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Midway

$88+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
DCA — MDW
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
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 November or January, booked 30 days in advance, depart on a Wednesday 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 August 21, 2025.

Round-trip from

$175
(Mytrip)

One-way from

$88
(CheapOair)

Popular in

October

Cheapest in

November

Average price

$294

Good round-trip deal

$229 or less

Good one-way deal

$155 or less
From Washington, D.C. Reagan-National to Chicago Midway
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One-way flight from Washington, D.C. Reagan-National to Chicago Midway
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High demand for flights, 4% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Washington, D.C. Reagan-National to Chicago Midway.
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Price to beat on a one-way flight from Washington, D.C. Reagan-National to Chicago Midway.
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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 August 21, 2025.

This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/116:00 pmDCA - MDW
1 stop22h 53mFrontier
Mon 9/154:48 pmMDW - DCA
1 stop28h 11mFrontier
Deal found 8/20$175
This Flightnetwork deal was found by Cheapflights users on 8/19. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:00 amDCA - MDW
1 stop9h 53mFrontier
Fri 10/106:24 pmMDW - DCA
1 stop26h 35mFrontier
Deal found 8/19$176
This Booking.com deal was found by Cheapflights users on 8/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/87:00 amDCA - MDW
1 stop9h 53mFrontier
Fri 9/124:48 pmMDW - DCA
1 stop23h 11mFrontier
Deal found 8/19$177
This Southwest deal was found by Cheapflights users on 8/21. 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 9/168:40 pmDCA - MDW
Nonstop2h 05mSouthwest
Thu 9/185:25 pmMDW - DCA
Nonstop1h 55mSouthwest
Deal found 8/21$197
This Booking.com deal was found by Cheapflights users on 8/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/157:00 amDCA - MDW
1 stop9h 53mFrontier
Mon 9/224:48 pmMDW - DCA
1 stop23h 11mFrontier
Deal found 8/19$202
This Gotogate deal was found by Cheapflights users on 8/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/57:00 amDCA - MDW
1 stop9h 53mFrontier
Mon 9/84:48 pmMDW - DCA
1 stop23h 11mFrontier
Deal found 8/21$207
This Booking.com deal was found by Cheapflights users on 8/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:00 amDCA - MDW
1 stop9h 53mFrontier
Fri 9/264:48 pmMDW - DCA
1 stop23h 11mFrontier
Deal found 8/19$208
This Southwest deal was found by Cheapflights users on 8/18. 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 10/188:25 amDCA - MDW
Nonstop2h 10mSouthwest
Tue 10/215:30 amMDW - DCA
2 stops7h 30mSouthwest
Deal found 8/18$212
This Delta deal was found by Cheapflights users on 8/21. 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.
Wed 9/176:00 amDCA - MDW
1 stop3h 40mDelta
Sat 9/201:08 pmMDW - DCA
1 stop3h 25mDelta
Deal found 8/21$217
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:00 amDCA - MDW
1 stop9h 53mFrontier
Mon 9/294:48 pmMDW - DCA
1 stop28h 11mFrontier
Deal found 8/18$220
This Southwest deal was found by Cheapflights users on 8/19. 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 10/99:40 pmDCA - MDW
Nonstop2h 00mSouthwest
Tue 10/147:40 amMDW - DCA
2 stops7h 35mSouthwest
Deal found 8/19$222

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 August 21, 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

Thu 9/11

6:00 pm-3:53 pm

1 stop22h 53m

Chicago Midway

Mon 9/15

4:48 pm-9:59 pm

1 stop28h 11m

$175

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 10/20

1:00 pm-12:24 am

1 stop12h 24m

Chicago Midway

Fri 10/24

12:11 pm-9:59 pm

1 stop8h 48m

$175

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 9/14

1:00 pm-3:53 pm

1 stop27h 53m

Chicago Midway

Fri 9/19

3:48 pm-4:59 pm

1 stop24h 11m

$175

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 11/6

9:35 pm-10:35 pm

Nonstop2h 00m

Chicago Midway

Tue 11/11

10:05 am-1:00 pm

Nonstop1h 55m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 9/17

6:05 am-7:00 am

Nonstop1h 55m

Chicago Midway

Mon 9/22

5:25 pm-8:20 pm

Nonstop1h 55m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 9/11

9:00 pm-10:00 pm

Nonstop2h 00m

Chicago Midway

Mon 9/15

5:30 am-8:20 am

Nonstop1h 50m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 10/14

8:55 pm-10:00 pm

Nonstop2h 05m

Chicago Midway

Thu 10/16

6:10 am-8:55 am

Nonstop1h 45m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/4

6:55 pm-8:00 pm

Nonstop2h 05m

Chicago Midway

Mon 12/8

8:10 pm-10:55 pm

Nonstop1h 45m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 10/27

9:40 pm-10:40 pm

Nonstop2h 00m

Chicago Midway

Wed 10/29

7:15 am-10:00 am

Nonstop1h 45m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 10/16

6:00 am-7:00 am

Nonstop2h 00m

Chicago Midway

Sat 10/18

11:00 am-1:45 pm

Nonstop1h 45m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 18 results
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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, the most affordable and convenient option to reach the airport.

Read more about DCAby Emily Zemler
MDW

Arrive at MDW and take the Orange Line train for a quick, 30-minute ride to Chicago's city center.

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 August 8, 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 30 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 August 21, 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 evening could potentially save you up to 10% 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 August 17, 2025.

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

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 August 21, 2025.
Get a feel of what it's like to fly with Southwest and Frontier 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
8.0
Very good
4,245 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,245 reviews

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 2h. There are 599 mi between Washington, D.C. Reagan-National Airport and Chicago Midway Airport. This flight may include one or multiple stops.

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

    Frontier, at $99, was found to be the cheapest airline from Washington, D.C. Reagan-National Airport to Chicago Midway Airport. An alternate airline flying to your destination would be Southwest. Frontier is 67% 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 $78. While the most popular route (Washington, D.C. Reagan-National - Chicago Midway) can be booked for $197 on average our data indicates $280 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 Chicago Midway Airport?

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

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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.
Reagan-National to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Baltimore to Midway flights
Dulles Intl to Midway flights

Top 2 airlines flying from Reagan-National to Midway

Discover the top 2 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$99Average$233FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$174Average$298FlexibilityNo cancel feeOn-time63%

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