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$210+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$410
(Kiwi.com)

One-way from

$210
(Kiwi.com)

Popular in

September

Cheapest in

January

Average price

$710
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. 3% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:22 pmSJO - MKE
1 stop24h 29mSpirit Airlines
Mon 12/81:56 pmMKE - SJO
1 stop21h 31mSpirit Airlines
Deal found 9/16$410
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Wed 10/111:37 amSJO - MKE
1 stop23h 21mSpirit Airlines
Sun 10/51:55 pmMKE - SJO
1 stop21h 46mSpirit Airlines
Deal found 9/17$412
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 11/1811:28 pmSJO - MKE
2 stops15h 39mUnited Airlines
Wed 11/263:49 pmMKE - SJO
2 stops19h 36mUnited Airlines
Deal found 9/15$417
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/182:31 pmSJO - MKE
1 stop9h 25mDelta
Tue 11/257:00 amMKE - SJO
1 stop15h 07mDelta
Deal found 9/15$418
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:22 amSJO - MKE
1 stop15h 09mAmerican Airlines
Tue 12/91:08 pmMKE - SJO
1 stop9h 20mAmerican Airlines
Deal found 9/16$426
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amSJO - MKE
2 stops16h 01mAmerican Airlines
Wed 12/108:53 amMKE - SJO
2 stops11h 56mAmerican Airlines
Deal found 9/15$430
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 11/228:45 amSJO - MKE
2 stops13h 58mUnited Airlines
Mon 11/245:52 pmMKE - SJO
2 stops17h 33mUnited Airlines
Deal found 9/15$438
This Delta deal was found by Cheapflights users on 9/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:00 amSJO - MKE
1 stop16h 56mDelta
Tue 11/257:00 amMKE - SJO
1 stop15h 07mDelta
Deal found 9/15$439

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 September 17, 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

Wed 11/19

11:28 pm-11:24 am

2 stops11h 56m

Milwaukee-Mitchell

Tue 11/25

5:52 pm-11:25 am

2 stops17h 33m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 12/5

7:00 am-11:56 pm

1 stop16h 56m

Milwaukee-Mitchell

Mon 12/8

5:45 am-1:06 pm

1 stop7h 21m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 12/5

7:00 am-8:18 pm

1 stop13h 18m

Milwaukee-Mitchell

Wed 12/10

7:00 am-10:12 pm

1 stop15h 12m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 11/18

11:28 pm-9:59 pm

2 stops22h 31m

Milwaukee-Mitchell

Tue 11/25

5:52 pm-11:25 am

2 stops17h 33m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 12/4

2:31 pm-11:56 pm

1 stop9h 25m

Milwaukee-Mitchell

Wed 12/10

11:38 am-10:12 pm

1 stop10h 34m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 11/21

11:28 pm-10:19 am

1 stop10h 51m

Milwaukee-Mitchell

Tue 11/25

5:52 pm-11:25 am

2 stops17h 33m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 12/3

2:31 pm-11:56 pm

1 stop9h 25m

Milwaukee-Mitchell

Tue 12/9

7:00 am-10:12 pm

1 stop15h 12m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 12/4

2:31 pm-11:56 pm

1 stop9h 25m

Milwaukee-Mitchell

Sun 12/7

3:17 pm-10:12 pm

1 stop6h 55m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Thu 11/20

7:00 am-8:18 pm

1 stop13h 18m

Milwaukee-Mitchell

Tue 11/25

7:00 am-10:07 pm

1 stop15h 07m

$417

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 11/16

2:20 pm-11:24 am

2 stops21h 04m

Milwaukee-Mitchell

Wed 11/26

5:13 pm-11:25 am

2 stops18h 12m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 20 results
1
2

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 September 12, 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 September 17, 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.

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 September 17, 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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

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 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, San José Province to Milwaukee?

    Airlines like United Airlines and Delta fly from San José, San José Province to Milwaukee in about 11h 56m. The time it takes to get you to your destination can typically vary by up to 5h. Airlines will cover a distance of 2286 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Southwest and American Airlines, with the lowest prices starting at $382 and $399, respectively. You may be able to fly from San José, San José Province to Milwaukee for 53% 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
Sheboygan
Oak Creek
New Berlin
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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$251Average$451FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$382Average$597FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$399Average$718FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$537FlexibilityNo cancel feeOn-time69%

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