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San José

$138+ Cheap flights from Milwaukee (MKE) to San José (SJO)

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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJO
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Milwaukee-Mitchell to San José Juan Santamaria Intl are usually found in September or August, booked 40 days in advance, depart on a Tuesday or Friday and return on a Tuesday

Find flight deals from Milwaukee to San José

Cheapest flights from Milwaukee to San José
Explore the most affordable flight options available from Milwaukee to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:15 pmMKE - SJO
1 stop15h 27mMultiple Airlines
Fri 1/92:58 pmSJO - MKE
2 stops28h 16mMultiple Airlines
Deal found 11/24$374
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:34 amMKE - SJO
1 stop25h 08mMultiple Airlines
Thu 12/1812:39 pmSJO - MKE
1 stop29h 47mMultiple Airlines
Deal found 11/24$390
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:34 amMKE - SJO
1 stop25h 08mMultiple Airlines
Thu 12/1812:39 pmSJO - MKE
1 stop29h 47mMultiple Airlines
Deal found 11/24$396
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:09 pmMKE - SJO
1 stop17h 33mMultiple Airlines
Thu 12/181:31 pmSJO - MKE
2 stops28h 55mMultiple Airlines
Deal found 11/24$417
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:09 pmMKE - SJO
1 stop17h 33mMultiple Airlines
Thu 12/1112:39 pmSJO - MKE
1 stop28h 30mMultiple Airlines
Deal found 11/26$418
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:34 amMKE - SJO
1 stop25h 08mSpirit Airlines
Wed 12/1712:39 pmSJO - MKE
1 stop30h 41mSpirit Airlines
Deal found 11/24$419
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:34 amMKE - SJO
1 stop25h 08mSpirit Airlines
Thu 12/1112:39 pmSJO - MKE
1 stop21h 00mSpirit Airlines
Deal found 11/25$424
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/810:34 amMKE - SJO
1 stop25h 08mSpirit Airlines
Wed 12/1712:39 pmSJO - MKE
1 stop30h 41mSpirit Airlines
Deal found 11/24$425

Cheap flight deals from Milwaukee to San José

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to San José (SJO). 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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$352
(American Airlines)

One-way from

$138
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$732
Provider with most accurate pricing for Milwaukee-Mitchell-San José Juan Santamaria Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-San José Juan Santamaria Intl flights.
Search Deals
From Milwaukee-Mitchell to San José Juan Santamaria Intl
Search Deals
One-way flight from Milwaukee-Mitchell to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to San José 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 November 26, 2025.
Use the filters below to find and compare flights from Milwaukee to San José that are best for you.

Fly from

Milwaukee

Fly to

San José

Route

Depart

Return

Price

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Mon 2/9

12:17 pm-10:15 pm

1 stop9h 58m

San José Juan Santamaria Intl

Mon 2/16

7:00 am-2:50 pm

1 stop7h 50m

$377

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Sat 1/31

9:30 am-10:30 pm

1 stop13h 00m

San José Juan Santamaria Intl

Sat 2/7

6:38 am-10:02 pm

2 stops15h 24m

$406

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 2/17

1:35 pm-10:02 pm

1 stop8h 27m

San José Juan Santamaria Intl

Tue 2/24

7:00 am-8:13 pm

1 stop13h 13m

$437

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Thu 2/19

12:20 pm-10:02 pm

1 stop9h 42m

San José Juan Santamaria Intl

Tue 2/24

7:00 am-5:34 pm

1 stop10h 34m

$462

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 12/9

3:17 pm-10:20 pm

1 stop7h 03m

San José Juan Santamaria Intl

Wed 12/17

7:00 am-4:16 pm

1 stop9h 16m

$468

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 12/9

3:17 pm-10:20 pm

1 stop7h 03m

San José Juan Santamaria Intl

Fri 12/19

2:31 pm-11:54 pm

1 stop9h 23m

$499

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Tue 12/2

10:25 am-10:20 pm

1 stop11h 55m

San José Juan Santamaria Intl

Thu 12/11

7:00 am-11:54 pm

1 stop16h 54m

$516

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Mon 12/8

5:45 am-10:20 pm

1 stop16h 35m

San José Juan Santamaria Intl

Mon 12/15

7:00 am-11:54 pm

1 stop16h 54m

$519

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Fri 1/30

3:59 pm-6:59 am

2 stops15h 00m

San José Juan Santamaria Intl

Sat 2/7

8:25 am-11:46 pm

2 stops15h 21m

$526

MilwaukeeSan José

MKE - SJO

MKESJO

Milwaukee-Mitchell

Wed 12/31

8:15 pm-11:42 am

1 stop15h 27m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 19 results
1
2

Compare providers for flights from Milwaukee to San José

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 Milwaukee to San José in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 Milwaukee-San José flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-San José flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Milwaukee-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-San José flights, Cheapflights users trust eDreams the most. eDreams 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 Milwaukee-San José 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 Milwaukee to San José

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

How far ahead should I book a flight from Milwaukee to San José?

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to San José. Price data was last updated on November 21, 2025.

The best time to book flights from Milwaukee to San José is 40 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, October is the cheapest month in which you can book a flight from Milwaukee to San José (average of $248). Flying from Milwaukee to San José in March is currently the most expensive (average of $364). 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.

What is the cheapest time of day to fly from MKE to SJO?

Find hourly flight availability from Milwaukee to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 26, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 65% on flights from Milwaukee to San José by exploring options for tickets in the afternoon.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated November 26, 2025.
Read through reviews of airlines operating flights from Milwaukee to San José, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,003 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,050 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,037 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,156 reviews
Southwest
8.0
Very good
4,254 reviews

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    For as low as $377, Delta can have you in San José from Milwaukee in 9h 58m. There are 2286 mi between Milwaukee and San José. This flight may include one or multiple stops.

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

    According to our current data, Spirit Airlines ($292), Delta ($385), and Southwest ($426) offers the cheapest pricing from Milwaukee to San José. You may be able to fly from Milwaukee to San José for 54% less than the average price by searching for these airlines.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Milwaukee to San José (average of $248). Flying from Milwaukee to San José in March is currently the most expensive (average of $364). 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 San José?

Book flights to San José if you plan to visit one of these locations
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
Dominical

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Top 5 airlines flying from Milwaukee to San José

Discover the top 5 airlines that operate flights from Milwaukee to San José. 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$292Average$454FlexibilityNo cancel feeOn-time65%
DeltaCheapest$385Average$690FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$426Average$682FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$486Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$505Average$800FlexibilityNo cancel feeOn-time69%

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