$287+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Aug 17 — Aug 241
Round-trip
1 adult, Economy
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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 July 18, 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 18, 2026.
This American Airlines deal was found by Cheapflights users on 7/13. 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 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 7/13![American Airlines logo]()
$483
This American Airlines deal was found by Cheapflights users on 7/12. 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 12/253:29 pm
SJO
- MKE
1 stop8h 30m
American Airlines
Mon 1/183:49 pm
MKE
- SJO
1 stop20h 49m
American Airlines
Deal found 7/12![American Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 7/15. 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.
Wed 9/301:19 pm
SJO
- MKE
1 stop9h 29m
Delta
Mon 10/125:40 am
MKE
- SJO
1 stop7h 18m
Delta
Deal found 7/15![Delta logo]()
$491
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 10/229:00 am
SJO
- MKE
1 stop7h 50m
Southwest
Mon 11/25:10 am
MKE
- SJO
1 stop8h 05m
Southwest
Deal found 7/13![Southwest logo]()
$515
This Southwest deal was found by Cheapflights users on 7/14. 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.
Wed 9/239:00 am
SJO
- MKE
2 stops10h 55m
Southwest
Tue 9/297:40 am
MKE
- SJO
2 stops12h 00m
Southwest
Deal found 7/14![Southwest logo]()
$519
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 18, 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 18, 2026.
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:00 pm
SJO
- MKE
1 stop21h 31m
American Airlines
Mon 11/26:48 pm
MKE
- SJO
2 stops18h 51m
American Airlines
Deal found 7/13![American Airlines logo]()
$512
This Southwest deal was found by Cheapflights users on 7/13. 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.
Thu 10/229:00 am
SJO
- MKE
1 stop7h 50m
Southwest
Mon 11/25:10 am
MKE
- SJO
1 stop8h 05m
Southwest
Deal found 7/13![Southwest logo]()
$515
This United Airlines deal was found by Cheapflights users on 7/14. 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 10/151:25 pm
SJO
- MKE
2 stops21h 05m
United Airlines
Wed 10/2110:42 am
MKE
- SJO
2 stops9h 55m
United Airlines
Deal found 7/14![United Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 7/14. 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 9/249:00 am
SJO
- MKE
2 stops10h 40m
Southwest
Mon 9/288:00 am
MKE
- SJO
2 stops11h 40m
Southwest
Deal found 7/14![Southwest logo]()
$519
This Southwest deal was found by Cheapflights users on 7/14. 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.
Wed 9/239:00 am
SJO
- MKE
1 stop11h 05m
Southwest
Tue 9/296:40 am
MKE
- SJO
2 stops13h 00m
Southwest
Deal found 7/14![Southwest logo]()
$519
This United Airlines deal was found by Cheapflights users on 7/13. 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 12/211:15 am
SJO
- MKE
2 stops21h 56m
United Airlines
Sun 1/35:00 am
MKE
- SJO
2 stops17h 32m
United Airlines
Deal found 7/13![United Airlines logo]()
$597
This Southwest deal was found by Cheapflights users on 7/14. 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.
Tue 10/139:00 am
SJO
- MKE
1 stop7h 35m
Southwest
Tue 10/208:20 am
MKE
- SJO
2 stops12h 20m
Southwest
Deal found 7/14![Southwest logo]()
$519
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Fri 12/251:55 pm
SJO
- MKE
1 stop27h 56m
United Airlines
Sun 1/35:00 am
MKE
- SJO
2 stops17h 32m
United Airlines
Deal found 7/17![United Airlines logo]()
$613
This Southwest deal was found by Cheapflights users on 7/14. 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.
Mon 10/129:00 am
SJO
- MKE
2 stops13h 45m
Southwest
Mon 10/198:15 am
MKE
- SJO
2 stops12h 25m
Southwest
Deal found 7/14![Southwest logo]()
$572
Last-minute flights from San José to MilwaukeeDiscover last-minute flight deals from San José to Milwaukee. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Milwaukee. Data last updated July 18, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/14. 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 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 7/14![American Airlines logo]()
$620
This Avianca deal was found by Cheapflights users on 7/16. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:40 am
SJO
- MKE
2 stops11h 59m
Multiple Airlines
Sat 8/221:19 pm
MKE
- SJO
2 stops11h 21m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$651
This American Airlines deal was found by Cheapflights users on 7/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:56 pm
SJO
- MKE
2 stops20h 51m
American Airlines
Mon 8/316:00 pm
MKE
- SJO
2 stops19h 03m
American Airlines
Deal found 7/15![American Airlines logo]()
$595
This Avianca deal was found by Cheapflights users on 7/15. 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 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 stops11h 59m
Multiple Airlines
Sat 9/510:43 am
MKE
- SJO
2 stops13h 57m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$624
This American Airlines deal was found by Cheapflights users on 7/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/232:56 pm
SJO
- MKE
2 stops19h 41m
American Airlines
Sun 9/65:50 pm
MKE
- SJO
2 stops19h 13m
American Airlines
Deal found 7/15![American Airlines logo]()
$602
This American Airlines deal was found by Cheapflights users on 7/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/232:56 pm
SJO
- MKE
2 stops19h 41m
American Airlines
Mon 9/76:28 am
MKE
- SJO
1 stop6h 58m
American Airlines
Deal found 7/13![American Airlines logo]()
$617
This American Airlines deal was found by Cheapflights users on 7/14. 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.
Sun 8/232:56 pm
SJO
- MKE
2 stops19h 41m
American Airlines
Sat 9/512:28 pm
MKE
- SJO
1 stop26h 24m
American Airlines
Deal found 7/14![American Airlines logo]()
$639
This American Airlines deal was found by Cheapflights users on 7/17. 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.
Mon 8/242:56 pm
SJO
- MKE
2 stops19h 41m
American Airlines
Sat 9/52:42 pm
MKE
- SJO
2 stops22h 25m
American Airlines
Deal found 7/17![American Airlines logo]()
$636
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 18, 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 18, 2026.
This Southwest deal was found by Cheapflights users on 7/14. 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 12/119:00 am
SJO
- MKE
1 stop10h 15m
Southwest
Deal found 7/14![Southwest logo]()
$287
This American Airlines deal was found by Cheapflights users on 7/13. 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 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 7/13![American Airlines logo]()
$300
This FlightHub deal was found by Cheapflights users on 7/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/19:45 am
SJO
- MKE
1 stop21h 13m
Frontier
Deal found 7/14![Frontier logo]()
$325
This United Airlines deal was found by Cheapflights users on 7/14. 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.
Mon 12/78:45 am
SJO
- MKE
2 stops25h 04m
United Airlines
Deal found 7/14![United Airlines logo]()
$335
This Orbitz deal was found by Cheapflights users on 7/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/272:02 pm
SJO
- MKE
2 stops17h 43m
JetBlue
Deal found 7/14![JetBlue logo]()
$343
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 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $483 (American Airlines) |
One-way from | $287 (Southwest) |
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 18, 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
1:00 pm-11:31 am
1 stop21h 31m
Milwaukee-Mitchell
Mon 11/2
6:48 pm-1:39 pm
2 stops18h 51m
$512
Quickest round-trip
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 10/22
9:00 am-5:50 pm
1 stop7h 50m
Milwaukee-Mitchell
Mon 11/2
5:10 am-1:15 pm
1 stop8h 05m
$515
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 9/24
9:00 am-8:40 pm
2 stops10h 40m
Milwaukee-Mitchell
Mon 9/28
8:00 am-6:40 pm
2 stops11h 40m
$519
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Wed 9/23
9:00 am-9:05 pm
1 stop11h 05m
Milwaukee-Mitchell
Tue 9/29
6:40 am-6:40 pm
2 stops13h 00m
$519
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Tue 10/13
9:00 am-5:35 pm
1 stop7h 35m
Milwaukee-Mitchell
Tue 10/20
8:20 am-7:40 pm
2 stops12h 20m
$519
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 10/15
1:25 pm-11:30 am
2 stops21h 05m
Milwaukee-Mitchell
Wed 10/21
10:42 am-7:37 pm
2 stops9h 55m
$557
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 10/12
9:00 am-11:45 pm
2 stops13h 45m
Milwaukee-Mitchell
Mon 10/19
8:15 am-7:40 pm
2 stops12h 25m
$572
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 12/21
1:15 am-11:11 pm
2 stops21h 56m
Milwaukee-Mitchell
Sun 1/3
5:00 am-10:32 pm
2 stops17h 32m
$597
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 12/25
1:55 pm-5:51 pm
1 stop27h 56m
Milwaukee-Mitchell
Sun 1/3
5:00 am-10:32 pm
2 stops17h 32m
$613
Cheapest one-way
Quickest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 12/11
9:00 am-7:15 pm
1 stop10h 15m
$287
Showing 1-10 of 18 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 $501). 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 18, 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.
Comfort
7.2
Food
6.4
Boarding
7.5
Overall
7.1
Crew
7.9
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
Comfort
7.2
Food
6.4
Boarding
7.5
Overall
7.1
Crew
7.9
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentLinda,Jul 2026
ROA - CLT
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 18, 2026.
San José and Milwaukee flights
Browse other San José and Milwaukee flight options. Last updated on July 18, 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 18, 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 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$541 | FlexibilityNo cancel fee | On-time71% |