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.

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).

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.

$78+ 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 January or July, booked 46 days in advance, depart on a Wednesday or Thursday 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	$144 (Southwest)
One-way from	$78 (Southwest)
Popular in	October
Cheapest in	January
Average price	$372
Good round-trip deal	$311 or less
Good one-way deal	$163 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

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Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).

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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 October 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 October 23, 2025.

Wed 12/243:20 pmDCA - MDW

Nonstop2h 10mSouthwest

Tue 1/63:35 pmMDW - DCA

Nonstop1h 45mSouthwest

Deal found 10/22

$149

Sat 11/158:15 amDCA - MDW

1 stop28h 15mFrontier

Mon 11/1712:30 pmMDW - DCA

1 stop8h 29mFrontier

Deal found 10/23

$150

Tue 12/96:00 amDCA - MDW

Nonstop2h 05mSouthwest

Wed 12/105:40 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 10/22

$155

Tue 12/166:55 pmDCA - MDW

Nonstop2h 05mSouthwest

Thu 12/258:10 pmMDW - DCA

Nonstop1h 45mSouthwest

Deal found 10/22

$159

Tue 12/911:35 amDCA - MDW

Nonstop2h 05mSouthwest

Wed 12/1711:25 amMDW - DCA

1 stop3h 45mSouthwest

Deal found 10/22

$160

Sun 11/98:15 amDCA - MDW

1 stop28h 15mFrontier

Thu 11/1312:30 pmMDW - DCA

1 stop23h 32mFrontier

Deal found 10/23

$163

Sun 11/22:00 pmDCA - MDW

1 stop22h 30mFrontier

Thu 11/612:30 pmMDW - DCA

1 stop23h 32mFrontier

Deal found 10/21

$165

Tue 12/98:45 pmDCA - MDW

Nonstop2h 10mSouthwest

Thu 12/115:40 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 10/22

$173

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 October 23, 2025.

Sat 1/1712:35 pmDCA - MDW

1 stop7h 25mSouthwest

Tue 1/205:25 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 10/22

$154

Fri 12/127:59 amDCA - MDW

1 stop4h 56mDelta

Mon 12/156:00 amMDW - DCA

1 stop4h 37mDelta

Deal found 10/22

$177

Tue 12/910:50 amDCA - MDW

2 stops6h 45mSouthwest

Wed 12/103:30 pmMDW - DCA

Nonstop1h 45mSouthwest

Deal found 10/23

$170

Mon 12/86:02 amDCA - MDW

1 stop3h 52mDelta

Tue 12/912:50 pmMDW - DCA

1 stop4h 50mDelta

Deal found 10/21

$177

Wed 12/176:00 amDCA - MDW

Nonstop2h 05mSouthwest

Mon 1/56:00 amMDW - DCA

Nonstop1h 45mSouthwest

Deal found 10/20

$173

Wed 12/36:02 amDCA - MDW

1 stop3h 52mDelta

Mon 12/81:14 pmMDW - DCA

1 stop4h 45mDelta

Deal found 10/21

$177

Thu 12/118:45 pmDCA - MDW

Nonstop2h 10mSouthwest

Sat 12/1310:40 amMDW - DCA

Nonstop1h 50mSouthwest

Deal found 10/22

$173

Wed 12/32:00 pmDCA - MDW

1 stop5h 18mDelta

Wed 12/249:29 amMDW - DCA

1 stop6h 11mDelta

Deal found 10/21

$177

Wed 12/176:02 amDCA - MDW

1 stop3h 52mDelta

Mon 1/55:25 pmMDW - DCA

1 stop4h 55mDelta

Deal found 10/20

$177

Thu 12/116:02 amDCA - MDW

1 stop3h 52mDelta

Sat 12/136:00 amMDW - DCA

1 stop4h 37mDelta

Deal found 10/21

$177

Last-minute flights from Reagan-National to Midway
Discover last-minute flight deals from Reagan-National to Midway. Data last updated October 23, 2025 and is based on user searches.

Thu 10/236:31 pmDCA - MDW

1 stop7h 05mFrontier

Thu 10/3012:30 pmMDW - DCA

1 stop23h 32mFrontier

Deal found 10/20

$192

Sun 10/262:00 pmDCA - MDW

1 stop11h 36mFrontier

Thu 10/3012:30 pmMDW - DCA

1 stop27h 29mFrontier

Deal found 10/21

$194

Wed 10/298:00 amDCA - MDW

1 stop28h 30mFrontier

Fri 10/3112:30 pmMDW - DCA

1 stop23h 34mFrontier

Deal found 10/21

$176

Wed 10/298:00 amDCA - MDW

1 stop28h 30mFrontier

Sun 11/212:30 pmMDW - DCA

1 stop8h 29mFrontier

Deal found 10/21

$193

Thu 10/308:00 amDCA - MDW

1 stop28h 30mFrontier

Mon 11/312:30 pmMDW - DCA

1 stop27h 29mFrontier

Deal found 10/21

$190

Sat 11/16:00 pmDCA - MDW

1 stop19h 30mFrontier

Mon 11/312:30 pmMDW - DCA

1 stop27h 29mFrontier

Deal found 10/20

$185

Sun 11/22:00 pmDCA - MDW

1 stop22h 30mFrontier

Thu 11/612:30 pmMDW - DCA

1 stop23h 32mFrontier

Deal found 10/21

$165

Sat 11/86:00 pmDCA - MDW

1 stop18h 30mFrontier

Mon 11/1012:30 pmMDW - DCA

1 stop27h 29mFrontier

Deal found 10/23

$170

Sun 11/98:15 amDCA - MDW

1 stop28h 15mFrontier

Thu 11/1312:30 pmMDW - DCA

1 stop23h 32mFrontier

Deal found 10/23

$163

Wed 11/122:00 pmDCA - MDW

1 stop22h 30mFrontier

Sun 11/1612:30 pmMDW - DCA

1 stop8h 29mFrontier

Deal found 10/23

$179

Thu 11/132:00 pmDCA - MDW

1 stop22h 30mFrontier

Sun 11/1612:30 pmMDW - DCA

1 stop23h 32mFrontier

Deal found 10/23

$181

Sat 11/158:15 amDCA - MDW

1 stop28h 15mFrontier

Mon 11/1712:30 pmMDW - DCA

1 stop8h 29mFrontier

Deal found 10/23

$150

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 October 23, 2025.

Tue 12/93:20 pmDCA - MDW

Nonstop2h 10mSouthwest

Deal found 10/21

$78

Sat 12/136:00 pmDCA - MDW

1 stop18h 08mFrontier

Deal found 10/23

$79

Sat 11/82:00 pmDCA - MDW

1 stop22h 30mFrontier

Deal found 10/23

$81

Wed 12/243:35 pmDCA - MDW

1 stop5h 40mSouthwest

Deal found 10/23

$82

Mon 12/86:02 amDCA - MDW

1 stop3h 52mDelta

Deal found 10/22

$89

Sun 12/76:02 amDCA - MDW

1 stop3h 52mDelta

Deal found 10/22

$92

Sun 11/92:00 pmDCA - MDW

1 stop22h 30mFrontier

Deal found 10/23

$94

Sun 11/28:00 amDCA - MDW

1 stop28h 30mFrontier

Deal found 10/23

$95

Thu 12/1111:35 amDCA - MDW

Nonstop2h 05mSouthwest

Deal found 10/23

$96

Thu 12/2511:40 amDCA - MDW

2 stops6h 30mSouthwest

Deal found 10/21

$97

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

Sat 1/17

12:35 pm-7:00 pm

1 stop7h 25m

Chicago Midway

Tue 1/20

5:25 pm-8:15 pm

Nonstop1h 50m

$154

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 12/9

10:50 am-4:35 pm

2 stops6h 45m

Chicago Midway

Wed 12/10

3:30 pm-6:15 pm

Nonstop1h 45m

$170

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/17

6:00 am-7:05 am

Nonstop2h 05m

Chicago Midway

Mon 1/5

6:00 am-8:45 am

Nonstop1h 45m

$173

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/11

8:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Sat 12/13

10:40 am-1:30 pm

Nonstop1h 50m

$173

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 12/12

7:59 am-11:55 am

1 stop4h 56m

Chicago Midway

Mon 12/15

6:00 am-11:37 am

1 stop4h 37m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 12/8

6:02 am-8:54 am

1 stop3h 52m

Chicago Midway

Tue 12/9

12:50 pm-6:40 pm

1 stop4h 50m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/3

6:02 am-8:54 am

1 stop3h 52m

Chicago Midway

Mon 12/8

1:14 pm-6:59 pm

1 stop4h 45m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/3

2:00 pm-6:18 pm

1 stop5h 18m

Chicago Midway

Wed 12/24

9:29 am-4:40 pm

1 stop6h 11m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Wed 12/17

6:02 am-8:54 am

1 stop3h 52m

Chicago Midway

Mon 1/5

5:25 pm-11:20 pm

1 stop4h 55m

$177

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 12/11

6:02 am-8:54 am

1 stop3h 52m

Chicago Midway

Sat 12/13

6:00 am-11:37 am

1 stop4h 37m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/23

Showing 1-10 of 21 results

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 October.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	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.

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 46 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 $99). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in November is currently the most expensive (average of $230). 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 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?

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

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, the most affordable and convenient option to reach the airport.

MDW

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

Our travel experts

Ramsey Qubein

Expert on MDW

Emily Zemler

Expert on DCA

Reviews of airlines servicing Midway

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

8.0

Very good

4,236 reviews

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

4,236 reviews

Southwest

8.0

Very good

4,236 reviews

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

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 7h 25m. There are 599 mi between Washington, D.C. Reagan-National Airport and Chicago Midway Airport.
What is the cheapest airline to fly from Washington, D.C. Reagan-National Airport to Chicago Midway Airport round-trip?
Southwest, at $179, 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 $108. While the most popular route (Washington, D.C. Reagan-National - Chicago Midway) can be booked for $144 on average, our data indicates $304 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 $99). Flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport in November is currently the most expensive (average of $230). 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

Merrillville

Lansing

Hammond

Porter

Benton Harbor

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Top airline flying from Reagan-National to Midway

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$179	Average$310	FlexibilityNo cancel fee	On-time63%

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$78+ 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 12/16. 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 January or July, booked 46 days in advance, depart on a Wednesday or Thursday 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 October 23, 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 October 23, 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 October.

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?

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?

What is the cheapest day to fly 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

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

Reviews of airlines servicing Midway

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.

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?

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

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 Chicago Midway Airport?

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.

Top airline flying from Reagan-National to Midway

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Book with Flexibility

Travel Smart

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 October 23, 2025.