$250+ 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
Sep 25 — Oct 21
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 August 26, 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 August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 9/247:55 am -
2 stops25h 12m
Mon 10/55:00 am -
2 stops31h 38m
Deal found 8/21![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 9/247:55 am -
2 stops22h 12m
Tue 10/63:52 pm -
2 stops20h 46m
Deal found 8/21![United Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 8/23. 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 10/71:25 pm -
1 stop9h 28m
Wed 10/145:30 am -
1 stop7h 30m
Deal found 8/23![Delta logo]()
$512
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/267:55 am -
1 stop13h 50m
Fri 10/26:15 am -
2 stops30h 23m
Deal found 8/21![United Airlines logo]()
$522
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm -
1 stop9h 29m
Tue 10/65:30 am -
1 stop7h 30m
Deal found 8/21![Delta logo]()
$529
This Southwest deal was found by Cheapflights users on 8/25. 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 10/89:00 am -
2 stops13h 45m
Mon 10/126:30 am -
2 stops14h 10m
Deal found 8/25![Southwest logo]()
$539
This United Airlines deal was found by Cheapflights users on 8/22. 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 12/192:25 pm -
2 stops19h 38m
Wed 12/307:45 am -
1 stop28h 30m
Deal found 8/22![United Airlines logo]()
$555
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:19 pm -
1 stop9h 29m
Tue 10/65:30 am -
1 stop7h 30m
Deal found 8/21![Delta logo]()
$557
This Faresmojo deal was found by Cheapflights users on 8/21. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm -
1 stop9h 29m
Mon 10/55:30 am -
1 stop7h 24m
Deal found 8/21![JetBlue logo]()
$566
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 9/227:55 am -
2 stops25h 05m
Mon 10/56:32 pm -
2 stops18h 06m
Deal found 8/21![United Airlines logo]()
$575
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 August 26, 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 August 26, 2026.
This United Airlines deal was found by Cheapflights users on 8/23. 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 1/201:15 am -
2 stops15h 58m
Tue 2/25:00 am -
2 stops13h 16m
Deal found 8/23![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/23. 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 1/181:15 am -
1 stop21h 31m
Tue 2/27:00 pm -
1 stop17h 15m
Deal found 8/23![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/26. 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 12/41:55 pm -
1 stop28h 13m
Wed 12/95:00 am -
2 stops14h 53m
Deal found 8/26![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 9/247:55 am -
2 stops32h 45m
Sat 10/36:47 pm -
2 stops25h 50m
Deal found 8/21![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/26. 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 1/171:15 am -
2 stops15h 58m
Sun 1/318:00 am -
1 stop10h 16m
Deal found 8/26![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/24. 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 1/211:25 pm -
1 stop9h 14m
Thu 1/2811:10 am -
1 stop8h 43m
Deal found 8/24![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/26. 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 1/161:15 am -
2 stops13h 49m
Sun 1/316:00 am -
2 stops14h 39m
Deal found 8/26![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/23. 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 1/181:15 am -
1 stop21h 31m
Sat 1/304:00 pm -
1 stop28h 39m
Deal found 8/23![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/26. 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 1/161:15 am -
2 stops15h 58m
Mon 2/12:50 pm -
2 stops29h 49m
Deal found 8/26![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/26. 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 1/171:15 am -
2 stops19h 39m
Tue 2/27:00 pm -
1 stop17h 15m
Deal found 8/26![United Airlines logo]()
$491
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/267:55 am -
1 stop8h 24m
Tue 10/66:15 am -
2 stops30h 23m
Deal found 8/21![United Airlines logo]()
$522
This United Airlines deal was found by Cheapflights users on 8/23. 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 1/171:15 am -
2 stops19h 39m
Thu 1/286:10 am -
1 stop13h 43m
Deal found 8/23![United Airlines logo]()
$522
Last-minute flights from San José to MilwaukeeDiscover last-minute flight deals from San José to Milwaukee. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Milwaukee. Data last updated August 26, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 9/227:55 am -
2 stops25h 05m
Mon 10/56:32 pm -
2 stops18h 06m
Deal found 8/21![United Airlines logo]()
$575
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 9/227:55 am -
1 stop13h 44m
Tue 10/66:40 pm -
1 stop17h 58m
Deal found 8/21![United Airlines logo]()
$607
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/231:19 pm -
1 stop9h 29m
Tue 10/65:30 am -
1 stop7h 30m
Deal found 8/21![Delta logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:07 am -
1 stop25h 01m
Sun 10/412:05 pm -
2 stops20h 05m
Deal found 8/21![Multiple Airlines logo]()
$593
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 9/247:55 am -
2 stops22h 12m
Mon 10/56:00 am -
1 stop30h 38m
Deal found 8/21![United Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Thu 9/247:55 am -
2 stops22h 12m
Sun 10/48:00 am -
1 stop29h 21m
Deal found 8/21![United Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm -
1 stop9h 29m
Tue 10/65:30 am -
1 stop7h 30m
Deal found 8/21![Delta logo]()
$529
This Faresmojo deal was found by Cheapflights users on 8/21. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm -
1 stop9h 29m
Mon 10/55:30 am -
1 stop7h 24m
Deal found 8/21![JetBlue logo]()
$566
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm -
1 stop9h 29m
Fri 10/25:30 am -
1 stop7h 24m
Deal found 8/21![Delta logo]()
$602
This Faresmojo deal was found by Cheapflights users on 8/21. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:19 pm -
1 stop9h 29m
Sun 10/45:30 am -
1 stop7h 24m
Deal found 8/21![JetBlue logo]()
$604
This Southwest deal was found by Cheapflights users on 8/26. 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 9/259:00 am -
1 stop10h 50m
Fri 10/28:15 am -
2 stops12h 25m
Deal found 8/26![Southwest logo]()
$612
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/267:55 am -
1 stop8h 24m
Tue 10/66:15 am -
2 stops30h 23m
Deal found 8/21![United Airlines logo]()
$522
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 August 26, 2026.
Search for one-way flight options from San José to Milwaukee. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/181:00 pm -
1 stop26h 53m
Deal found 8/24![American Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 8/25. 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 2/1712:35 pm -
2 stops25h 08m
Deal found 8/25![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop16h 54m
Deal found 8/21![Delta logo]()
$264
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Tue 11/1711:28 pm -
2 stops15h 30m
Deal found 8/21![United Airlines logo]()
$268
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Fri 11/2011:28 pm -
1 stop23h 22m
Deal found 8/21![United Airlines logo]()
$272
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 11/141:55 pm -
1 stop8h 20m
Deal found 8/21![United Airlines logo]()
$295
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sun 11/1512:35 pm -
2 stops21h 38m
Deal found 8/21![United Airlines logo]()
$306
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 August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $459 (United Airlines) |
One-way from | $250 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $571 |
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 7,457,451 searches. Data last updated August 26, 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 San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Wed 1/20
1:15 am-5:13 pm
2 stops15h 58m
Milwaukee-Mitchell
Tue 2/2
5:00 am-6:16 pm
2 stops13h 16m
$459
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Mon 1/18
1:15 am-10:46 pm
1 stop21h 31m
Milwaukee-Mitchell
Tue 2/2
7:00 pm-12:15 pm
1 stop17h 15m
$459
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Fri 12/4
1:55 pm-6:08 pm
1 stop28h 13m
Milwaukee-Mitchell
Wed 12/9
5:00 am-7:53 pm
2 stops14h 53m
$459
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Thu 9/24
7:55 am-5:40 pm
2 stops32h 45m
Milwaukee-Mitchell
Sat 10/3
6:47 pm-7:37 pm
2 stops25h 50m
$491
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Sun 1/17
1:15 am-5:13 pm
2 stops15h 58m
Milwaukee-Mitchell
Sun 1/31
8:00 am-6:16 pm
1 stop10h 16m
$491
Quickest round-trip
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Thu 1/21
1:25 pm-10:39 pm
1 stop9h 14m
Milwaukee-Mitchell
Thu 1/28
11:10 am-7:53 pm
1 stop8h 43m
$491
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Sat 1/16
1:15 am-3:04 pm
2 stops13h 49m
Milwaukee-Mitchell
Sun 1/31
6:00 am-8:39 pm
2 stops14h 39m
$491
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Mon 1/18
1:15 am-10:46 pm
1 stop21h 31m
Milwaukee-Mitchell
Sat 1/30
4:00 pm-8:39 pm
1 stop28h 39m
$491
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Sat 1/16
1:15 am-5:13 pm
2 stops15h 58m
Milwaukee-Mitchell
Mon 2/1
2:50 pm-8:39 pm
2 stops29h 49m
$491
San JoséMilwaukee
SJO San José Juan Santamaria Intl - MKE Milwaukee-Mitchell
SJOMKE
San José Juan Santamaria Intl
Sun 1/17
1:15 am-8:54 pm
2 stops19h 39m
Milwaukee-Mitchell
Tue 2/2
7:00 pm-12:15 pm
1 stop17h 15m
$491
Showing 1-10 of 19 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 August.
| 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?
Airfare is below average for this route at the moment.
San José to Milwaukee flights typically cost between $538 and $619 in January.The cheapest round-trip price found within the last 5 days was $459 on United Airlines (Jan 18-Feb 3).
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 August 26, 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.
Overall
7.1
Boarding
7.5
Entertainment
6.8
Crew
7.9
Comfort
7.2
Food
6.4
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
Overall
7.1
Boarding
7.5
Entertainment
6.8
Crew
7.9
Comfort
7.2
Food
6.4
Reviews
1 / 20
2.0
MediocreSherif,Aug 2026
YYZ - ORD
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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Alternative routes for San José to Milwaukee
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Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
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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 August 26, 2026.
San José and Milwaukee flights
Browse other San José and Milwaukee flight options. Last updated on August 26, 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 August 26, 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 7,457,451 searches. Data last updated August 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$488 | Average$557 | FlexibilityNo cancel fee | On-time71% |