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$252+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Apr 2 — Apr 91
Thu 4/2
Thu 4/9
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 March 3, 2026.

This United Airlines deal was found by Cheapflights users on 3/2. 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.
Fri 4/247:55 am
SJO
-
MKE
1 stop25h 15m
United Airlines
Wed 5/63:51 pm
MKE
-
SJO
1 stop21h 30m
United Airlines
Deal found 3/2$382
This Avianca deal was found by Cheapflights users on 2/27. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:05 am
SJO
-
MKE
2 stops11h 03m
Multiple Airlines
Sun 9/610:30 am
MKE
-
SJO
2 stops14h 10m
Multiple Airlines
Deal found 2/27$473
This Avianca deal was found by Cheapflights users on 2/27. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:05 am
SJO
-
MKE
2 stops12h 50m
Multiple Airlines
Sat 9/510:30 am
MKE
-
SJO
2 stops14h 10m
Multiple Airlines
Deal found 2/27$474
This United Airlines deal was found by Cheapflights users on 3/2. 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.
Fri 5/11:25 pm
SJO
-
MKE
2 stops22h 46m
United Airlines
Tue 5/55:56 pm
MKE
-
SJO
2 stops19h 25m
United Airlines
Deal found 3/2$479
This Avianca deal was found by Cheapflights users on 2/26. 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.
Tue 3/175:00 am
SJO
-
MKE
2 stops16h 45m
Multiple Airlines
Wed 4/2912:10 pm
MKE
-
SJO
2 stops12h 30m
Multiple Airlines
Deal found 2/26$503
This Southwest deal was found by Cheapflights users on 2/27. 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.
Fri 4/249:00 am
SJO
-
MKE
2 stops13h 00m
Southwest
Mon 4/278:00 am
MKE
-
SJO
2 stops12h 00m
Southwest
Deal found 2/27$517
This Faresmojo deal was found by Cheapflights users on 3/3. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:25 pm
SJO
-
MKE
1 stop9h 31m
JetBlue
Mon 5/116:43 pm
MKE
-
SJO
1 stop18h 21m
JetBlue
Deal found 3/3$540
This United Airlines deal was found by Cheapflights users on 2/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/231:25 pm
SJO
-
MKE
1 stop8h 30m
United Airlines
Tue 4/2812:10 pm
MKE
-
SJO
1 stop8h 27m
United Airlines
Deal found 2/27$546
This United Airlines deal was found by Cheapflights users on 2/28. 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.
Wed 6/312:30 am
SJO
-
MKE
1 stop8h 35m
United Airlines
Mon 6/85:56 pm
MKE
-
SJO
1 stop17h 15m
United Airlines
Deal found 2/28$555

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 March 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$382
(United Airlines)

One-way from

$252
(Delta)

Popular in

October

Cheapest in

April

Average price

$574
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. 8% potential increase in price ($51 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 March 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 March 3, 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

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 4/24

7:55 am-10:10 am

1 stop25h 15m

Milwaukee-Mitchell

Wed 5/6

3:51 pm-12:21 pm

1 stop21h 30m

$382

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 5/1

1:25 pm-1:11 pm

2 stops22h 46m

Milwaukee-Mitchell

Tue 5/5

5:56 pm-12:21 pm

2 stops19h 25m

$479

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 3/17

7:45 am-10:45 pm

1 stop14h 00m

Milwaukee-Mitchell

Wed 4/29

12:10 pm-7:37 pm

1 stop8h 27m

$561

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 7/23

8:45 am-9:45 pm

1 stop12h 00m

Milwaukee-Mitchell

Thu 7/30

5:00 am-12:45 pm

1 stop8h 45m

$576

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 5/31

1:25 pm-11:08 am

2 stops20h 43m

Milwaukee-Mitchell

Sun 6/7

2:50 pm-10:11 am

2 stops20h 21m

$580

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 5/23

2:40 pm-11:59 pm

1 stop8h 19m

Milwaukee-Mitchell

Thu 8/27

5:55 am-11:56 am

1 stop7h 01m

$588

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 4/16

9:00 am-10:50 pm

1 stop12h 50m

$257

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 4/16

7:55 am-10:00 am

2 stops25h 05m

$263

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 4/15

12:20 pm-11:26 am

2 stops22h 06m

$274

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 4/7

11:13 am-10:10 am

1 stop21h 57m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/26

Showing 1-10 of 16 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 March.
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, May is the cheapest month in which you can book a flight from San José to Milwaukee (average of $188). Flying from San José to Milwaukee in July is currently the most expensive (average of $320). 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 March 3, 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
9,377 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
United Airlines
7.4
Good
9,377 reviews
United Airlines
7.4
Good
9,377 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats
American Airlines
7.1
Good
11,375 reviews
United Airlines
7.4
Good
9,377 reviews

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
6.0
Good

Gerry,Jan 2026

YVR - DEN

Seats were uncomfortable. Second leg of my flight on United had much more comfortable seats

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 $382, United Airlines can have you in Milwaukee from San José in 25h 15m. 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 26% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from San José to Milwaukee one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $218. Users have also found prices from $248 and $305 on United Airlines and Southwest, respectively.

  • 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, May is the cheapest month in which you can book a flight from San José to Milwaukee (average of $188). Flying from San José to Milwaukee in July is currently the most expensive (average of $320). 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
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 March 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$557FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$537FlexibilityNo cancel feeOn-time69%

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