Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

DCA - MDW

$87 Find cheap flights from Reagan Washington National Airport to Chicago Midway Airport

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 5/30. 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
Sat 6/15
Sat 6/22

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 42,211,976 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Reagan-National to Midway (DCA-MDW)

 
These are the cheapest deals for flights from Reagan-National to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 Reagan-National to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Reagan-National to Midway.

Recent one-way flight deals from Reagan-National to Midway

Only flying one-way? Below are some of the best one-way flight deals from Reagan-National to Midway found on KAYAK recently.

Recent last minute flight deals from Reagan-National to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Reagan-National to Midway.

Recent direct flight deals from Reagan-National to Midway

The latest deals for direct flights from Reagan-National to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Reagan-National to Midway

Find recent round-trip train or bus tickets from Reagan-National to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:57 pm - 11:09 amDCA-MDW
17h 12m1 stop
10:01 pm - 12:03 pmMDW-DCA
13h 02m1 stop
$183Frontier
Find Deal
Wed, May 29 - Sat, Jun 1
10:00 am - 12:43 pmDCA-MDW
3h 43m1 stop
5:45 pm - 11:11 pmMDW-DCA
4h 26m1 stop
$188Delta
Find Deal
Tue, Jun 25 - Wed, Jul 3
6:57 pm - 11:09 amDCA-MDW
17h 12m1 stop
10:01 pm - 12:03 pmMDW-DCA
13h 02m1 stop
$190Frontier
Find Deal
Tue, May 28 - Sat, Jun 1
6:57 pm - 11:09 amDCA-MDW
17h 12m1 stop
5:01 am - 6:07 pmMDW-DCA
12h 06m1 stop
$192Frontier
Find Deal
Tue, May 28 - Thu, May 30
12:35 pm - 5:04 pmDCA-MDW
5h 29m1 stop
5:59 pm - 10:47 pmMDW-DCA
3h 48m1 stop
$198Delta
Find Deal
Tue, Jul 30 - Sat, Aug 10
12:35 pm - 5:04 pmDCA-MDW
5h 29m1 stop
9:35 am - 3:30 pmMDW-DCA
4h 55m1 stop
$203Delta
Find Deal
Tue, Jul 30 - Fri, Aug 9
12:20 pm - 5:04 pmDCA-MDW
5h 44m1 stop
5:45 pm - 11:09 pmMDW-DCA
4h 24m1 stop
$208Delta
Find Deal
Tue, Jun 18 - Mon, Jun 24
10:00 am - 12:31 pmDCA-MDW
3h 31m1 stop
2:05 pm - 8:14 pmMDW-DCA
5h 09m1 stop
$213Delta
Find Deal
Mon, Sep 9 - Sat, Sep 14
6:57 pm - 11:09 amDCA-MDW
17h 12m1 stop
5:55 am - 6:05 pmMDW-DCA
11h 10m1 stop
$225Frontier
Find Deal
Wed, May 29 - Wed, Jun 5
6:57 pm - 9:54 pmDCA-MDW
27h 57m1 stop
5:01 am - 9:57 pmMDW-DCA
15h 56m1 stop
$226Frontier
Find Deal
Sat, Jun 1 - Thu, Jun 6
12:55 pm - 9:27 pmDCA-MDW
9h 32m1 stop
$87Frontier
Find Deal
Thu, May 30
12:55 pm - 9:27 pmDCA-MDW
9h 32m1 stop
$88Frontier
Find Deal
Thu, May 30
12:55 pm - 9:27 pmDCA-MDW
9h 32m1 stop
$92Frontier
Find Deal
Thu, May 30
12:55 pm - 11:09 amDCA-MDW
23h 14m1 stop
$93Frontier
Find Deal
Wed, May 29
6:05 am - 8:38 amDCA-MDW
3h 33m1 stop
$94Delta
Find Deal
Tue, Jul 9
1:15 pm - 5:14 pmDCA-MDW
4h 59m1 stop
$104Delta
Find Deal
Sat, Aug 17
9:15 am - 10:20 amDCA-MDW
2h 05mnonstop
$119Southwest
Find Deal
Wed, Jun 5
7:25 am - 3:00 pmDCA-MDW
8h 35m2 stops
$133Southwest
Find Deal
Wed, Jun 5
5:00 pm - 6:30 pmDCA-MDW
26h 30m3 stops
$475WestJet
Find Deal
Fri, Jun 14
5:08 pm - 11:02 amDCA-MDW
18h 54m3 stops
$532WestJet
Find Deal
Sat, May 25
12:55 pm - 4:13 pmDCA-MDW
4h 18m1 stop
2:15 pm - 10:00 pmMDW-DCA
6h 45m1 stop
$338Delta
Find Deal
Sat, May 18 - Wed, Jun 5
6:05 am - 11:02 amDCA-MDW
5h 57m1 stop
9:34 am - 4:35 pmMDW-DCA
6h 01m1 stop
$358Delta
Find Deal
Sat, May 18 - Mon, Jun 17
3:40 pm - 4:45 pmDCA-MDW
2h 05mnonstop
6:45 pm - 9:40 pmMDW-DCA
1h 55mnonstop
$470Southwest
Find Deal
Mon, May 20 - Tue, May 21
4:50 pm - 8:30 pmDCA-MDW
4h 40m1 stop
9:35 am - 12:25 pmMDW-DCA
1h 50mnonstop
$479Southwest
Find Deal
Mon, May 20 - Tue, May 21
7:00 pm - 8:00 pmDCA-MDW
2h 00mnonstop
8:30 am - 5:00 pmMDW-DCA
7h 30m2 stops
$484Southwest
Find Deal
Mon, May 20 - Tue, May 21
8:00 am - 1:35 pmDCA-MDW
6h 35m1 stop
2:15 pm - 10:00 pmMDW-DCA
6h 45m1 stop
$509Delta
Find Deal
Sun, May 19 - Mon, Jun 3
6:10 am - 9:06 amDCA-MDW
3h 56m1 stop
1:21 pm - 7:30 pmMDW-DCA
5h 09m1 stop
$518Delta
Find Deal
Sun, May 19 - Wed, May 22
7:00 am - 1:49 pmDCA-MDW
7h 49m1 stop
5:05 am - 6:07 pmMDW-DCA
12h 02m1 stop
$702Frontier
Find Deal
Tue, May 21 - Sat, May 25
12:55 pm - 11:09 amDCA-MDW
23h 14m1 stop
10:01 pm - 6:08 pmMDW-DCA
19h 07m1 stop
$705Frontier
Find Deal
Tue, May 21 - Sat, May 25
7:00 am - 11:13 amDCA-MDW
29h 13m1 stop
6:15 am - 12:09 pmMDW-DCA
28h 54m1 stop
$708Frontier
Find Deal
Fri, May 17 - Mon, Aug 5

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 Sunday and more expensive on a Monday. 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 April, where tickets cost $69 on average. On the other hand, the most expensive months are October and November, where the average cost of tickets is $432 and $399 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 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 ($87) and Delta ($94). The cheapest round-trip tickets were found on Frontier ($183) and Delta ($188).

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

Each day, there are between 9 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 02m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 81 flights. The most frequent day of departure is Thursday, 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.

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 6:10 am and will be landing in Chicago Midway Airport at 7:10 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 9:25 pm and lands at 10:25 pm.

Good to know

Low season

November

High season

October

Cheapest flight

$87
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly with an average 5% 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 $87 for a one-way ticket and $183 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

 
See real verified KAYAK customer reviews for airlines flying from Washington, D.C. to Chicago. 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 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 verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10673 reviews
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
7.9Comfort
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

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.
5/30Thu
1 stopFrontier
9h 32mDCA-MDW
$87
5/30Thu
1 stopFrontier
9h 32mDCA-MDW
$88
5/30Thu
1 stopFrontier
9h 32mDCA-MDW
$92
5/29Wed
1 stopFrontier
23h 14mDCA-MDW
$93
7/9Tue
1 stopDelta
3h 33mDCA-MDW
$94
8/17Sat
1 stopDelta
4h 59mDCA-MDW
$104
6/5Wed
nonstopSouthwest
2h 05mDCA-MDW
$119
6/5Wed
2 stopsSouthwest
8h 35mDCA-MDW
$133
6/14Fri
3 stopsWestJet
26h 30mDCA-MDW
$475
5/25Sat
3 stopsWestJet
18h 54mDCA-MDW
$532

Search by stops

Search by airline

Search by price

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.
5/18Sat
multi-stopDelta
4h 18mDCA-MDW
6/5Wed
multi-stopDelta
6h 45mMDW-DCA
$338
5/18Sat
multi-stopDelta
5h 57mDCA-MDW
6/17Mon
multi-stopDelta
6h 01mMDW-DCA
$358
5/20Mon
nonstopSouthwest
2h 05mDCA-MDW
5/21Tue
nonstopSouthwest
1h 55mMDW-DCA
$470
5/20Mon
multi-stopSouthwest
4h 40mDCA-MDW
5/21Tue
nonstopSouthwest
1h 50mMDW-DCA
$479
5/20Mon
nonstopSouthwest
2h 00mDCA-MDW
5/21Tue
multi-stopSouthwest
7h 30mMDW-DCA
$484
5/19Sun
multi-stopDelta
6h 35mDCA-MDW
6/3Mon
multi-stopDelta
6h 45mMDW-DCA
$509
5/19Sun
multi-stopDelta
3h 56mDCA-MDW
5/22Wed
multi-stopDelta
5h 09mMDW-DCA
$518
5/21Tue
multi-stopFrontier
7h 49mDCA-MDW
5/25Sat
multi-stopFrontier
12h 02mMDW-DCA
$702
5/21Tue
multi-stopFrontier
23h 14mDCA-MDW
5/25Sat
multi-stopFrontier
19h 07mMDW-DCA
$705
5/17Fri
multi-stopFrontier
29h 13mDCA-MDW
8/5Mon
multi-stopFrontier
28h 54mMDW-DCA
$708

Search by stops

Search by airline

Search by price

Reagan Washington National Airport - Chicago Midway Airport Flights

Departure:

Reagan Washington National Airport (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Reagan Washington National Airport

Cabin classes:

$378