$194+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
May 17 — May 241
Round-trip
1 adult, Economy
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Find cheap flights from San José to Milwaukee with Cheapflights
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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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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 April 17, 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 April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:07 am
SJO
- MKE
1 stop23h 54m
Multiple Airlines
Fri 6/1912:08 pm
MKE
- SJO
2 stops21h 12m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$509
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/2111:13 am
SJO
- MKE
1 stop10h 32m
United Airlines
Mon 5/258:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/16![United Airlines logo]()
$536
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:00 am
SJO
- MKE
1 stop10h 45m
Southwest
Mon 8/315:35 am
MKE
- SJO
1 stop8h 10m
Southwest
Deal found 4/13![Southwest logo]()
$542
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/812:35 pm
SJO
- MKE
1 stop21h 55m
American Airlines
Mon 5/116:42 pm
MKE
- SJO
1 stop17h 53m
American Airlines
Deal found 4/14![American Airlines logo]()
$547
This Southwest deal was found by Cheapflights users on 4/16. 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.
Tue 8/189:00 am
SJO
- MKE
2 stops10h 30m
Southwest
Mon 8/315:35 am
MKE
- SJO
1 stop8h 10m
Southwest
Deal found 4/16![Southwest logo]()
$555
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 April 17, 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 April 17, 2026.
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/2111:13 am
SJO
- MKE
1 stop10h 32m
United Airlines
Mon 5/258:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/16![United Airlines logo]()
$536
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:00 am
SJO
- MKE
1 stop10h 45m
Southwest
Mon 8/315:35 am
MKE
- SJO
1 stop8h 10m
Southwest
Deal found 4/13![Southwest logo]()
$542
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:20 pm
SJO
- MKE
1 stop9h 33m
Delta
Thu 8/135:55 am
MKE
- SJO
1 stop7h 01m
Delta
Deal found 4/16![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 4/13. 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.
Sat 5/167:55 am
SJO
- MKE
2 stops39h 04m
United Airlines
Mon 6/15:29 pm
MKE
- SJO
2 stops17h 42m
United Airlines
Deal found 4/13![United Airlines logo]()
$605
This Delta deal was found by Cheapflights users on 4/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:20 pm
SJO
- MKE
1 stop9h 39m
Delta
Thu 8/275:55 am
MKE
- SJO
1 stop7h 01m
Delta
Deal found 4/15![Delta logo]()
$651
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 5/141:25 pm
SJO
- MKE
2 stops27h 07m
United Airlines
Thu 8/135:05 am
MKE
- SJO
2 stops39h 32m
United Airlines
Deal found 4/15![United Airlines logo]()
$617
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Sat 5/3012:30 am
SJO
- MKE
2 stops19h 16m
United Airlines
Sun 6/78:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/14![United Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Thu 5/2811:13 am
SJO
- MKE
2 stops22h 55m
United Airlines
Sun 5/318:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/14![United Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Fri 5/2912:30 am
SJO
- MKE
2 stops12h 44m
United Airlines
Sat 6/610:46 am
MKE
- SJO
1 stop12h 53m
United Airlines
Deal found 4/15![United Airlines logo]()
$665
Last-minute flights from San José to MilwaukeeDiscover last-minute flight deals from San José to Milwaukee. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Milwaukee. Data last updated April 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:00 am
SJO
- MKE
1 stop25h 01m
Multiple Airlines
Fri 5/1512:09 pm
MKE
- SJO
2 stops28h 09m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$587
This American Airlines deal was found by Cheapflights users on 4/14. 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 5/812:35 pm
SJO
- MKE
1 stop21h 55m
American Airlines
Mon 5/116:42 pm
MKE
- SJO
1 stop17h 53m
American Airlines
Deal found 4/14![American Airlines logo]()
$547
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 am
SJO
- MKE
1 stop25h 01m
Multiple Airlines
Mon 6/112:09 pm
MKE
- SJO
2 stops28h 02m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/2111:13 am
SJO
- MKE
1 stop10h 32m
United Airlines
Mon 5/258:00 am
MKE
- SJO
1 stop15h 39m
United Airlines
Deal found 4/16![United Airlines logo]()
$536
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 April 17, 2026.
Search for one-way flight options from San José to Milwaukee. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Priceline deal was found by Cheapflights users on 4/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/69:35 am
SJO
- MKE
1 stop21h 26m
Frontier
Deal found 4/15![Frontier logo]()
$194
This Priceline deal was found by Cheapflights users on 4/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/89:35 am
SJO
- MKE
1 stop21h 23m
Frontier
Deal found 4/13![Frontier logo]()
$231
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/141:25 pm
SJO
- MKE
1 stop8h 34m
United Airlines
Deal found 4/16![United Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/137:55 am
SJO
- MKE
2 stops28h 16m
United Airlines
Deal found 4/16![United Airlines logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:00 am
SJO
- MKE
1 stop25h 01m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$268
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:00 am
SJO
- MKE
1 stop10h 45m
Southwest
Deal found 4/14![Southwest logo]()
$295
This Expedia deal was found by Cheapflights users on 4/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:40 pm
SJO
- MKE
2 stops18h 11m
JetBlue
Deal found 4/15![JetBlue logo]()
$301
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:00 am
SJO
- MKE
1 stop10h 45m
Southwest
Deal found 4/14![Southwest logo]()
$306
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/161:00 pm
SJO
- MKE
1 stop8h 33m
United Airlines
Deal found 4/16![United Airlines logo]()
$325
This Avianca deal was found by Cheapflights users on 4/14. 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 8/255:05 am
SJO
- MKE
2 stops11h 03m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$328
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 April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $509 (Kiwi.com) |
One-way from | $194 (Priceline) |
Popular in | July |
Cheapest in | January |
Average price | $525 |
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 April 17, 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 5/21
11:13 am-10:45 pm
1 stop10h 32m
Milwaukee-Mitchell
Mon 5/25
8:00 am-10:39 pm
1 stop15h 39m
$536
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 8/21
9:00 am-8:45 pm
1 stop10h 45m
Milwaukee-Mitchell
Mon 8/31
5:35 am-12:45 pm
1 stop8h 10m
$542
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sat 5/16
7:55 am-11:59 pm
2 stops39h 04m
Milwaukee-Mitchell
Mon 6/1
5:29 pm-10:11 am
2 stops17h 42m
$605
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 5/14
1:25 pm-5:32 pm
2 stops27h 07m
Milwaukee-Mitchell
Thu 8/13
5:05 am-7:37 pm
2 stops39h 32m
$617
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sat 5/30
12:30 am-8:46 pm
2 stops19h 16m
Milwaukee-Mitchell
Sun 6/7
8:00 am-10:39 pm
1 stop15h 39m
$618
Quickest round-trip
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 5/14
1:20 pm-11:53 pm
1 stop9h 33m
Milwaukee-Mitchell
Thu 8/13
5:55 am-11:56 am
1 stop7h 01m
$625
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 5/28
11:13 am-11:08 am
2 stops22h 55m
Milwaukee-Mitchell
Sun 5/31
8:00 am-10:39 pm
1 stop15h 39m
$639
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Sat 5/23
1:20 pm-11:59 pm
1 stop9h 39m
Milwaukee-Mitchell
Thu 8/27
5:55 am-11:56 am
1 stop7h 01m
$651
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 5/29
12:30 am-2:14 pm
2 stops12h 44m
Milwaukee-Mitchell
Sat 6/6
10:46 am-10:39 pm
1 stop12h 53m
$665
Cheapest one-way
Quickest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Tue 5/19
1:20 pm-11:53 pm
1 stop9h 33m
$259
Showing 1-10 of 17 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 April.
| 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 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 April 17, 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.
Crew
8.1
Food
6.6
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Food
6.6
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
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 April 17, 2026.
San José and Milwaukee flights
Browse other San José and Milwaukee flight options. Last updated on April 17, 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 April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$554 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$458 | Average$537 | FlexibilityNo cancel fee | On-time69% |