$291+ 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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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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
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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
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Best
Last-minute
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Cheapest flights from San José to MilwaukeeExplore 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 2, 2026.
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 2, 2026.
This American Airlines deal was found by Cheapflights users on 6/28. 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 6/28![American Airlines logo]()
$519
This American Airlines deal was found by Cheapflights users on 6/28. 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 stops20h 51m
American Airlines
Mon 8/317:00 pm
MKE
- SJO
2 stops18h 03m
American Airlines
Deal found 6/28![American Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 6/30. 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 10/127:55 am
SJO
- MKE
1 stop13h 50m
United Airlines
Tue 10/206:40 pm
MKE
- SJO
1 stop17h 58m
United Airlines
Deal found 6/30![United Airlines logo]()
$548
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/1![American Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 6/27. 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 6/27![United Airlines logo]()
$567
This American Airlines deal was found by Cheapflights users on 6/27. 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 8/231:29 pm
SJO
- MKE
2 stops19h 22m
American Airlines
Mon 8/316:00 pm
MKE
- SJO
2 stops19h 03m
American Airlines
Deal found 6/27![American Airlines logo]()
$575
This United Airlines deal was found by Cheapflights users on 6/27. 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 7/2412:30 am
SJO
- MKE
2 stops11h 18m
United Airlines
Sat 8/85:00 am
MKE
- SJO
2 stops18h 39m
United Airlines
Deal found 6/27![United Airlines logo]()
$590
Best flights from San José to MilwaukeeDiscover carefully curated flight deals from San José to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from San José to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/1![American Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 6/30. 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 10/127:55 am
SJO
- MKE
1 stop13h 50m
United Airlines
Tue 10/206:40 pm
MKE
- SJO
1 stop17h 58m
United Airlines
Deal found 6/30![United Airlines logo]()
$548
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/297:15 am
SJO
- MKE
1 stop15h 19m
United Airlines
Wed 8/58:00 am
MKE
- SJO
1 stop29h 21m
United Airlines
Deal found 7/1![United Airlines logo]()
$548
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/277:15 am
SJO
- MKE
1 stop10h 11m
United Airlines
Thu 7/3010:28 am
MKE
- SJO
2 stops24h 43m
United Airlines
Deal found 6/30![United Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 6/27. 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 7/2512:44 pm
SJO
- MKE
1 stop9h 50m
United Airlines
Sat 8/85:00 am
MKE
- SJO
1 stop7h 55m
United Airlines
Deal found 6/27![United Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 6/29. 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 12/222:05 pm
SJO
- MKE
1 stop8h 34m
United Airlines
Sun 1/36:00 am
MKE
- SJO
2 stops14h 39m
United Airlines
Deal found 6/29![United Airlines logo]()
$590
Last-minute flights from San José to MilwaukeeDiscover last-minute flight deals from San José to Milwaukee. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Milwaukee. Data last updated July 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/27. 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 7/2412:30 am
SJO
- MKE
2 stops11h 18m
United Airlines
Sat 8/85:00 am
MKE
- SJO
2 stops18h 39m
United Airlines
Deal found 6/27![United Airlines logo]()
$590
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Mon 7/276:00 am
SJO
- MKE
2 stops16h 44m
American Airlines
Thu 7/3012:09 pm
MKE
- SJO
1 stop11h 29m
American Airlines
Deal found 6/30![American Airlines logo]()
$603
This United Airlines deal was found by Cheapflights users on 7/1. 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 7/297:15 am
SJO
- MKE
1 stop15h 19m
United Airlines
Wed 8/58:00 am
MKE
- SJO
1 stop29h 21m
United Airlines
Deal found 7/1![United Airlines logo]()
$548
This American Airlines deal was found by Cheapflights users on 6/27. 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 8/132:56 pm
SJO
- MKE
2 stops19h 41m
American Airlines
Sun 8/166:48 pm
MKE
- SJO
2 stops18h 38m
American Airlines
Deal found 6/27![American Airlines logo]()
$519
This American Airlines deal was found by Cheapflights users on 6/28. 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 stops20h 51m
American Airlines
Mon 8/317:00 pm
MKE
- SJO
2 stops18h 03m
American Airlines
Deal found 6/28![American Airlines logo]()
$527
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/1![American Airlines logo]()
$561
This American Airlines deal was found by Cheapflights users on 6/27. 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 8/231:29 pm
SJO
- MKE
2 stops19h 22m
American Airlines
Mon 8/316:28 am
MKE
- SJO
1 stop6h 58m
American Airlines
Deal found 6/27![American Airlines logo]()
$575
This American Airlines deal was found by Cheapflights users on 6/28. 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 8/231:29 pm
SJO
- MKE
2 stops19h 22m
American Airlines
Sun 9/64:25 pm
MKE
- SJO
2 stops20h 38m
American Airlines
Deal found 6/28![American Airlines logo]()
$609
One-way flights from San José to MilwaukeeSearch for one-way flight options from San José to Milwaukee. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from San José to Milwaukee. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This American Airlines deal was found by Cheapflights users on 6/28. 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 9/181:00 pm
SJO
- MKE
1 stop26h 53m
American Airlines
Deal found 6/28![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 6/30. 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 9/111:00 pm
SJO
- MKE
1 stop26h 53m
American Airlines
Deal found 6/30![American Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 7/1. 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 9/41:25 pm
SJO
- MKE
2 stops32h 11m
United Airlines
Deal found 7/1![United Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 6/28. 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.
Mon 8/246:00 am
SJO
- MKE
2 stops16h 14m
American Airlines
Deal found 6/28![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 6/28. 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 8/231:29 pm
SJO
- MKE
2 stops19h 22m
American Airlines
Deal found 6/28![American Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/161:25 pm
SJO
- MKE
1 stop8h 20m
United Airlines
Deal found 6/30![United Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/177:55 am
SJO
- MKE
2 stops22h 05m
United Airlines
Deal found 6/30![United Airlines logo]()
$369
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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $519 (American Airlines) |
One-way from | $291 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $655 |
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 2, 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
Cheapest round-trip
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 10/22
3:01 pm-11:12 am
2 stops19h 11m
Milwaukee-Mitchell
Mon 11/2
6:48 pm-12:09 pm
2 stops17h 21m
$519
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 10/12
7:55 am-10:45 pm
1 stop13h 50m
Milwaukee-Mitchell
Tue 10/20
6:40 pm-11:38 am
1 stop17h 58m
$548
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Wed 7/29
7:15 am-11:34 pm
1 stop15h 19m
Milwaukee-Mitchell
Wed 8/5
8:00 am-12:21 pm
1 stop29h 21m
$548
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 7/27
7:15 am-6:26 pm
1 stop10h 11m
Milwaukee-Mitchell
Thu 7/30
10:28 am-10:11 am
2 stops24h 43m
$590
Quickest round-trip
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sat 7/25
12:44 pm-11:34 pm
1 stop9h 50m
Milwaukee-Mitchell
Sat 8/8
5:00 am-11:55 am
1 stop7h 55m
$590
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Tue 12/22
2:05 pm-10:39 pm
1 stop8h 34m
Milwaukee-Mitchell
Sun 1/3
6:00 am-8:39 pm
2 stops14h 39m
$590
Cheapest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 9/18
1:00 pm-4:53 pm
1 stop26h 53m
$291
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 9/11
1:00 pm-11:07 am
2 stops21h 07m
$296
Quickest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sat 9/5
7:55 am-9:00 pm
2 stops12h 05m
$325
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 9/4
1:25 pm-5:09 pm
1 stop26h 44m
$325
Showing 1-10 of 11 resultsSorted by cheapest first
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.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
SJO-MKE
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 2, 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.
Crew
7.9
Entertainment
6.8
Boarding
7.5
Food
6.4
Overall
7.1
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
Crew
7.9
Entertainment
6.8
Boarding
7.5
Food
6.4
Overall
7.1
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
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.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
Port Washington
New Berlin
Oak Creek
Wauwatosa
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Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 2, 2026.
San José and Milwaukee flights
Browse other San José and Milwaukee flight options. Last updated on July 2, 2026.
Other flights from San José
Browse through other flights departing from San José. Flights are based on user searches made on Cheapflights and were last updated on July 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$541 | FlexibilityNo cancel fee | On-time71% |