Is Southwest the cheapest airline to fly with from Washington, D.C. to Milwaukee?

With an average price of $355 return, Southwest is not the cheapest airline to fly from Washington, D.C. to Milwaukee with. Instead, for the lowest price, our data suggests flying with Delta, where a return flight costs $255 on average.

What is the cheapest Southwest flight from Washington, D.C. to Milwaukee?

In the last 3 days, the lowest price for a flight with Southwest from Washington, D.C. to Milwaukee was $245 for a return flight and $130 for a one-way flight.

Does Southwest fly direct to Milwaukee from Washington, D.C.?

Yes, Southwest does offer direct flights for the route, with around 12 flights per week.

What’s the cheapest day of the week to fly from Washington, D.C. to Milwaukee with Southwest?

On average, the cheapest day of the week to fly from Washington, D.C. to Milwaukee with Southwest is Friday, when prices are around $112. The most expensive day is generally Sunday, where the average price is around $154.

What’s the cheapest month to fly from Washington, D.C. to Milwaukee with Southwest?

The cheapest month for Southwest flights to Milwaukee from Washington, D.C. is generally September, where plane tickets cost $119 on average. If possible, try to avoid the most expensive months of April and February, where tickets cost $340 and $405 respectively.

$136 Cheap Southwest Flights from Washington, D.C. to Milwaukee

WAS - MKE

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Flight Deals

Cheap Southwest Flight Deals from Washington, D.C. to Milwaukee

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Washington, D.C. to Milwaukee that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Washington, D.C. to Milwaukee

Tue, Dec 2 - Sat, Dec 6

3:40 pm - 4:50 pmDCA-MKE

2h 10mnonstop

12:10 pm - 3:00 pmMKE-DCA

1h 50mnonstop

$251Southwest

Find Deal

Tue, Dec 2 - Sat, Dec 6

2:40 pm - 8:35 pmDCA-MKE

6h 55m1 stop

12:10 pm - 3:00 pmMKE-DCA

1h 50mnonstop

$261Southwest

Find Deal

Tue, Dec 2 - Sat, Dec 6

2:40 pm - 8:35 pmDCA-MKE

6h 55m1 stop

5:45 am - 3:40 pmMKE-DCA

8h 55m2 stops

$276Southwest

Find Deal

Sat, Feb 14 - Sat, Feb 21

6:55 am - 2:30 pmDCA-MKE

8h 35m1 stop

4:30 pm - 8:55 amMKE-DCA

15h 25m2 stops

$292Southwest

Find Deal

Wed, Dec 24 - Thu, Dec 25

8:40 pm - 9:45 pmBWI-MKE

2h 05mnonstop

6:40 am - 9:30 amMKE-BWI

1h 50mnonstop

$305Southwest

Find Deal

Sat, Feb 14 - Sun, Feb 22

8:15 am - 9:40 amDCA-MKE

2h 25mnonstop

9:45 am - 12:30 pmMKE-DCA

1h 45mnonstop

$306Southwest

Find Deal

Wed, Dec 24 - Thu, Dec 25

8:40 pm - 9:45 pmBWI-MKE

2h 05mnonstop

3:55 pm - 10:50 pmMKE-BWI

5h 55m1 stop

$315Southwest

Find Deal

Thu, Dec 18 - Sun, Dec 21

3:55 pm - 5:05 pmDCA-MKE

2h 10mnonstop

3:20 pm - 6:10 pmMKE-DCA

1h 50mnonstop

$316Southwest

Find Deal

Wed, Dec 24 - Tue, Dec 30

8:40 pm - 9:45 pmBWI-MKE

2h 05mnonstop

6:40 am - 6:15 pmMKE-BWI

10h 35m1 stop

$319Southwest

Find Deal

Wed, Dec 24 - Mon, Dec 29

3:40 pm - 4:50 pmDCA-MKE

2h 10mnonstop

5:50 am - 4:15 pmMKE-DCA

9h 25m1 stop

$322Southwest

Find Deal

Useful Info

Low season	January
High season	July
Cheapest flight	$136
Average price round-trip	$312
Good deal one-way	$270

Best time to beat the crowds but there is an average 9% increase in price.

Most popular time to fly with an average 1% increase in price.

Flight from Reagan Washington National Airport to Milwaukee

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Washington, D.C. to Milwaukee

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Washington, D.C. to Milwaukee?
With an average price of $355 return, Southwest is not the cheapest airline to fly from Washington, D.C. to Milwaukee with. Instead, for the lowest price, our data suggests flying with Delta, where a return flight costs $255 on average.
What is the cheapest Southwest flight from Washington, D.C. to Milwaukee?
In the last 3 days, the lowest price for a flight with Southwest from Washington, D.C. to Milwaukee was $245 for a return flight and $130 for a one-way flight.
Does Southwest fly direct to Milwaukee from Washington, D.C.?
Yes, Southwest does offer direct flights for the route, with around 12 flights per week.
What’s the cheapest day of the week to fly from Washington, D.C. to Milwaukee with Southwest?
On average, the cheapest day of the week to fly from Washington, D.C. to Milwaukee with Southwest is Friday, when prices are around $112. The most expensive day is generally Sunday, where the average price is around $154.
What’s the cheapest month to fly from Washington, D.C. to Milwaukee with Southwest?
The cheapest month for Southwest flights to Milwaukee from Washington, D.C. is generally September, where plane tickets cost $119 on average. If possible, try to avoid the most expensive months of April and February, where tickets cost $340 and $405 respectively.

8.0

Very good4,240 verified ratings

8.1Boarding

8.0Comfort

8.6Crew

7.5Entertainment

7.0Food

Pros +

Cons -

Show reviews that mention

10.0 Wonderful

James, Oct 2025

TUS-LAS

Very good

8.0 Very good

Greg, Oct 2025

OAK-BUR

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 Very good

Margaret, Oct 2025

SAV-HOU

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 Very good

TODD, Oct 2025

CMH-HOU

Tried watching free movie and it kept freezing so I couldn’t finish.

10.0 Wonderful

Antonio, Oct 2025

PVD-MCO

Always reliable

10.0 Wonderful

Verified traveler, Oct 2025

MDW-BWI

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

4.0 Mediocre

Mike, Oct 2025

GRR-MDW

Staff/crew very good. 4 hour delay not good.

10.0 Wonderful

Stacy, Oct 2025

SMF-DEN

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Everything you need to know for your flight from Washington, D.C. to Milwaukee

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Cabin class types available on flights to Milwaukee

First Class flights from Washington, D.C. to Milwaukee

Business Class flights from Washington, D.C. to Milwaukee

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WAS - MKE

$136 Find Cheap Southwest Flights from Washington, D.C. to Milwaukee

Search hundreds of travel sites at once for deals on Southwest flights from Washington, D.C. to Milwaukee

Cheap Southwest Flight Deals from Washington, D.C. to Milwaukee

Recent round-trip Southwest flight deals from Washington, D.C. to Milwaukee

Recent one-way Southwest flight deals from Washington, D.C. to Milwaukee

Recent last minute Southwest flight deals from Washington, D.C. to Milwaukee

Recent direct Southwest flight deals from Washington, D.C. to Milwaukee

Good to know

When to Book Flights with Southwest from Washington, D.C. to Milwaukee

FAQs for flying to Milwaukee with Southwest

Is Southwest the cheapest airline to fly with from Washington, D.C. to Milwaukee?

What is the cheapest Southwest flight from Washington, D.C. to Milwaukee?

Does Southwest fly direct to Milwaukee from Washington, D.C.?

What’s the cheapest day of the week to fly from Washington, D.C. to Milwaukee with Southwest?

What’s the cheapest month to fly from Washington, D.C. to Milwaukee with Southwest?

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Everything you need to know for your flight from Washington, D.C. to Milwaukee

Cabin class types available on flights to Milwaukee

Cabin classes available on flights to Washington, D.C.. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Milwaukee with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.