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$212+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
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 San José Juan Santamaria Intl to Milwaukee-Mitchell are usually found in January or April, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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 December 2, 2025.

This Delta deal was found by Cheapflights users on 12/1. 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.
Tue 12/237:00 amSJO - MKE
1 stop13h 17mDelta
Fri 1/27:25 amMKE - SJO
1 stop14h 30mDelta
Deal found 12/1$497
This United Airlines deal was found by Cheapflights users on 11/30. 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 12/266:30 amSJO - MKE
1 stop16h 15mUnited Airlines
Fri 1/97:50 amMKE - SJO
1 stop10h 26mUnited Airlines
Deal found 11/30$506
This eDestinos deal was found by Cheapflights users on 12/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:52 pmSJO - MKE
2 stops50h 29mFrontier
Fri 1/210:48 amMKE - SJO
2 stops22h 33mFrontier
Deal found 12/2$529
This American Airlines deal was found by Cheapflights users on 11/30. 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 12/2312:34 amSJO - MKE
1 stop21h 22mAmerican Airlines
Tue 12/307:45 amMKE - SJO
1 stop12h 29mAmerican Airlines
Deal found 11/30$536
This American Airlines deal was found by Cheapflights users on 12/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2212:34 amSJO - MKE
1 stop10h 29mAmerican Airlines
Fri 1/27:52 amMKE - SJO
1 stop12h 22mAmerican Airlines
Deal found 12/2$540
This United Airlines deal was found by Cheapflights users on 12/1. 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.
Tue 12/211:28 pmSJO - MKE
2 stops15h 40mUnited Airlines
Tue 12/96:00 amMKE - SJO
2 stops14h 39mUnited Airlines
Deal found 12/1$544
This United Airlines deal was found by Cheapflights users on 12/2. 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.
Sat 12/206:30 amSJO - MKE
1 stop16h 15mUnited Airlines
Sat 1/38:30 amMKE - SJO
2 stops28h 45mUnited Airlines
Deal found 12/2$548

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 December 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$353
(Kiwi.com)

One-way from

$212
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$511
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. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 2, 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

Thu 2/19

12:35 pm-6:45 pm

1 stop30h 10m

Milwaukee-Mitchell

Mon 2/23

7:40 pm-11:40 am

1 stop16h 00m

$396

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 2/22

12:35 pm-9:53 am

2 stops21h 18m

Milwaukee-Mitchell

Mon 2/23

7:40 pm-11:40 am

1 stop16h 00m

$419

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 2/22

12:35 pm-9:53 am

2 stops21h 18m

Milwaukee-Mitchell

Sat 2/28

6:02 pm-11:40 am

1 stop17h 38m

$420

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 2/19

1:45 pm-10:40 pm

1 stop8h 55m

Milwaukee-Mitchell

Wed 2/25

5:30 am-7:30 pm

2 stops14h 00m

$464

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 1/14

6:30 am-10:34 am

2 stops28h 04m

Milwaukee-Mitchell

Wed 1/21

2:32 pm-12:56 pm

1 stop22h 24m

$476

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 2/19

7:00 am-5:34 pm

1 stop10h 34m

Milwaukee-Mitchell

Wed 2/25

7:05 am-10:02 pm

1 stop14h 57m

$476

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 2/17

11:28 pm-2:05 pm

2 stops14h 37m

Milwaukee-Mitchell

Sun 2/22

8:00 am-6:16 pm

1 stop10h 16m

$476

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 2/20

7:00 am-11:48 pm

1 stop16h 48m

Milwaukee-Mitchell

Wed 2/25

7:05 am-10:02 pm

1 stop14h 57m

$476

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 2/18

11:28 pm-10:58 am

1 stop11h 30m

Milwaukee-Mitchell

Wed 2/25

5:00 am-8:39 pm

2 stops15h 39m

$476

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 2/17

11:28 pm-10:58 am

1 stop11h 30m

Milwaukee-Mitchell

Tue 2/24

8:00 am-6:16 pm

1 stop10h 16m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 21 results
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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 December.
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 November 28, 2025.

To ensure you get the cheapest price possible for a flight from San José to Milwaukee, you should look to book at least 42 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 $195). Flying from San José to Milwaukee in December 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.

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 December 2, 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.

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 December 2, 2025.
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
9,063 reviews

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

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
9,063 reviews
United Airlines
7.4
Good
9,063 reviews

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

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
11,044 reviews
United Airlines
7.4
Good
9,063 reviews

Entertainment

7.1

Boarding

7.7

Crew

8.1

Comfort

7.3

Food

6.6

Overall

7.4

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 $464, Southwest can have you in Milwaukee from San José in 8h 55m. 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 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 Spirit Airlines. According to our data, you can fly for as low as $193. Users have also found prices from $228 and $248 on American Airlines and United Airlines, 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, October is the cheapest month in which you can book a flight from San José to Milwaukee (average of $195). Flying from San José to Milwaukee in December 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

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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 December 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$690FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$537FlexibilityNo cancel feeOn-time69%

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