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$54 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 1/13. 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
0 bags

Search 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

Best District of Columbia Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Washington, D.C.
Baltimorenonstop$65

Good to know

Low season

March

High season

October

Cheapest flight

$54
Best time to beat the crowds but there is an average 81% increase in price.
Most popular time to fly and prices are also 49% lower on average.
Flight from Chicago Midway Airport to Reagan Washington National 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 to District of Columbia from Chicago Midway Airport 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 to District of Columbia with an airline and back to Chicago Midway Airport 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 to District of Columbia from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to District of Columbia

  • Morning departure is around 6% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 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.
8.1
SouthwestOverall score based on 5035 reviews
8.1Comfort
8.7Crew
8.3Boarding
7.7Entertainment
7.2Food
Airline reviews

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

6.0 Goodjohn, Nov 2024TPA - BWI
Read more Southwest reviews

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

Bottom seat cushion is almost non existent. Very uncomfortable seat.

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

Average, boarding was ok, the eye scanner broken mid way through boarding they ahd to do it manually. Did not eat any food, Not even water was offered for free.

Boarding attendant was rude. Crew on the plan were more interested in talking amongst themselves and did not ask parentage if they needed anything or even walk down the isles.

Flight was ok with exception of the multiple delays. As with all Spirit flights, the sights are extremely uncomfortable and lack leg space. However, the price savings is the plus.

I upgraded my ticket at the ticket counter and was not informed of the huge bottleneck at TSA pre check. It took me over an hour to get through the line at this small airport and although I ran to the gate and reached it prior to scheduled departure, it had already pushed pack. I missed the flight. Spirit rebooked me on a flight to Orlando that evening, which would require me to then rent a car and drive to FLL. For scheduling reasons, I determined it be would better to rent a car in Pensacola and drive it to my destination in FLL. Spirit called me that evening and asked me if I was going to board the plane. I explained no, for scheduling reasons. The person apologized and said I would receive a refund, but I have not heard back. Certainly, I ought to be refunded the upgrade I paid for at the counter.

The staff from LAX to New Orleans were rude but the staff from New Orleans to LAX were nice!

Did what they needed to do. Brought us from point A to point B timely and without issue. Boarding through deplaning smooth.

Direct 2.5 hour flight good. Free snacks and coffee, water, or soft drinks not available...bad.

Atlanta airport gate area floor and nearly all seats disgusting. Spirit airlines crew fantastic!!

Over 2 hour delay due to “weather” but all other flights were taking off with no issues. We felt lied to the entire time as well.

Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂

Booked direct in July '24. Turned into a 14 hr layover (both ways) in Denver. My 5 day vaca turned into a 1 day . Not good, BUT,... Thank you for the people @ Frontier who were professionally friendly & approachable.

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

We understand and comply with Frontier’s bag sizes. We’ve had some problems in past while having to await other passengers who do not understand the baggage restrictions or have not prepaid and that is usually our biggest concern (others delaying us) with flying Frontier. Flying OUT of ONT, however, has always been a great experience. I’ve also noted even on delayed Frontier flights very knowledgeable pilots who manage expectations well.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

The crew was ghetto lol I felt like I was on an inner city field trip

Horrible! The short distance flight ended up taking 5 hrs! There was a 3 hr delay for the flight to take off and there was a 70 min wait on the tarmac for some bogus reason that the pilot said the gate he was supposed to board was taken up. After a 30 min wait he said the plane that was supposed to push out of the gate called a medical emergency and 40 min later he ended up boarding another gate. For the initial 3 hr delay there was no information/alert about the gate or delay in the app or the boards up until the boarding time and even beyond! Had to walk all the way to the end of the terminal to find the frontier staff to ask what was going on. Avoid this airline at all costs! If you have carryon bags or checked bags , their prices come equivalent to the prices of more reliable airlines. They are the worst in timeliness at 60% (reported as delayed) this year (check the data) by a high margin even compared to the second worst airline. If you are ok with having a miserable flight experience with the odds close to flip of a coin, feel free to try them. If you value your time , money and flying experience, stay away.

There was nothing to like, flight delayed had to move to different departure areas, disorganized to say the leasr

Delayed for two hours due to trivial issues. No reimbursment. Also on arrival further delay due to terminal malfunction.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

Allowed me to chose my seat without extra charge (I purchased full-price ticket) and boarding was in group1. Didn't even serve water.

Book cheap flights from Chicago to District of Columbia

Recent round-trip flight deals

 
These are the cheapest round-trip flights from Chicago to District of Columbia found on KAYAK in the last 72 hours.
2/6Thu
1 stopFrontier
8h 44mMDW-DCA
2/10Mon
1 stopFrontier
7h 17mDCA-MDW
$108
12/13Fri
1 stopFrontier
10h 19mMDW-IAD
12/17Tue
1 stopFrontier
10h 49mIAD-MDW
$118
12/10Tue
1 stopFrontier
7h 44mMDW-DCA
12/11Wed
1 stopFrontier
12h 12mDCA-MDW
$128
12/13Fri
1 stopFrontier
10h 19mMDW-IAD
12/16Mon
1 stopFrontier
24h 57mIAD-MDW
$128
12/10Tue
nonstopSouthwest
1h 50mMDW-DCA
12/11Wed
nonstopSouthwest
2h 05mDCA-MDW
$198
12/10Tue
nonstopSouthwest
1h 45mMDW-DCA
12/11Wed
1 stopSouthwest
6h 50mDCA-MDW
$207
12/18Wed
1 stopDelta
4h 58mMDW-DCA
1/1Wed
1 stopDelta
3h 50mDCA-MDW
$216
12/10Tue
1 stopDelta
6h 18mMDW-IAD
12/11Wed
1 stopDelta
7h 52mIAD-MDW
$216
12/17Tue
1 stopPorter Airlines
10h 09mMDW-IAD
12/21Sat
1 stopPorter Airlines
10h 40mIAD-MDW
$604
12/15Sun
1 stopAir Transat
10h 09mMDW-IAD
12/22Sun
1 stopAir Transat
10h 40mIAD-MDW
$664

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to District of Columbia found on KAYAK in the last 72 hours.
1/13Mon
1 stopFrontier
8h 47mMDW-DCA
$54
12/18Wed
1 stopFrontier
5h 00mMDW-IAD
$54
2/12Wed
nonstopSouthwest
1h 50mMDW-DCA
$99
2/23Sun
1 stopAllegiant Air
13h 35mMDW-IAD
$107
3/4Tue
1 stopDelta
5h 48mMDW-DCA
$108
12/18Wed
1 stopDelta
6h 18mMDW-IAD
$108
12/16Mon
nonstopSouthwest
1h 45mMDW-DCA
$109
2/20Thu
1 stopAllegiant Air
13h 35mMDW-IAD
$114
1/30Thu
3 stops
24h 59mMDW-IAD
$192
1/23Thu
3 stops
24h 59mMDW-IAD
$201

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Last minute flights from Midway to District of Columbia

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to District of Columbia that are departing in the next 10 days.
11/21Thu
multi-stopFrontier
7h 50mMDW-IAD
12/6Fri
multi-stopFrontier
5h 58mIAD-MDW
$238
11/21Thu
multi-stopFrontier
7h 50mMDW-IAD
11/26Tue
multi-stopFrontier
9h 24mIAD-MDW
$278
11/21Thu
multi-stopFrontier
7h 50mMDW-IAD
11/23Sat
multi-stopFrontier
14h 25mIAD-MDW
$318
11/21Thu
multi-stopFrontier
7h 50mMDW-IAD
12/5Thu
multi-stopFrontier
4h 58mIAD-MDW
$338
11/22Fri
multi-stopFrontier
23h 10mMDW-DCA
12/5Thu
multi-stopFrontier
18h 13mDCA-MDW
$350
11/23Sat
multi-stopDelta
7h 55mMDW-IAD
12/8Sun
multi-stopDelta
4h 50mIAD-MDW
$387
11/22Fri
multi-stop
13h 18mMDW-DCA
1/4Sat
multi-stop
6h 08mDCA-MDW
$437
11/23Sat
multi-stopDelta
7h 55mMDW-IAD
12/5Thu
multi-stopDelta
3h 50mIAD-MDW
$457
11/21Thu
nonstopSouthwest
1h 45mMDW-DCA
12/2Mon
multi-stopSouthwest
4h 55mDCA-MDW
$514
11/23Sat
nonstopSouthwest
1h 45mMDW-DCA
11/27Wed
nonstopSouthwest
2h 10mDCA-MDW
$520

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

Information on your arrival and departure airports