$75 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 3/25. 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.
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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$58

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 and deals for you by selecting your travel dates.
Choose your dates
6:40 am - 4:59 pmMDW-DCA
9h 19m1 stop
1:03 pm - 12:21 amDCA-MDW
12h 18m1 stop
$150Frontier
Find Deal
Tue, Apr 1 - Wed, Apr 2
10:11 am - 7:44 pmMDW-IAD
8h 33m1 stop
12:53 pm - 9:33 pmIAD-MDW
9h 40m1 stop
$150Frontier
Find Deal
Tue, Apr 1 - Wed, Apr 9
10:11 am - 7:44 pmMDW-IAD
8h 33m1 stop
5:54 pm - 11:24 pmIAD-MDW
6h 30m1 stop
$151Frontier
Find Deal
Tue, Apr 1 - Tue, Apr 8
8:20 pm - 11:05 pmMDW-DCA
1h 45mnonstop
8:50 pm - 9:55 pmDCA-MDW
2h 05mnonstop
$177Southwest
Find Deal
Wed, Mar 26 - Wed, Apr 2
8:10 pm - 11:00 pmMDW-DCA
1h 50mnonstop
6:20 pm - 7:25 pmDCA-MDW
2h 05mnonstop
$178Southwest
Find Deal
Thu, May 22 - Sun, May 25
8:20 pm - 11:05 pmMDW-DCA
1h 45mnonstop
1:00 pm - 3:20 pmDCA-MDW
3h 20m1 stop
$183Southwest
Find Deal
Wed, Mar 26 - Wed, Apr 2
4:25 pm - 10:55 pmMDW-DCA
5h 30m1 stop
11:55 am - 1:00 pmDCA-MDW
2h 05mnonstop
$187Southwest
Find Deal
Mon, Mar 17 - Wed, Mar 19
9:25 am - 4:23 pmMDW-IAD
5h 58m1 stop
6:00 am - 8:45 amIAD-MDW
3h 45m1 stop
$197Delta
Find Deal
Thu, Mar 27 - Mon, Mar 31
6:42 pm - 11:00 pmMDW-IAD
3h 18m1 stop
6:00 am - 8:43 amIAD-MDW
3h 43m1 stop
$214Delta
Find Deal
Mon, Mar 31 - Thu, Apr 3
6:42 pm - 11:00 pmMDW-IAD
3h 18m1 stop
6:00 am - 8:45 amIAD-MDW
3h 45m1 stop
$217Delta
Find Deal
Mon, Mar 17 - Thu, Mar 20

Good to know

Low season

January

High season

October

Cheapest flight

$75
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 43% 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.

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. $108 one-way - $211 round-trip
  • High season is considered to be October, November and December. The cheapest month to fly from Chicago is October.
  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.1
SouthwestOverall score based on 4330 reviews
7.1Food
8.2Boarding
8.1Comfort
8.7Crew
7.6Entertainment
Airline reviews

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

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

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

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

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

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Would be great if Frontier can Assign Seats together under one PNR

Early arrival. Great landing. Pilot updates. Too cold in plane.

Better to put road truck seat in plain it so uncomfortable can not adjustable and fill metal don’t have cushions at all it’s very hard to travel for five hours

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

food not having to pay for it, reclining seat would be nice, more leg room, HEAT!!!!!!!

An absolutely fraudulent experience. Extremely unprofessional. Terrible in all ways possible. Rude staff, flight attendants, and deceptive "policies."

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

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

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