IAD - MDW

$85 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 7/19. 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

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

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flights from Dulles Intl to Midway

 
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.

Recent round-trip flight deals from Dulles Intl to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Dulles Intl to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
3:32 pm - 11:39 pmIAD-MDW
9h 07m1 stop
Frontier Logo
6:15 am - 6:31 amMDW-IAD
23h 16m1 stop
$171Frontier
Find Deal
Thu, May 15 - Mon, May 19
Frontier Logo
3:32 pm - 11:39 pmIAD-MDW
9h 07m1 stop
Frontier Logo
10:48 am - 4:34 pmMDW-IAD
4h 46m1 stop
$181Frontier
Find Deal
Thu, May 15 - Sat, May 17
Frontier Logo
7:31 am - 2:48 pmIAD-MDW
32h 17m1 stop
Frontier Logo
1:19 pm - 4:36 pmMDW-IAD
26h 17m1 stop
$191Frontier
Find Deal
Sun, May 11 - Thu, May 15
Delta Logo
3:37 pm - 9:13 pmIAD-MDW
6h 36m1 stop
Delta Logo
6:00 am - 11:41 amMDW-IAD
4h 41m1 stop
$197Delta
Find Deal
Sat, May 24 - Sun, May 25
Frontier Logo
4:59 pm - 10:36 pmIAD-MDW
6h 37m1 stop
Frontier Logo
6:10 am - 4:04 pmMDW-IAD
8h 54m1 stop
$198Frontier
Find Deal
Wed, May 28 - Sat, May 31
Delta Logo
5:40 pm - 9:27 pmIAD-MDW
4h 47m1 stop
Delta Logo
1:08 pm - 5:37 pmMDW-IAD
3h 29m1 stop
$199Delta
Find Deal
Fri, May 30 - Sat, May 31
Allegiant Air Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
Allegiant Air Logo
11:45 am - 2:23 pmMDW-IAD
25h 38m2 stops
$294Allegiant Air
Find Deal
Thu, Jun 19 - Sun, Jun 22
 Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
 Logo
8:05 am - 11:26 amMDW-IAD
26h 21m3 stops
Thu, Jun 5 - Mon, Jun 9
Allegiant Air Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
Allegiant Air Logo
11:45 am - 2:23 pmMDW-IAD
25h 38m2 stops
$315Allegiant Air
Find Deal
Thu, Jun 5 - Sun, Jun 8
 Logo
9:10 pm - 2:03 pmIAD-MDW
17h 53m2 stops
 Logo
8:05 am - 11:26 amMDW-IAD
26h 21m3 stops
Thu, Jun 5 - Mon, Jun 9
Useful Info

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 seasonApril
High seasonOctober
Cheapest flight$85
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 31% 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 $85 for a one-way ticket and $171 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?

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Washington Dulles Airport to Chicago Midway Airport flight 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.

  • 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.

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.
8.0
DeltaOverall score based on 7934 reviews
7.9Entertainment
7.3Food
8.5Crew
7.9Comfort
8.2Boarding
Airline reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

8.0 ExcellentFredrick, Apr 2025GSO - DTW
Read more Delta reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

When I booked it on Kayak it aaid that I wasn't allowed hamd luggage. I called United Airlines and it took them 6 minutes to figure out if I was allowed free hand luggage. Surely something that simple they should be able to tell me instantly.

We were delayed in Toronto on the tarmac for THREE hours with no clear indication as to why except that it was not a safety hazard. Pilot did apologize more than once but even he was unable to explain why exactly we were delayed. I overheard the stewards saying that the captain was very frustrated with the situation as well because he was not able to explain why except it had something to do with water supply or system on the aircraft and now we needed to wait for an engineer to approve the aircraft for flight. It was very frustrating and distressing as a passenger and we should have been given complimentary meals at the very least.

Flight was cramped with every seat taken. The food was fine, nothing crazy to write home about. The plane felt dated and needing some TLC, the button for the window shade didn't work and there were no AC outlets to use. When communicating with staff all except one nice lady never seemed happy to help me almost like I was bothering them when asked for things like a glass of water or a snack. The flight was overall fine. It did what was needed which is get me from point A to point B. But it certainly was not special. I don't expect much in economy but I believe economy on a host of other airlines is more memorable and better experience.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

The flight was heavily booked so boarding was a lengthy process. The FA’s were rather abrupt during this process but became more gracious as the flight went on. Breakfast (puffed pastry and chewy sausage) was pretty horrible but there was fruit and yogurt which they didn’t mess up. Overall it was fine.

Liked nothing. As per previous segment it was delay delay delay.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.