$41 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 3/5. 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.
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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$53

Good to know

Low season

March

High season

October

Cheapest flight

$41
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 44% 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. $114 one-way - $229 round-trip
  • High season is considered to be October, November and December. The cheapest month to fly from Chicago is April.
  • Morning departure is around 5% 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 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 4587 reviews
7.1Food
8.7Crew
7.7Entertainment
8.2Boarding
8.1Comfort
Airline reviews

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.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

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.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Very easy with the app to board and staff skills

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

Boarding was very well executed. Got my bag right away.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

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.
3/4Tue
1 stopFrontier
7h 25mMDW-IAD
3/11Tue
1 stopFrontier
6h 23mIAD-MDW
$95
3/4Tue
1 stopFrontier
7h 25mMDW-IAD
3/11Tue
1 stopFrontier
6h 23mIAD-MDW
$100
3/4Tue
1 stopFrontier
7h 25mMDW-IAD
3/8Sat
1 stopFrontier
7h 36mIAD-MDW
$101
3/4Tue
1 stopFrontier
13h 54mMDW-DCA
3/11Tue
1 stopFrontier
7h 17mDCA-MDW
$110
2/19Wed
1 stopFrontier
5h 27mMDW-IAD
2/19Wed
1 stopFrontier
26h 26mIAD-MDW
$110
2/20Thu
nonstopSouthwest
1h 50mMDW-DCA
2/20Thu
nonstopSouthwest
2h 10mDCA-MDW
$172
2/20Thu
nonstopSouthwest
1h 50mMDW-DCA
2/24Mon
nonstopSouthwest
2h 05mDCA-MDW
$177
3/3Mon
1 stopDelta
7h 21mMDW-IAD
3/6Thu
1 stopDelta
5h 12mIAD-MDW
$197
2/12Wed
1 stopDelta
5h 19mMDW-IAD
2/20Thu
1 stopDelta
3h 51mIAD-MDW
$207
2/13Thu
1 stop
13h 35mMDW-IAD
2/17Mon
3 stops
25h 02mIAD-MDW
$536

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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.
3/5Wed
1 stopFrontier
5h 51mMDW-IAD
$41
3/5Wed
1 stopFrontier
5h 51mMDW-IAD
$46
4/16Wed
nonstopSouthwest
1h 50mMDW-DCA
$89
2/12Wed
nonstopSouthwest
1h 50mMDW-DCA
$90
3/27Thu
1 stopDelta
6h 44mMDW-DCA
$99
2/27Thu
1 stopDelta
4h 57mMDW-IAD
$99
2/23Sun
1 stopAllegiant Air
13h 35mMDW-IAD
$120
2/23Sun
1 stopAllegiant Air
13h 35mMDW-IAD
$125
4/14Mon
3 stops
25h 51mMDW-IAD
$215
6/9Mon
3 stops
12h 04mMDW-IAD
$249

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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.
2/4Tue
multi-stopFrontier
7h 44mMDW-DCA
2/10Mon
multi-stopFrontier
7h 17mDCA-MDW
$250
2/4Tue
multi-stopFrontier
7h 44mMDW-DCA
2/9Sun
multi-stopFrontier
7h 17mDCA-MDW
$260
2/4Tue
multi-stopFrontier
12h 44mMDW-DCA
2/5Wed
multi-stopFrontier
12h 16mDCA-MDW
$278
2/4Tue
nonstopSouthwest
1h 50mMDW-DCA
2/5Wed
nonstopSouthwest
2h 05mDCA-MDW
$483
2/4Tue
nonstopSouthwest
1h 50mMDW-DCA
2/5Wed
multi-stopSouthwest
5h 20mDCA-MDW
$493
2/1Sat
multi-stopDelta
5h 05mMDW-IAD
2/5Wed
multi-stopDelta
3h 51mIAD-MDW
$538
2/4Tue
multi-stopDelta
3h 55mMDW-DCA
2/8Sat
multi-stopDelta
3h 51mDCA-MDW
$559
2/4Tue
multi-stopDelta
3h 45mMDW-IAD
2/10Mon
multi-stopDelta
3h 51mIAD-MDW
$559
2/1Sat
nonstopSouthwest
1h 50mMDW-DCA
2/9Sun
nonstopSouthwest
2h 15mDCA-MDW
$589
2/1Sat
multi-stopSouthwest
3h 45mMDW-DCA
2/9Sun
nonstopSouthwest
2h 05mDCA-MDW
$595

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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

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