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 1/15. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$223
Overall average: $395
Southwest
sáb. 1/17dom. 1/18
DCA - MDW • Non-stop
Cheapest one-way
$87
Typical prices: $164-$243
Frontier
jue. 1/15
DCA - MDW • 1 stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
DCA is easily accessible via the city's metro line.
The CTA Orange Line connects MDW to downtown quickly.
Expert advice
Expert advice
Expert advice
Expert advice
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 57% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 19% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Reagan-National to Midway

sáb., ene. 17 - dom., ene. 18
Southwest Logo
6:05 am - 7:20 am
DCA
-
MDW
2h 15mnonstop
Southwest Logo
3:35 pm - 6:20 pm
MDW
-
DCA
1h 45mnonstop
$223Southwest
sáb., ene. 17 - lun., ene. 19
Southwest Logo
8:25 am - 9:45 am
DCA
-
MDW
2h 20mnonstop
Southwest Logo
5:20 pm - 8:15 pm
MDW
-
DCA
1h 55mnonstop
$226Southwest
sáb., feb. 14 - mar., feb. 17
Southwest Logo
3:40 pm - 4:55 pm
DCA
-
MDW
2h 15mnonstop
Southwest Logo
9:10 am - 12:00 pm
MDW
-
DCA
1h 50mnonstop
$227Southwest
sáb., ene. 24 - mar., ene. 27
Southwest Logo
8:25 am - 9:45 am
DCA
-
MDW
2h 20mnonstop
Southwest Logo
10:15 am - 1:00 pm
MDW
-
DCA
1h 45mnonstop
$231Southwest
jue., ene. 15 - lun., ene. 19
Frontier Logo
6:00 pm - 7:54 pm
DCA
-
MDW
26h 54m1 stop
Frontier Logo
9:09 pm - 9:59 pm
MDW
-
DCA
23h 50m1 stop
$233Frontier
sáb., ene. 17 - lun., ene. 19
Southwest Logo
11:50 am - 7:45 pm
DCA
-
MDW
8h 55m1 stop
Southwest Logo
6:00 am - 8:55 am
MDW
-
DCA
1h 55mnonstop
$236Southwest
mié., feb. 11 - sáb., feb. 14
Southwest Logo
2:55 pm - 7:05 pm
DCA
-
MDW
5h 10m1 stop
Southwest Logo
5:55 pm - 8:45 pm
MDW
-
DCA
1h 50mnonstop
$237Southwest
sáb., ene. 17 - dom., ene. 18
Southwest Logo
6:30 am - 4:25 pm
DCA
-
MDW
10h 55m2 stops
Southwest Logo
10:15 am - 1:00 pm
MDW
-
DCA
1h 45mnonstop
$238Southwest
sáb., ene. 17 - lun., ene. 19
Southwest Logo
6:30 am - 4:25 pm
DCA
-
MDW
10h 55m2 stops
Southwest Logo
8:10 pm - 10:55 pm
MDW
-
DCA
1h 45mnonstop
$241Southwest
dom., ene. 18 - dom., ene. 18
Delta Logo
9:54 am - 12:48 pm
DCA
-
MDW
3h 54m1 stop
Delta Logo
5:59 pm - 11:32 pm
MDW
-
DCA
4h 33m1 stop
$243Delta
Booking Insights

KAYAK's insights & trends for Reagan-National to Midway flights

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 round-trip 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 Wednesday, and avoid Mondays 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 round-trip 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 July, where tickets cost $263 (return) on average. On the other hand, the most expensive months are January and November, where the average cost of round-trip tickets is $395 and $393 respectively.

Can I save money by flying with a layover from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $306 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

To get a below average price on the flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, you should book around 4 weeks before departure, which saves you about 57% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Find deals
Expert advice

Expert advice for your flight from Reagan-National to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
DCA

DCA is easily accessible via the city’s metro line, reaching the terminal in under 30 minutes, making it convenient for business travelers.

Read more about DCABy Ramsey Qubein
MDW

The CTA Orange Line offers a direct route from MDW to downtown Chicago in about 25-30 minutes, ideal for quick city access.

Read more about MDWBy Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on DCA

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Good to know

Low seasonJanuary
Cheapest flight$87
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 12% lower on average.
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 $202 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?

    American Airlines, Alaska Airlines, Delta, and JetBlue offer 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 Boeing 737 MAX 8 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.

KAYAK’s top tips for finding a cheap flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $167 or less one-way and $312 or less round-trip.

Prefer to fly direct from Reagan Washington National Airport to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Washington, D.C. Reagan-National to Chicago Midway.
Find which airlines fly direct from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct 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

Direct 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

Reviews of the 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
SouthwestOverall score based on 4251 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

8.0 ExcellentMaggie, Dec 2025
BWI - LAS
Read more Southwest reviews

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

Everything you need to know for your flight from Reagan-National to Midway

Information on your arrival and departure airports

Reagan Washington National Airport (DCA)
Midway (MDW)