$73 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 3/18. 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
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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

Thu, Feb 19 - Sat, Feb 28
Frontier Logo
9:05 am - 4:43 pm
MDW
-
IAD
6h 38m
1 stop
Frontier Logo
10:29 am - 9:39 pm
IAD
-
MDW
12h 10m
1 stop
$138Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
9:05 am - 4:43 pm
MDW
-
IAD
6h 38m
1 stop
Frontier Logo
11:22 am - 10:29 pm
IAD
-
MDW
12h 07m
1 stop
$148Frontier
Thu, Feb 19 - Thu, Feb 26
Frontier Logo
9:05 am - 4:43 pm
MDW
-
IAD
6h 38m
1 stop
Frontier Logo
11:22 am - 4:16 pm
IAD
-
MDW
5h 54m
1 stop
$150Frontier
Thu, Feb 26 - Thu, Mar 5
Frontier Logo
6:25 am - 4:43 pm
MDW
-
IAD
9h 18m
1 stop
Frontier Logo
11:22 am - 4:16 pm
IAD
-
MDW
5h 54m
1 stop
$153Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
9:05 am - 4:43 pm
MDW
-
IAD
6h 38m
1 stop
Frontier Logo
5:22 pm - 10:29 pm
IAD
-
MDW
6h 07m
1 stop
$154Frontier
Tue, Feb 17 - Wed, Feb 18
Southwest Logo
6:00 am - 8:55 am
MDW
-
DCA
1h 55mnonstop
Southwest Logo
6:00 am - 7:15 am
DCA
-
MDW
2h 15mnonstop
$197Southwest
Tue, Feb 17 - Wed, Feb 18
Southwest Logo
5:20 pm - 8:15 pm
MDW
-
DCA
1h 55mnonstop
Southwest Logo
8:00 am - 2:20 pm
DCA
-
MDW
7h 20m
1 stop
$207Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
8:35 pm - 11:20 pm
MDW
-
DCA
1h 45mnonstop
Southwest Logo
6:00 am - 7:15 am
DCA
-
MDW
2h 15mnonstop
$214Southwest
Tue, Feb 24 - Tue, Mar 3
Delta Logo
9:34 am - 5:04 pm
MDW
-
DCA
6h 30m
1 stop
Delta Logo
12:00 pm - 6:40 pm
DCA
-
MDW
7h 40m
1 stop
$217Delta
Sat, Feb 21 - Mon, Feb 23
Southwest Logo
6:25 am - 9:20 am
MDW
-
DCA
1h 55mnonstop
Southwest Logo
9:00 pm - 10:15 pm
DCA
-
MDW
2h 15mnonstop
$218Southwest
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 $177 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Washington, D.C. Reagan-National Airport (DCA), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $199.

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 $224 on average.

Good to know

Low seasonSeptember
Cheapest flight$73
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 8% 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.

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

    The cheapest time of day to fly to District of Columbia is generally in the evening, when round-trip flights cost $280 on average. Morning departures are around 6% 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 $297.

Top tips for finding cheap flights to District of Columbia

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Washington, D.C. $146 one-way - $260 round-trip

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 4268 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

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

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

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.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

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

Information on your arrival and departure airports