What are the most popular airlines that fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport?

Before booking your flight from Washington, D.C. Reagan-National Airport to Chicago Midway Airport check out the most popular airlines for this route: Delta, Frontier or Southwest.

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

Flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport are found to be more expensive on Saturday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago Midway Airport.

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.

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.

$86+ Flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

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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 Thursday or Friday and return on a Wednesday

Cheap flight deals from Reagan-National to Midway

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$178 (Frontier)
One-way from	$86 (Frontier)
Popular in	July
Cheapest in	November
Average price	$307
Good round-trip deal	$253 or less
Good one-way deal	$171 or less

Provider with most accurate pricing for Washington, D.C. Reagan-National-Chicago Midway flight deals.

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Provider most trusted by Cheapflights users for Washington, D.C. Reagan-National-Chicago Midway flights.

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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

Search Deals

Highest demand for flights based on searches. 13% potential increase in price ($51 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).

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Average for round-trip flights in April 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 April 11, 2025.

Tue 4/151:03 pmDCA - MDW

1 stop12h 18mFrontier

Wed 4/166:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 4/10

$178

Wed 5/289:35 amDCA - MDW

Nonstop1h 55mSouthwest

Sat 5/315:35 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 4/10

$179

Sat 4/1912:30 pmDCA - MDW

1 stop6h 50mDelta

Sun 4/206:04 amMDW - DCA

1 stop4h 21mDelta

Deal found 4/10

$217

Best flights from Reagan-National to Midway
Discover carefully curated flight deals from Reagan-National to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 11, 2025.

Tue 4/151:03 pmDCA - MDW

1 stop12h 18mFrontier

Wed 4/166:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 4/10

$178

Wed 5/289:35 amDCA - MDW

Nonstop1h 55mSouthwest

Sat 5/315:35 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 4/10

$179

Sat 4/1912:30 pmDCA - MDW

1 stop6h 50mDelta

Sun 4/206:04 amMDW - DCA

1 stop4h 21mDelta

Deal found 4/10

$217

Last-minute flights from Reagan-National to Midway
Discover last-minute flight deals from Reagan-National to Midway. Data last updated April 11, 2025 and is based on user searches.

Tue 4/151:03 pmDCA - MDW

1 stop12h 18mFrontier

Wed 4/166:45 amMDW - DCA

1 stop9h 14mFrontier

Deal found 4/10

$178

Wed 4/161:03 pmDCA - MDW

1 stop12h 18mFrontier

Tue 4/226:45 amMDW - DCA

1 stop28h 24mFrontier

Deal found 4/10

$180

Sat 4/1912:30 pmDCA - MDW

1 stop6h 50mDelta

Sun 4/206:04 amMDW - DCA

1 stop4h 21mDelta

Deal found 4/10

$217

Sat 4/199:40 amDCA - MDW

Nonstop1h 55mSouthwest

Sun 4/207:55 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 4/10

$339

Wed 5/289:35 amDCA - MDW

Nonstop1h 55mSouthwest

Sat 5/315:35 pmMDW - DCA

Nonstop1h 55mSouthwest

Deal found 4/10

$179

One-way flights from Reagan-National to Midway
Search for one-way flight options from Reagan-National to Midway. Find affordable one-way fares based on user searches. Data last updated April 11, 2025.

Thu 5/17:00 amDCA - MDW

1 stop13h 08mFrontier

Deal found 4/10

$86

Sun 4/209:35 pmDCA - MDW

Nonstop1h 55mSouthwest

Deal found 4/10

$90

Sat 5/106:00 amDCA - MDW

1 stop4h 40mDelta

Deal found 4/10

$99

Cheapflights Fare Finder

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

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 4/15

1:03 pm-12:21 am

1 stop12h 18m

Chicago Midway

Wed 4/16

6:45 am-4:59 pm

1 stop9h 14m

$178

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 5/28

9:35 am-10:30 am

Nonstop1h 55m

Chicago Midway

Sat 5/31

5:35 pm-8:30 pm

Nonstop1h 55m

$179

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 4/19

12:30 pm-6:20 pm

1 stop6h 50m

Chicago Midway

Sun 4/20

6:04 am-11:25 am

1 stop4h 21m

$217

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/1

7:00 am-7:08 pm

1 stop13h 08m

$86

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sun 4/20

9:35 pm-10:30 pm

Nonstop1h 55m

$90

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 5/29

6:00 am-8:40 am

1 stop3h 40m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Compare providers for flights from Reagan-National to Midway

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 April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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

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.

MDW

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

Our travel experts

Ramsey Qubein

Expert on MDW

Emily Zemler

Expert on DCA

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 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?

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 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?

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

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

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

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

4,279 reviews

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

4,279 reviews

Southwest

8.0

Very good

4,279 reviews

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

7,910 reviews

Southwest

8.0

Very good

4,279 reviews

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

3,277 reviews

Southwest

8.0

Very good

4,279 reviews

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

What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport round-trip?
Frontier, at $178, 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 Southwest and Delta. Frontier 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?
$86 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $90 and $99, 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 $93. While the most popular route (Washington, D.C. Reagan-National - Chicago Midway) can be booked for $161 on average our data indicates $287 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

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Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

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Top 3 airlines flying from Reagan-National to Midway

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$120	Average$233	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$177	Average$317	FlexibilityNo cancel fee	On-time63%
Delta	Cheapest$177	Average$498	FlexibilityNo cancel fee	On-timeN/A

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$86+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Reagan-National to Midway with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

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 Thursday or Friday and return on a Wednesday

Cheap flight deals from Reagan-National to Midway

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Reagan-National to Midway

Cheapest flights from Reagan-National to MidwayExplore 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 April 11, 2025.

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 April 11, 2025.

Cheapflights Fare Finder

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.

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 April.

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

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

MDW

Our travel experts

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.

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 April 4, 2025.

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

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 April 11, 2025.

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 30, 2025.

Rainfall in Midway by month

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

Temperature in Midway by month

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

Reviews of airlines servicing Midway

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?

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

What are the cheapest flights 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?

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

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

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

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

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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.

Top 3 airlines flying from Reagan-National to Midway

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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 April 11, 2025.