$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 5/10. 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

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$107

Cheap Flight Deals from Midway to District of Columbia (MDW-USDC)

 
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.

Recent round-trip flight deals from Midway to District of Columbia

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to District of Columbia.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Frontier Logo
8:30 am - 2:23 pmMDW-IAD
4h 53m1 stop
Frontier Logo
3:32 pm - 11:47 pmIAD-MDW
9h 15m1 stop
$158Frontier
Find Deal
Fri, May 9 - Mon, May 12
Frontier Logo
8:03 pm - 4:59 pmMDW-DCA
19h 56m1 stop
Frontier Logo
6:00 pm - 7:08 pmDCA-MDW
26h 08m1 stop
$159Frontier
Find Deal
Sun, May 4 - Wed, May 7
Southwest Logo
9:20 am - 12:10 pmMDW-DCA
1h 50mnonstop
Southwest Logo
6:10 am - 7:10 amDCA-MDW
2h 00mnonstop
$161Southwest
Find Deal
Sat, May 10 - Sun, May 11
Southwest Logo
12:25 pm - 3:15 pmMDW-DCA
1h 50mnonstop
Southwest Logo
1:10 pm - 3:20 pmDCA-MDW
3h 10m1 stop
$167Southwest
Find Deal
Tue, May 6 - Wed, May 7
Delta Logo
4:59 pm - 11:39 pmMDW-DCA
5h 40m1 stop
Delta Logo
6:00 am - 8:40 amDCA-MDW
3h 40m1 stop
$197Delta
Find Deal
Tue, Apr 29 - Wed, Apr 30
Delta Logo
9:20 am - 4:39 pmMDW-IAD
6h 19m1 stop
Delta Logo
12:29 pm - 4:12 pmIAD-MDW
4h 43m1 stop
$197Delta
Find Deal
Tue, Apr 29 - Tue, May 6
 Logo
6:56 pm - 8:17 pmMDW-IAD
24h 21m1 stop
 Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
Thu, Jun 5 - Sun, Jun 8
 Logo
3:55 pm - 10:20 amMDW-IAD
17h 25m2 stops
 Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
Thu, Jun 26 - Sun, Jun 29
Allegiant Air Logo
7:00 pm - 9:05 pmMDW-IAD
25h 05m2 stops
Allegiant Air Logo
8:22 pm - 2:26 pmIAD-MDW
19h 04m1 stop
$274Allegiant Air
Find Deal
Fri, May 30 - Sun, Jun 1
Allegiant Air Logo
11:45 am - 2:23 pmMDW-IAD
25h 38m2 stops
Allegiant Air Logo
3:58 pm - 7:15 amIAD-MDW
16h 17m1 stop
$345Allegiant Air
Find Deal
Thu, Jun 19 - Sun, Jun 22

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 $96 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 $96.

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 at night, when round-trip flights cost $269 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 in the afternoon, which is peak travel time and where the average cost of a ticket is $443.

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 $125 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $326 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 Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from District of Columbia, Wednesday is the cheapest day to fly and Tuesday is the most expensive.

How far in advance should I book a flight from Chicago Midway Airport to District of Columbia?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.
To get a below average price on the flight from Chicago Midway Airport to District of Columbia, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low season

January

High season

October

Cheapest flight

$78
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 46% 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.

See more FAQs

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. $123 one-way - $227 round-trip

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 4274 reviews
7.6Entertainment
8.2Boarding
7.1Food
8.0Comfort
8.6Crew
Airline reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

6.0 GoodCarolynn, Mar 2025KOA - SMF
Read more Southwest reviews

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

1.5 hour delay, poor service, no compassion from the crew. Terrible experience

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Very good. Sad to learn Southwest is going start to charge for bags

Our flight was diverted from being a non-stop to getting within 150 miles and requiring another plane. We heard 4 or 5 different versions from SW as to why we had to stop, then wait for a replacement plane. Five hour delay, weather did not come up as a single excuse.... communication was not clear and well explained. No one really took charge!

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

WiFi on the flight was not working. Thus, entertainment options were limited.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Great staff. Wifi is terrible. Signing up for skylines is a painstaking process. Had to call customer service just to get my flight itinerary and confirmation sent to me. Consistent delays. A well staffed company that is run so poorly. Upper management needs to be renewed.

The WiFi didn't seem as fast as it normally is

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

The crew was wonderful and attentive. The seats near exit row were restrictive. Offer healthy snacks please

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Landing in terminal 2, but my luggage is terminal 3. We (and others) were looking for it in terminal 1. We probably missed the crew broadcast, but the communication could have been clearer for non native (or elderly) passengers.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

Bag should not be so much money. This is how Frontier takes advantage of customers

The plane was comfortable. The time to board was way too slow and very unorganized! The crew was not as friendly as normally. The was not a single time that they offered water nor anything!!!

They switched my flight to Spirit, Never using Kayak again,

i was denied boarding, even though i had an assigned seat, checked in on line and was at airport early. Then they refused to fully refund the the fair and replacement fair because they claimed it was "no show/denied boarding". I will never fly this airline again

I was not permitted on my flight and had to purchase another flight ticket to Las Vegas.

This was a full flight and I was in Zone 1, however upon boarding, several other zones went in ahead of me, leaving no overhead cabin space near my seat. This created a challenging disembarkment process.

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

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