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WAS - MDW

Find cheap flights from Washington, D.C. to Chicago Midway Airport from $39

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 5/1. 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
0 bags
Fri 5/24
Fri 5/31

Search 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
In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

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

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

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
4:10 pm - 5:13 pmBWI-MDW
2h 03mnonstop
12:28 pm - 3:16 pmMDW-BWI
1h 48mnonstop
$58Frontier
Find Deal
Wed, May 8 - Wed, May 15
9:00 pm - 11:52 amBWI-MDW
15h 52m1 stop
12:28 pm - 3:16 pmMDW-BWI
1h 48mnonstop
$67Frontier
Find Deal
Sat, May 11 - Wed, May 15
7:16 pm - 8:15 pmBWI-MDW
1h 59mnonstop
3:36 pm - 6:26 pmMDW-BWI
1h 50mnonstop
$70Frontier
Find Deal
Wed, May 22 - Wed, May 29
4:10 pm - 5:13 pmBWI-MDW
2h 03mnonstop
7:00 am - 7:32 pmMDW-BWI
11h 32m1 stop
$72Frontier
Find Deal
Wed, May 8 - Wed, May 15
6:10 am - 8:51 amBWI-MDW
3h 41m1 stop
5:47 pm - 11:18 pmMDW-BWI
4h 31m1 stop
$176Delta
Find Deal
Sun, May 26 - Thu, May 30
6:10 am - 9:06 amBWI-MDW
3h 56m1 stop
9:32 am - 5:12 pmMDW-BWI
6h 40m1 stop
$177Delta
Find Deal
Wed, May 22 - Tue, May 28
6:00 am - 9:06 amIAD-MDW
4h 06m1 stop
5:45 pm - 10:58 pmMDW-IAD
4h 13m1 stop
$178Delta
Find Deal
Wed, Jun 5 - Tue, Jun 18
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
$539Porter Airlines
Find Deal
Fri, May 10 - Sun, May 12
1:00 pm - 9:37 pmIAD-MDW
9h 37m1 stop
8:00 am - 3:52 pmMDW-IAD
6h 52m1 stop
$548Porter Airlines
Find Deal
Mon, May 13 - Wed, May 22
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
8:00 am - 3:52 pmMDW-IAD
6h 52m1 stop
$558Porter Airlines
Find Deal
Wed, May 8 - Wed, May 15

Flights from Washington, D.C. to Midway - Travel Insights & Trends

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 one-way flights from Washington, D.C. to Chicago Midway Airport.
Our data shows that the cheapest route for a one-way flight from Washington, D.C. to Chicago Midway Airport cost $24 and was between Baltimore and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $38.

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

The average price of all flights from Washington, D.C. to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Washington, D.C. to Chicago Midway Airport, you should consider leaving on a Friday and avoid Mondays if you are looking for the best rates. For your return to Washington, D.C., you’ll find the best rates on Wednesdays and the most expensive ones on Tuesdays.

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 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 September, where tickets cost $204 on average. On the other hand, the most expensive months are May and December, where the average cost of tickets is $477 and $470 respectively.

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

The average 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 $153, 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 daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Washington, D.C. to Chicago Midway Airport, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 9 days before departure.

Which airlines provide the cheapest flights from Washington, D.C. to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Washington, D.C. to Chicago Midway Airport were found on Frontier ($58) and Delta ($176). Frontier proposed the cheapest one-way flight at $39.

Which airlines fly non-stop between Washington, D.C. and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Washington, D.C. to Chicago Midway Airport.
There are 2 airlines that fly nonstop from Washington, D.C. to Chicago Midway Airport. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best one-way deal found costing $61. On average, the best prices for this route can be found at Frontier.

How many flights are there between Washington, D.C. and Chicago Midway Airport per day?

Each day, there are between 8 and 13 nonstop flights that take off from Washington, D.C. and land in Chicago Midway Airport, with an average flight time of 2h 02m. The most common departure time is 6:00 pm and most flights take off in the morning. Each week, there are 82 flights. The most frequent day of departure is Friday, when 16% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Washington, D.C. and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Washington, D.C. to Chicago Midway Airport take?

Direct flights cover the 597 miles separating Washington, D.C. to Chicago Midway Airport in about 1h 59m.

What’s the earliest departure time from Washington, D.C. to Chicago Midway Airport?

Early birds can take the earliest flight from Washington, D.C. at 6:25 am and will be landing in Chicago Midway Airport at 7:25 am.

What’s the latest departure time from Washington, D.C. to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Washington, D.C. to Chicago Midway Airport jets off at 9:55 pm and lands at 10:55 pm.

Good to know

Low season

January

High season

December

Cheapest flight

$39
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 30% increase in price.
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 $39 for a one-way ticket and $58 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, and Alaska Airlines 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 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, 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 $481 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $136 and an overall rating of 6.3.

  • 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.

See more FAQs

Top tips for finding a cheap flight from Washington, D.C. to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $37 or less one-way and $79 or less round-trip.

Prefer to fly non-stop from Washington, D.C. to Chicago Midway Airport?

Find which airlines fly direct from Washington, D.C. to Midway, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

Top 4 airlines serving 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
DeltaOverall score based on 11004 reviews
7.5food
7.9comfort
8.6crew
8.0entertainment
8.2boarding
Airline reviews

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

2.0 MediocreMarisol, Apr 2024DFW - ATL
Read more about Delta reviews

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The flights from Ottawa to Albuquerque went smoothly enough though on on flight they didn't have how water for coffee or tea and on another there there was no ice. The return flights from Albuquerque were delayed by mechanical problems on both flights. Ottawa was a ground crew maintenance issue.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap flights from Washington, D.C. to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Washington, D.C. to Chicago found on KAYAK in the last 72 hours.
5/1Wed
nonstopFrontier
2h 03mBWI-MDW
$39
10/16Wed
nonstopFrontier
1h 59mBWI-MDW
$40
5/17Fri
nonstopFrontier
1h 59mBWI-MDW
$41
5/22Wed
nonstopFrontier
1h 59mBWI-MDW
$42
7/1Mon
1 stopDelta
3h 44mBWI-MDW
$88
5/28Tue
1 stopDelta
4h 06mIAD-MDW
$89
6/24Mon
2 stops
11h 58mBWI-MDW
$204
5/16Thu
3 stops
26h 32mIAD-MDW
$264
5/10Fri
1 stopPorter Airlines
5h 17mIAD-MDW
$282
5/24Fri
1 stopPorter Airlines
5h 17mIAD-MDW
$346

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Last minute flights from Washington, D.C. to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Washington, D.C. to Chicago that are departing in the next 10 days.
4/27Sat
multi-stopFrontier
10h 43mBWI-MDW
5/1Wed
nonstopFrontier
1h 48mMDW-BWI
$110
4/27Sat
multi-stopFrontier
10h 43mBWI-MDW
5/6Mon
multi-stopFrontier
12h 45mMDW-BWI
$120
4/29Mon
multi-stopFrontier
5h 47mBWI-MDW
5/6Mon
nonstopFrontier
1h 48mMDW-BWI
$128
4/28Sun
multi-stop
19h 56mBWI-MDW
5/6Mon
multi-stop
4h 43mMDW-BWI
$349
4/26Fri
multi-stopDelta
4h 59mDCA-MDW
6/8Sat
multi-stopDelta
4h 11mMDW-DCA
$405
4/28Sun
multi-stop
19h 56mBWI-MDW
5/3Fri
multi-stop
30h 55mMDW-BWI
$463
4/27Sat
multi-stopDelta
3h 50mIAD-MDW
4/27Sat
multi-stopDelta
7h 14mMDW-IAD
$482
4/25Thu
multi-stopPorter Airlines
5h 17mIAD-MDW
5/2Thu
multi-stopPorter Airlines
6h 52mMDW-IAD
$1,055
4/27Sat
multi-stopPorter Airlines
5h 12mIAD-MDW
4/29Mon
multi-stopPorter Airlines
6h 52mMDW-IAD
$1,132
4/25Thu
multi-stopWestJet
18h 31mDCA-MDW
4/26Fri
multi-stopWestJet
23h 25mMDW-DCA
$1,289

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Flights to Chicago Midway Airport