$106 Find Cheap Flights from San Jose to Wisconsin

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Wisconsin departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Wisconsin

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Wisconsin, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Wisconsin, as well as popular online travel agencies
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Flight Deals

Cheap Flights from San Jose to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$341
Madison
Madison1 stop$305
Appleton
Appleton1 stop$369
Green Bay
Green Bay2 stops$374
Wausau
Wausau1 stop$522
La Crosse
La Crosse2 stops$688
Rhinelander
Rhinelander2 stops$517
Minneapolis
Minneapolis2 stops$272
Duluth
Duluth1 stop$516
Chicago
Chicago1 stop$270
Milwaukee
Milwaukee1 stop$341
Madison
Madison1 stop$305
Appleton
Appleton1 stop$369
Green Bay
Green Bay2 stops$374
Wausau
Wausau1 stop$522
La Crosse
La Crosse2 stops$688
Rhinelander
Rhinelander2 stops$517
Minneapolis
Minneapolis2 stops$272
Duluth
Duluth1 stop$516
Chicago
Chicago1 stop$270

Book Cheap San Jose to Wisconsin Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Wisconsin that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Jose to Wisconsin

Sat, Jun 27 - Fri, Jul 10
Frontier Logo
8:25 pm - 6:19 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$270Frontier
Mon, May 18 - Wed, May 27
Multiple Airlines Logo
12:57 pm - 4:02 pm
SJC
-
MSP
25h 05m
2 stops
Multiple Airlines Logo
8:10 am - 11:59 am
MSP
-
SJC
29h 49m
1 stop
$272Multiple Airlines
Wed, May 27 - Tue, Jun 9
Alaska Airlines Logo
12:59 pm - 1:14 pm
SJC
-
ORD
22h 15m
1 stop
Alaska Airlines Logo
7:40 am - 1:40 pm
ORD
-
SJC
8h 00m
1 stop
$272Alaska Airlines
Wed, May 27 - Sat, May 30
Delta Logo
12:12 pm - 10:44 pm
SJC
-
MSN
8h 32m
1 stop
Delta Logo
2:33 pm - 8:38 pm
MSN
-
SJC
8h 05m
1 stop
$305Delta
Wed, May 27 - Sat, May 30
American Airlines Logo
7:24 pm - 10:38 am
SJC
-
MSN
13h 14m
2 stops
American Airlines Logo
5:39 pm - 10:43 pm
MSN
-
SJC
7h 04m
1 stop
$310American Airlines
Wed, May 27 - Sat, May 30
American Airlines Logo
7:24 pm - 10:38 am
SJC
-
MSN
13h 14m
2 stops
American Airlines Logo
2:03 pm - 10:43 pm
MSN
-
SJC
10h 40m
2 stops
$315American Airlines
Wed, Jul 8 - Mon, Jul 13
Delta Logo
6:20 am - 2:04 pm
SJC
-
MSN
5h 44m
1 stop
Delta Logo
2:45 pm - 8:35 pm
MSN
-
SJC
7h 50m
1 stop
$337Delta
Tue, May 19 - Sat, May 23
United Airlines Logo
12:56 pm - 10:59 pm
SJC
-
MKE
8h 03m
1 stop
United Airlines Logo
5:29 pm - 10:35 pm
MKE
-
SJC
7h 06m
1 stop
$341United Airlines
Tue, May 19 - Thu, Jun 4
United Airlines Logo
6:30 am - 4:50 pm
SJC
-
ATW
8h 20m
1 stop
United Airlines Logo
5:30 pm - 10:30 pm
ATW
-
SJC
7h 00m
1 stop
$369United Airlines
Wed, Jun 10 - Wed, Jun 10
Southwest Logo
6:00 am - 2:00 pm
SJC
-
MKE
6h 00m
1 stop
Southwest Logo
6:55 pm - 11:00 pm
MKE
-
SJC
6h 05m
1 stop
$406Southwest
Booking Insights

KAYAK's insights & trends for San Jose to Wisconsin flights

Get data-powered insights and trends into flights from San Jose to Wisconsin to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from San Jose, California to Wisconsin?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Jose, California to Wisconsin departing in May.

What is the cheapest month to fly from San Jose to Wisconsin?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Wisconsin, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Jose to Wisconsin is July, when tickets cost $171 (return) on average. On the other hand, the most expensive months are February and January, when the average cost of round-trip tickets is $429 and $353 respectively.

Good to know

Low seasonFebruary
Cheapest flight$106
Best time to beat the crowds but there is an average 28% increase in price.
Flight from San Jose to Chicago O'Hare Airport

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from San Jose to Wisconsin?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Jose to Wisconsin.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Wisconsin?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose to Wisconsin is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Jose to Wisconsin?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from San Jose to Wisconsin with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Wisconsin?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from San Jose to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from San Jose to the following destinations at these prices or less: Minneapolis $163 one-way - $340 round-trip; Chicago $304 one-way - $453 round-trip

Reviews of the top 4 airlines serving from San Jose to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Wisconsin. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Jose to Wisconsin? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4314 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

OK, we were delayed and had to de plane and reboard.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

Boarding gate at LAX was too crowded—two gates next to one another

On time departure and early arrival. Flight attendant very nice.

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

there are no options s for snack besides cookies would ve nice to have a salty option n

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Everything you need to know for your flight from San Jose to Wisconsin

Information on your arrival and departure airports