SJC - MSN

$213 Find Cheap Flights from San Jose to Madison - Compare and Save

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 Madison departing on 8/30. 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

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Everything you should know

Cheapest round-trip
$343
Typical prices: $338-$392
United Airlines
Wed 9/9Sat 9/12
SJC - MSN • 1 stop
Cheapest one-way
$213
Typical prices: $282-$508
Multiple Airlines
Sun 8/30
SJC - MSN • 2 stops
Top airlines
Cheapest • from $343 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between San Jose and Madison. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $575 (round-trip)
Shortest trip • 6h 14m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 52% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San Jose to Madison (SJC-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Madison 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 Madison

Wed, Sep 9 - Sat, Sep 12
United Airlines Logo
6:30 am - 2:59 pm
SJC
-
MSN
6h 29m
1 stop
United Airlines Logo
2:50 pm - 8:54 pm
MSN
-
SJC
8h 04m
1 stop
$343United Airlines
Tue, Oct 13 - Tue, Oct 20
Delta Logo
1:34 pm - 10:57 pm
SJC
-
MSN
7h 23m
1 stop
Delta Logo
6:00 am - 12:39 pm
MSN
-
SJC
8h 39m
1 stop
$343Delta
Wed, Oct 14 - Tue, Oct 20
Delta Logo
1:34 pm - 8:55 pm
SJC
-
MSN
5h 21m
1 stop
Delta Logo
6:00 am - 12:39 pm
MSN
-
SJC
8h 39m
1 stop
$343Delta
Mon, Oct 12 - Tue, Oct 20
Delta Logo
10:40 pm - 10:23 am
SJC
-
MSN
9h 43m
1 stop
Delta Logo
6:00 am - 12:39 pm
MSN
-
SJC
8h 39m
1 stop
$351Delta
Fri, Aug 21 - Sun, Aug 23
American Airlines Logo
12:42 pm - 12:10 am
SJC
-
MSN
9h 28m
2 stops
American Airlines Logo
8:00 am - 11:57 am
MSN
-
SJC
5h 57m
1 stop
$364American Airlines
Thu, Aug 27 - Thu, Sep 3
American Airlines Logo
12:42 pm - 12:10 am
SJC
-
MSN
9h 28m
2 stops
American Airlines Logo
8:00 am - 11:57 am
MSN
-
SJC
5h 57m
1 stop
$364American Airlines
Tue, Nov 3 - Sat, Nov 7
United Airlines Logo
6:30 am - 5:02 pm
SJC
-
MSN
8h 32m
1 stop
United Airlines Logo
4:04 pm - 10:59 pm
MSN
-
SJC
8h 55m
1 stop
$443United Airlines
Sat, Aug 15 - Tue, Aug 18
United Airlines Logo
6:20 am - 2:51 pm
SJC
-
MSN
6h 31m
1 stop
United Airlines Logo
3:55 pm - 10:50 pm
MSN
-
SJC
8h 55m
1 stop
$454United Airlines
Tue, Nov 3 - Sat, Nov 7
Alaska Airlines Logo
7:15 am - 11:12 pm
SJC
-
MSN
13h 57m
2 stops
Alaska Airlines Logo
2:56 pm - 9:34 pm
MSN
-
SJC
8h 38m
1 stop
$644Alaska Airlines
Tue, Nov 3 - Sat, Nov 7
Alaska Airlines Logo
7:43 pm - 8:25 am
SJC
-
MSN
10h 42m
2 stops
Alaska Airlines Logo
9:35 am - 7:40 pm
MSN
-
SJC
12h 05m
2 stops
$649Alaska Airlines
Booking Insights

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

Get data-powered insights and trends into flights from San Jose to Madison 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 Madison?

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 Madison departing in October.

Flight prices are below average for this route right now.

Flights to Madison from San Jose, California usually cost between $510 and $1,022 in October.
The lowest price found in the past 5 days was $343 on Delta (Oct 13-Oct 20).

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Madison, 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 Madison is March, where tickets cost $309 (return) on average. On the other hand, the most expensive months are December and August, where the average cost of round-trip tickets is $1,449 and $757 respectively.

Good to know

Low season

March

Cheapest flight

$213
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from San Jose to Madison

When to book flights from San Jose to Madison

Are your dates flexible? Find out the best times to travel from San Jose to Madison based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from San Jose to Madison

  • What is the cheapest flight from San Jose to Madison?

    In the last 5 days, the lowest price for a flight from San Jose to Madison was $213 for a one-way ticket and $343 for a round-trip.

  • Do I need a passport to fly between San Jose and Madison?

    A passport is not required to fly from San Jose to Madison.

  • Which aircraft models fly most regularly from San Jose to Madison?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from San Jose to Madison?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between San Jose and Madison, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from San Jose to Madison, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from San Jose to Madison are Delta and United Airlines. With an average price for the route of $563 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $754 and an overall rating of 7.4.

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

    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 Madison.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from San Jose 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 Madison?

    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 to Madison with an airline and back to San Jose with another airline. Booking your flights between San Jose and MSN can sometimes prove cheaper using this method.

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

    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 to Madison from San Jose up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from San Jose to Madison

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Madison. 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 Madison? 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.
7.8
DeltaOverall score based on 8493 reviews
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

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

6.0 GoodCarl, Mar 2026
ATL - ATW
Read more Delta reviews

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

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Flight was late, the only reason I almost missed my flight was that my connection was also late.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

It was a short, comfortable flight. It did leave an hour late due to the pilot having to be replaced (family emergency) but that didn’t inconvenience myself & my friend. The situation was explained, eventually.

UA594 was delayed multiple times. I ended up getting picked up so I can make it in time for work 6AM on Monday, 7/6/2026

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

A good, solid, no frills experience. Departed and arrived on time, staff were pleasant and attentive. Loved the Bluetooth connectivity on the SJC to IAH leg. Being able to watch movies and listen to them with my noise cancelling headphones was lovely. Missed that on the IAH to LHR leg (so I put the wired buds on and my over ear Quiet Comforts over those).

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

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

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

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

Information on your arrival and departure airports