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WAS - MDW

$37 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 7/13. 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
Wed 7/10
Wed 7/17

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 42,898,604 times on KAYAK, and here is why:

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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
7:09 pm - 8:08 pmBWI-MDW
1h 59mnonstop
3:28 pm - 6:19 pmMDW-BWI
1h 51mnonstop
$58Frontier
Find Deal
Mon, Aug 26 - Fri, Sep 6
7:09 pm - 8:08 pmBWI-MDW
1h 59mnonstop
3:28 pm - 6:19 pmMDW-BWI
1h 51mnonstop
$60Frontier
Find Deal
Fri, Sep 13 - Mon, Sep 16
7:09 pm - 8:08 pmBWI-MDW
1h 59mnonstop
3:28 pm - 6:19 pmMDW-BWI
1h 51mnonstop
$68Frontier
Find Deal
Fri, Sep 27 - Mon, Sep 30
6:55 pm - 7:53 pmBWI-MDW
1h 58mnonstop
3:29 pm - 6:17 pmMDW-BWI
1h 48mnonstop
$75Frontier
Find Deal
Sat, Jun 29 - Wed, Jul 3
6:00 am - 8:38 amBWI-MDW
3h 38m1 stop
5:43 pm - 11:20 pmMDW-BWI
4h 37m1 stop
$176Delta
Find Deal
Thu, Jul 11 - Wed, Jul 17
6:00 am - 9:38 amIAD-MDW
4h 38m1 stop
5:45 pm - 11:03 pmMDW-IAD
4h 18m1 stop
$188Delta
Find Deal
Sun, Sep 1 - Sat, Sep 7
7:30 am - 8:17 pmIAD-MDW
37h 47m2 stops
8:00 am - 3:52 pmMDW-IAD
6h 52m1 stop
Sun, Jul 7 - Wed, Jul 17
5:20 pm - 9:37 pmIAD-MDW
5h 17m1 stop
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
$501Porter Airlines
Find Deal
Thu, Jul 18 - Sun, Jul 21
2:50 pm - 7:02 pmIAD-MDW
5h 12m1 stop
5:15 pm - 11:37 amMDW-IAD
17h 22m1 stop
$538Porter Airlines
Find Deal
Sat, Jul 20 - Tue, Jul 23
5:35 pm - 11:18 amIAD-MDW
18h 43m3 stops
8:40 am - 5:02 pmMDW-IAD
7h 22m1 stop
Thu, Jul 4 - Sun, Jul 7

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 $26 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 $44.

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 Sundays.

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 April, where tickets cost $69 on average. On the other hand, the most expensive months are October and November, where the average cost of tickets is $432 and $399 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 $164, prices are generally cheapest when you fly direct.

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 $37.

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 $58. 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 10 and 25 nonstop flights that take off from Washington, D.C. and land in Chicago Midway Airport, with an average flight time of 2h 00m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 119 flights. The most frequent day of departure is Friday, when 21% 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 55m.

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 6:10 am and will be landing in Chicago Midway Airport at 7:10 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

May

Cheapest flight

$37
Best time to beat the crowds with an average 54% drop in price.
Most popular time to fly with an average 2% 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 $37 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, Delta, JetBlue, 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 $477 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 $133 and an overall rating of 6.2.

  • 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 $41 or less one-way and $93 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 10295 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.9Comfort
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

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

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

The CX617 from HK to BKK was delayed more than 1.5 hours.

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.

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

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.
7/13Sat
nonstopFrontier
1h 56mBWI-MDW
$37
6/26Wed
nonstopFrontier
1h 58mBWI-MDW
$39
7/5Fri
nonstopFrontier
1h 56mBWI-MDW
$41
7/11Thu
1 stopDelta
3h 38mBWI-MDW
$88
7/2Tue
1 stopDelta
3h 39mIAD-MDW
$94
7/8Mon
2 stops
11h 57mBWI-MDW
$201
10/12Sat
3 stops
22h 30mIAD-MDW
$223
7/1Mon
1 stopPorter Airlines
9h 37mIAD-MDW
$254
6/29Sat
1 stopPorter Airlines
5h 12mIAD-MDW
$262
6/18Tue
3 stopsWestJet
34h 51mDCA-MDW
$582

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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.
6/15Sat
nonstopFrontier
1h 58mBWI-MDW
6/24Mon
nonstopFrontier
1h 48mMDW-BWI
$151
6/15Sat
nonstopFrontier
1h 58mBWI-MDW
6/21Fri
nonstopFrontier
1h 48mMDW-BWI
$171
6/15Sat
nonstopFrontier
1h 58mBWI-MDW
6/18Tue
multi-stopFrontier
12h 45mMDW-BWI
$177
6/15Sat
nonstopFrontier
1h 58mBWI-MDW
6/17Mon
nonstopFrontier
1h 48mMDW-BWI
$180
6/15Sat
nonstopFrontier
1h 58mBWI-MDW
6/19Wed
nonstopFrontier
1h 48mMDW-BWI
$181
6/15Sat
multi-stopFrontier
18h 35mBWI-MDW
6/18Tue
multi-stopFrontier
12h 45mMDW-BWI
$188
6/15Sat
multi-stopDelta
3h 43mBWI-MDW
6/22Sat
multi-stopDelta
4h 37mMDW-BWI
$296
6/12Wed
multi-stopDelta
3h 43mBWI-MDW
6/17Mon
multi-stopDelta
4h 34mMDW-BWI
$392
6/15Sat
multi-stopDelta
3h 43mBWI-MDW
6/19Wed
multi-stopDelta
4h 37mMDW-BWI
$412
6/14Fri
multi-stop
15h 33mBWI-MDW
6/17Mon
multi-stop
8h 11mMDW-BWI
$617

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Flights to Chicago Midway Airport