$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
Jul 22 — Jul 291
Round-trip
1 adult, Economy
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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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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 June 22, 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 June 22, 2026.
This Southwest deal was found by Cheapflights users on 6/18. 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.
Thu 10/159:00 am
SJO
- MKE
1 stop12h 20m
Southwest
Mon 10/265:00 am
MKE
- SJO
1 stop8h 00m
Southwest
Deal found 6/18![Southwest logo]()
$515
This United Airlines deal was found by Cheapflights users on 6/18. 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 10/157:55 am
SJO
- MKE
2 stops30h 16m
United Airlines
Sun 10/255:00 am
MKE
- SJO
2 stops30h 25m
United Airlines
Deal found 6/18![United Airlines logo]()
$516
This American Airlines deal was found by Cheapflights users on 6/18. 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 01m
American Airlines
Mon 11/27:03 pm
MKE
- SJO
2 stops17h 19m
American Airlines
Deal found 6/18![American Airlines logo]()
$519
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:29 pm
SJO
- MKE
1 stop8h 30m
American Airlines
Mon 8/316:28 am
MKE
- SJO
1 stop6h 58m
American Airlines
Deal found 6/20![American Airlines logo]()
$525
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:22 am
SJO
- MKE
1 stop15h 09m
American Airlines
Sun 11/296:48 pm
MKE
- SJO
2 stops17h 21m
American Airlines
Deal found 6/17![American Airlines logo]()
$529
This United Airlines deal was found by Cheapflights users on 6/17. 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 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 53m
United Airlines
Mon 11/27:00 pm
MKE
- SJO
2 stops16h 25m
United Airlines
Deal found 6/17![United Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 6/18. 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 6/18![American Airlines logo]()
$531
This United Airlines deal was found by Cheapflights users on 6/18. 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 9/231:25 pm
SJO
- MKE
2 stops21h 05m
United Airlines
Sun 9/277:18 am
MKE
- SJO
2 stops30h 03m
United Airlines
Deal found 6/18![United Airlines logo]()
$535
This American Airlines deal was found by Cheapflights users on 6/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:29 pm
SJO
- MKE
1 stop8h 30m
American Airlines
Tue 8/2512:28 pm
MKE
- SJO
1 stop26h 24m
American Airlines
Deal found 6/20![American Airlines logo]()
$538
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 June 22, 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 June 22, 2026.
This United Airlines deal was found by Cheapflights users on 6/20. 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.
Fri 9/41:25 pm
SJO
- MKE
2 stops28h 30m
United Airlines
Mon 9/146:00 pm
MKE
- SJO
1 stop19h 21m
United Airlines
Deal found 6/20![United Airlines logo]()
$553
This American Airlines deal was found by Cheapflights users on 6/21. 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
1 stop9h 28m
American Airlines
Mon 9/77:00 pm
MKE
- SJO
2 stops19h 52m
American Airlines
Deal found 6/21![American Airlines logo]()
$609
This United Airlines deal was found by Cheapflights users on 6/18. 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 7/2411:13 am
SJO
- MKE
2 stops20h 55m
United Airlines
Mon 7/273:11 pm
MKE
- SJO
2 stops20h 00m
United Airlines
Deal found 6/18![United Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/1412:30 am
SJO
- MKE
2 stops17h 18m
United Airlines
Sun 8/28:50 am
MKE
- SJO
2 stops26h 21m
United Airlines
Deal found 6/20![United Airlines logo]()
$716
This United Airlines deal was found by Cheapflights users on 6/19. 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 8/912:30 am
SJO
- MKE
1 stop21h 15m
United Airlines
Thu 8/136:15 am
MKE
- SJO
2 stops31h 06m
United Airlines
Deal found 6/19![United Airlines logo]()
$731
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/157:15 am
SJO
- MKE
2 stops22h 45m
United Airlines
Wed 7/226:20 am
MKE
- SJO
2 stops17h 19m
United Airlines
Deal found 6/21![United Airlines logo]()
$734
This United Airlines deal was found by Cheapflights users on 6/20. 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.
Sat 6/277:55 am
SJO
- MKE
2 stops13h 34m
United Airlines
Sat 7/117:23 pm
MKE
- SJO
2 stops28h 16m
United Airlines
Deal found 6/20![United Airlines logo]()
$808
Last-minute flights from San José to MilwaukeeDiscover last-minute flight deals from San José to Milwaukee. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Milwaukee. Data last updated June 22, 2026 and is based on user searches.
This KAYAK deal was found by Cheapflights users on 6/17. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:15 am
SJO
- MKE
1 stop15h 19m
Multiple Airlines
Mon 7/137:23 pm
MKE
- SJO
2 stops25h 14m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$749
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/1412:30 am
SJO
- MKE
2 stops17h 18m
United Airlines
Sun 8/28:50 am
MKE
- SJO
2 stops26h 21m
United Airlines
Deal found 6/19![United Airlines logo]()
$716
This American Airlines deal was found by Cheapflights users on 6/21. 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 7/152:11 pm
SJO
- MKE
1 stop8h 23m
American Airlines
Sun 8/27:01 am
MKE
- SJO
1 stop6h 59m
American Airlines
Deal found 6/21![American Airlines logo]()
$615
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/157:15 am
SJO
- MKE
2 stops22h 45m
United Airlines
Wed 7/226:20 am
MKE
- SJO
2 stops17h 19m
United Airlines
Deal found 6/21![United Airlines logo]()
$734
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/212:11 pm
SJO
- MKE
1 stop8h 23m
American Airlines
Tue 7/286:17 pm
MKE
- SJO
1 stop19h 43m
American Airlines
Deal found 6/19![American Airlines logo]()
$612
This United Airlines deal was found by Cheapflights users on 6/18. 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 7/2312:30 am
SJO
- MKE
1 stop21h 15m
United Airlines
Mon 7/271:30 pm
MKE
- SJO
2 stops21h 41m
United Airlines
Deal found 6/18![United Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 6/18. 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 7/277:55 am
SJO
- MKE
2 stops22h 05m
United Airlines
Thu 7/308:50 am
MKE
- SJO
2 stops26h 21m
United Airlines
Deal found 6/18![United Airlines logo]()
$590
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 June 22, 2026.
Search for one-way flight options from San José to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
This American Airlines deal was found by Cheapflights users on 6/18. 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 9/182:57 pm
SJO
- MKE
2 stops20h 51m
American Airlines
Deal found 6/18![American Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 6/19. 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 9/1812:44 pm
SJO
- MKE
1 stop9h 53m
United Airlines
Deal found 6/19![United Airlines logo]()
$292
This American Airlines deal was found by Cheapflights users on 6/21. 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 6/21![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/21. 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
1 stop9h 28m
American Airlines
Deal found 6/21![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 6/21. 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 8/241:29 pm
SJO
- MKE
1 stop23h 35m
American Airlines
Deal found 6/21![American Airlines logo]()
$338
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 June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $515 (Southwest) |
One-way from | $291 (American Airlines) |
Popular in | June |
Cheapest in | January |
Average price | $737 |
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 June 22, 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
Fri 9/4
1:25 pm-6:55 pm
2 stops28h 30m
Milwaukee-Mitchell
Mon 9/14
6:00 pm-12:21 pm
1 stop19h 21m
$553
Quickest round-trip
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sun 8/23
1:29 pm-11:57 pm
1 stop9h 28m
Milwaukee-Mitchell
Mon 9/7
7:00 pm-1:52 pm
2 stops19h 52m
$609
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 7/24
11:13 am-9:08 am
2 stops20h 55m
Milwaukee-Mitchell
Mon 7/27
3:11 pm-10:11 am
2 stops20h 00m
$647
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Tue 7/14
12:30 am-6:48 pm
2 stops17h 18m
Milwaukee-Mitchell
Sun 8/2
8:50 am-10:11 am
2 stops26h 21m
$716
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sun 8/9
12:30 am-10:45 pm
1 stop21h 15m
Milwaukee-Mitchell
Thu 8/13
6:15 am-12:21 pm
2 stops31h 06m
$731
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Wed 7/15
7:15 am-7:00 am
2 stops22h 45m
Milwaukee-Mitchell
Wed 7/22
6:20 am-10:39 pm
2 stops17h 19m
$734
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sat 6/27
7:55 am-10:29 pm
2 stops13h 34m
Milwaukee-Mitchell
Sat 7/11
7:23 pm-10:39 pm
2 stops28h 16m
$808
Cheapest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 9/18
12:44 pm-11:37 pm
1 stop9h 53m
$292
Quickest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sun 8/23
1:29 pm-11:57 pm
1 stop9h 28m
$334
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 8/24
1:29 pm-2:04 pm
1 stop23h 35m
$338
Showing 1-10 of 12 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 June.
| 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, 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 June is currently the most expensive (average of $737). 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 June 22, 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
Comfort
7.2
Food
6.4
Entertainment
6.8
Boarding
7.5
Overall
7.1
Reviews
1 / 20
10.0
ExcellentBeatriz,May 2026
HEL - DFW
Crew
7.9
Comfort
7.2
Food
6.4
Entertainment
6.8
Boarding
7.5
Overall
7.1
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 June 22, 2026.
San José and Milwaukee flights
Browse other San José and Milwaukee flight options. Last updated on June 22, 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 June 22, 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 June 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$541 | FlexibilityNo cancel fee | On-time71% |