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$99+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — MDW
Jun 7 — Jun 141
Sun 6/7
Sun 6/14
1 adult, Economy
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Cheapflights Tip: The best prices from Washington, D.C. Reagan-National to Chicago Midway are usually found in July or September, booked 75 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

Cheap 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 May 8, 2026.

This Southwest deal was found by Cheapflights users on 5/4. 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.
Sat 6/612:35 pm
DCA
-
MDW
1 stop5h 15m
Southwest
Tue 6/95:20 pm
MDW
-
DCA
1 stop4h 55m
Southwest
Deal found 5/4$228
This Southwest deal was found by Cheapflights users on 5/6. 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.
Wed 5/272:40 pm
DCA
-
MDW
2 stops8h 05m
Southwest
Sat 5/306:35 pm
MDW
-
DCA
Nonstop1h 55m
Southwest
Deal found 5/6$233
This Southwest deal was found by Cheapflights users on 5/7. 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.
Sat 6/612:35 pm
DCA
-
MDW
1 stop5h 15m
Southwest
Tue 6/1611:25 am
MDW
-
DCA
1 stop6h 30m
Southwest
Deal found 5/7$238
This Southwest deal was found by Cheapflights users on 5/8. 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.
Mon 6/17:55 am
DCA
-
MDW
Nonstop2h 05m
Southwest
Thu 6/48:10 pm
MDW
-
DCA
Nonstop1h 50m
Southwest
Deal found 5/8$239
This Southwest deal was found by Cheapflights users on 5/7. 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.
Wed 8/56:05 am
DCA
-
MDW
Nonstop1h 55m
Southwest
Thu 8/68:55 am
MDW
-
DCA
Nonstop1h 55m
Southwest
Deal found 5/7$247
This Delta deal was found by Cheapflights users on 5/7. 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.
Sat 5/306:05 am
DCA
-
MDW
1 stop3h 38m
Delta
Tue 6/21:22 pm
MDW
-
DCA
1 stop4h 37m
Delta
Deal found 5/7$248
This Southwest deal was found by Cheapflights users on 5/8. 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.
Thu 5/289:35 pm
DCA
-
MDW
Nonstop2h 00m
Southwest
Mon 6/13:50 pm
MDW
-
DCA
1 stop7h 00m
Southwest
Deal found 5/8$249
This Southwest deal was found by Cheapflights users on 5/8. 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.
Mon 6/12:45 pm
DCA
-
MDW
1 stop4h 05m
Southwest
Tue 6/21:55 pm
MDW
-
DCA
1 stop3h 45m
Southwest
Deal found 5/8$250
This Southwest deal was found by Cheapflights users on 5/6. 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.
Wed 6/106:00 am
DCA
-
MDW
Nonstop2h 00m
Southwest
Thu 6/118:00 am
MDW
-
DCA
1 stop6h 50m
Southwest
Deal found 5/6$253

Find 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 May 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Delta)

One-way from

$99
(Delta)

Popular in

November

Cheapest in

July

Average price

$319

Good round-trip deal

$332 or less

Good one-way deal

$215 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. 10% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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

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 May 8, 2026.
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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 5/26

9:05 am-3:45 pm

2 stops7h 40m

Chicago Midway

Sat 5/30

12:45 pm-6:25 pm

1 stop4h 40m

$233
Quickest round-trip

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/16

6:00 am-7:00 am

Nonstop2h 00m

Chicago Midway

Thu 6/18

6:00 am-8:45 am

Nonstop1h 45m

$233

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 6/6

6:05 am-8:43 am

1 stop3h 38m

Chicago Midway

Tue 6/9

9:17 am-4:34 pm

1 stop6h 17m

$238

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 6/29

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

Wed 7/1

3:55 pm-10:50 pm

1 stop5h 55m

$253

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/27

9:05 am-3:45 pm

2 stops7h 40m

Chicago Midway

Fri 5/29

8:05 pm-10:55 pm

Nonstop1h 50m

$258

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 8/1

4:30 pm-5:30 pm

Nonstop2h 00m

Chicago Midway

Tue 8/4

8:50 am-3:50 pm

2 stops6h 00m

$258

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 6/30

9:39 am-12:46 pm

1 stop4h 07m

Chicago Midway

Fri 7/3

1:26 pm-6:59 pm

1 stop4h 33m

$268

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 7/4

12:05 pm-1:05 pm

Nonstop2h 00m

Chicago Midway

Wed 7/8

11:15 am-2:00 pm

Nonstop1h 45m

$289

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 6/22

6:55 pm-8:05 pm

Nonstop2h 10m

Chicago Midway

Mon 6/29

6:00 am-8:45 am

Nonstop1h 45m

$297

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/28

12:00 pm-1:05 pm

Nonstop2h 05m

Chicago Midway

Mon 6/1

5:00 pm-7:55 pm

Nonstop1h 55m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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.

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?

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 73 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, July is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport (average of $263). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in November is currently the most expensive (average of $393). 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 May 8, 2026.

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 in the morning tend to be the most expensive. A flight at noon could potentially save you up to 13% 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 May 2, 2026.

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

How much does it cost to fly round-trip from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

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

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Washington, D.C. Reagan-National Airport to Chicago Midway Airport trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on MDW

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 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

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 May 8, 2026.
Get a feel of what it's like to fly with Southwest from Washington, D.C. Reagan-National Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,302 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,302 reviews
Southwest
7.9
Good
4,302 reviews

Entertainment

7.5

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

  • How long is the flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

    Departing from Washington, D.C. Reagan-National Airport to Chicago Midway Airport will take you 3h 38m. There are 599 mi between Washington, D.C. Reagan-National Airport and Chicago Midway Airport. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport round-trip?

    Southwest, at $191, was found to be the cheapest airline from Washington, D.C. Reagan-National Airport to Chicago Midway Airport.. Southwest is 42% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 $119. While the most popular route (Washington, D.C. Reagan-National - Chicago Midway) can be booked for $197 on average, our data indicates $355 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, July is the cheapest month in which you can book a flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport (average of $263). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in November is currently the most expensive (average of $393). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Reagan-National to Midway

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

Top airline flying from Reagan-National to Midway

Discover the top airline 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 May 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$191Average$324FlexibilityNo cancel feeOn-time63%

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