WAS - MDW

$99 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 5/26. 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
$205
Typical prices: $324-$222
Frontier
Tue 6/9Thu 6/11
BWI - MDW • 1 stop
Cheapest non-stop
$207
Typical prices: $323-$217
Southwest
Sat 6/13Wed 6/17
BWI - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
DCA is conveniently close to downtown D.C. for quick access.
From MDW, use the CTA Orange Line to reach downtown fast.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $205 (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 2h 03m
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 $195 (round-trip)
Shortest trip • 3h 44m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 41% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
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, Jun 9 - Thu, Jun 11
Frontier Logo
6:28 am - 11:12 am
BWI
-
MDW
5h 44m
1 stop
Frontier Logo
6:00 am - 3:33 pm
MDW
-
BWI
8h 33m
1 stop
$205Frontier
Sat, May 16 - Wed, Jun 17
Frontier Logo
6:45 am - 11:04 am
BWI
-
MDW
5h 19m
1 stop
Frontier Logo
6:00 am - 4:22 pm
MDW
-
BWI
9h 22m
1 stop
$206Frontier
Sat, Jun 13 - Wed, Jun 17
Southwest Logo
6:15 am - 7:15 am
BWI
-
MDW
2h 00mnonstop
Southwest Logo
7:25 am - 10:15 am
MDW
-
BWI
1h 50mnonstop
$207Southwest
Wed, May 13 - Thu, May 14
Frontier Logo
6:45 am - 11:09 am
BWI
-
MDW
5h 24m
1 stop
Frontier Logo
6:00 am - 3:46 pm
MDW
-
BWI
8h 46m
1 stop
$208Frontier
Wed, May 13 - Sat, May 16
Frontier Logo
6:45 am - 11:09 am
BWI
-
MDW
5h 24m
1 stop
Frontier Logo
6:00 am - 4:49 pm
MDW
-
BWI
9h 49m
1 stop
$209Frontier
Wed, May 27 - Sat, May 30
Southwest Logo
6:30 am - 7:35 am
BWI
-
MDW
2h 05mnonstop
Southwest Logo
12:05 pm - 2:55 pm
MDW
-
BWI
1h 50mnonstop
$212Southwest
Wed, Jul 1 - Sun, Jul 5
Multiple Airlines Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Multiple Airlines Logo
2:48 pm - 2:26 pm
MDW
-
IAD
22h 38m
1 stop
$223Multiple Airlines
Mon, May 25 - Wed, May 27
Delta Logo
6:00 am - 8:43 am
IAD
-
MDW
3h 43m
1 stop
Delta Logo
6:36 pm - 10:56 pm
MDW
-
IAD
3h 20m
1 stop
$228Delta
Wed, May 27 - Thu, Jun 4
Delta Logo
6:05 am - 8:43 am
DCA
-
MDW
3h 38m
1 stop
Delta Logo
10:59 am - 5:15 pm
MDW
-
DCA
5h 16m
1 stop
$228Delta
Mon, May 18 - Thu, May 21
Multiple Airlines Logo
6:17 pm - 11:09 am
IAD
-
MDW
17h 52m
1 stop
Multiple Airlines Logo
9:14 am - 5:28 pm
MDW
-
IAD
7h 14m
1 stop
$229Multiple 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 June.

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 $219 on the route between Baltimore (BWI) 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. The most popular route is between Washington, D.C. Reagan-National Airport (DCA) and Chicago Midway Airport (MDW).

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 $77 (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 $286 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 1% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Baltimore to Chicago Midway Airport

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

Are your dates flexible? Find out the best times to travel from Washington, D.C. to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Washington, D.C. to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Washington, D.C. to Chicago Midway Airport was $99 for a one-way ticket and $205 for a round-trip.

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

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

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

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

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

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

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

    The Boeing 737 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 Frontier?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and Frontier. With an average price for the route of $308 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $205 and an overall rating of 5.6.

  • 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 $200 or less one-way and $305 or less round-trip.

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

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

Direct departures

Washington, D.C. to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Washington, D.C.

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Washington, D.C. to Midway

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Washington, D.C. to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4314 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

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

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

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

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.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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

Information on your arrival and departure airports