HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Milwaukee

$269+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Aug 7 — Aug 141
Fri 8/7
Fri 8/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San José to Milwaukee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 July 8, 2026.

This United Airlines deal was found by Cheapflights users on 7/8. 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 10/161:25 pm
SJO
-
MKE
2 stops16h 42m
United Airlines
Mon 10/263:48 pm
MKE
-
SJO
2 stops28h 05m
United Airlines
Deal found 7/8$468
This American Airlines deal was found by Cheapflights users on 7/8. 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 10/223:01 pm
SJO
-
MKE
2 stops19h 11m
American Airlines
Mon 11/26:48 pm
MKE
-
SJO
2 stops17h 21m
American Airlines
Deal found 7/8$481
This American Airlines deal was found by Cheapflights users on 7/8. 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 10/163:01 pm
SJO
-
MKE
2 stops20h 07m
American Airlines
Tue 10/276:10 am
MKE
-
SJO
2 stops14h 55m
American Airlines
Deal found 7/8$491
This United Airlines deal was found by Cheapflights users on 7/8. 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 9/1912:44 pm
SJO
-
MKE
1 stop9h 53m
United Airlines
Wed 9/306:00 pm
MKE
-
SJO
1 stop26h 37m
United Airlines
Deal found 7/8$499
This Southwest deal was found by Cheapflights users on 7/8. 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.
Fri 10/169:00 am
SJO
-
MKE
1 stop7h 50m
Southwest
Mon 10/265:00 am
MKE
-
SJO
1 stop8h 35m
Southwest
Deal found 7/8$510
This United Airlines deal was found by Cheapflights users on 7/7. 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 10/207:55 am
SJO
-
MKE
1 stop8h 24m
United Airlines
Wed 10/216:32 pm
MKE
-
SJO
2 stops18h 06m
United Airlines
Deal found 7/7$513
This American Airlines deal was found by Cheapflights users on 7/7. 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
Fri 8/216:28 am
MKE
-
SJO
1 stop6h 58m
American Airlines
Deal found 7/7$516
This KAYAK deal was found by Cheapflights users on 7/8. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1612:44 pm
SJO
-
MKE
1 stop9h 53m
Copa Airlines
Tue 10/276:10 am
MKE
-
SJO
1 stop13h 43m
Copa Airlines
Deal found 7/8$526
This Faresmojo deal was found by Cheapflights users on 7/8. 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 8/147:15 am
SJO
-
MKE
1 stop15h 22m
JetBlue
Sun 8/167:05 pm
MKE
-
SJO
1 stop17h 33m
JetBlue
Deal found 7/8$572
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sun 7/2612:30 am
SJO
-
MKE
1 stop8h 35m
United Airlines
Sat 8/297:18 am
MKE
-
SJO
2 stops13h 19m
United Airlines
Deal found 7/3$590
This American Airlines deal was found by Cheapflights users on 7/8. 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 8/142:56 pm
SJO
-
MKE
2 stops20h 51m
American Airlines
Tue 8/257:00 am
MKE
-
SJO
1 stop7h 52m
American Airlines
Deal found 7/8$599

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 July 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$513
(United Airlines)

One-way from

$273
(American Airlines)

Popular in

June

Cheapest in

February

Average price

$655
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. 15% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 8, 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

Fri 10/16

12:44 pm-11:37 pm

1 stop9h 53m

Milwaukee-Mitchell

Tue 10/27

5:00 am-7:39 pm

2 stops15h 39m

$468

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 10/16

1:25 pm-7:07 am

2 stops16h 42m

Milwaukee-Mitchell

Mon 10/26

3:48 pm-6:53 pm

2 stops28h 05m

$468

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sat 9/19

12:44 pm-11:37 pm

1 stop9h 53m

Milwaukee-Mitchell

Wed 9/30

5:00 am-7:37 pm

2 stops15h 37m

$499
Quickest round-trip

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 12/25

7:00 am-5:45 pm

1 stop10h 45m

Milwaukee-Mitchell

Mon 1/18

5:55 am-12:45 pm

1 stop6h 50m

$590

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 7/27

12:30 am-10:05 am

1 stop8h 35m

Milwaukee-Mitchell

Wed 8/26

6:15 am-7:37 pm

2 stops14h 22m

$590

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 7/24

12:30 am-4:42 pm

2 stops15h 12m

Milwaukee-Mitchell

Thu 9/3

3:15 pm-7:37 pm

2 stops29h 22m

$590

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 7/27

12:30 am-12:48 pm

2 stops11h 18m

Milwaukee-Mitchell

Tue 8/25

7:18 am-8:19 pm

2 stops14h 01m

$590

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Mon 7/27

12:30 am-4:42 pm

2 stops15h 12m

Milwaukee-Mitchell

Thu 8/27

11:40 am-8:19 pm

1 stop9h 39m

$590

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Sun 7/26

12:30 am-5:06 pm

1 stop15h 36m

Milwaukee-Mitchell

Thu 9/3

3:15 pm-7:37 pm

2 stops29h 22m

$590
Cheapest one-way

San JoséMilwaukee

SJO - MKE

SJOMKE

San José Juan Santamaria Intl

Fri 9/11

7:55 am-6:55 pm

2 stops34h 00m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 14 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 July.
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, February is the cheapest month in which you can book a flight from San José to Milwaukee (average of $493). Flying from San José to Milwaukee in June is currently the most expensive (average of $798). 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 July 8, 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
11,783 reviews

Overall

7.1

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.8

Boarding

7.5

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
11,783 reviews
American Airlines
7.1
Good
11,783 reviews

Overall

7.1

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.8

Boarding

7.5

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 $513, United Airlines can have you in Milwaukee from San José in 8h 24m. 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 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 31% 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, February is the cheapest month in which you can book a flight from San José to Milwaukee (average of $493). Flying from San José to Milwaukee in June is currently the most expensive (average of $798). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 July 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$399Average$541FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights