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$286+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jun 24 — Jul 11
Wed 6/24
Wed 7/1
1 adult, Economy
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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 May 25, 2026.

This United Airlines deal was found by Cheapflights users on 5/20. 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 10/131:25 pm
SJO
-
MKE
2 stops24h 46m
United Airlines
Tue 10/208:00 am
MKE
-
SJO
1 stop12h 37m
United Airlines
Deal found 5/20$506
This United Airlines deal was found by Cheapflights users on 5/23. 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 9/17:55 am
SJO
-
MKE
2 stops30h 17m
United Airlines
Tue 9/86:00 pm
MKE
-
SJO
1 stop26h 37m
United Airlines
Deal found 5/23$516
This United Airlines deal was found by Cheapflights users on 5/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2212:44 pm
SJO
-
MKE
1 stop9h 52m
United Airlines
Mon 11/27:00 pm
MKE
-
SJO
2 stops16h 25m
United Airlines
Deal found 5/25$519
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Thu 10/222:45 pm
SJO
-
MKE
2 stops19h 47m
American Airlines
Mon 11/26:48 pm
MKE
-
SJO
2 stops17h 21m
American Airlines
Deal found 5/22$540
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/42:57 pm
SJO
-
MKE
2 stops20h 14m
American Airlines
Sat 10/104:26 pm
MKE
-
SJO
2 stops19h 39m
American Airlines
Deal found 5/24$592
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:56 pm
SJO
-
MKE
2 stops19h 41m
American Airlines
Mon 8/315:50 pm
MKE
-
SJO
2 stops19h 13m
American Airlines
Deal found 5/24$602
This United Airlines deal was found by Cheapflights users on 5/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:55 am
SJO
-
MKE
1 stop13h 50m
United Airlines
Wed 6/245:56 pm
MKE
-
SJO
1 stop29h 43m
United Airlines
Deal found 5/24$620
This American Airlines deal was found by Cheapflights users on 5/22. 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.
Sat 8/222:52 pm
SJO
-
MKE
2 stops20h 55m
American Airlines
Sat 9/54:12 pm
MKE
-
SJO
2 stops20h 22m
American Airlines
Deal found 5/22$623
This United Airlines deal was found by Cheapflights users on 5/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/232:05 pm
SJO
-
MKE
1 stop10h 04m
United Airlines
Thu 1/76:00 am
MKE
-
SJO
2 stops14h 39m
United Airlines
Deal found 5/24$625

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 May 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$506
(United Airlines)

One-way from

$286
(Mytrip)

Popular in

July

Cheapest in

January

Average price

$498
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. 6% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 25, 2026.
Use the filters below to find and compare flights from San José to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 10/13

1:25 pm-3:11 pm

2 stops24h 46m

Milwaukee-Mitchell

Tue 10/20

8:00 am-7:37 pm

1 stop12h 37m

$506

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 9/11

12:44 pm-11:30 am

2 stops21h 46m

Milwaukee-Mitchell

Wed 9/16

6:00 am-11:38 am

1 stop30h 38m

$506

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 7/20

11:13 am-7:00 am

2 stops18h 47m

Milwaukee-Mitchell

Wed 7/29

8:50 am-10:11 am

2 stops26h 21m

$625

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 11/20

2:20 pm-5:13 pm

2 stops26h 53m

Milwaukee-Mitchell

Tue 11/24

10:45 am-1:15 pm

2 stops26h 30m

$633
Quickest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 8/19

1:14 pm-11:53 pm

1 stop9h 39m

Milwaukee-Mitchell

Mon 8/24

5:34 am-11:49 am

1 stop7h 15m

$652

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 8/23

8:45 am-7:07 am

2 stops21h 22m

Milwaukee-Mitchell

Sat 9/5

10:44 am-8:19 am

2 stops22h 35m

$684

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 8/23

1:14 pm-11:53 pm

1 stop9h 39m

Milwaukee-Mitchell

Sun 9/6

5:34 am-11:49 am

1 stop7h 15m

$684

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 7/13

11:13 am-7:00 am

2 stops18h 47m

Milwaukee-Mitchell

Tue 7/21

8:00 am-10:11 am

1 stop27h 11m

$688
Cheapest one-way

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 6/24

7:55 am-10:45 pm

1 stop13h 50m

$313
Quickest one-way

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Tue 7/21

2:11 pm-11:34 pm

1 stop8h 23m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

Showing 1-10 of 15 resultsSorted by cheapest first
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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San José-Milwaukee flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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

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

Currently, January is the cheapest month in which you can book a flight from San José to Milwaukee (average of $480). Flying from San José to Milwaukee in July is currently the most expensive (average of $655). 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.

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 May 25, 2026.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.1
Good
11,626 reviews

Boarding

7.5

Entertainment

6.9

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.
American Airlines
7.1
Good
11,626 reviews
American Airlines
7.1
Good
11,626 reviews

Boarding

7.5

Entertainment

6.9

Crew

7.9

Comfort

7.2

Food

6.4

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

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 $506, United Airlines can have you in Milwaukee from San José in 24h 46m. Airlines will cover a distance of 2286 mi.

  • What is the cheapest airline to fly from San José to Milwaukee round-trip?

    American Airlines, at $399, was found to be the cheapest airline from San José to Milwaukee.. Users have found that American Airlines is 26% 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, January is the cheapest month in which you can book a flight from San José to Milwaukee (average of $480). Flying from San José to Milwaukee in July is currently the most expensive (average of $655). 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
Port Washington
New Berlin
Oak Creek
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for San José to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
San José to O'Hare Intl flights
San José to Minneapolis flights
Liberia to Minneapolis flights
San José to Green Bay flights

Top airline flying from San José to Milwaukee

Discover the top airline 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 May 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$541FlexibilityNo cancel feeOn-time71%

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