$164+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MKE
Jun 7 — Jun 141
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
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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 Jose to Milwaukee
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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 May 8, 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 May 8, 2026.
This Southwest deal was found by Cheapflights users on 5/6. 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 6/83:30 pm
SJC
- MKE
1 stop8h 25m
Southwest
Tue 6/166:55 pm
MKE
- SJC
1 stop6h 05m
Southwest
Deal found 5/6![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 5/5. 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 5/2610:55 pm
SJC
- MKE
1 stop10h 00m
Southwest
Thu 5/286:30 pm
MKE
- SJC
1 stop5h 55m
Southwest
Deal found 5/5![Southwest logo]()
$352
This Southwest deal was found by Cheapflights users on 5/7. 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 6/112:30 pm
SJC
- MKE
1 stop7h 50m
Southwest
Thu 6/42:30 pm
MKE
- SJC
1 stop8h 30m
Southwest
Deal found 5/7![Southwest logo]()
$355
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:40 pm
SJC
- MKE
1 stop6h 57m
American Airlines
Thu 5/281:43 pm
MKE
- SJC
2 stops11h 00m
American Airlines
Deal found 5/5![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:40 pm
SJC
- MKE
1 stop6h 57m
American Airlines
Fri 5/297:18 am
MKE
- SJC
1 stop8h 24m
American Airlines
Deal found 5/5![American Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 5/7. 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.
Wed 5/276:45 am
SJC
- MKE
1 stop7h 20m
Southwest
Sat 5/301:05 pm
MKE
- SJC
1 stop6h 15m
Southwest
Deal found 5/7![Southwest logo]()
$386
This Southwest deal was found by Cheapflights users on 5/5. 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 8/2511:30 am
SJC
- MKE
2 stops7h 55m
Southwest
Thu 9/33:05 pm
MKE
- SJC
1 stop6h 30m
Southwest
Deal found 5/5![Southwest logo]()
$388
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Wed 5/276:00 am
SJC
- MKE
2 stops11h 57m
American Airlines
Sat 5/3012:11 pm
MKE
- SJC
2 stops12h 32m
American Airlines
Deal found 5/7![American Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 5/4. 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 6/165:00 pm
SJC
- MKE
1 stop5h 55m
Southwest
Fri 6/195:25 am
MKE
- SJC
1 stop6h 15m
Southwest
Deal found 5/4![Southwest logo]()
$402
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 May 8, 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 May 8, 2026.
This Southwest deal was found by Cheapflights users on 5/4. 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 7/24:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Wed 7/86:55 pm
MKE
- SJC
1 stop6h 05m
Southwest
Deal found 5/4![Southwest logo]()
$447
This Alaska Airlines deal was found by Cheapflights users on 5/4. 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.
Tue 6/28:00 am
SJC
- MKE
2 stops11h 04m
Alaska Airlines
Wed 6/35:00 am
MKE
- SJC
2 stops10h 40m
Alaska Airlines
Deal found 5/4![Alaska Airlines logo]()
$451
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:10 am
SJC
- MKE
1 stop6h 05m
Delta
Mon 8/247:30 am
MKE
- SJC
1 stop7h 24m
Delta
Deal found 5/8![Delta logo]()
$485
This Southwest deal was found by Cheapflights users on 5/5. 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.
Sun 8/25:05 pm
SJC
- MKE
1 stop5h 55m
Southwest
Thu 8/66:25 pm
MKE
- SJC
1 stop5h 50m
Southwest
Deal found 5/5![Southwest logo]()
$477
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/231:40 pm
SJC
- MKE
1 stop6h 03m
Delta
Wed 8/53:59 pm
MKE
- SJC
1 stop6h 25m
Delta
Deal found 5/6![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 5/4. 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 6/194:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Mon 6/225:15 pm
MKE
- SJC
1 stop8h 10m
Southwest
Deal found 5/4![Southwest logo]()
$477
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/179:20 am
SJC
- MKE
2 stops11h 25m
Southwest
Fri 7/246:35 pm
MKE
- SJC
1 stop6h 20m
Southwest
Deal found 5/8![Southwest logo]()
$482
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/154:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Fri 6/193:15 pm
MKE
- SJC
2 stops10h 10m
Southwest
Deal found 5/8![Southwest logo]()
$482
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/2510:20 am
SJC
- MKE
2 stops7h 25m
Southwest
Wed 7/16:25 am
MKE
- SJC
2 stops8h 50m
Southwest
Deal found 5/8![Southwest logo]()
$482
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/114:05 pm
SJC
- MKE
1 stop7h 10m
Southwest
Mon 6/156:35 pm
MKE
- SJC
1 stop6h 20m
Southwest
Deal found 5/8![Southwest logo]()
$494
Last-minute flights from San Jose to MilwaukeeDiscover last-minute flight deals from San Jose to Milwaukee. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Milwaukee. Data last updated May 8, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 5/5. 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 5/2610:55 pm
SJC
- MKE
1 stop10h 00m
Southwest
Thu 5/286:30 pm
MKE
- SJC
1 stop5h 55m
Southwest
Deal found 5/5![Southwest logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:40 pm
SJC
- MKE
1 stop6h 57m
American Airlines
Thu 5/281:43 pm
MKE
- SJC
2 stops11h 00m
American Airlines
Deal found 5/5![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:40 pm
SJC
- MKE
1 stop6h 57m
American Airlines
Fri 5/297:18 am
MKE
- SJC
1 stop8h 24m
American Airlines
Deal found 5/5![American Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 5/7. 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.
Wed 5/276:45 am
SJC
- MKE
1 stop7h 20m
Southwest
Sat 5/301:05 pm
MKE
- SJC
1 stop6h 15m
Southwest
Deal found 5/7![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Wed 5/276:00 am
SJC
- MKE
2 stops11h 57m
American Airlines
Sat 5/3012:11 pm
MKE
- SJC
2 stops12h 32m
American Airlines
Deal found 5/7![American Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 5/7. 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 6/112:30 pm
SJC
- MKE
1 stop7h 50m
Southwest
Thu 6/42:30 pm
MKE
- SJC
1 stop8h 30m
Southwest
Deal found 5/7![Southwest logo]()
$355
This CheapOair deal was found by Cheapflights users on 5/7. 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.
Sat 6/61:14 pm
SJC
- MKE
1 stop8h 45m
Alaska Airlines
Wed 6/106:02 am
MKE
- SJC
1 stop9h 18m
Alaska Airlines
Deal found 5/7![Alaska Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 5/6. 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 6/83:30 pm
SJC
- MKE
1 stop8h 25m
Southwest
Tue 6/166:55 pm
MKE
- SJC
1 stop6h 05m
Southwest
Deal found 5/6![Southwest logo]()
$351
This Southwest deal was found by Cheapflights users on 5/4. 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 6/165:00 pm
SJC
- MKE
1 stop5h 55m
Southwest
Fri 6/195:25 am
MKE
- SJC
1 stop6h 15m
Southwest
Deal found 5/4![Southwest logo]()
$402
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 May 8, 2026.
Search for one-way flight options from San Jose to Milwaukee. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This American Airlines deal was found by Cheapflights users on 5/4. 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 5/2612:40 pm
SJC
- MKE
1 stop6h 57m
American Airlines
Deal found 5/4![American Airlines logo]()
$164
This Southwest deal was found by Cheapflights users on 5/5. 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 6/243:30 pm
SJC
- MKE
2 stops7h 25m
Southwest
Deal found 5/5![Southwest logo]()
$169
This Delta deal was found by Cheapflights users on 5/5. 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.
Tue 6/26:20 am
SJC
- MKE
1 stop6h 49m
Delta
Deal found 5/5![Delta logo]()
$174
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:20 am
SJC
- MKE
1 stop6h 49m
Delta
Deal found 5/4![Delta logo]()
$178
This Southwest deal was found by Cheapflights users on 5/5. 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.
Thu 6/46:00 am
SJC
- MKE
1 stop13h 55m
Southwest
Deal found 5/5![Southwest logo]()
$183
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:20 am
SJC
- MKE
1 stop6h 49m
Delta
Deal found 5/8![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 5/4. 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 7/710:40 am
SJC
- MKE
2 stops10h 30m
Southwest
Deal found 5/4![Southwest logo]()
$214
This American Airlines deal was found by Cheapflights users on 5/4. 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 6/312:38 pm
SJC
- MKE
2 stops8h 56m
American Airlines
Deal found 5/4![American Airlines logo]()
$218
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/32:34 pm
SJC
- MKE
1 stop7h 25m
Alaska Airlines
Deal found 5/8![Alaska Airlines logo]()
$219
This United Airlines deal was found by Cheapflights users on 5/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:45 am
SJC
- MKE
1 stop6h 09m
United Airlines
Deal found 5/5![United Airlines logo]()
$228
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $351 (Southwest) |
One-way from | $164 (American Airlines) |
Popular in | March |
Cheapest in | September |
Average price | $424 |
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 May 8, 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
Thu 7/2
4:05 pm-1:15 am
1 stop7h 10m
Milwaukee-Mitchell
Wed 7/8
6:55 pm-11:00 pm
1 stop6h 05m
$447
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Tue 6/2
8:00 am-9:04 pm
2 stops11h 04m
Milwaukee-Mitchell
Wed 6/3
5:00 am-1:40 pm
2 stops10h 40m
$451
Quickest round-trip
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Sun 8/2
5:05 pm-1:00 am
1 stop5h 55m
Milwaukee-Mitchell
Thu 8/6
6:25 pm-10:15 pm
1 stop5h 50m
$477
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Fri 6/19
4:05 pm-1:15 am
1 stop7h 10m
Milwaukee-Mitchell
Mon 6/22
5:15 pm-11:25 pm
1 stop8h 10m
$477
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Fri 7/17
9:20 am-10:45 pm
2 stops11h 25m
Milwaukee-Mitchell
Fri 7/24
6:35 pm-10:55 pm
1 stop6h 20m
$482
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Mon 6/15
4:05 pm-1:15 am
1 stop7h 10m
Milwaukee-Mitchell
Fri 6/19
3:15 pm-11:25 pm
2 stops10h 10m
$482
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Thu 6/25
10:20 am-7:45 pm
2 stops7h 25m
Milwaukee-Mitchell
Wed 7/1
6:25 am-1:15 pm
2 stops8h 50m
$482
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Sat 8/22
6:10 am-2:15 pm
1 stop6h 05m
Milwaukee-Mitchell
Mon 8/24
7:30 am-12:54 pm
1 stop7h 24m
$485
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Thu 7/23
1:40 pm-9:43 pm
1 stop6h 03m
Milwaukee-Mitchell
Wed 8/5
3:59 pm-8:24 pm
1 stop6h 25m
$487
San JoseMilwaukee
SJC - MKE
SJCMKE
San Jose
Thu 6/11
4:05 pm-1:15 am
1 stop7h 10m
Milwaukee-Mitchell
Mon 6/15
6:35 pm-10:55 pm
1 stop6h 20m
$494
Showing 1-10 of 21 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 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 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 $338). 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 May 8, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican Airlines 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.
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Entertainment
7.5
Boarding
8.1
Food
7.0
Crew
8.6
Overall
7.9
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
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Top 3 airlines flying from San Jose to Milwaukee
Discover the top 3 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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$267 | Average$462 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$282 | Average$386 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$300 | Average$353 | FlexibilityNo cancel fee | On-time71% |