Milwaukee

$298+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jun 22 — Jun 291
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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 23, 2026.

This United Airlines deal was found by Cheapflights users on 5/19. 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 9/241:25 pm
SJO
-
MKE
2 stops16h 42m
United Airlines
Mon 10/55:00 am
MKE
-
SJO
2 stops32h 21m
United Airlines
Deal found 5/19$506
This American Airlines deal was found by Cheapflights users on 5/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/222:45 pm
SJO
-
MKE
2 stops19h 47m
American Airlines
Mon 11/26:48 pm
MKE
-
SJO
2 stops17h 21m
American Airlines
Deal found 5/19$519
This United Airlines deal was found by Cheapflights users on 5/20. 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 11/26:00 am
MKE
-
SJO
2 stops30h 42m
United Airlines
Deal found 5/20$525
This American Airlines deal was found by Cheapflights users on 5/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:52 pm
SJO
-
MKE
2 stops19h 45m
American Airlines
Tue 9/86:46 pm
MKE
-
SJO
2 stops17h 19m
American Airlines
Deal found 5/19$530
This United Airlines deal was found by Cheapflights users on 5/19. 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 10/2910:28 pm
SJO
-
MKE
1 stop23h 59m
United Airlines
Mon 11/26:00 am
MKE
-
SJO
2 stops29h 25m
United Airlines
Deal found 5/19$544
This Avianca deal was found by Cheapflights users on 5/19. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:05 am
SJO
-
MKE
2 stops11h 03m
Multiple Airlines
Sat 10/38:00 am
MKE
-
SJO
2 stops11h 50m
Multiple Airlines
Deal found 5/19$546
This Southwest deal was found by Cheapflights users on 5/19. 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 9/19:00 am
SJO
-
MKE
1 stop11h 05m
Southwest
Tue 9/87:40 am
MKE
-
SJO
2 stops12h 00m
Southwest
Deal found 5/19$554
This United Airlines deal was found by Cheapflights users on 5/19. 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 9/241:25 pm
SJO
-
MKE
2 stops19h 35m
United Airlines
Fri 10/25:56 pm
MKE
-
SJO
1 stop19h 25m
United Airlines
Deal found 5/19$565
This Southwest deal was found by Cheapflights users on 5/19. 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 10/19:00 am
SJO
-
MKE
2 stops13h 05m
Southwest
Thu 10/85:00 am
MKE
-
SJO
1 stop8h 00m
Southwest
Deal found 5/19$573

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 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$506
(United Airlines)

One-way from

$298
(United Airlines)

Popular in

July

Cheapest in

January

Average price

$498
Provider with most accurate pricing for San José Juan Santamaria Intl-Milwaukee-Mitchell flight deals.
Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Milwaukee-Mitchell flights.
From San José Juan Santamaria Intl to Milwaukee-Mitchell
One-way flight from San José Juan Santamaria Intl to Milwaukee-Mitchell
Highest demand for flights based on searches. 6% potential increase in price ($34 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in May 2026

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 23, 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

Tue 10/13

12:44 pm-10:53 am

1 stop21h 09m

Milwaukee-Mitchell

Tue 10/20

10:41 am-7:37 pm

1 stop9h 56m

$506

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 10/22

7:55 am-7:07 am

2 stops22h 12m

Milwaukee-Mitchell

Mon 11/2

6:00 am-11:25 am

2 stops29h 25m

$525

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 9/24

12:44 pm-11:36 pm

1 stop9h 52m

Milwaukee-Mitchell

Sat 10/3

5:56 pm-12:21 pm

1 stop19h 25m

$565

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 9/24

12:44 pm-11:36 pm

1 stop9h 52m

Milwaukee-Mitchell

Fri 10/2

5:56 pm-12:21 pm

1 stop19h 25m

$565

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 9/1

9:00 am-9:05 pm

1 stop11h 05m

Milwaukee-Mitchell

Tue 9/8

6:05 am-12:45 pm

1 stop7h 40m

$568

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 10/1

9:00 am-10:20 pm

1 stop12h 20m

Milwaukee-Mitchell

Thu 10/8

5:00 am-12:00 pm

1 stop8h 00m

$568
Quickest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 9/26

1:25 pm-11:25 pm

1 stop9h 00m

Milwaukee-Mitchell

Sun 10/4

5:55 am-11:54 am

1 stop6h 59m

$578

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 10/29

10:28 pm-6:08 pm

1 stop18h 40m

Milwaukee-Mitchell

Mon 11/2

7:00 pm-11:25 am

2 stops16h 25m

$622

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 8/22

2:52 pm-12:47 pm

2 stops20h 55m

Milwaukee-Mitchell

Sat 9/5

4:12 pm-11:34 am

2 stops20h 22m

$623

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 8/23

5:45 am-7:07 am

2 stops24h 22m

Milwaukee-Mitchell

Sat 9/5

10:45 am-10:58 am

2 stops25h 13m

$684

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/19

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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 23, 2026.
Peruse reviews from past customers who have flown with 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.

Entertainment

6.9

Boarding

7.5

Crew

7.9

Food

6.4

Comfort

7.2

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

Entertainment

6.9

Boarding

7.5

Crew

7.9

Food

6.4

Comfort

7.2

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

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 $568, United Airlines can have you in Milwaukee from San José in 11h 05m. Airlines will cover a distance of 2286 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from San José to Milwaukee round-trip?

    American Airlines, at $399, was found to be the cheapest airline from San José to Milwaukee.. Users have found that American Airlines is 26% 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

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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.

Top airline flying from San José to Milwaukee

Discover the top airline 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 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$541FlexibilityNo cancel feeOn-time71%

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