to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Dulles Intl to Midway departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$139
Frontier
Thu 12/25Wed 12/31
IAD - MDW • 1 stop
Cheapest one-way
$78
Typical prices: $127-$161
Frontier
Sat 12/6
IAD - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $139 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Dulles Intl to Midway (IAD-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Dulles Intl to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Dulles Intl to Midway

Thu, Dec 25 - Wed, Dec 31
Frontier Logo
5:35 am - 5:38 pmIAD-MDW
13h 03m1 stop
Frontier Logo
8:15 am - 5:47 pmMDW-IAD
8h 32m1 stop
$139Frontier
Find Deal
Fri, Dec 5 - Mon, Dec 8
Frontier Logo
5:19 pm - 10:12 pmIAD-MDW
5h 53m1 stop
Frontier Logo
6:15 am - 5:25 pmMDW-IAD
10h 10m1 stop
$140Frontier
Find Deal
Fri, Nov 14 - Mon, Nov 17
Frontier Logo
5:34 pm - 10:08 pmIAD-MDW
5h 34m1 stop
Frontier Logo
1:37 pm - 12:11 amMDW-IAD
9h 34m1 stop
$143Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
5:19 pm - 10:12 pmIAD-MDW
5h 53m1 stop
Frontier Logo
6:15 am - 4:24 pmMDW-IAD
9h 09m1 stop
$144Frontier
Find Deal
Fri, Dec 5 - Sat, Dec 6
Frontier Logo
5:19 pm - 10:12 pmIAD-MDW
5h 53m1 stop
Frontier Logo
2:59 pm - 11:09 amMDW-IAD
19h 10m1 stop
$145Frontier
Find Deal
Fri, Dec 12 - Sun, Dec 14
Frontier Logo
5:19 pm - 10:12 pmIAD-MDW
5h 53m1 stop
Frontier Logo
2:59 pm - 3:05 pmMDW-IAD
23h 06m1 stop
$146Frontier
Find Deal
Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
3:00 pm - 6:46 pmIAD-MDW
4h 46m1 stop
Multiple Airlines Logo
5:30 pm - 7:45 amMDW-IAD
13h 15m1 stop
$177Multiple Airlines
Find Deal
Sat, Jan 17 - Mon, Jan 19
Delta Logo
5:59 pm - 10:09 pmIAD-MDW
5h 10m1 stop
Delta Logo
6:17 pm - 12:24 amMDW-IAD
5h 07m1 stop
$248Delta
Find Deal
Wed, Dec 3 - Wed, Dec 10
Delta Logo
6:00 am - 8:54 amIAD-MDW
3h 54m1 stop
Delta Logo
12:50 pm - 6:21 pmMDW-IAD
4h 31m1 stop
$257Delta
Find Deal
Sat, Jan 17 - Mon, Jan 19
Delta Logo
6:00 am - 8:54 amIAD-MDW
3h 54m1 stop
Delta Logo
6:00 am - 11:44 amMDW-IAD
4h 44m1 stop
$258Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Dulles Intl to Midway flights

Get data-powered insights and trends into flights from Dulles Intl to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Washington Dulles Airport to Chicago Midway Airport?

The average price of all round-trip flights from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Tuesday and more expensive on a Wednesday. On your return trip to Washington Dulles Airport, you should consider flying back on a Thursday, and avoid Thursdays for better deals.

Good to know

Low seasonSeptember
Cheapest flight$78
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Washington Dulles Airport to Chicago Midway Airport

When to book flights from Dulles Intl to Midway

Are your dates flexible? Find out the best times to travel from Dulles Intl to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Washington Dulles Airport to Chicago Midway Airport flights

  • What is the cheapest flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport was $78 for a one-way ticket and $139 for a round-trip.

  • Do I need a passport to fly between Washington Dulles Airport and Chicago Midway Airport?

    A passport is not required to fly from Washington Dulles Airport to Chicago Midway Airport.

  • Which airports will I be using when flying from Washington Dulles Airport to Chicago Midway Airport?

    When flying out of Washington Dulles Airport you will be using Washington, D.C. Dulles Intl. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which aircraft models fly most regularly from Washington Dulles Airport to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Washington Dulles Airport to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Washington Dulles Airport and Chicago Midway Airport.

  • Which is the best airline for flights from Washington, D.C. to Chicago, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Delta and Frontier. With an average price for the route of $327 and an overall rating of 7.9, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $185 and an overall rating of 5.8.

  • How does KAYAK find such low prices on flights from Washington Dulles Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Washington Dulles Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Washington Dulles Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Washington Dulles Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Washington Dulles Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Washington Dulles Airport with another airline. Booking your flights between Washington Dulles Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington Dulles Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Washington Dulles Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Dulles Intl to Midway

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Dulles Intl to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 7993 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Everything you need to know for your flight from Dulles Intl to Midway

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