$184+ Cheap flights from San Jose, CA to Milwaukee (SJC - 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MKE
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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Find cheap flights from San Jose 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 Jose to Milwaukee
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Best
Last-minute
One-way
Cheapest flights from San Jose to MilwaukeeExplore the most affordable flight options available from San Jose to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.
Explore the most affordable flight options available from San Jose to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:00 am
SJC
- MKE
1 stop9h 00m
American Airlines
Tue 8/252:39 pm
MKE
- SJC
1 stop5h 51m
American Airlines
Deal found 6/9![American Airlines logo]()
$269
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:35 am
SJC
- MKE
2 stops8h 30m
Southwest
Tue 8/2512:40 pm
MKE
- SJC
2 stops8h 30m
Southwest
Deal found 6/9![Southwest logo]()
$281
This CheapOair deal was found by Cheapflights users on 6/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:15 am
SJC
- MKE
1 stop7h 33m
Alaska Airlines
Mon 11/164:44 pm
MKE
- SJC
1 stop19h 01m
Alaska Airlines
Deal found 6/9![Alaska Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 am
SJC
- MKE
1 stop10h 50m
Southwest
Mon 8/313:05 pm
MKE
- SJC
1 stop7h 50m
Southwest
Deal found 6/8![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:00 pm
SJC
- MKE
1 stop5h 55m
Southwest
Tue 7/146:10 am
MKE
- SJC
1 stop6h 50m
Southwest
Deal found 6/9![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:30 am
SJC
- MKE
1 stop5h 43m
Delta
Mon 10/267:15 am
MKE
- SJC
1 stop7h 13m
Delta
Deal found 6/8![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 6/9. 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 10/102:08 pm
SJC
- MKE
1 stop6h 51m
United Airlines
Fri 10/162:39 pm
MKE
- SJC
1 stop8h 19m
United Airlines
Deal found 6/9![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:45 am
SJC
- MKE
1 stop7h 00m
Southwest
Sat 10/39:45 am
MKE
- SJC
1 stop11h 10m
Southwest
Deal found 6/8![Southwest logo]()
$376
Best flights from San Jose to MilwaukeeDiscover carefully curated flight deals from San Jose to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
Discover carefully curated flight deals from San Jose to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/189:35 am
SJC
- MKE
2 stops8h 30m
Southwest
Tue 8/2512:40 pm
MKE
- SJC
2 stops8h 30m
Southwest
Deal found 6/9![Southwest logo]()
$281
This Southwest deal was found by Cheapflights users on 6/6. 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 7/34:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Tue 7/76:25 am
MKE
- SJC
2 stops8h 50m
Southwest
Deal found 6/6![Southwest logo]()
$397
This Southwest deal was found by Cheapflights users on 6/5. 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 7/34:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Fri 7/101:50 pm
MKE
- SJC
1 stop8h 35m
Southwest
Deal found 6/5![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 6/5. 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 7/155:00 pm
SJC
- MKE
1 stop5h 55m
Southwest
Sun 7/198:15 pm
MKE
- SJC
1 stop12h 45m
Southwest
Deal found 6/5![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 6/7. 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 8/78:15 am
SJC
- MKE
1 stop6h 45m
Southwest
Mon 8/103:05 pm
MKE
- SJC
1 stop7h 50m
Southwest
Deal found 6/7![Southwest logo]()
$456
This Southwest deal was found by Cheapflights users on 6/7. 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 8/311:40 am
SJC
- MKE
2 stops10h 30m
Southwest
Tue 8/1111:40 am
MKE
- SJC
2 stops7h 45m
Southwest
Deal found 6/7![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 6/6. 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 6/246:00 am
SJC
- MKE
1 stop7h 40m
Southwest
Tue 6/304:10 pm
MKE
- SJC
1 stop9h 15m
Southwest
Deal found 6/6![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:05 pm
SJC
- MKE
1 stop7h 15m
Southwest
Sun 7/198:15 pm
MKE
- SJC
1 stop12h 45m
Southwest
Deal found 6/8![Southwest logo]()
$482
This Southwest deal was found by Cheapflights users on 6/6. 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 7/1210:35 am
SJC
- MKE
1 stop7h 00m
Southwest
Sun 7/198:15 pm
MKE
- SJC
1 stop12h 45m
Southwest
Deal found 6/6![Southwest logo]()
$482
Last-minute flights from San Jose to MilwaukeeDiscover last-minute flight deals from San Jose to Milwaukee. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Milwaukee. Data last updated June 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/5. 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 6/303:30 pm
SJC
- MKE
2 stops7h 25m
Southwest
Wed 7/86:25 am
MKE
- SJC
1 stop6h 20m
Southwest
Deal found 6/5![Southwest logo]()
$422
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:17 am
SJC
- MKE
1 stop15h 42m
Alaska Airlines
Tue 8/46:02 am
MKE
- SJC
1 stop9h 18m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$442
This Southwest deal was found by Cheapflights users on 6/6. 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 7/34:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Tue 7/76:25 am
MKE
- SJC
2 stops8h 50m
Southwest
Deal found 6/6![Southwest logo]()
$397
This Delta deal was found by Cheapflights users on 6/7. 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 7/46:20 am
SJC
- MKE
1 stop6h 48m
Delta
Wed 7/153:59 pm
MKE
- SJC
1 stop6h 36m
Delta
Deal found 6/7![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Sat 7/46:01 am
SJC
- MKE
2 stops9h 52m
American Airlines
Sat 7/1112:12 pm
MKE
- SJC
2 stops12h 29m
American Airlines
Deal found 6/7![American Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/75:00 pm
SJC
- MKE
1 stop5h 55m
Southwest
Tue 7/146:10 am
MKE
- SJC
1 stop6h 50m
Southwest
Deal found 6/9![Southwest logo]()
$367
This Delta deal was found by Cheapflights users on 6/7. 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.
Tue 7/71:10 pm
SJC
- MKE
1 stop6h 31m
Delta
Tue 7/148:00 am
MKE
- SJC
1 stop6h 01m
Delta
Deal found 6/7![Delta logo]()
$417
This Alaska Airlines deal was found by Cheapflights users on 6/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:16 pm
SJC
- MKE
1 stop7h 43m
Alaska Airlines
Wed 7/156:02 am
MKE
- SJC
1 stop9h 18m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 6/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:10 pm
SJC
- MKE
1 stop9h 35m
Southwest
Wed 7/156:10 am
MKE
- SJC
2 stops10h 15m
Southwest
Deal found 6/9![Southwest logo]()
$427
This Southwest deal was found by Cheapflights users on 6/5. 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 7/153:30 pm
SJC
- MKE
2 stops7h 25m
Southwest
Sun 7/198:15 pm
MKE
- SJC
1 stop12h 45m
Southwest
Deal found 6/5![Southwest logo]()
$433
One-way flights from San Jose to MilwaukeeSearch for one-way flight options from San Jose to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
Search for one-way flight options from San Jose to Milwaukee. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
SJC
- MKE
1 stop7h 40m
Southwest
Deal found 6/8![Southwest logo]()
$184
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:16 pm
SJC
- MKE
1 stop7h 43m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$209
This CheapOair deal was found by Cheapflights users on 6/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:16 pm
SJC
- MKE
1 stop7h 43m
Alaska Airlines
Deal found 6/7![Alaska Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 6/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2811:47 am
SJC
- MKE
1 stop9h 47m
American Airlines
Deal found 6/9![American Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 6/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:44 pm
SJC
- MKE
1 stop8h 15m
Alaska Airlines
Deal found 6/8![Alaska Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:10 pm
SJC
- MKE
1 stop6h 31m
Delta
Deal found 6/8![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 6/5. 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.
Fri 7/106:20 am
SJC
- MKE
1 stop6h 49m
Delta
Deal found 6/5![Delta logo]()
$244
This Southwest deal was found by Cheapflights users on 6/6. 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 6/303:30 pm
SJC
- MKE
2 stops7h 25m
Southwest
Deal found 6/6![Southwest logo]()
$245
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/292:23 pm
SJC
- MKE
1 stop7h 11m
American Airlines
Deal found 6/6![American Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 6/6. 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 7/611:40 am
SJC
- MKE
2 stops10h 30m
Southwest
Deal found 6/6![Southwest logo]()
$261
Find flight deals from San Jose to Milwaukee
Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $269 (American Airlines) |
One-way from | $184 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $493 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 10, 2026.
Use the filters below to find and compare flights from San Jose to Milwaukee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Tue 8/18
9:35 am-8:05 pm
2 stops8h 30m
Milwaukee-Mitchell
Tue 8/25
12:40 pm-7:10 pm
2 stops8h 30m
$281
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Fri 7/3
4:05 pm-1:15 am
1 stop7h 10m
Milwaukee-Mitchell
Tue 7/7
6:25 am-1:15 pm
2 stops8h 50m
$397
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Fri 7/3
4:05 pm-1:15 am
1 stop7h 10m
Milwaukee-Mitchell
Fri 7/10
1:50 pm-8:25 pm
1 stop8h 35m
$422
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Wed 7/15
5:00 pm-12:55 am
1 stop5h 55m
Milwaukee-Mitchell
Sun 7/19
8:15 pm-7:00 am
1 stop12h 45m
$427
Quickest round-trip
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Fri 8/7
8:15 am-5:00 pm
1 stop6h 45m
Milwaukee-Mitchell
Mon 8/10
3:05 pm-8:55 pm
1 stop7h 50m
$456
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Mon 8/3
11:40 am-12:10 am
2 stops10h 30m
Milwaukee-Mitchell
Tue 8/11
11:40 am-5:25 pm
2 stops7h 45m
$457
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Wed 6/24
6:00 am-3:40 pm
1 stop7h 40m
Milwaukee-Mitchell
Tue 6/30
4:10 pm-11:25 pm
1 stop9h 15m
$482
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Fri 7/17
4:05 pm-1:20 am
1 stop7h 15m
Milwaukee-Mitchell
Sun 7/19
8:15 pm-7:00 am
1 stop12h 45m
$482
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Sun 7/12
10:35 am-7:35 pm
1 stop7h 00m
Milwaukee-Mitchell
Sun 7/19
8:15 pm-7:00 am
1 stop12h 45m
$482
Cheapest one-way
Quickest one-way
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Tue 6/30
6:20 am-3:08 pm
1 stop6h 48m
$184
Showing 1-10 of 17 resultsSorted by cheapest first
Compare providers for flights from San Jose 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 Jose to Milwaukee in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on San Jose, California-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Milwaukee flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Jose, California-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 Jose, California-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 Jose to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from San Jose with our price prediction graph.
SJC-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 Jose to Milwaukee
What is the cheapest month to book a flight from San Jose, California to Milwaukee?
Currently, September is the cheapest month in which you can book a flight from San Jose, California to Milwaukee (average of $364). Flying from San Jose, California to Milwaukee in March is currently the most expensive (average of $567). 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 Jose, California to Milwaukee?
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated June 10, 2026.
Get a feel of what it's like to fly with Southwest and Delta from San Jose to Milwaukee by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Overall
7.9
Boarding
8.1
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Related info for your journey
Find useful and relevant information for your journey from San Jose 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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Top 2 airlines flying from San Jose to Milwaukee
Discover the top 2 airlines that operate flights from San Jose to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$504 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$336 | Average$441 | FlexibilityNo cancel fee | On-timeN/A |