$293+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MKE
Jun 12 — Jun 191
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
Cheapest
Best
Last-minute
One-way
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 May 13, 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 May 13, 2026.
This Mytrip deal was found by Cheapflights users on 5/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/249:35 am
SJO
- MKE
1 stop21h 23m
Frontier
Wed 9/212:08 pm
MKE
- SJO
2 stops21h 12m
Frontier
Deal found 5/10![Frontier logo]()
$457
This United Airlines deal was found by Cheapflights users on 5/9. 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
1 stop8h 35m
United Airlines
Sat 6/68:00 am
MKE
- SJO
1 stop12h 37m
United Airlines
Deal found 5/9![United Airlines logo]()
$536
This Orbitz deal was found by Cheapflights users on 5/10. 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 8/249:35 am
SJO
- MKE
1 stop21h 23m
Multiple Airlines
Wed 9/29:36 am
MKE
- SJO
3 stops27h 09m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$538
This American Airlines deal was found by Cheapflights users on 5/10. 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 5/3111:59 pm
SJO
- MKE
1 stop22h 45m
American Airlines
Sun 6/77:18 am
MKE
- SJO
1 stop16h 25m
American Airlines
Deal found 5/10![American Airlines logo]()
$551
This Avianca deal was found by Cheapflights users on 5/12. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:05 am
SJO
- MKE
2 stops11h 03m
Multiple Airlines
Sat 10/310:41 am
MKE
- SJO
2 stops13h 59m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$552
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sun 8/239:00 am
SJO
- MKE
2 stops11h 50m
Southwest
Wed 9/26:40 am
MKE
- SJO
2 stops13h 00m
Southwest
Deal found 5/11![Southwest logo]()
$573
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 May 13, 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 May 13, 2026.
This Southwest deal was found by Cheapflights users on 5/11. 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.
Sun 8/239:00 am
SJO
- MKE
2 stops11h 50m
Southwest
Mon 8/317:00 am
MKE
- SJO
2 stops12h 40m
Southwest
Deal found 5/11![Southwest logo]()
$573
This United Airlines deal was found by Cheapflights users on 5/12. 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 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
1 stop8h 35m
United Airlines
Sat 6/610:46 am
MKE
- SJO
1 stop12h 53m
United Airlines
Deal found 5/12![United Airlines logo]()
$575
This Southwest deal was found by Cheapflights users on 5/10. 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 8/249:00 am
SJO
- MKE
1 stop10h 45m
Southwest
Wed 9/26:05 am
MKE
- SJO
1 stop7h 40m
Southwest
Deal found 5/10![Southwest logo]()
$587
This United Airlines deal was found by Cheapflights users on 5/9. 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 6/1911:13 am
SJO
- MKE
2 stops26h 23m
United Airlines
Wed 6/245:56 pm
MKE
- SJO
1 stop29h 43m
United Airlines
Deal found 5/9![United Airlines logo]()
$605
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:25 pm
SJO
- MKE
2 stops19h 24m
United Airlines
Mon 11/28:45 pm
MKE
- SJO
2 stops16h 30m
United Airlines
Deal found 5/12![United Airlines logo]()
$612
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:45 am
SJO
- MKE
2 stops15h 24m
United Airlines
Mon 11/27:00 pm
MKE
- SJO
2 stops16h 25m
United Airlines
Deal found 5/12![United Airlines logo]()
$612
Last-minute flights from San José to MilwaukeeDiscover last-minute flight deals from San José to Milwaukee. Data last updated May 13, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Milwaukee. Data last updated May 13, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/9. 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
1 stop8h 35m
United Airlines
Sat 6/68:00 am
MKE
- SJO
1 stop12h 37m
United Airlines
Deal found 5/9![United Airlines logo]()
$536
This American Airlines deal was found by Cheapflights users on 5/10. 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 5/3111:59 pm
SJO
- MKE
1 stop22h 45m
American Airlines
Sun 6/77:18 am
MKE
- SJO
1 stop16h 25m
American Airlines
Deal found 5/10![American Airlines logo]()
$551
This United Airlines deal was found by Cheapflights users on 5/9. 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 5/3111:13 am
SJO
- MKE
2 stops28h 33m
United Airlines
Sun 6/711:55 am
MKE
- SJO
2 stops23h 16m
United Airlines
Deal found 5/9![United Airlines logo]()
$632
This United Airlines deal was found by Cheapflights users on 5/9. 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 6/66:40 am
SJO
- MKE
1 stop9h 24m
United Airlines
Sat 6/131:30 pm
MKE
- SJO
2 stops23h 08m
United Airlines
Deal found 5/9![United Airlines logo]()
$613
This United Airlines deal was found by Cheapflights users on 5/9. 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 6/1912:44 pm
SJO
- MKE
1 stop9h 50m
United Airlines
Wed 6/245:56 pm
MKE
- SJO
1 stop29h 43m
United Airlines
Deal found 5/9![United Airlines logo]()
$605
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 May 13, 2026.
Search for one-way flight options from San José to Milwaukee. Find affordable one-way fares based on user searches. Data last updated May 13, 2026.
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:13 am
SJO
- MKE
2 stops26h 23m
United Airlines
Deal found 5/8![United Airlines logo]()
$293
This American Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:59 pm
SJO
- MKE
1 stop10h 21m
American Airlines
Deal found 5/8![American Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 5/10. 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 6/2312:30 am
SJO
- MKE
2 stops19h 26m
United Airlines
Deal found 5/10![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:55 am
SJO
- MKE
2 stops25h 02m
United Airlines
Deal found 5/12![United Airlines logo]()
$308
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:55 am
SJO
- MKE
2 stops29h 41m
United Airlines
Deal found 5/8![United Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2812:30 am
SJO
- MKE
1 stop21h 15m
United Airlines
Deal found 5/12![United Airlines logo]()
$332
This United Airlines deal was found by Cheapflights users on 5/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:55 am
SJO
- MKE
1 stop8h 11m
United Airlines
Deal found 5/12![United Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 5/286:00 am
SJO
- MKE
2 stops16h 34m
American Airlines
Deal found 5/12![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 5/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/239:00 am
SJO
- MKE
2 stops12h 30m
Southwest
Deal found 5/12![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 5/11. 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
1 stop25h 10m
United Airlines
Deal found 5/11![United Airlines logo]()
$355
This Copa Airlines deal was found by Cheapflights users on 5/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:17 pm
SJO
- MKE
2 stops24h 34m
Copa Airlines
Deal found 5/12![Copa Airlines logo]()
$361
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 May 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $457 (Mytrip) |
One-way from | $293 (United Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $498 |
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 May 13, 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
Sun 8/23
9:00 am-9:50 pm
2 stops11h 50m
Milwaukee-Mitchell
Mon 8/31
7:00 am-6:40 pm
2 stops12h 40m
$573
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 5/29
12:30 am-10:05 am
1 stop8h 35m
Milwaukee-Mitchell
Sat 6/6
10:46 am-10:39 pm
1 stop12h 53m
$575
Quickest round-trip
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 8/24
9:00 am-8:45 pm
1 stop10h 45m
Milwaukee-Mitchell
Wed 9/2
6:05 am-12:45 pm
1 stop7h 40m
$587
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 6/19
11:13 am-2:36 pm
2 stops26h 23m
Milwaukee-Mitchell
Wed 6/24
5:56 pm-10:39 pm
1 stop29h 43m
$605
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 10/22
1:25 pm-9:49 am
2 stops19h 24m
Milwaukee-Mitchell
Mon 11/2
8:45 pm-1:15 pm
2 stops16h 30m
$612
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Thu 10/29
7:45 am-12:09 am
2 stops15h 24m
Milwaukee-Mitchell
Mon 11/2
7:00 pm-11:25 am
2 stops16h 25m
$612
Cheapest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 6/5
11:13 am-2:36 pm
2 stops26h 23m
$293
Quickest one-way
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 6/8
12:30 am-10:05 am
1 stop8h 35m
$298
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Mon 6/8
7:55 am-9:57 am
2 stops25h 02m
$308
San JoséMilwaukee
SJO - MKE
SJOMKE
San José Juan Santamaria Intl
Fri 5/29
7:55 am-11:19 am
2 stops26h 24m
$332
Showing 1-10 of 13 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 May.
| 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 May 13, 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.
Overall
7.4
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Overall
7.4
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Crew
8.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Overall
7.4
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Food
6.6
Crew
8.1
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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Complete your trip
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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 May 13, 2026.
San José and Milwaukee flights
Browse other San José and Milwaukee flight options. Last updated on May 13, 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 May 13, 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 May 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$399 | Average$541 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$458 | Average$537 | FlexibilityNo cancel fee | On-time69% |