DCA - MDW

$107 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 10/18. 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

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
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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

Mon, Oct 20 - Thu, Oct 23
Frontier Logo
7:00 am - 12:24 amDCA-MDW
18h 24m1 stop
Frontier Logo
6:24 pm - 12:04 pmMDW-DCA
16h 40m1 stop
$175Frontier
Find Deal
Thu, Oct 23 - Fri, Oct 24
Frontier Logo
7:00 am - 12:36 amDCA-MDW
18h 36m1 stop
Frontier Logo
12:11 pm - 12:04 pmMDW-DCA
22h 53m1 stop
$177Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
2:00 pm - 11:30 amDCA-MDW
22h 30m1 stop
Frontier Logo
12:30 pm - 9:59 pmMDW-DCA
8h 29m1 stop
$209Frontier
Find Deal
Wed, Oct 15 - Tue, Oct 21
Southwest Logo
3:30 pm - 4:30 pmDCA-MDW
2h 00mnonstop
Southwest Logo
7:15 am - 10:00 amMDW-DCA
1h 45mnonstop
$237Southwest
Find Deal
Wed, Nov 19 - Wed, Nov 19
Southwest Logo
6:00 am - 7:05 amDCA-MDW
2h 05mnonstop
Southwest Logo
11:25 am - 4:10 pmMDW-DCA
3h 45m1 stop
$243Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 8
Southwest Logo
6:50 pm - 7:50 pmDCA-MDW
2h 00mnonstop
Southwest Logo
10:20 am - 6:55 pmMDW-DCA
7h 35m1 stop
$247Southwest
Find Deal
Tue, Oct 7 - Thu, Oct 9
Southwest Logo
3:30 pm - 4:30 pmDCA-MDW
2h 00mnonstop
Southwest Logo
6:00 pm - 8:55 pmMDW-DCA
1h 55mnonstop
$250Southwest
Find Deal
Tue, Oct 7 - Wed, Oct 15
Delta Logo
12:31 pm - 4:09 pmDCA-MDW
4h 38m1 stop
Delta Logo
5:04 pm - 10:40 pmMDW-DCA
4h 36m1 stop
$257Delta
Find Deal
Sat, Oct 18 - Mon, Oct 20
Delta Logo
6:20 pm - 10:14 pmDCA-MDW
4h 54m1 stop
Delta Logo
6:23 pm - 10:59 pmMDW-DCA
3h 36m1 stop
$280Delta
Find Deal
Sat, Oct 25 - Mon, Oct 27
Delta Logo
6:10 am - 10:30 amDCA-MDW
5h 20m1 stop
Delta Logo
6:23 pm - 10:59 pmMDW-DCA
3h 36m1 stop
$281Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
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
Top airlines
Frontier
Cheapest • from $175 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 53% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 19% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$175
Overall average: $363
Frontier
Mon 10/20Thu 10/23
DCA - MDW • 1 stop
Cheapest non-stop
$237
Typical prices: $290-445
Southwest
Wed 10/15Wed 10/22
DCA - MDW • Non-stop
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!
Expert advice

Expert advice for your flight from Reagan-National to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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
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 Monday. On your return trip to Reagan Washington National Airport, you should consider flying back on a Wednesday, and avoid Sundays 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 January, where tickets cost $247 (return) on average. On the other hand, the most expensive months are October and June, where the average cost of round-trip tickets is $363 and $356 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 53% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$107
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 18% 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 $107 for a one-way ticket and $175 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, Hawaiian Airlines, and Delta 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.

  • Which is the best airline for flights from Washington, D.C. to Chicago, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Washington, D.C. to Chicago are Southwest and Frontier. With an average price for the route of $304 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $219 and an overall rating of 5.8.

  • 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 $154 or less one-way and $271 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 airlines 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 4242 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

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