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DCA - MDW

Find cheap flights from Reagan Washington National Airport to Chicago Midway Airport from $79

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Reagan-National to Midway departing on 5/11. 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
Thu 4/18
Thu 4/25

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, 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 Washington, D.C. to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 47,600,107 times on KAYAK, and here is why:

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Cheap flight deals from Reagan-National to Midway

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Reagan-National to Midway 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.
6:50 am - 7:50 amDCA-MDW
2h 00mnonstop
12:45 pm - 3:25 pmMDW-DCA
1h 40mnonstop
$120Southwest
Find Deal
Wed, Apr 17 - Wed, Apr 24
10:05 am - 12:45 pmDCA-MDW
3h 40m1 stop
5:45 pm - 10:46 pmMDW-DCA
4h 01m1 stop
$176Delta
Find Deal
Wed, Apr 17 - Sat, Apr 20
6:00 am - 8:50 amDCA-MDW
3h 50m1 stop
5:45 pm - 10:46 pmMDW-DCA
4h 01m1 stop
$177Delta
Find Deal
Sat, Apr 13 - Sat, Apr 20
10:05 am - 12:45 pmDCA-MDW
3h 40m1 stop
11:00 am - 5:05 pmMDW-DCA
5h 05m1 stop
$178Delta
Find Deal
Tue, Apr 9 - Sat, Apr 13
6:00 am - 8:44 amDCA-MDW
3h 44m1 stop
1:10 pm - 7:15 pmMDW-DCA
5h 05m1 stop
$192Delta
Find Deal
Thu, Jul 4 - Tue, Jul 9
11:00 am - 12:00 pmDCA-MDW
2h 00mnonstop
11:00 am - 3:00 pmMDW-DCA
3h 00m1 stop
$193Southwest
Find Deal
Wed, Apr 17 - Wed, Apr 24
10:05 am - 12:45 pmDCA-MDW
3h 40m1 stop
12:45 pm - 7:14 pmMDW-DCA
5h 29m1 stop
$197Delta
Find Deal
Thu, Apr 11 - Wed, Apr 17
6:50 pm - 8:24 amDCA-MDW
14h 34m1 stop
5:30 am - 6:01 pmMDW-DCA
11h 31m1 stop
$230Frontier
Find Deal
Mon, Apr 8 - Wed, Apr 10
12:50 pm - 10:03 pmDCA-MDW
10h 13m1 stop
10:55 pm - 12:00 pmMDW-DCA
12h 05m1 stop
$236Frontier
Find Deal
Thu, Apr 25 - Tue, Apr 30
7:00 am - 8:36 amDCA-MDW
26h 36m1 stop
10:53 pm - 9:59 pmMDW-DCA
22h 06m1 stop
$240Frontier
Find Deal
Wed, Apr 24 - Thu, Apr 25

Flights from Reagan-National to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Reagan-National to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Reagan Washington National Airport to Chicago Midway Airport?

The average price of all flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Wednesday and more expensive on a Sunday. On your return trip to Reagan Washington National Airport, you should consider flying back on a Tuesday, and avoid Thursdays for better deals.

What is the cheapest month to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, 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 Washington, D.C. Reagan-National Airport to Chicago Midway Airport is September, where tickets cost $204 on average. On the other hand, the most expensive months are May and December, where the average cost of tickets is $477 and $470 respectively.

How far in advance should I book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 9 days before departure.

Which airlines provide the cheapest flights from Reagan Washington National Airport to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($79) and Delta ($87). The cheapest round-trip tickets were found on Southwest ($120) and Delta ($176).

How many flights are there between Washington, D.C. Reagan-National Airport and Chicago Midway Airport per day?

Each day, there are between 8 and 12 nonstop flights that take off from Washington, D.C. Reagan-National Airport and land in Chicago Midway Airport, with an average flight time of 2h 05m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 79 flights. The most frequent day of departure is Tuesday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Washington, D.C. Reagan-National Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Reagan Washington National Airport to Chicago Midway Airport take?

Nonstop flights from Reagan Washington National Airport generally make it to Chicago Midway Airport in 2h 00m. The flying distance between the two cities is 599 miles.

What’s the earliest departure time from Reagan Washington National Airport to Chicago Midway Airport?

Early birds can take the earliest flight from Washington, D.C. Reagan-National Airport at 6:00 am and will be landing in Chicago Midway Airport at 7:05 am.

What’s the latest departure time from Reagan Washington National Airport to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport jets off at 9:15 pm and lands at 10:10 pm.

Good to know

Low season

November

High season

October

Cheapest flight

$79
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 13% increase in price.
Flight from Reagan Washington National Airport to Chicago Midway Airport

When to book flights from Reagan-National to Midway

Are your dates flexible? Find out the best times to travel from Reagan-National to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Reagan Washington National Airport to Chicago Midway Airport flights

  • What is the cheapest flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport was $79 for a one-way ticket and $120 for a round-trip.

  • Do I need a passport to fly between Reagan Washington National Airport and Chicago Midway Airport?

    No

  • Which airports will I be using when flying from Reagan Washington National Airport to Chicago Midway Airport?

    When flying out of Reagan Washington National Airport you will be using Washington, D.C. Reagan-National. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Reagan Washington National Airport to Chicago Midway Airport?

    Only American Airlines offers inflight Wi-Fi service on the Reagan Washington National Airport to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Reagan Washington National Airport to Chicago Midway Airport?

    The Airbus A319 is the aircraft model that flies most regularly on the Reagan Washington National Airport to Chicago Midway Airport flight route.

  • On which days can I fly direct from Reagan Washington National Airport to Chicago Midway Airport?

    There are nonstop flights from Reagan Washington National Airport to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Reagan Washington National Airport to Chicago Midway Airport?

    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 Reagan Washington National Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Reagan Washington National Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Reagan Washington National 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 Reagan Washington National Airport to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Reagan Washington National Airport with another airline. Booking your flights between Reagan Washington National Airport and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Reagan Washington National Airport to Chicago Midway Airport?

    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 Chicago Midway Airport from Reagan Washington National Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Reagan Washington National Airport to Chicago Midway Airport?

Find which airlines fly direct from Reagan-National to Midway, which days they fly and book direct flights.

Nonstop departures

Washington, D.C. Reagan-National to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Chicago Midway to Washington, D.C. Reagan-National

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top airline flying from Reagan-National to Midway

Need help choosing which airline to fly with from Reagan-National to Midway? 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 KAYAK reviews.
8.0
DeltaOverall score based on 11551 reviews
79comfort
86crew
81entertainment
75food
82boarding
81overall
Airline reviews

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Read more about Delta

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

Mario was great. Made a night flight on a small aircraft pleasant and memorable.

I wouldn't say I liked being forced to check my small roller bag at the gate; too many people had bags and were in a higher boarding group.

Book cheap flights from Washington, D.C. to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Washington, D.C. to Chicago found on KAYAK in the last 72 hours.
5/11Sat
1 stopFrontier
10h 38mDCA-MDW
$79
4/23Tue
1 stopDelta
4h 49mDCA-MDW
$87
5/30Thu
1 stopDelta
3h 36mDCA-MDW
$88
5/5Sun
1 stopDelta
3h 50mDCA-MDW
$89
4/23Tue
nonstopSouthwest
2h 15mDCA-MDW
$95
4/8Mon
1 stopFrontier
14h 34mDCA-MDW
$100
5/29Wed
1 stopDelta
3h 28mDCA-MDW
$104
5/28Tue
1 stopDelta
3h 28mDCA-MDW
$114
4/23Tue
2 stopsSouthwest
9h 45mDCA-MDW
$128
5/3Fri
1 stopSouthwest
5h 05mDCA-MDW
$153

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Last minute flights from Reagan-National to Midway

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 Washington, D.C. to Chicago that are departing in the next 10 days.
3/23Sat
multi-stopDelta
3h 46mDCA-MDW
3/30Sat
multi-stopDelta
4h 04mMDW-DCA
$420
3/23Sat
multi-stopDelta
4h 21mDCA-MDW
3/26Tue
multi-stopDelta
5h 18mMDW-DCA
$462
3/19Tue
nonstopSouthwest
2h 00mDCA-MDW
3/20Wed
nonstopSouthwest
1h 45mMDW-DCA
$521
3/21Thu
multi-stopDelta
3h 33mDCA-MDW
3/31Sun
multi-stopDelta
6h 40mMDW-DCA
$528
3/19Tue
multi-stopSouthwest
6h 00mDCA-MDW
3/19Tue
nonstopSouthwest
1h 45mMDW-DCA
$530
3/19Tue
multi-stopSouthwest
7h 40mDCA-MDW
3/19Tue
nonstopSouthwest
1h 45mMDW-DCA
$535
3/23Sat
multi-stopDelta
3h 46mDCA-MDW
3/26Tue
multi-stopDelta
3h 16mMDW-DCA
$540
3/22Fri
multi-stopFrontier
9h 20mDCA-MDW
3/26Tue
multi-stopFrontier
15h 49mMDW-DCA
$620
3/22Fri
multi-stopFrontier
9h 20mDCA-MDW
3/27Wed
multi-stopFrontier
7h 39mMDW-DCA
$688
3/22Fri
multi-stopFrontier
9h 20mDCA-MDW
4/11Thu
multi-stopFrontier
7h 43mMDW-DCA
$701

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Reagan Washington National Airport - Chicago Midway Airport Flights

Departure:

Reagan Washington National Airport (DCA)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Reagan Washington National Airport

Cabin classes:

$520