WAS - MDW

$89 Find Cheap Flights from Washington, D.C. to Chicago Midway Airport - Compare and Save

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 10/28. 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.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$198
Typical prices: $144-$278
Southwest
Sat 9/12Sat 9/19
BWI - MDW • 2 stops
Cheapest non-stop
$201
Typical prices: $139-$279
Southwest
Sat 10/10Sat 10/10
BWI - MDW • Non-stop
Top airlines
Cheapest • from $197 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 1h 58m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Top routes
Cheapest • 1% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $187 (round-trip)
Shortest trip • 3h 41m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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Flight Deals
Booking Insights
Expert advice
Flight 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

Sat, Sep 12 - Sat, Sep 19
Southwest Logo
8:30 am - 2:10 pm
BWI
-
MDW
6h 40m
2 stops
Southwest Logo
11:45 am - 4:00 pm
MDW
-
BWI
3h 15m
1 stop
$198Southwest
Tue, Nov 3 - Mon, Nov 9
Southwest Logo
4:50 pm - 9:30 pm
BWI
-
MDW
5h 40m
2 stops
Southwest Logo
12:50 pm - 5:55 pm
MDW
-
BWI
4h 05m
1 stop
$198Southwest
Wed, Oct 14 - Sat, Oct 17
Southwest Logo
11:00 am - 2:35 pm
BWI
-
MDW
4h 35m
1 stop
Southwest Logo
2:20 pm - 10:45 pm
MDW
-
BWI
7h 25m
2 stops
$198Southwest
Sat, Sep 12 - Fri, Sep 18
Frontier Logo
7:50 am - 5:51 pm
IAD
-
MDW
11h 01m
1 stop
Frontier Logo
6:25 am - 5:18 pm
MDW
-
IAD
9h 53m
1 stop
$200Frontier
Fri, Aug 28 - Sat, Aug 29
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$200Frontier
Wed, Aug 26 - Wed, Sep 2
Frontier Logo
6:20 am - 10:55 am
IAD
-
MDW
5h 35m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$200Frontier
Sun, Sep 6 - Wed, Sep 9
Delta Logo
6:00 am - 10:10 am
BWI
-
MDW
5h 10m
1 stop
Delta Logo
6:05 am - 12:58 pm
MDW
-
BWI
5h 53m
1 stop
$202Delta
Mon, Aug 31 - Sun, Sep 6
Delta Logo
6:00 am - 9:59 am
BWI
-
MDW
4h 59m
1 stop
Delta Logo
6:05 am - 1:05 pm
MDW
-
BWI
6h 00m
1 stop
$202Delta
Sun, Aug 16 - Sun, Aug 23
Multiple Airlines Logo
6:30 pm - 2:59 pm
IAD
-
MDW
21h 29m
2 stops
Multiple Airlines Logo
9:26 pm - 6:29 pm
MDW
-
IAD
20h 03m
1 stop
$363Multiple Airlines
Thu, Oct 8 - Sun, Oct 11
Multiple Airlines Logo
1:30 pm - 10:58 am
IAD
-
MDW
22h 28m
2 stops
Multiple Airlines Logo
11:38 am - 6:45 pm
MDW
-
IAD
6h 07m
1 stop
$454Multiple Airlines
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.

How much is a round-trip flight from Washington, D.C. to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Washington, D.C. to Chicago Midway Airport departing in September.

Flight prices are below average for this route right now.

Flights to Chicago Midway Airport from Washington, D.C. usually cost between $270 and $378 in September.
The lowest price found in the past 5 days was $198 on Southwest (Sep 12-Sep 19).

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Washington, D.C. to Chicago Midway Airport costs $177 on the route between Washington, D.C. Reagan-National Airport (DCA) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 1% cheaper than other Washington, D.C.-Chicago Midway Airport routes. It is also the most popular route.

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 September, where tickets cost $265 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $425 and $379 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $304 on average.

Expert advice

Expert advice for your flight from Washington, D.C. to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Ramsey Qubein

Ramsey Qubein

Expert on DCA

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Good to know

Low season

February

Cheapest flight

$89
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 23% 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 5 days, the lowest price for a flight from Washington, D.C. to Chicago Midway Airport was $89 for a one-way ticket and $197 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 MAX 8 is the aircraft model that flies most regularly on the Washington, D.C. to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Washington, D.C. to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Washington, D.C. and Chicago Midway Airport.

  • 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 United Airlines?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and United Airlines. With an average price for the route of $350 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $348 and an overall rating of 7.4.

  • 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 $186 or less one-way and $291 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 3 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
SouthwestOverall score based on 4227 reviews
8.0Comfort
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

Almost 2 hour delay in boarding with all standing ready to board at original time. No explanation given.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

The trip was unremarkable which is good. Crew was very professional and courteous.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

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

Information on your arrival and departure airports