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$268+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
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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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$294
(Kiwi.com)

One-way from

$268
(Kiwi.com)

Popular in

October

Cheapest in

January

Average price

$373
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. 9% potential increase in price ($58 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 January 2026
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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 January 15, 2026.

This United Airlines deal was found by Cheapflights users on 1/13. 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 2/52:05 pm
SJO
-
MKE
1 stop8h 51m
United Airlines
Sun 2/85:00 am
MKE
-
SJO
1 stop7h 56m
United Airlines
Deal found 1/13$419
This Avianca deal was found by Cheapflights users on 1/14. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:40 am
SJO
-
MKE
2 stops10h 26m
Multiple Airlines
Tue 9/110:20 am
MKE
-
SJO
2 stops14h 20m
Multiple Airlines
Deal found 1/14$452
This Southwest deal was found by Cheapflights users on 1/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:00 am
SJO
-
MKE
1 stop12h 50m
Southwest
Sun 4/1911:45 am
MKE
-
SJO
1 stop8h 15m
Southwest
Deal found 1/15$487
This United Airlines deal was found by Cheapflights users on 1/15. 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.
Mon 4/1311:13 am
SJO
-
MKE
1 stop21h 57m
United Airlines
Sun 4/195:10 am
MKE
-
SJO
2 stops30h 01m
United Airlines
Deal found 1/15$489
This Avianca deal was found by Cheapflights users on 1/14. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:40 am
SJO
-
MKE
2 stops10h 26m
Multiple Airlines
Sat 9/510:20 am
MKE
-
SJO
2 stops14h 20m
Multiple Airlines
Deal found 1/14$511
This Faresmojo deal was found by Cheapflights users on 1/14. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:25 pm
SJO
-
MKE
1 stop9h 02m
JetBlue
Mon 5/115:55 am
MKE
-
SJO
1 stop7h 09m
JetBlue
Deal found 1/14$521
This United Airlines deal was found by Cheapflights users on 1/14. 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 3/135:30 am
SJO
-
MKE
1 stop16h 15m
United Airlines
Tue 3/175:00 am
MKE
-
SJO
1 stop7h 56m
United Airlines
Deal found 1/14$523
This United Airlines deal was found by Cheapflights users on 1/14. 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 3/185:30 am
SJO
-
MKE
2 stops15h 20m
United Airlines
Sun 3/225:00 am
MKE
-
SJO
2 stops17h 32m
United Airlines
Deal found 1/14$530
This United Airlines deal was found by Cheapflights users on 1/13. 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 6/112:30 am
SJO
-
MKE
1 stop15h 24m
United Airlines
Mon 6/225:10 am
MKE
-
SJO
2 stops30h 01m
United Airlines
Deal found 1/13$549
This American Airlines deal was found by Cheapflights users on 1/14. 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.
Fri 3/136:00 am
SJO
-
MKE
1 stop13h 25m
American Airlines
Tue 3/176:20 am
MKE
-
SJO
1 stop16h 23m
American Airlines
Deal found 1/14$555

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 January 15, 2026.
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 2/5

2:05 pm-10:56 pm

1 stop8h 51m

Milwaukee-Mitchell

Sun 2/8

5:00 am-12:56 pm

1 stop7h 56m

$419

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 4/13

9:00 am-10:50 pm

1 stop12h 50m

Milwaukee-Mitchell

Sun 4/19

11:45 am-7:00 pm

1 stop8h 15m

$487

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 4/13

11:13 am-11:32 am

2 stops23h 19m

Milwaukee-Mitchell

Sun 4/19

7:50 am-12:21 pm

2 stops29h 31m

$489

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 5/8

1:25 pm-11:27 pm

1 stop9h 02m

Milwaukee-Mitchell

Mon 5/11

5:55 am-12:04 pm

1 stop7h 09m

$521

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 6/1

12:30 am-11:13 am

1 stop9h 43m

Milwaukee-Mitchell

Tue 6/23

5:40 pm-10:11 am

1 stop17h 31m

$523

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 3/13

5:30 am-10:45 pm

1 stop16h 15m

Milwaukee-Mitchell

Tue 3/17

5:00 am-11:56 am

1 stop7h 56m

$523

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 2/2

1:30 pm-5:58 pm

2 stops28h 28m

$268

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 2/1

1:30 pm-9:58 am

3 stops20h 28m

$279

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 4/8

7:55 am-9:49 pm

2 stops36h 54m

$292

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Wed 4/8

11:35 pm-11:00 am

1 stop10h 25m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 13 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 January.
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

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.

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 January 15, 2026.
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
9,164 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,164 reviews
United Airlines
7.4
Good
9,164 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,136 reviews
United Airlines
7.4
Good
9,164 reviews

Comfort

7.3

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 $419, United Airlines can have you in Milwaukee from San José in 8h 51m. 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 27% 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 American Airlines. According to our data, you can fly for as low as $218. Users have also found prices from $248 and $253 on United Airlines and Delta, 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$458Average$535FlexibilityNo cancel feeOn-time69%

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