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$219+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from San José Juan Santamaria Intl to Milwaukee-Mitchell are usually found in January or April, booked 15 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$433
(Kiwi.com)

One-way from

$219
(eDestinos)

Popular in

October

Cheapest in

January

Average price

$691
Provider with most accurate pricing for San José Juan Santamaria Intl-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for San José Juan Santamaria Intl-Milwaukee-Mitchell flights.
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From San José Juan Santamaria Intl to Milwaukee-Mitchell
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One-way flight from San José Juan Santamaria Intl to Milwaukee-Mitchell
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Highest demand for flights based on searches. 6% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:39 pmSJO - MKE
1 stop25h 28mMultiple Airlines
Fri 1/91:56 pmMKE - SJO
1 stop21h 31mMultiple Airlines
Deal found 10/28$433
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 12/2412:39 pmSJO - MKE
1 stop11h 02mMultiple Airlines
Sun 1/42:45 pmMKE - SJO
1 stop20h 57mMultiple Airlines
Deal found 10/26$452
This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:39 pmSJO - MKE
1 stop11h 02mMultiple Airlines
Sat 1/38:15 pmMKE - SJO
2 stops16h 10mMultiple Airlines
Deal found 10/26$470
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/2612:39 pmSJO - MKE
1 stop25h 28mMultiple Airlines
Fri 1/27:30 amMKE - SJO
1 stop28h 12mMultiple Airlines
Deal found 10/26$477

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 October 28, 2025.
Use the filters below to find and compare flights from San José to Milwaukee that are best for you.

Fly from

San José

Fly to

Milwaukee

Route

Depart

Return

Price

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 12/26

12:39 pm-2:07 pm

1 stop25h 28m

Milwaukee-Mitchell

Fri 1/9

1:56 pm-11:27 am

1 stop21h 31m

$433

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 12/24

12:39 pm-11:41 pm

1 stop11h 02m

Milwaukee-Mitchell

Sat 1/3

8:15 pm-12:25 pm

2 stops16h 10m

$470

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 3/31

7:55 am-3:04 pm

2 stops30h 09m

Milwaukee-Mitchell

Wed 4/15

8:29 am-8:19 pm

2 stops12h 50m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 3/25

10:28 pm-9:50 pm

2 stops22h 22m

Milwaukee-Mitchell

Wed 4/15

2:24 pm-10:11 am

2 stops20h 47m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 3/25

1:05 pm-10:30 am

1 stop20h 25m

Milwaukee-Mitchell

Wed 4/22

11:10 am-8:19 pm

1 stop10h 09m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 3/31

11:13 am-9:49 am

2 stops21h 36m

Milwaukee-Mitchell

Mon 4/20

2:00 pm-10:11 am

1 stop21h 11m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 3/31

11:13 am-3:04 pm

2 stops26h 51m

Milwaukee-Mitchell

Wed 4/22

7:00 am-7:37 pm

2 stops13h 37m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 3/31

7:55 am-3:04 pm

2 stops30h 09m

Milwaukee-Mitchell

Tue 4/21

8:00 am-7:37 pm

1 stop12h 37m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 3/25

1:05 pm-10:30 am

1 stop20h 25m

Milwaukee-Mitchell

Mon 4/20

3:53 pm-10:11 am

2 stops19h 18m

$480

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 3/25

1:05 pm-10:43 pm

1 stop8h 38m

Milwaukee-Mitchell

Tue 4/21

8:00 am-12:26 pm

1 stop29h 26m

$480

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 19 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on San José-Milwaukee flight deals on Cheapflights vs. eDreams >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 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 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

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

Use this chart to determine the optimal time to book a round-trip flight from San José to Milwaukee. Price data was last updated on October 24, 2025.

To ensure you get the cheapest price possible for a flight from San José to Milwaukee, you should look to book at least 15 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, October is the cheapest month in which you can book a flight from San José to Milwaukee (average of $196). Flying from San José to Milwaukee in March is currently the most expensive (average of $329). 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 SJO to MKE?

Find hourly flight availability from San José to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

It’s optimal to fly from San José to Milwaukee in the afternoon. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the morning.

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 October 28, 2025.
Peruse reviews from past customers who have flown with United Airlines, American Airlines, and Spirit 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
8,996 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,996 reviews
United Airlines
7.4
Good
8,996 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,033 reviews
United Airlines
7.4
Good
8,996 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
Spirit Airlines
6.3
Okay
8,112 reviews
United Airlines
7.4
Good
8,996 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 $480, United Airlines can have you in Milwaukee from San José in 30h 09m. Airlines will cover a distance of 2286 mi.

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

    Spirit Airlines, at $251, was found to be the cheapest airline from San José to Milwaukee.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Users have found that Spirit Airlines is 54% 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, October is the cheapest month in which you can book a flight from San José to Milwaukee (average of $196). Flying from San José to Milwaukee in March is currently the most expensive (average of $329). 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

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Top 3 airlines flying from San José to Milwaukee

Discover the top 3 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$451FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$399Average$690FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$484FlexibilityNo cancel feeOn-time69%

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