$79 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 10/16. 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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Best District of Columbia Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Washington, D.C.
Baltimorenonstop$97
Washington, D.C.
Baltimorenonstop$97

Cheap Flights from Midway to District of Columbia

 
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, Aug 7 - Mon, Aug 11
Southwest Logo
9:20 am - 12:10 pmMDW-DCA
1h 50mnonstop
Southwest Logo
11:55 am - 12:50 pmDCA-MDW
1h 55mnonstop
$157Southwest
Find Deal
Fri, Jun 27 - Sun, Jun 29
Frontier Logo
6:20 am - 3:29 pmMDW-IAD
8h 09m1 stop
Frontier Logo
4:31 pm - 11:18 pmIAD-MDW
7h 47m1 stop
$160Frontier
Find Deal
Wed, Jun 25 - Mon, Jul 14
Frontier Logo
11:39 am - 12:04 amMDW-IAD
11h 25m1 stop
Frontier Logo
4:24 pm - 11:17 pmIAD-MDW
7h 53m1 stop
$161Frontier
Find Deal
Wed, Jun 25 - Sun, Jun 29
Frontier Logo
11:39 am - 12:04 amMDW-IAD
11h 25m1 stop
Frontier Logo
4:31 pm - 11:18 pmIAD-MDW
7h 47m1 stop
$162Frontier
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
8:30 pm - 11:25 pmMDW-DCA
1h 55mnonstop
Southwest Logo
3:20 pm - 8:25 pmDCA-MDW
6h 05m1 stop
$167Southwest
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Thu, Jun 26 - Tue, Jul 1
Frontier Logo
2:55 pm - 12:04 amMDW-IAD
8h 09m1 stop
Frontier Logo
6:10 am - 10:41 amIAD-MDW
5h 31m1 stop
$170Frontier
Find Deal
Thu, Aug 14 - Mon, Aug 18
Delta Logo
9:31 am - 4:33 pmMDW-DCA
6h 02m1 stop
Delta Logo
3:50 pm - 9:49 pmDCA-MDW
6h 59m1 stop
$197Delta
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Tue, Aug 5 - Wed, Aug 6
Delta Logo
9:25 am - 4:43 pmMDW-IAD
6h 18m1 stop
Delta Logo
6:00 am - 9:45 amIAD-MDW
4h 45m1 stop
$197Delta
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Sun, Jul 13 - Sun, Jul 20
Allegiant Air Logo
11:37 am - 2:23 pmMDW-IAD
25h 46m2 stops
Allegiant Air Logo
3:53 pm - 7:13 amIAD-MDW
16h 20m1 stop
$272Allegiant Air
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Fri, Jun 27 - Sun, Jun 29
Allegiant Air Logo
9:12 am - 1:55 pmMDW-IAD
27h 43m1 stop
Allegiant Air Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
$277Allegiant Air
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to District of Columbia.

The cheapest ticket to District of Columbia from Chicago Midway Airport found in the last 72 hours was to Baltimore, at $95 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 $95.

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 $232 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 $139 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $365 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
High seasonMay
Cheapest flight$79
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 8% 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 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 $272 on average. Morning departures are around 1% 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 $443.

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 4285 reviews
8.2Boarding
7.6Entertainment
7.1Food
8.0Comfort
8.6Crew
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

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

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