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 Sunday. 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.

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.

$89+ Flights from Washington, D.C. Reagan-National Airport to Chicago Midway Airport

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

Find a great deal and save up to 77% by booking at least 49 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Washington, D.C. Reagan-National Airport to Chicago Midway Airport within the next two weeks, with the cheapest ticket starting at $259.

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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 30 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Reagan-National to Midway

Round-trip from	$167 (Southwest)
One-way from	$89 (Southwest)
Popular in	October
Cheapest in	November
Average price	$339
Good round-trip deal	$256 or less
Good one-way deal	$160 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, 2% potential price rise

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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).

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Average for round-trip flights in June 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 June 14, 2025.

Mon 8/1111:55 amDCA - MDW

Nonstop1h 55mSouthwest

Wed 8/139:00 amMDW - DCA

1 stop6h 00mSouthwest

Deal found 6/13

$167

Thu 8/146:00 amDCA - MDW

1 stop3h 35mDelta

Tue 8/196:04 amMDW - DCA

1 stop5h 36mDelta

Deal found 6/13

$197

Sat 6/281:00 pmDCA - MDW

1 stop8h 53mFrontier

Fri 7/412:35 pmMDW - DCA

1 stop8h 24mFrontier

Deal found 6/14

$200

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 June 14, 2025.

Mon 8/1111:55 amDCA - MDW

Nonstop1h 55mSouthwest

Wed 8/139:00 amMDW - DCA

1 stop6h 00mSouthwest

Deal found 6/13

$167

Thu 8/146:00 amDCA - MDW

1 stop3h 35mDelta

Tue 8/196:04 amMDW - DCA

1 stop5h 36mDelta

Deal found 6/13

$197

Sat 6/281:00 pmDCA - MDW

1 stop8h 53mFrontier

Fri 7/412:35 pmMDW - DCA

1 stop8h 24mFrontier

Deal found 6/14

$200

Last-minute flights from Reagan-National to Midway
Discover last-minute flight deals from Reagan-National to Midway. Data last updated June 14, 2025 and is based on user searches.

Sun 6/226:00 pmDCA - MDW

1 stop18h 40mFrontier

Sat 6/282:44 pmMDW - DCA

1 stop20h 16mFrontier

Deal found 6/12

$457

Mon 6/239:30 amDCA - MDW

Nonstop2h 00mSouthwest

Tue 7/19:50 amMDW - DCA

Nonstop1h 50mSouthwest

Deal found 6/13

$389

Mon 6/236:05 amDCA - MDW

1 stop3h 36mDelta

Fri 7/44:26 pmMDW - DCA

1 stop6h 20mDelta

Deal found 6/13

$409

Sat 6/281:00 pmDCA - MDW

1 stop8h 53mFrontier

Fri 7/412:35 pmMDW - DCA

1 stop8h 24mFrontier

Deal found 6/14

$200

Mon 6/306:50 pmDCA - MDW

Nonstop2h 00mSouthwest

Wed 7/23:30 pmMDW - DCA

Nonstop1h 50mSouthwest

Deal found 6/11

$179

Tue 7/19:39 amDCA - MDW

1 stop3h 50mDelta

Sat 7/59:24 amMDW - DCA

1 stop6h 09mDelta

Deal found 6/13

$199

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 June 14, 2025.

Tue 8/56:55 amDCA - MDW

1 stop6h 15mSouthwest

Deal found 6/13

$89

Mon 6/309:39 amDCA - MDW

1 stop3h 50mDelta

Deal found 6/13

$100

Fri 8/296:00 pmDCA - MDW

1 stop7h 24mFrontier

Deal found 6/13

$139

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

Mon 8/11

11:55 am-12:50 pm

Nonstop1h 55m

Chicago Midway

Wed 8/13

9:00 am-4:00 pm

1 stop6h 00m

$167

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Thu 8/14

6:00 am-8:35 am

1 stop3h 35m

Chicago Midway

Tue 8/19

6:04 am-12:40 pm

1 stop5h 36m

$197

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Sat 6/28

1:00 pm-8:53 pm

1 stop8h 53m

Chicago Midway

Fri 7/4

12:35 pm-9:59 pm

1 stop8h 24m

$200

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Tue 8/5

6:55 am-12:10 pm

1 stop6h 15m

$89

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Mon 6/30

9:39 am-12:29 pm

1 stop3h 50m

$100

Washington, D.C.Chicago

DCA - MDW

DCAMDW

Washington, D.C. Reagan-National

Fri 8/29

6:00 pm-12:24 am

1 stop7h 24m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

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

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 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?

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 11% 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 afternoons 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

4,283 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,283 reviews

Southwest

8.0

Very good

4,283 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,956 reviews

Southwest

8.0

Very good

4,283 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Frontier

5.9

Fair

3,296 reviews

Southwest

8.0

Very good

4,283 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What are the cheapest airlines flying from Washington, D.C. Reagan-National Airport to Chicago Midway Airport round-trip?
Southwest, at $167, 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 45% 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 $100 and $139, 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 $89. While the most popular route (Washington, D.C. Reagan-National - Chicago Midway) can be booked for $157 on average our data indicates $283 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

Merrillville

Lansing

Benton Harbor

Porter

Hammond

Valparaiso

Chesterton

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Top 2 airlines flying from Reagan-National to Midway

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$163	Average$235	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$177	Average$305	FlexibilityNo cancel fee	On-time63%

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$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 8/5. 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 30 days in advance, depart on a Wednesday or Thursday and return on a Wednesday

Cheap flight deals from Reagan-National to Midway

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 June 14, 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 June 14, 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.

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 June 9, 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 June 14, 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 June 8, 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

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 June 14, 2025.

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 2 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 June 14, 2025.