$94 Find Cheap Flights from Chicago Midway Airport to District of Columbia

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to District of Columbia departing on 4/8. 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 District of Columbia

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to District of Columbia, 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 Chicago to District of Columbia, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Midway to District of Columbia Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to District of Columbia 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 Midway to District of Columbia

Wed, Apr 8 - Tue, Apr 21
Frontier Logo
2:56 pm - 12:36 am
MDW
-
IAD
8h 40m
1 stop
Frontier Logo
8:20 am - 7:31 pm
IAD
-
MDW
12h 11m
1 stop
$199Frontier
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
2:15 pm - 12:36 am
MDW
-
IAD
9h 21m
1 stop
Frontier Logo
8:20 am - 7:31 pm
IAD
-
MDW
12h 11m
1 stop
$200Frontier
Wed, Apr 1 - Wed, Apr 8
Frontier Logo
6:00 am - 2:20 pm
MDW
-
IAD
7h 20m
1 stop
Frontier Logo
3:15 pm - 10:19 pm
IAD
-
MDW
8h 04m
1 stop
$201Frontier
Mon, Mar 30 - Tue, Apr 7
Frontier Logo
2:41 pm - 12:31 am
MDW
-
IAD
8h 50m
1 stop
Frontier Logo
3:15 pm - 10:19 pm
IAD
-
MDW
8h 04m
1 stop
$205Frontier
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
7:25 pm - 10:15 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
3:40 pm - 4:50 pm
DCA
-
MDW
2h 10mnonstop
$209Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
1:55 pm - 6:40 pm
MDW
-
DCA
3h 45m
1 stop
Southwest Logo
3:40 pm - 4:50 pm
DCA
-
MDW
2h 10mnonstop
$215Southwest
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
4:20 pm - 7:10 pm
MDW
-
DCA
1h 50mnonstop
Southwest Logo
4:55 pm - 10:15 pm
DCA
-
MDW
6h 20m
1 stop
$219Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
1:55 pm - 6:40 pm
MDW
-
DCA
3h 45m
1 stop
Southwest Logo
9:05 am - 1:30 pm
DCA
-
MDW
5h 25m
1 stop
$224Southwest
Tue, Apr 7 - Wed, Apr 8
Delta Logo
6:34 pm - 10:51 pm
MDW
-
DCA
3h 17m
1 stop
Delta Logo
6:00 am - 8:53 am
DCA
-
MDW
3h 53m
1 stop
$229Delta
Mon, Apr 13 - Tue, Apr 14
Delta Logo
1:24 pm - 6:59 pm
MDW
-
DCA
4h 35m
1 stop
Delta Logo
6:00 am - 8:47 am
DCA
-
MDW
3h 47m
1 stop
$244Delta
Booking Insights

KAYAK's insights & trends for Midway to District of Columbia flights

Get data-powered insights and trends into flights from Midway to District of Columbia to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to District of Columbia flight route?

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

The cheapest ticket to District of Columbia from Chicago Midway Airport found in the last 72 hours was to Baltimore, at $233 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Baltimore (BWI), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $233.

What is the cheapest time of day to fly to District of Columbia?

The average price for all round-trip flights from Chicago Midway Airport to District of Columbia depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to District of Columbia is generally in the evening, when round-trip flights cost $292 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to District of Columbia is generally at night, which is peak travel time and where the average cost of a ticket is $316.

Can I save money by flying with a layover from Chicago Midway Airport to District of Columbia?

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 $234 on average.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 24% lower on average.
Flight from Chicago Midway Airport to Washington Dulles Airport

FAQs - booking District of Columbia flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to District of Columbia?

    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 Chicago Midway Airport to District of Columbia.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to District of Columbia?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to District of Columbia 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 Chicago Midway Airport to District of Columbia?

    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 from Chicago Midway Airport to District of Columbia with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to District of Columbia?

    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 from Chicago Midway Airport to District of Columbia up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Midway to District of Columbia

 
See real verified KAYAK customer reviews for airlines flying from Chicago to District of Columbia. 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 Midway to District of Columbia? 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 4324 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Everything you need to know for your flight from Midway to District of Columbia

Information on your arrival and departure airports