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Find cheap Southwest flights to Milwaukee

RDU — MKE
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Find Southwest flight deals to Milwaukee

Cheapest Southwest flights from USA to Milwaukee
Explore the most affordable Southwest flight options available from USA to Milwaukee. Find the lowest fares with prices last updated on July 27, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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 8/255:25 am
BOS
-
MKE
2 stops6h 40m
Southwest
Sat 8/291:00 pm
MKE
-
BOS
1 stop4h 55m
Southwest
Deal found 7/23$242
This Southwest deal was found by Cheapflights users on 7/27. 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.
Wed 8/265:25 am
BOS
-
MKE
2 stops6h 40m
Southwest
Wed 9/26:40 am
MKE
-
BOS
2 stops8h 20m
Southwest
Deal found 7/27$247
This Southwest deal was found by Cheapflights users on 7/23. 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 8/131:15 pm
HOU
-
MKE
1 stop7h 30m
Southwest
Sun 8/168:40 am
MKE
-
HOU
1 stop7h 00m
Southwest
Deal found 7/23$259

Flights to Milwaukee with Southwest at a glance

Find detailed information about Southwest flights from USA to Milwaukee. Explore the options provided by Southwest to plan your journey from USA to Milwaukee. Data last updated July 27, 2026.

Popular in

March

Cheapest in

October

Average price

$405

Round-trip from

$237

One-way from

$119

Good one-way deal

$153 or less
Highest demand for flights to Milwaukee with Southwest; 3% potential price increase.
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Best time to find cheap flights to Milwaukee with Southwest; 1% potential price drop.
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Average price for flights to Milwaukee with Southwest (round-trip).
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Southwest
  • Southwest
  • 9/9-9/16
  • 2 total stops
  • 12h 10m total
  • USA to Milwaukee
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Southwest
  • Southwest
  • 10/7
  • 1 total stop
  • 7h 20m total
  • USA to Milwaukee
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Price to beat on a one-way flight from the United States to Milwaukee with Southwest.
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Cheapflights Insights

Find cheap Southwest flights to Milwaukee

How long is the flight to Milwaukee with Southwest?

On average, Southwest flights from the United States to Milwaukee take 2 hours 10 minutes. Flights to Milwaukee from other popular cities in the United States will vary in length. Below are a few examples of popular routes and their flight times.

Southwest weekly flight availability to Milwaukee

The most flights to Milwaukee operated by Southwest are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

When is the best time to book a flight to Milwaukee with Southwest?

The best time to book a flight to Milwaukee with Southwest is 77 days before departure. On average, fares are higher if you book 1 day before departure.

When is the cheapest time to fly to Milwaukee with Southwest?

Users looking for the cheapest Southwest fares to Milwaukee should consider flying on Tuesday evenings, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday at noon, when prices are usually at their highest.

FAQs about flights to Milwaukee with Southwest

  • Which airport do Southwest flights arrive at when travelling to Milwaukee?

    Southwest flights on this route tend to land at Milwaukee-Mitchell Airport.

  • Is Southwest the cheapest airline for a flight to Milwaukee?

    Flight prices will depend on many factors like date, time and cabin class so it is worth comparing flights before booking. Based on Cheapflights data the cheapest average return price for flights to Milwaukee tends to be with Sun Country Air.

  • Are there alternative airlines other than Southwest that fly to Milwaukee?

    Delta, American Airlines and United Airlines all fly to Milwaukee and offer an alternative to Southwest.

  • How much is a flight to Milwaukee with Southwest?

    The average price for a return flight with Southwest is $432; with a one-way flight around $266.

See more FAQs

Reviews of Southwest

See what Cheapflights users have to say about their Southwest experience.
Southwest
8.0
Very good
4,229 reviews
Overview

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Popular Southwest flights

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