WAS - MDW

$99 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 7/8. 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, 0 bags

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
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Everything you should know

Cheapest round-trip
$224
Typical prices: $308-$157
Southwest
Tue 8/11Sat 8/15
BWI - MDW • 1 stop
Cheapest non-stop
$225
Typical prices: $349-$165
Southwest
Tue 7/28Wed 7/29
BWI - MDW • Non-stop
Top airlines
Cheapest • from $224 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 01m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 3% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $202 (round-trip)
Shortest trip • 3h 39m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 46% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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We hope you love your trip to Midway!
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

Tue, Aug 11 - Sat, Aug 15
Southwest Logo
6:40 pm - 10:20 pm
BWI
-
MDW
4h 40m
1 stop
Southwest Logo
5:55 am - 8:40 am
MDW
-
BWI
1h 45mnonstop
$224Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
10:50 am - 1:05 pm
BWI
-
MDW
3h 15m
1 stop
Southwest Logo
12:45 pm - 5:00 pm
MDW
-
BWI
3h 15m
1 stop
$225Southwest
Mon, Aug 10 - Wed, Aug 12
Southwest Logo
4:10 pm - 7:30 pm
BWI
-
MDW
4h 20m
1 stop
Southwest Logo
12:35 pm - 4:40 pm
MDW
-
BWI
3h 05m
1 stop
$226Southwest
Sat, Aug 15 - Wed, Aug 19
Southwest Logo
10:50 am - 1:05 pm
BWI
-
MDW
3h 15m
1 stop
Southwest Logo
8:45 am - 2:00 pm
MDW
-
BWI
4h 15m
1 stop
$227Southwest
Tue, Sep 1 - Thu, Sep 17
Delta Logo
6:15 am - 9:17 am
BWI
-
MDW
4h 02m
1 stop
Delta Logo
1:00 pm - 7:35 pm
MDW
-
BWI
5h 35m
1 stop
$234Delta
Thu, Aug 27 - Sun, Aug 30
Frontier Logo
11:11 am - 10:11 pm
IAD
-
MDW
12h 00m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$247Frontier
Fri, Aug 21 - Sun, Aug 23
Frontier Logo
11:12 am - 10:11 pm
IAD
-
MDW
11h 59m
1 stop
Frontier Logo
6:00 am - 4:20 pm
MDW
-
IAD
9h 20m
1 stop
$248Frontier
Fri, Jul 3 - Mon, Jul 13
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Frontier Logo
6:05 am - 5:14 pm
MDW
-
IAD
10h 09m
1 stop
$250Frontier
Wed, Sep 16 - Mon, Sep 21
Delta Logo
6:10 am - 9:07 am
DCA
-
MDW
3h 57m
1 stop
Delta Logo
5:10 pm - 11:43 pm
MDW
-
DCA
5h 33m
1 stop
$251Delta
Tue, Jul 14 - Wed, Jul 15
Delta Logo
10:21 am - 4:15 pm
IAD
-
MDW
6h 54m
1 stop
Delta Logo
6:00 am - 11:37 am
MDW
-
IAD
4h 37m
1 stop
$253Delta
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 August.

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 $211 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, 3% 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 April, where tickets cost $70 (return) on average. On the other hand, the most expensive months are March and February, where the average cost of round-trip tickets is $236 and $187 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 $278 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 seasonFebruary
Cheapest flight$99
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Washington Dulles Airport 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 $99 for a one-way ticket and $224 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 $331 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $313 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 $180 or less one-way and $310 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.
7.9
SouthwestOverall score based on 4235 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
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.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

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

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

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

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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

Information on your arrival and departure airports