WAS - MDW

$56 Find Cheap Flights from Washington, D.C. 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 Washington, D.C. to Midway departing on 9/19. 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
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
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
Booking Insights
Flights Deals

Cheap Flights from Washington, D.C. to Midway (WAS-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Washington, D.C. 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 Washington, D.C. to Midway

Fri, Oct 3 - Mon, Oct 6
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$80Frontier
Find Deal
Sun, Sep 21 - Thu, Sep 25
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$89Frontier
Find Deal
Fri, Oct 17 - Mon, Oct 20
Frontier Logo
2:29 pm - 3:33 pmBWI-MDW
2h 04mnonstop
Frontier Logo
1:59 pm - 4:55 pmMDW-BWI
1h 56mnonstop
$102Frontier
Find Deal
Thu, Sep 11 - Sun, Sep 14
Frontier Logo
5:40 pm - 6:43 pmBWI-MDW
2h 03mnonstop
Frontier Logo
1:49 pm - 4:50 pmMDW-BWI
2h 01mnonstop
$107Frontier
Find Deal
Sat, Oct 18 - Thu, Oct 23
Frontier Logo
5:55 pm - 6:59 pmBWI-MDW
2h 04mnonstop
Frontier Logo
1:59 pm - 4:55 pmMDW-BWI
1h 56mnonstop
$108Frontier
Find Deal
Wed, Sep 3 - Sat, Sep 6
Southwest Logo
1:25 pm - 2:20 pmBWI-MDW
1h 55mnonstop
Southwest Logo
7:00 am - 9:50 amMDW-BWI
1h 50mnonstop
$161Southwest
Find Deal
Mon, Aug 18 - Fri, Aug 22
Allegiant Air Logo
1:22 pm - 6:17 pmIAD-MDW
5h 55m1 stop
Allegiant Air Logo
9:32 am - 3:23 pmMDW-IAD
4h 51m1 stop
$174Allegiant Air
Find Deal
Sat, Aug 30 - Tue, Sep 2
Southwest Logo
7:05 pm - 8:05 pmDCA-MDW
2h 00mnonstop
Southwest Logo
12:15 pm - 3:10 pmMDW-DCA
1h 55mnonstop
$217Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
Delta Logo
5:25 pm - 9:12 pmIAD-MDW
4h 47m1 stop
Delta Logo
9:30 am - 11:26 pmMDW-IAD
12h 56m1 stop
$227Delta
Find Deal
Sat, Aug 30 - Wed, Sep 3
Delta Logo
12:29 pm - 6:37 pmDCA-MDW
7h 08m1 stop
Delta Logo
4:25 pm - 11:46 pmMDW-DCA
6h 21m1 stop
$227Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Washington, D.C. to Midway flights

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

What is the cheapest Washington, D.C. to Chicago Midway Airport flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Washington, D.C. to Chicago Midway Airport.

Our data shows that the cheapest route for a return flight from Washington, D.C. to Chicago Midway Airport cost $109 and was between Baltimore (BWI) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $109.

What’s the cheapest day of the week to fly from Washington, D.C. to Chicago Midway Airport?

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

If you are looking for a flight deal from Washington, D.C. to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Friday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Washington, D.C. to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Washington, D.C. to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Washington, D.C. to Chicago Midway Airport is February, where tickets cost $181 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $329 and $322 respectively.

Can I save money by flying with a layover from Washington, D.C. to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $223, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Washington, D.C. to Chicago Midway Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Washington, D.C. to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Washington, D.C. to Chicago Midway Airport, you should book around 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$56
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Baltimore to Chicago Midway Airport

When to book flights from Washington, D.C. to Midway

Are your dates flexible? Find out the best times to travel from Washington, D.C. 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, D.C. to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Washington, D.C. to Chicago Midway Airport was $56 for a one-way ticket and $80 for a round-trip.

  • Do I need a passport to fly between Washington, D.C. and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Washington, D.C. to Chicago Midway Airport?

    When flying out of Washington, D.C. you will be using one of these airports: Washington, D.C. Reagan-National or Washington, D.C. Dulles Intl. You will be landing at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Washington, D.C. to Chicago Midway Airport?

    American Airlines, Alaska Airlines, Hawaiian Airlines, and Delta offer inflight Wi-Fi service on the Washington, D.C. to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Washington, D.C. to Chicago Midway Airport?

    The Boeing 737-800 Passenger/BBJ2 (winglets) is the aircraft model that flies most regularly on the Washington, D.C. to Chicago Midway Airport flight route.

  • On which days can I fly direct from Washington, D.C. to Chicago Midway Airport?

    There are nonstop flights from Washington, D.C. to Chicago Midway Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and Frontier. With an average price for the route of $293 and an overall rating of 8.0, Southwest 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 5.9.

  • How does KAYAK find such low prices on flights from Washington, D.C. 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, D.C. 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, D.C. 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, D.C. 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, D.C. 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, D.C. with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Washington, D.C. 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, D.C. up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Washington, D.C. to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $136 or less one-way and $186 or less round-trip.

Prefer to fly direct from Washington, D.C. to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Washington, D.C. to Chicago Midway.
Find which airlines fly direct from Washington, D.C. to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Washington, D.C. to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Washington, D.C.

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Washington, D.C. 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 Washington, D.C. 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
SouthwestOverall score based on 4241 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

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

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Everything you need to know for your flight from Washington, D.C. 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.