$129 Find Cheap Flights from San José 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 José to Wisconsin departing on 2/7. 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 José 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 José to Wisconsin, as well as popular online travel agencies
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Cheap Flights from San José to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$420
Green Bay
Green Bay2 stops$534
Chicago
Chicago1 stop$257
Milwaukee
Milwaukee1 stop$420
Green Bay
Green Bay2 stops$534
Chicago
Chicago1 stop$257

Book Cheap San José 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 José 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 José to Wisconsin

Fri, Feb 6 - Sun, Feb 15
Spirit Airlines Logo
1:30 pm - 11:47 pm
SJO
-
ORD
10h 17m
1 stop
Spirit Airlines Logo
7:00 am - 12:22 pm
ORD
-
SJO
29h 22m
1 stop
$257Spirit Airlines
Fri, Feb 13 - Sun, Mar 1
Spirit Airlines Logo
1:31 pm - 11:47 pm
SJO
-
ORD
10h 16m
1 stop
Spirit Airlines Logo
8:59 am - 11:40 am
ORD
-
SJO
26h 41m
2 stops
$261Spirit Airlines
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
1:31 pm - 11:24 pm
SJO
-
ORD
9h 53m
1 stop
Multiple Airlines Logo
8:16 pm - 12:22 pm
ORD
-
SJO
16h 06m
1 stop
$267Multiple Airlines
Tue, Apr 21 - Wed, May 20
JetBlue Logo
1:25 pm - 11:25 pm
SJO
-
MKE
9h 00m
1 stop
JetBlue Logo
5:55 am - 12:04 pm
MKE
-
SJO
7h 09m
1 stop
$420JetBlue
Wed, Feb 18 - Mon, Feb 23
Multiple Airlines Logo
12:35 pm - 7:32 pm
SJO
-
MSP
30h 57m
1 stop
Multiple Airlines Logo
10:00 am - 12:22 pm
MSP
-
SJO
26h 22m
2 stops
$430Multiple Airlines
Fri, Mar 13 - Tue, Mar 17
American Airlines Logo
6:00 am - 3:53 pm
SJO
-
MKE
8h 53m
1 stop
American Airlines Logo
12:14 pm - 7:12 pm
MKE
-
SJO
7h 58m
1 stop
$515American Airlines
Fri, Mar 13 - Tue, Mar 17
American Airlines Logo
7:00 am - 11:59 pm
SJO
-
MKE
15h 59m
1 stop
American Airlines Logo
12:14 pm - 9:43 pm
MKE
-
SJO
10h 29m
2 stops
$519American Airlines
Fri, May 8 - Mon, May 11
JetBlue Logo
1:25 pm - 11:27 pm
SJO
-
MKE
9h 02m
1 stop
JetBlue Logo
5:55 am - 12:04 pm
MKE
-
SJO
7h 09m
1 stop
$521JetBlue
Fri, Mar 13 - Tue, Mar 17
United Airlines Logo
1:05 pm - 10:14 pm
SJO
-
MKE
8h 09m
1 stop
United Airlines Logo
5:00 am - 11:56 am
MKE
-
SJO
7h 56m
1 stop
$523United Airlines
Fri, Mar 13 - Tue, Mar 17
United Airlines Logo
1:05 pm - 10:14 pm
SJO
-
MKE
8h 09m
1 stop
United Airlines Logo
9:44 am - 9:32 pm
MKE
-
SJO
12h 48m
2 stops
$527United Airlines
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San José 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 José to Wisconsin is January, when tickets cost $373 (return) on average. On the other hand, the most expensive months are October and February, when the average cost of round-trip tickets is $700 and $675 respectively.

Good to know

Low seasonOctober
Cheapest flight$129
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from San José to Chicago O'Hare Airport

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from San José 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 José to Wisconsin.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San José 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 José 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 José 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 José 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 José 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 José to the following destinations at these prices or less: Chicago $150 one-way - $296 round-trip

Reviews of the top airlines flying from San José to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from San José 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 José 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.
7.4
United AirlinesOverall score based on 9191 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
Airline reviews

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

4.0 OkayAnonymous, Jan 2026
ALB - IAD
Read more United Airlines reviews

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Mean flight attendant. I wanted to reuse my plastic cup, but he (Matthew) said he can't for safety. I then said "I don't want water then" and he poured me a glass. I hope Matthew gets herpes and spends the rest of his life poor, lonely, and homeless.

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The seats were comfortable and we had leg room. Great entertainment.

The flight crew where really good. Better then the crew from BNE to SFO

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

When I got to the waiting area, it was full but when the time came to board, rgete was no plane. The women where you would show your ticket, gave the news saying there was a maintenance problem and that it be an extra half hour wait. We never did see the plane but ultimately, Noone ever saw the plane because there was a fire on one engine. Needless to say, the wait time before it was announced what really happened, was a few hours. Many, many missed their plane transfer because they entered their first train. Also, the electronic info panels up on the different wall for all to see the status of each flight, never stated anything having to do with the long, long hold up. Many people had major problems because they had to swith planes during their trip and that never happened...

It was a good trip. Flight Attendants were friendly and responsive.

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

Information on your arrival and departure airports