$78 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 10/5. 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

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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Cheap Flights from Midway to District of Columbia

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Washington, D.C.
Baltimorenonstop$92
Washington, D.C.
Baltimorenonstop$92

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

Fri, Oct 3 - Sun, Oct 5
Frontier Logo
5:15 pm - 11:39 pmMDW-IAD
5h 24m1 stop
Frontier Logo
7:14 pm - 7:23 amIAD-MDW
13h 09m1 stop
$143Frontier
Find Deal
Sat, Oct 18 - Mon, Oct 20
Frontier Logo
11:31 am - 8:53 pmMDW-IAD
8h 22m1 stop
Frontier Logo
4:45 pm - 11:46 pmIAD-MDW
8h 01m1 stop
$144Frontier
Find Deal
Sun, Sep 28 - Tue, Sep 30
Frontier Logo
6:21 am - 9:19 pmMDW-IAD
13h 58m1 stop
Frontier Logo
9:15 am - 3:58 pmIAD-MDW
7h 43m1 stop
$145Frontier
Find Deal
Thu, Oct 2 - Sun, Oct 5
Frontier Logo
4:56 pm - 11:39 pmMDW-IAD
5h 43m1 stop
Frontier Logo
7:14 pm - 7:23 amIAD-MDW
13h 09m1 stop
$146Frontier
Find Deal
Sun, Dec 7 - Wed, Dec 10
Frontier Logo
6:00 am - 12:49 pmMDW-IAD
5h 49m1 stop
Frontier Logo
8:00 am - 9:32 pmIAD-MDW
14h 32m1 stop
$147Frontier
Find Deal
Tue, Nov 18 - Thu, Nov 20
Multiple Airlines Logo
1:56 pm - 8:20 pmMDW-IAD
5h 24m1 stop
Multiple Airlines Logo
8:23 pm - 1:21 pmIAD-MDW
17h 58m1 stop
$193Multiple Airlines
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
5:40 pm - 8:35 pmMDW-DCA
1h 55mnonstop
Southwest Logo
11:45 am - 12:50 pmDCA-MDW
2h 05mnonstop
$237Southwest
Find Deal
Wed, Oct 8 - Sat, Oct 11
Southwest Logo
8:10 pm - 10:55 pmMDW-DCA
1h 45mnonstop
Southwest Logo
6:45 pm - 7:45 pmDCA-MDW
2h 00mnonstop
$247Southwest
Find Deal
Sat, Oct 25 - Sat, Nov 1
Delta Logo
4:23 pm - 9:43 pmMDW-DCA
4h 20m1 stop
Delta Logo
6:10 am - 10:30 amDCA-MDW
5h 20m1 stop
$277Delta
Find Deal
Fri, Feb 20 - Mon, Feb 23
Delta Logo
1:00 pm - 7:20 pmMDW-DCA
5h 20m1 stop
Delta Logo
6:00 am - 8:50 amDCA-MDW
3h 50m1 stop
$280Delta
Find Deal
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 $72 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 $72.

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 $204 on average.

What is the cheapest month to fly from Chicago Midway Airport to District of Columbia?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to District of Columbia, 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 Chicago Midway Airport to District of Columbia is October, when tickets cost $137 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $275 and $275 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to District of Columbia?

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

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

Good to know

Low seasonJanuary
Cheapest flight$78
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 1% 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 at night, when round-trip flights cost $266 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to District of Columbia is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $319.

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. $112 one-way - $240 round-trip

Reviews of the top 3 airlines serving 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 4242 reviews
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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