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$204+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$388
(United Airlines)

One-way from

$204
(Mytrip)

Popular in

November

Cheapest in

January

Average price

$494
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. 21% potential increase in price ($167 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($65 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 18, 2025.

This United Airlines deal was found by Cheapflights users on 8/15. 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 9/197:55 amSJO - MKE
1 stop12h 16mUnited Airlines
Sun 9/217:15 pmMKE - SJO
2 stops25h 22mUnited Airlines
Deal found 8/15$388
This Expedia deal was found by Cheapflights users on 8/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/301:00 pmSJO - MKE
2 stops25h 43mJetBlue
Sat 10/44:38 pmMKE - SJO
2 stops20h 17mJetBlue
Deal found 8/17$429
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/47:55 amSJO - MKE
1 stop8h 18mUnited Airlines
Tue 9/95:54 pmMKE - SJO
1 stop26h 43mUnited Airlines
Deal found 8/17$433
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/2512:44 pmSJO - MKE
1 stop9h 40mUnited Airlines
Thu 10/28:00 amMKE - SJO
1 stop12h 37mUnited Airlines
Deal found 8/17$438
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2412:18 pmSJO - MKE
2 stops27h 21mSpirit Airlines
Sun 9/712:53 pmMKE - SJO
1 stop22h 34mSpirit Airlines
Deal found 8/16$464
This Expedia deal was found by Cheapflights users on 8/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/71:00 pmSJO - MKE
2 stops25h 43mJetBlue
Sat 9/204:38 pmMKE - SJO
2 stops20h 17mJetBlue
Deal found 8/17$466
This Delta deal was found by Cheapflights users on 8/16. 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.
Thu 11/207:00 amSJO - MKE
1 stop9h 17mDelta
Fri 12/52:45 pmMKE - SJO
1 stop7h 30mDelta
Deal found 8/16$480
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Mon 12/226:30 amSJO - MKE
2 stops15h 43mUnited Airlines
Sun 1/45:00 amMKE - SJO
2 stops17h 32mUnited Airlines
Deal found 8/17$501
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Thu 11/2010:08 amSJO - MKE
2 stops26h 43mMultiple Airlines
Fri 12/51:56 pmMKE - SJO
1 stop21h 31mMultiple Airlines
Deal found 8/17$511

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 August 18, 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 9/19

7:55 am-9:11 pm

1 stop12h 16m

Milwaukee-Mitchell

Sun 9/21

7:15 pm-7:37 pm

2 stops25h 22m

$388

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 9/30

1:00 pm-3:43 pm

2 stops25h 43m

Milwaukee-Mitchell

Sat 10/4

4:38 pm-11:55 am

2 stops20h 17m

$429

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 9/4

7:55 am-5:13 pm

1 stop8h 18m

Milwaukee-Mitchell

Tue 9/9

5:54 pm-7:37 pm

1 stop26h 43m

$433

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 9/5

7:55 am-3:09 pm

2 stops30h 14m

Milwaukee-Mitchell

Wed 9/10

8:00 am-12:26 pm

1 stop29h 26m

$433

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 9/25

12:44 pm-11:24 pm

1 stop9h 40m

Milwaukee-Mitchell

Thu 10/2

8:00 am-7:37 pm

1 stop12h 37m

$438

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 11/20

11:28 pm-1:58 pm

2 stops14h 30m

Milwaukee-Mitchell

Fri 12/5

3:50 pm-12:55 pm

2 stops21h 05m

$438

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 8/30

7:30 am-11:06 pm

1 stop14h 36m

$204

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 8/28

12:18 pm-4:39 pm

2 stops27h 21m

$230

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 8/30

12:18 pm-11:06 pm

3 stops33h 48m

$231

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 8/29

7:30 am-11:06 pm

1 stop14h 36m

$236

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 13 results
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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, San José Province 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 August 8, 2025.

The price you pay for your flight from San José, San José Province to Milwaukee may vary depending on when you book. For the best chance of a lower fare, look to book 15 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, February is the cheapest month in which you can book a flight from San José, San José Province to Milwaukee (average of $280). Flying from San José, San José Province to Milwaukee in June is currently the most expensive (average of $376). 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 August 18, 2025.

It’s optimal to fly from San José, San José Province to Milwaukee at noon. By choosing this option you can save up to 15% 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, San José Province 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 August 18, 2025.
Peruse reviews from past customers who have flown with Southwest, 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.
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,038 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

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

    Flying on Spirit Airlines is currently your cheapest option to Milwaukee, with prices starting at $251. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $350 and $382, respectively. You may be able to fly from San José, San José Province to Milwaukee for 59% less than the average price by searching for these airlines.

  • 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, San José Province to Milwaukee?

    Currently, February is the cheapest month in which you can book a flight from San José, San José Province to Milwaukee (average of $280). Flying from San José, San José Province to Milwaukee in June is currently the most expensive (average of $376). 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
Mequon
Oak Creek
Sheboygan
Wauwatosa

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Top 4 airlines flying from San José to Milwaukee

Discover the top 4 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$451FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$350Average$588FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$382Average$597FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$458Average$484FlexibilityNo cancel feeOn-time69%

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