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$243+ Cheap flights from San José (SJO) to Milwaukee (MKE)

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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
1 adult, Economy
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Cheap flight deals from San José to Milwaukee

Cheapest flights from San José to Milwaukee
Explore the most affordable flight options available from San José to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.

This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:44 pm
SJO
-
MKE
1 stop9h 52m
United Airlines
Sun 11/18:00 am
MKE
-
SJO
1 stop27h 25m
United Airlines
Deal found 5/2$457
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:44 pm
SJO
-
MKE
1 stop9h 52m
United Airlines
Mon 11/27:00 pm
MKE
-
SJO
2 stops18h 15m
United Airlines
Deal found 5/1$471
This United Airlines deal was found by Cheapflights users on 5/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:55 am
SJO
-
MKE
2 stops34h 56m
United Airlines
Sun 9/67:00 pm
MKE
-
SJO
2 stops18h 21m
United Airlines
Deal found 5/4$476
This United Airlines deal was found by Cheapflights users on 5/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/132:20 pm
SJO
-
MKE
2 stops23h 23m
United Airlines
Mon 3/16:10 am
MKE
-
SJO
1 stop13h 43m
United Airlines
Deal found 5/5$489
This Southwest deal was found by Cheapflights users on 5/2. 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 7/158:45 am
SJO
-
MKE
1 stop11h 05m
Southwest
Sun 8/25:00 am
MKE
-
SJO
1 stop7h 00m
Southwest
Deal found 5/2$518
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:20 pm
SJO
-
MKE
1 stop9h 39m
Delta
Thu 8/275:55 am
MKE
-
SJO
1 stop7h 01m
Delta
Deal found 5/1$520
This Ovago deal was found by Cheapflights users on 5/2. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:25 pm
SJO
-
MKE
2 stops19h 24m
Multiple Airlines
Mon 11/27:00 pm
MKE
-
SJO
2 stops16h 25m
Multiple Airlines
Deal found 5/2$521
This United Airlines deal was found by Cheapflights users on 5/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:30 am
SJO
-
MKE
1 stop8h 35m
United Airlines
Sat 6/68:00 am
MKE
-
SJO
1 stop15h 39m
United Airlines
Deal found 5/1$529

Find flight deals from San José to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$457
(United Airlines)

One-way from

$243
(CheapOair)

Popular in

July

Cheapest in

January

Average price

$494
Provider with most accurate pricing for San José Juan Santamaria Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Milwaukee-Mitchell flights.
Search Deals
From San José Juan Santamaria Intl to Milwaukee-Mitchell
Search Deals
One-way flight from San José Juan Santamaria Intl to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San José to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 5, 2026.
Use the filters below to find and compare flights from San José to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 9/3

1:25 pm-10:00 am

2 stops19h 35m

Milwaukee-Mitchell

Sun 9/6

7:00 pm-12:21 pm

2 stops18h 21m

$471

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 10/22

1:25 pm-9:49 am

2 stops19h 24m

Milwaukee-Mitchell

Mon 11/2

7:00 pm-11:25 am

2 stops16h 25m

$471
Quickest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 5/23

1:20 pm-11:59 pm

1 stop9h 39m

Milwaukee-Mitchell

Thu 8/27

5:34 am-11:49 am

1 stop7h 15m

$520

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 5/29

12:30 am-10:05 am

1 stop8h 35m

Milwaukee-Mitchell

Sat 6/6

8:00 am-10:39 pm

1 stop15h 39m

$529
Cheapest one-way

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 8/24

9:35 am-7:58 am

1 stop21h 23m

$243

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 6/5

7:55 am-10:45 pm

1 stop13h 50m

$258

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 5/28

7:55 am-11:19 am

2 stops26h 24m

$258
Quickest one-way

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 7/14

12:30 am-10:05 am

1 stop8h 35m

$258

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 9/10

9:00 am-8:45 pm

1 stop10h 45m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/5

Sorted by cheapest first

Compare providers for flights from San José to Milwaukee

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 San José to Milwaukee in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 San José-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San José-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San José-Milwaukee 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 San José-Milwaukee 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 San José to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from San José 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 San José to Milwaukee

What is the cheapest month to book a flight from San José to Milwaukee?

Currently, January is the cheapest month in which you can book a flight from San José to Milwaukee (average of $480). Flying from San José to Milwaukee in July is currently the most expensive (average of $655). 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.

How much does it cost to fly round-trip from San José to Milwaukee?

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated May 5, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from San José to Milwaukee to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,684 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
United Airlines
7.4
Good
9,684 reviews
United Airlines
7.4
Good
9,684 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.
American Airlines
7.1
Good
11,666 reviews
United Airlines
7.4
Good
9,684 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Apr 2026

DFW - EWR

The flight was on time. Crew was friendly. Will fly again. The seats was comfortable.

Related info for your journey

Find useful and relevant information for your journey from San José to Milwaukee. 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 San José to Milwaukee?

    For as low as $471, United Airlines can have you in Milwaukee from San José in 19h 35m. Airlines will cover a distance of 2286 mi.

  • What are the cheapest airlines flying from San José to Milwaukee round-trip?

    American Airlines, at $399, was found to be the cheapest airline from San José to Milwaukee. An alternate airline flying to your destination would be United Airlines. Users have found that American Airlines is 25% cheaper than the other options available to this destination.

  • Can I find deals for flights from San José to Milwaukee that include hotel bookings?

    Yes. In addition to deals on San José to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Milwaukee.

  • Can I find deals for business class flights from San José to Milwaukee?

    Yes. Cheapflights offers flight deals from San José to Milwaukee 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 San José to Milwaukee?

    Currently, January is the cheapest month in which you can book a flight from San José to Milwaukee (average of $480). Flying from San José to Milwaukee in July is currently the most expensive (average of $655). 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

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for San José to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
San José to O'Hare Intl flights
San José to Minneapolis flights
Liberia to Minneapolis flights
San José to Green Bay flights

Top 2 airlines flying from San José to Milwaukee

Discover the top 2 airlines that operate flights from San José to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$554FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$537FlexibilityNo cancel feeOn-time69%

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