HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$89+ Cheap flights from Reagan-National (DCA) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — MDW
Mar 30 — Apr 61
Sun 3/30
Sun 4/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Reagan-National to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago Midway are usually found in November or January, booked 24 days in advance, depart on a Friday or Thursday and return on a Wednesday

Cheap flight deals from Reagan-National to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Reagan-National (DCA) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

July

Cheapest in

November

Average price

$346

Good round-trip deal

$245 or less

Good one-way deal

$159 or less
Provider with most accurate pricing for Washington, D.C. Reagan-National-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Washington, D.C. Reagan-National-Chicago Midway flights.
Search Deals
From Washington, D.C. Reagan-National to Chicago Midway
Search Deals
One-way flight from Washington, D.C. Reagan-National to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals
Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Washington, D.C. Reagan-National to Chicago Midway.
Search Deals

Find flight deals from Reagan-National to Midway

Cheapest flights from Reagan-National to Midway
Explore the most affordable flight options available from Reagan-National to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2025.

This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/227:30 amDCA - MDW
Nonstop2h 00mSouthwest
Tue 4/293:20 pmMDW - DCA
Nonstop1h 50mSouthwest
Deal found 3/23$177
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/246:00 amDCA - MDW
1 stop3h 40mDelta
Sat 4/263:02 pmMDW - DCA
1 stop6h 20mDelta
Deal found 3/24$217
This Frontier deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/21:03 pmDCA - MDW
1 stop12h 18mFrontier
Wed 4/96:45 amMDW - DCA
1 stop9h 14mFrontier
Deal found 3/24$218

Cheapflights Fare Finder

Customize your flight search to find flights from Reagan-National to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 25, 2025.
Use the filters below to find and compare flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport that are best for you.

Fly from

Reagan-National

Fly to

Midway

Route

Depart

Return

Price

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/22

7:30 am-8:30 am

Nonstop2h 00m

Chicago Midway

Tue 4/29

3:20 pm-6:10 pm

Nonstop1h 50m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 4/2

1:03 pm-12:21 am

1 stop12h 18m

Chicago Midway

Wed 4/9

6:45 am-4:59 pm

1 stop9h 14m

$218

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/10

9:39 am-12:29 pm

1 stop3h 50m

Chicago Midway

Wed 6/25

12:41 pm-7:36 pm

1 stop5h 55m

$223

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/10

9:00 am-10:15 am

Nonstop2h 15m

$89

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 4/28

6:00 am-8:40 am

1 stop3h 40m

$99

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 4/18

6:00 pm-12:21 am

1 stop7h 21m

$110

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Compare providers for flights from Reagan-National to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Reagan-National to Midway in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Washington, D.C. Reagan-National Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Washington, D.C. Reagan-National Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Washington, D.C. Reagan-National Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Washington, D.C. Reagan-National Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

The best insider tips for Washington, D.C. Reagan-National Airport to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago Midway Airport trip
Airports
DCA

For a stress-free departure, use DCA's Metro stop on the Yellow and Blue lines for easy access and affordable travel.

Read more about DCAby Emily Zemler
MDW

Use the 'L' train's Orange Line for a quick, 30-minute ride to Chicago's city center from MDW.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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
Emily Zemler

Emily Zemler

Expert on DCA

Emily Zemler

Emily Zemler

Emily is a freelance writer and book author based in London covering entertainment and travel. Her work has appeared in Los Angeles Times, Observer, and Conde Nast Traveler She has ventured to more than 40 countries and all seven continents, always in search of a great art museum. She has written extensively about hotels, luxury travel, and aviation.

Read more

Best time to book a flight from Reagan-National to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Reagan-National with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Reagan-National to Midway. Price data was last updated on March 21, 2025.

To ensure you get the cheapest price possible for a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport, you should look to book at least 24 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport (average of $160). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DCA to MDW?

Find hourly flight availability from Reagan-National to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 25, 2025.

One of the essential ways to save on airfare from Washington, D.C. Reagan-National Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 6% on airfare.

What is the cheapest day to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Reagan-National to Midway. Price data was last updated on March 23, 2025.

Travelers seeking maximum savings on their Washington, D.C. Reagan-National Airport to Chicago Midway Airport flight should consider departing on Thursday at noon when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated March 25, 2025.
To help decide which airline to fly from Washington, D.C. to Chicago, see what other customers have to say about Southwest, Delta and Frontier. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,890 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,273 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Reagan-National to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport round-trip?

    Southwest, at $177, was found to be the cheapest airline from Washington, D.C. Reagan-National Airport to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Frontier. Southwest is 43% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport one-way?

    $89 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $99 and $108, respectively.

  • What are the cheapest flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $88. While the most popular route (Washington, D.C. Reagan-National - Chicago Midway) can be booked for $177 on average our data indicates $272 when flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport.

  • Can I find deals for flights from Reagan-National to Midway that include hotel bookings?

    Yes. In addition to deals on Reagan-National to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Reagan-National to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Reagan-National to Midway.

  • Can I find deals for business class flights from Reagan-National to Midway?

    Yes. Cheapflights offers flight deals from Reagan-National to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport (average of $160). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Washington, D.C. Reagan-National Airport?

Book flights to Washington, D.C. Reagan-National Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Reagan-National to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Dulles Intl to Midway flights
Baltimore to Midway flights

Top 3 airlines flying from Reagan-National to Midway

Discover the top 3 airlines that operate flights from Reagan-National to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$120Average$233FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$312FlexibilityNo cancel feeOn-time63%
DeltaCheapest$177Average$498FlexibilityNo cancel feeOn-timeN/A
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.