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 10/24. 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

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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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

Wed, Oct 15 - Tue, Oct 21
Frontier Logo
9:00 am - 1:38 pmIAD-MDW
5h 38m1 stop
Frontier Logo
8:05 am - 7:46 pmMDW-IAD
10h 41m1 stop
$140Frontier
Find Deal
Tue, Oct 28 - Tue, Nov 4
Frontier Logo
8:47 am - 12:41 pmIAD-MDW
28h 54m1 stop
Frontier Logo
1:56 pm - 8:20 pmMDW-IAD
5h 24m1 stop
$141Frontier
Find Deal
Tue, Oct 28 - Tue, Nov 4
Frontier Logo
8:47 am - 12:41 pmIAD-MDW
28h 54m1 stop
Frontier Logo
1:56 pm - 8:20 pmMDW-IAD
5h 24m1 stop
$142Frontier
Find Deal
Sat, Oct 25 - Mon, Oct 27
Frontier Logo
4:22 pm - 10:47 pmIAD-MDW
7h 25m1 stop
Frontier Logo
12:03 pm - 11:22 pmMDW-IAD
10h 19m1 stop
$143Frontier
Find Deal
Thu, Sep 25 - Fri, Sep 26
Frontier Logo
7:14 pm - 8:53 amIAD-MDW
14h 39m1 stop
Frontier Logo
5:15 pm - 12:15 amMDW-IAD
6h 00m1 stop
$144Frontier
Find Deal
Fri, Oct 3 - Sun, Oct 5
Frontier Logo
1:55 pm - 11:41 pmIAD-MDW
10h 46m1 stop
Frontier Logo
6:21 am - 9:24 pmMDW-IAD
14h 03m1 stop
$145Frontier
Find Deal
Tue, Oct 28 - Mon, Nov 10
Frontier Logo
8:47 am - 12:41 pmIAD-MDW
28h 54m1 stop
Frontier Logo
6:15 am - 4:34 pmMDW-IAD
9h 19m1 stop
$146Frontier
Find Deal
Sat, Oct 18 - Mon, Oct 20
Frontier Logo
4:22 pm - 10:47 pmIAD-MDW
7h 25m1 stop
Frontier Logo
9:45 am - 7:14 pmMDW-IAD
8h 29m1 stop
$149Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
1:07 pm - 4:09 pmIAD-MDW
28h 02m1 stop
Frontier Logo
9:45 am - 7:14 pmMDW-IAD
8h 29m1 stop
$150Frontier
Find Deal
Tue, Sep 23 - Fri, Sep 26
Frontier Logo
9:15 am - 3:58 pmIAD-MDW
7h 43m1 stop
Frontier Logo
6:20 am - 12:55 pmMDW-IAD
5h 35m1 stop
$152Frontier
Find Deal

Everything you should know

Cheapest round-trip
$140
Frontier
Wed 10/15Tue 10/21
IAD - MDW • 1 stop
Cheapest one-way
$78
Frontier
Fri 10/24
IAD - MDW • 1 stop
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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!
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 seasonDecember
Cheapest flight$78
Best time to beat the crowds with an average 20% 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 $78 for a one-way ticket and $140 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 $304 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 $183 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 7954 reviews
8.5Crew
7.3Food
7.9Comfort
7.9Entertainment
8.2Boarding
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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