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Find cheap Southwest flights to Milwaukee from $94

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Flights Deals

Cheap Southwest Flight Deals to Milwaukee

 
Here are some of the best deals found on KAYAK recently from Southwest 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.

Recent round-trip Southwest flight deals to Milwaukee

KAYAK's recommended round-trip Southwest deals departing in the coming months to Milwaukee.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
7:20 pm - 11:25 pmBOS-MKE
5h 05m1 stop
Southwest Logo
5:35 pm - 11:10 pmMKE-BOS
4h 35m1 stop
$207Southwest
Find Deal
Mon, Jun 30 - Tue, Jul 8
Southwest Logo
5:30 am - 9:40 amBOS-MKE
5h 10m1 stop
Southwest Logo
5:15 pm - 11:15 pmMKE-BOS
5h 00m1 stop
$227Southwest
Find Deal
Thu, May 29 - Fri, May 30
Southwest Logo
6:30 am - 6:30 pmSEA-MKE
10h 00m1 stop
Southwest Logo
7:45 am - 1:30 pmMKE-SEA
7h 45m1 stop
$231Southwest
Find Deal
Thu, Sep 18 - Sun, Sep 21
Southwest Logo
7:30 pm - 10:50 pmDEN-MKE
2h 20mnonstop
Southwest Logo
5:25 am - 7:00 amMKE-DEN
2h 35mnonstop
$237Southwest
Find Deal
Thu, May 22 - Mon, May 26
Southwest Logo
7:40 pm - 11:40 pmBOS-MKE
5h 00m1 stop
Southwest Logo
6:30 pm - 11:40 pmMKE-BOS
4h 10m1 stop
$242Southwest
Find Deal
Fri, Jul 11 - Sat, Jul 12
Southwest Logo
7:20 pm - 11:25 pmBOS-MKE
5h 05m1 stop
Southwest Logo
3:40 pm - 11:55 pmMKE-BOS
7h 15m1 stop
$247Southwest
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Fri, Jul 25 - Mon, Jul 28
Southwest Logo
6:55 pm - 11:00 pmBOS-MKE
5h 05m1 stop
Southwest Logo
7:45 am - 5:30 pmMKE-BOS
8h 45m1 stop
$252Southwest
Find Deal
Fri, Sep 12 - Sun, Sep 14
Southwest Logo
7:20 pm - 11:25 pmBOS-MKE
5h 05m1 stop
Southwest Logo
5:00 am - 3:40 pmMKE-BOS
9h 40m2 stops
$257Southwest
Find Deal
Mon, Jun 30 - Tue, Jul 8
Southwest Logo
9:25 am - 12:40 pmDEN-MKE
2h 15mnonstop
Southwest Logo
7:10 pm - 8:50 pmMKE-DEN
2h 40mnonstop
$257Southwest
Find Deal
Thu, May 29 - Thu, May 29
Southwest Logo
7:30 pm - 10:50 pmDEN-MKE
2h 20mnonstop
Southwest Logo
3:45 pm - 10:30 pmMKE-DEN
7h 45m1 stop
$262Southwest
Find Deal
Thu, May 22 - Sat, May 24
Useful Info

Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$94
Average price round-trip$325
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Boston to Milwaukee
(price for this month)

When to book flights with Southwest to Milwaukee

Average price per month
Flight prices as travel date approaches

FAQs for flying to Milwaukee with Southwest

  • Which other airlines fly to Milwaukee?

    Along with Southwest, you can also fly to Milwaukee with Air Wisconsin, Spirit Airlines, American Airlines, Delta, Delta, United Airlines, Spirit Airlines, Sun Country Air and Hawaiian Airlines.

  • How much is a flight to Milwaukee with Southwest?

    On average, Southwest flights to Milwaukee cost $180 one-way.

  • Which airport do Southwest flights to Milwaukee fly into?

    You’ll fly into Milwaukee-Mitchell Airport when flying to Milwaukee with Southwest.

Top tips for your flights to Milwaukee with Southwest

  • The cheapest flight to Milwaukee with Southwest found on KAYAK in the last 2 weeks departed from St. Louis and cost $127.

Southwest customer reviews

8.0
Very goodBased on 4,294 verified guest reviews
8.0Comfort
8.2Boarding
7.1Food
8.6Crew
7.6Entertainment
Pros +
Cons -
Show reviews that mention
Traveler rating:
Sort by:
K
8.0 Very good
Start drink service earlier. We were rushed.
J
8.0 Very good
It is southwest seat was ok. Not the most comfortable seat
H
6.0 Okay
They were more than 2 hours late.
H
10.0 Wonderful
Good
J
8.0 Very good
I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight
J
6.0 Okay
The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.
A
10.0 Wonderful
Plz don't take away free bags and free seating
D
6.0 Okay
The seats were a bit cramped and worn, but otherwise okay.
D
6.0 Okay
The seats were a bit cramped, but otherwise okay.
A
8.0 Very good
It departed late
Read more about Southwest

Everything you need to know for your flight to Milwaukee

Other airlines flying to Milwaukee

Flight deals from the most popular airlines with KAYAK users flying the route
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