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DCA - MDW

Find cheap flights from Reagan Washington National Airport to Chicago Midway Airport from $85

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 6/5. 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.
1 adult
0 bags
Fri 6/7
Fri 6/14

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 43,968,530 times on KAYAK, and here is why:

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

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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:00 am - 1:49 pmDCA-MDW
7h 49m1 stop
10:22 pm - 9:59 pmMDW-DCA
22h 37m1 stop
$177Frontier
Find Deal
Tue, May 21 - Thu, May 23
6:05 am - 8:49 amDCA-MDW
3h 44m1 stop
5:45 pm - 11:09 pmMDW-DCA
4h 24m1 stop
$188Delta
Find Deal
Mon, Jul 1 - Wed, Jul 10
12:20 pm - 5:04 pmDCA-MDW
5h 44m1 stop
10:11 am - 3:57 pmMDW-DCA
4h 46m1 stop
$198Delta
Find Deal
Wed, Jun 12 - Sat, Aug 24
6:10 am - 9:06 amDCA-MDW
3h 56m1 stop
1:21 pm - 7:30 pmMDW-DCA
5h 09m1 stop
$203Delta
Find Deal
Wed, May 29 - Wed, Jun 5
12:20 pm - 5:04 pmDCA-MDW
5h 44m1 stop
5:45 pm - 11:09 pmMDW-DCA
4h 24m1 stop
$208Delta
Find Deal
Wed, Jun 12 - Thu, Jun 20
12:55 pm - 1:49 pmDCA-MDW
25h 54m1 stop
10:22 pm - 9:59 pmMDW-DCA
22h 37m1 stop
$217Frontier
Find Deal
Mon, May 20 - Thu, May 23
6:05 am - 11:02 amDCA-MDW
5h 57m1 stop
3:45 pm - 11:57 pmMDW-DCA
7h 12m1 stop
$218Delta
Find Deal
Sat, Jun 1 - Sat, Jun 1
12:35 pm - 5:05 pmDCA-MDW
5h 30m1 stop
5:45 pm - 10:58 pmMDW-DCA
4h 13m1 stop
$223Delta
Find Deal
Wed, Jul 3 - Sat, Jul 6
6:05 am - 8:48 amDCA-MDW
3h 43m1 stop
5:45 pm - 11:09 pmMDW-DCA
4h 24m1 stop
$228Delta
Find Deal
Mon, Jun 17 - Thu, Jun 20
9:10 pm - 10:10 pmDCA-MDW
2h 00mnonstop
7:20 pm - 10:10 pmMDW-DCA
1h 50mnonstop
$330Southwest
Find Deal
Thu, Jun 20 - Fri, Jun 21

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 Southwest ($85) and Frontier ($90). The cheapest round-trip tickets were found on Frontier ($177) 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 7 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 03m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 76 flights. The most frequent day of departure is Tuesday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

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 6:10 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

$85
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly with an average 6% 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 $85 for a one-way ticket and $177 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 10789 reviews
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
7.4Food
Airline reviews

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.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

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.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

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.
6/5Wed
nonstopSouthwest
2h 00mDCA-MDW
$85
9/24Tue
1 stopFrontier
17h 53mDCA-MDW
$90
9/25Wed
1 stopDelta
4h 31mDCA-MDW
$94
8/28Wed
1 stopDelta
3h 44mDCA-MDW
$104
6/1Sat
1 stopDelta
5h 57mDCA-MDW
$109
6/2Sun
1 stopDelta
3h 56mDCA-MDW
$114
5/21Tue
1 stopFrontier
7h 49mDCA-MDW
$117
5/21Tue
1 stopFrontier
7h 49mDCA-MDW
$119
7/11Thu
1 stopFrontier
7h 20mDCA-MDW
$127
5/30Thu
1 stopFrontier
9h 32mDCA-MDW
$129

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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.
5/13Mon
multi-stopFrontier
23h 48mDCA-MDW
5/20Mon
multi-stopFrontier
15h 48mMDW-DCA
$287
5/13Mon
multi-stopFrontier
17h 47mDCA-MDW
5/17Fri
multi-stopFrontier
15h 58mMDW-DCA
$295
5/13Mon
multi-stopFrontier
23h 48mDCA-MDW
5/31Fri
multi-stopFrontier
12h 06mMDW-DCA
$317
5/13Mon
nonstopSouthwest
2h 05mDCA-MDW
5/16Thu
nonstopSouthwest
1h 50mMDW-DCA
$444
5/13Mon
multi-stopSouthwest
5h 25mDCA-MDW
5/16Thu
multi-stopSouthwest
3h 05mMDW-DCA
$462
5/11Sat
multi-stopDelta
3h 41mDCA-MDW
5/11Sat
multi-stopDelta
4h 00mMDW-DCA
$488
5/11Sat
multi-stopDelta
3h 41mDCA-MDW
5/12Sun
multi-stopDelta
4h 55mMDW-DCA
$504
5/13Mon
multi-stopSouthwest
8h 10mDCA-MDW
5/16Thu
multi-stopSouthwest
6h 50mMDW-DCA
$534
5/10Fri
multi-stopDelta
3h 35mDCA-MDW
5/14Tue
multi-stopDelta
4h 32mMDW-DCA
$581
5/10Fri
multi-stopDelta
3h 35mDCA-MDW
5/14Tue
multi-stopDelta
4h 32mMDW-DCA
$588

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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:

$520