DCA - MDW

$78 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 12/4. 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
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Everything you should know

Cheapest round-trip
$200
Overall average: $330
Frontier
Thu 12/4Mon 12/8
DCA - MDW • 1 stop
Cheapest non-stop
$223
Typical prices: $230-$369
Southwest
Wed 12/3Sun 12/7
DCA - MDW • Non-stop
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 $200 (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 • 22% 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

Thu, Dec 4 - Mon, Dec 8
Frontier Logo
8:00 am - 11:08 amDCA-MDW
28h 08m1 stop
Frontier Logo
12:18 pm - 9:59 pmMDW-DCA
8h 41m1 stop
$200Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
2:00 pm - 11:08 amDCA-MDW
22h 08m1 stop
Frontier Logo
12:18 pm - 1:06 pmMDW-DCA
23h 48m1 stop
$201Frontier
Find Deal
Thu, Dec 11 - Mon, Dec 15
Frontier Logo
6:00 pm - 11:08 amDCA-MDW
18h 08m1 stop
Frontier Logo
12:18 pm - 1:06 pmMDW-DCA
23h 48m1 stop
$202Frontier
Find Deal
Wed, Dec 3 - Sun, Dec 7
Southwest Logo
11:35 am - 12:40 pmDCA-MDW
2h 05mnonstop
Southwest Logo
9:00 pm - 11:45 pmMDW-DCA
1h 45mnonstop
$223Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
11:35 am - 12:40 pmDCA-MDW
2h 05mnonstop
Southwest Logo
8:10 am - 4:05 pmMDW-DCA
6h 55m1 stop
$233Southwest
Find Deal
Thu, Dec 25 - Thu, Dec 25
Southwest Logo
11:35 am - 12:40 pmDCA-MDW
2h 05mnonstop
Southwest Logo
3:30 pm - 6:15 pmMDW-DCA
1h 45mnonstop
$237Southwest
Find Deal
Sat, Dec 6 - Sun, Dec 7
Southwest Logo
6:30 am - 3:20 pmDCA-MDW
9h 50m2 stops
Southwest Logo
9:15 am - 12:00 pmMDW-DCA
1h 45mnonstop
$238Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7
Delta Logo
9:36 am - 12:34 pmDCA-MDW
3h 58m1 stop
Delta Logo
6:40 pm - 11:08 pmMDW-DCA
3h 28m1 stop
$243Delta
Find Deal
Wed, Dec 31 - Thu, Jan 1
Delta Logo
6:00 am - 11:06 amDCA-MDW
6h 06m1 stop
Delta Logo
6:00 am - 12:57 pmMDW-DCA
5h 57m1 stop
$257Delta
Find Deal
Wed, Dec 3 - Mon, Dec 8
Delta Logo
9:36 am - 12:34 pmDCA-MDW
3h 58m1 stop
Delta Logo
6:40 pm - 11:08 pmMDW-DCA
3h 28m1 stop
$265Delta
Find Deal
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 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 November, where the average cost of round-trip tickets is $372 and $370 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.

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

Good to know

Low seasonJanuary
Cheapest flight$78
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 8% 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 $78 for a one-way ticket and $200 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, Hawaiian Airlines, 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.

  • 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 $309 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 $182 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 $156 or less one-way and $302 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 4240 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

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

Information on your arrival and departure airports