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$167+ Cheap flights from San Jose to Madison (SJC - MSN)

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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — MSN
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheapflights Tip: The best prices from San Jose to Madison Truax Field are usually found in September or March, booked 72 days in advance, depart on a Wednesday or Saturday and return on a Friday

Cheap flight deals from San Jose to Madison

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Madison (MSN). 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 July 29, 2025.

Round-trip from

$269
(Mytrip)

One-way from

$167
(FlightHub)

Popular in

February

Cheapest in

September

Average price

$510
From San Jose to Madison Truax Field
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One-way flight from San Jose to Madison Truax Field
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Highest demand for flights based on searches. 6% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from San Jose to Madison

Cheapest flights from San Jose to Madison
Explore the most affordable flight options available from San Jose to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:14 pmSJC - MSN
1 stop27h 00mFrontier
Thu 9/187:59 pmMSN - SJC
1 stop17h 31mFrontier
Deal found 7/28$269
This Delta deal was found by Cheapflights users on 7/26. 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 9/241:30 pmSJC - MSN
1 stop7h 04mDelta
Wed 10/16:00 amMSN - SJC
1 stop8h 24mDelta
Deal found 7/26$289
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 12/249:00 amSJC - MSN
2 stops10h 03mUnited Airlines
Thu 1/12:23 pmMSN - SJC
1 stop10h 14mUnited Airlines
Deal found 7/27$369
This American Airlines deal was found by Cheapflights users on 7/26. 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 9/276:00 amSJC - MSN
1 stop8h 52mAmerican Airlines
Wed 10/16:40 amMSN - SJC
1 stop7h 59mAmerican Airlines
Deal found 7/26$379
This Alaska Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 11/69:32 amSJC - MSN
2 stops21h 49mAlaska Airlines
Mon 11/105:40 pmMSN - SJC
2 stops17h 15mAlaska Airlines
Deal found 7/27$519

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Madison 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 July 29, 2025.
Use the filters below to find and compare flights from San Jose to Madison that are best for you.

Fly from

San Jose

Fly to

Madison

Route

Depart

Return

Price

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Thu 9/11

2:14 pm-7:14 pm

1 stop27h 00m

Madison Truax Field

Thu 9/18

7:59 pm-11:30 am

1 stop17h 31m

$269

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Wed 9/24

1:30 pm-10:34 pm

1 stop7h 04m

Madison Truax Field

Sun 9/28

6:00 am-12:24 pm

1 stop8h 24m

$289

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Wed 12/24

9:00 am-9:03 pm

2 stops10h 03m

Madison Truax Field

Thu 1/1

2:23 pm-10:37 pm

1 stop10h 14m

$369

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Sat 9/27

6:00 am-4:52 pm

1 stop8h 52m

Madison Truax Field

Wed 10/1

6:40 am-12:39 pm

1 stop7h 59m

$379

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Thu 11/6

9:32 am-9:21 am

2 stops21h 49m

Madison Truax Field

Mon 11/10

5:40 pm-8:55 am

2 stops17h 15m

$519

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Thu 8/21

12:22 pm-6:58 pm

1 stop28h 36m

$167

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Wed 10/22

7:15 am-10:33 pm

2 stops13h 18m

$184

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Tue 8/19

9:49 am-11:27 pm

2 stops11h 38m

$215

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Wed 8/6

7:00 am-8:56 pm

2 stops11h 56m

$234

San JoseMadison

SJC - MSN

SJCMSN

San Jose

Tue 8/19

6:00 am-9:39 am

3 stops25h 39m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 11 results
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Best time to book a flight from San Jose to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from San Jose with our price prediction graph.
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 Madison

How far ahead should I book a flight from San Jose to Madison?

Use this chart to determine the optimal time to book a round-trip flight from San Jose to Madison. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from San Jose to Madison, you should look to book at least 72 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from San Jose to Madison?

Currently, January is the cheapest month in which you can book a flight from San Jose to Madison (average of $338). Flying from San Jose to Madison in March is currently the most expensive (average of $422). 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.

What is the cheapest time of day to fly from SJC to MSN?

Find hourly flight availability from San Jose to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

One of the essential ways to save on airfare from San Jose to Madison is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 19% on airfare.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated July 29, 2025.
Read through reviews of airlines operating flights from San Jose to Madison, such as Alaska Airlines, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Frontier
5.9
Fair
3,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from San Jose to Madison round-trip?

    According to our current data, Frontier ($269), Delta ($289), and United Airlines ($369) offers the cheapest pricing from San Jose to Madison. Frontier is 45% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from San Jose to Madison one-way?

    The cheapest airlines for a one-way flight from San Jose to Madison are Frontier ($167), Delta ($184), and American Airlines ($215).

  • Can I find deals for flights from San Jose to Madison that include hotel bookings?

    Yes. In addition to deals on San Jose to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Madison.

  • Can I find deals for business class flights from San Jose to Madison?

    Yes. Cheapflights offers flight deals from San Jose to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, January is the cheapest month in which you can book a flight from San Jose to Madison (average of $338). Flying from San Jose to Madison in March is currently the most expensive (average of $422). 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.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Top 3 airlines flying from San Jose to Madison

Discover the top 3 airlines that operate flights from San Jose to Madison. 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$298Average$517FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$338Average$518FlexibilityNo cancel feeOn-time71%

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