IAD - MDW

$87 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 4/8. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$200
Frontier
Tue 5/5Thu 5/7
IAD - MDW • 1 stop
Cheapest one-way
$89
Frontier
Wed 4/8
IAD - MDW • 1 stop
Top airlines
Cheapest • from $200 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Dulles Intl and Midway. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $203 (round-trip)
Shortest trip • 4h 17m (one-way)
Insights
Insights
Insights
Insights
Start a new search
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

Tue, May 5 - Thu, May 7
Frontier Logo
5:26 pm - 11:09 am
IAD
-
MDW
18h 43m
1 stop
Frontier Logo
6:00 am - 4:21 pm
MDW
-
IAD
9h 21m
1 stop
$200Frontier
Thu, Apr 23 - Mon, Apr 27
Frontier Logo
9:41 am - 7:31 pm
IAD
-
MDW
10h 50m
1 stop
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$201Frontier
Tue, May 26 - Sun, May 31
Multiple Airlines Logo
7:53 pm - 7:00 am
IAD
-
MDW
12h 07m
1 stop
Multiple Airlines Logo
2:47 pm - 2:18 pm
MDW
-
IAD
22h 31m
1 stop
$202Multiple Airlines
Thu, May 7 - Fri, May 15
Frontier Logo
7:27 pm - 3:57 pm
IAD
-
MDW
21h 30m
1 stop
Frontier Logo
4:52 pm - 6:32 pm
MDW
-
IAD
24h 40m
1 stop
$203Frontier
Thu, Apr 23 - Sat, Apr 25
Frontier Logo
9:41 am - 7:31 pm
IAD
-
MDW
10h 50m
1 stop
Frontier Logo
7:34 pm - 8:56 am
MDW
-
IAD
12h 22m
1 stop
$204Frontier
Tue, Apr 28 - Sun, May 3
Frontier Logo
7:15 am - 7:31 pm
IAD
-
MDW
13h 16m
1 stop
Frontier Logo
6:00 am - 12:36 am
MDW
-
IAD
17h 36m
1 stop
$205Frontier
Mon, Apr 20 - Sat, Apr 25
Frontier Logo
6:00 am - 10:19 pm
IAD
-
MDW
17h 19m
1 stop
Frontier Logo
7:34 pm - 8:56 am
MDW
-
IAD
12h 22m
1 stop
$206Frontier
Fri, Apr 17 - Tue, Apr 21
Frontier Logo
12:24 pm - 10:26 pm
IAD
-
MDW
11h 02m
1 stop
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
$207Frontier
Sat, May 2 - Sun, May 3
Frontier Logo
10:51 am - 6:37 pm
IAD
-
MDW
8h 46m
1 stop
Frontier Logo
6:00 am - 12:36 am
MDW
-
IAD
17h 36m
1 stop
$210Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
7:27 pm - 3:57 pm
IAD
-
MDW
21h 30m
1 stop
Frontier Logo
6:00 am - 5:12 pm
MDW
-
IAD
10h 12m
1 stop
$212Frontier
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.

Which airlines provide the cheapest flights from Washington Dulles Airport to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Washington Dulles Airport to Chicago Midway Airport were found on Frontier ($200) and Delta ($229).

Good to know

Low seasonDecember
Cheapest flight$89
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly and prices are also 28% 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 $87 for a one-way ticket and $200 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 5.7.

  • 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 8292 reviews
7.2Food
7.8Entertainment
8.1Boarding
8.5Crew
7.9Comfort
Airline reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

2.0 MediocreSusan, Mar 2026
JAX - ATL
Read more Delta reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

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

Information on your arrival and departure airports