IAD - MDW

$71 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 2/28. 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
$160
Frontier
Tue 1/13Thu 1/15
IAD - MDW • 1 stop
Cheapest one-way
$71
Frontier
Sat 2/28
IAD - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $162 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Jan 13 - Thu, Jan 15
Frontier Logo
6:00 am - 10:34 am
IAD
-
MDW
5h 34m1 stop
Frontier Logo
8:19 pm - 1:03 pm
MDW
-
IAD
15h 44m1 stop
$160Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
8:15 am - 2:26 pm
IAD
-
MDW
7h 11m1 stop
Frontier Logo
6:25 am - 4:43 pm
MDW
-
IAD
9h 18m1 stop
$162Frontier
Thu, Jan 1 - Wed, Jan 7
Frontier Logo
5:35 am - 10:12 pm
IAD
-
MDW
17h 37m1 stop
Frontier Logo
3:01 pm - 1:01 pm
MDW
-
IAD
21h 00m1 stop
$163Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
6:00 am - 11:31 am
IAD
-
MDW
6h 31m1 stop
Frontier Logo
6:10 am - 3:27 pm
MDW
-
IAD
8h 17m1 stop
$168Frontier
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
2:58 pm - 11:09 pm
IAD
-
MDW
9h 11m2 stops
Multiple Airlines Logo
6:10 am - 3:27 pm
MDW
-
IAD
8h 17m1 stop
$171Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Frontier Logo
5:37 pm - 10:19 pm
IAD
-
MDW
5h 42m1 stop
Frontier Logo
5:01 pm - 4:28 pm
MDW
-
IAD
22h 27m1 stop
$174Frontier
Thu, Jan 1 - Fri, Jan 9
Frontier Logo
5:35 am - 10:12 pm
IAD
-
MDW
17h 37m1 stop
Frontier Logo
3:01 pm - 1:16 pm
MDW
-
IAD
21h 15m1 stop
$175Frontier
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
8:40 am - 11:09 pm
IAD
-
MDW
15h 29m1 stop
Frontier Logo
6:10 am - 3:27 pm
MDW
-
IAD
8h 17m1 stop
$180Frontier
Thu, Jan 8 - Mon, Jan 12
Frontier Logo
1:46 pm - 2:06 pm
IAD
-
MDW
25h 20m1 stop
Frontier Logo
6:10 am - 3:27 pm
MDW
-
IAD
8h 17m1 stop
$181Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
6:00 am - 11:33 am
IAD
-
MDW
6h 33m1 stop
Frontier Logo
6:00 am - 6:43 pm
MDW
-
IAD
11h 43m1 stop
$184Frontier
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.

How much is a round-trip flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Washington, D.C. Dulles Intl Airport to Chicago Midway Airport departing in January.

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 seasonDecember
Cheapest flight$71
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 11% 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 $71 for a one-way ticket and $160 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 8008 reviews
7.3Food
7.9Comfort
8.1Boarding
8.5Crew
7.9Entertainment
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

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

Information on your arrival and departure airports