WAS - MDW

$64 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 1/28. 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.
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
$128
Overall average: $296
Frontier
Wed 1/28Wed 2/4
BWI - MDW • 1 stop
Cheapest non-stop
$139
Typical prices: $174-$357
Southwest
Tue 1/13Tue 1/20
BWI - MDW • Non-stop
Our travelers' advice
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
Southwest
Cheapest • from $139 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
BWI-MDW
Cheapest • 28% average savings
DCA-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 33% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Jan 28 - Wed, Feb 4
Frontier Logo
7:10 am - 12:05 pm
BWI
-
MDW
5h 55m1 stop
Frontier Logo
1:20 pm - 12:21 am
MDW
-
BWI
10h 01m1 stop
$128Frontier
Wed, Jan 28 - Wed, Feb 4
Frontier Logo
7:10 am - 12:05 pm
BWI
-
MDW
5h 55m1 stop
Frontier Logo
1:20 pm - 12:21 am
MDW
-
BWI
10h 01m1 stop
$129Frontier
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
7:45 am - 9:05 am
BWI
-
MDW
2h 20mnonstop
Southwest Logo
5:15 pm - 8:10 pm
MDW
-
BWI
1h 55mnonstop
$139Southwest
Thu, Feb 19 - Tue, Feb 24
Frontier Logo
6:08 pm - 10:34 pm
BWI
-
MDW
5h 26m1 stop
Frontier Logo
6:10 am - 5:13 pm
MDW
-
BWI
10h 03m1 stop
$145Frontier
Wed, Jan 7 - Wed, Jan 21
Frontier Logo
11:45 am - 10:17 pm
BWI
-
MDW
11h 32m1 stop
Frontier Logo
1:20 pm - 12:21 am
MDW
-
BWI
10h 01m1 stop
$146Frontier
Mon, Jan 12 - Thu, Jan 15
Southwest Logo
10:25 am - 11:35 am
BWI
-
MDW
2h 10mnonstop
Southwest Logo
1:25 pm - 4:10 pm
MDW
-
BWI
1h 45mnonstop
$149Southwest
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
6:00 am - 11:27 am
BWI
-
MDW
6h 27m1 stop
Frontier Logo
5:16 pm - 12:31 am
MDW
-
BWI
6h 15m1 stop
$153Frontier
Fri, Jan 16 - Sat, Jan 17
Southwest Logo
8:15 pm - 9:25 pm
BWI
-
MDW
2h 10mnonstop
Southwest Logo
12:15 pm - 3:00 pm
MDW
-
BWI
1h 45mnonstop
$158Southwest
Wed, Jan 7 - Thu, Jan 8
Southwest Logo
5:50 pm - 7:00 pm
BWI
-
MDW
2h 10mnonstop
Southwest Logo
5:15 pm - 8:10 pm
MDW
-
BWI
1h 55mnonstop
$159Southwest
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
2:58 pm - 11:09 pm
IAD
-
MDW
9h 11m2 stops
Multiple Airlines Logo
6:10 am - 3:27 pm
MDW
-
IAD
8h 17m1 stop
$171Multiple 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 January.

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 $139 on the route between Baltimore (BWI) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 28% 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’s the cheapest day of the week to fly from Washington, D.C. to Chicago Midway Airport?

The average price of all round-trip flights from Washington, D.C. to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Washington, D.C. to Chicago Midway Airport, look for departures on Tuesdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Thursday is the cheapest day to fly and Thursday is the most expensive.

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 February, where tickets cost $184 (return) on average. On the other hand, the most expensive months are December and November, where the average cost of round-trip tickets is $418 and $330 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.
Airports
DCA

DCA is conveniently close to downtown D.C., making it easy to reach via metro in under 30 minutes, ideal for quick departures.

MDW

From MDW, take the CTA Orange Line to reach downtown Chicago in about 25-30 minutes, avoiding traffic delays.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

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.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on DCA

Ramsey Qubein

Ramsey Qubein

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.

Read more

Good to know

Low seasonFebruary
Cheapest flight$64
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 5% 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 $64 for a one-way ticket and $128 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, Delta, and JetBlue 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 $302 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $204 and an overall rating of 5.8.

  • 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 $159 or less one-way and $263 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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

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

Information on your arrival and departure airports