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$194+ Cheap flights from Oakland, CA to Madison (OAK - 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MSN
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Cheap flight deals from Oakland to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) 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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$598
(Delta)

One-way from

$194
(Delta)

Popular in

June

Cheapest in

February

Average price

$403
Provider with most accurate pricing for Oakland-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Oakland-Madison Truax Field flights.
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From Oakland to Madison Truax Field
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One-way flight from Oakland to Madison Truax Field
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Highest demand for flights based on searches. 4% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Oakland to Madison

Cheapest flights from Oakland to Madison
Explore the most affordable flight options available from Oakland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 12, 2025.

This Delta deal was found by Cheapflights users on 11/9. 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 12/165:55 amOAK - MSN
2 stops28h 55mDelta
Wed 12/242:56 pmMSN - OAK
2 stops33h 51mDelta
Deal found 11/9$630
This Delta deal was found by Cheapflights users on 11/9. 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.
Mon 12/155:55 amOAK - MSN
2 stops28h 55mDelta
Wed 12/242:56 pmMSN - OAK
2 stops33h 51mDelta
Deal found 11/9$640
This Delta deal was found by Cheapflights users on 11/10. 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 12/245:53 amOAK - MSN
2 stops14h 16mDelta
Tue 12/3010:50 amMSN - OAK
2 stops37h 57mDelta
Deal found 11/10$800
This Delta deal was found by Cheapflights users on 11/9. 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 12/1612:30 pmOAK - MSN
2 stops8h 27mDelta
Tue 12/307:00 amMSN - OAK
2 stops11h 04mDelta
Deal found 11/9$823
This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 12/1912:30 pmOAK - MSN
2 stops8h 32mDelta
Wed 12/242:56 pmMSN - OAK
2 stops9h 51mDelta
Deal found 11/9$838
This Delta deal was found by Cheapflights users on 11/9. 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 12/1712:30 pmOAK - MSN
2 stops8h 27mDelta
Tue 12/307:00 amMSN - OAK
2 stops11h 04mDelta
Deal found 11/9$859
This Delta deal was found by Cheapflights users on 11/9. 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.
Mon 12/1512:30 pmOAK - MSN
2 stops8h 27mDelta
Tue 12/307:00 amMSN - OAK
2 stops11h 04mDelta
Deal found 11/9$908
This Delta deal was found by Cheapflights users on 11/9. 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.
Fri 12/1912:30 pmOAK - MSN
2 stops8h 32mDelta
Tue 12/307:00 amMSN - OAK
2 stops11h 04mDelta
Deal found 11/9$958
This Delta deal was found by Cheapflights users on 11/9. 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 12/1612:30 pmOAK - MSN
2 stops8h 27mDelta
Thu 1/12:56 pmMSN - OAK
2 stops9h 51mDelta
Deal found 11/9$973
This Delta deal was found by Cheapflights users on 11/9. 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 12/1712:30 pmOAK - MSN
2 stops8h 27mDelta
Wed 12/312:56 pmMSN - OAK
2 stops9h 51mDelta
Deal found 11/9$1,009
This Delta deal was found by Cheapflights users on 11/9. 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 12/1612:30 pmOAK - MSN
2 stops8h 27mDelta
Fri 12/262:56 pmMSN - OAK
2 stops11h 02mDelta
Deal found 11/9$1,013
This Delta deal was found by Cheapflights users on 11/9. 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 12/1712:30 pmOAK - MSN
2 stops8h 27mDelta
Fri 12/262:56 pmMSN - OAK
2 stops11h 02mDelta
Deal found 11/9$1,049

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland 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 November 12, 2025.
Use the filters below to find and compare flights from Oakland to Madison that are best for you.

Fly from

Oakland

Fly to

Madison

Route

Depart

Return

Price

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 3/10

5:55 am-5:10 pm

2 stops9h 15m

Madison Truax Field

Wed 3/11

2:00 pm-11:53 pm

2 stops11h 53m

$598

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Wed 12/17

5:55 am-10:57 pm

2 stops15h 02m

Madison Truax Field

Wed 12/24

2:56 pm-10:47 pm

2 stops33h 51m

$630

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 12/16

5:55 am-12:50 pm

2 stops28h 55m

Madison Truax Field

Wed 12/24

2:56 pm-10:47 pm

2 stops33h 51m

$630

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 12/16

12:30 pm-10:57 pm

2 stops8h 27m

Madison Truax Field

Tue 12/30

7:00 am-4:04 pm

2 stops11h 04m

$823

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Fri 1/9

12:38 pm-10:40 pm

2 stops8h 02m

Madison Truax Field

Tue 1/13

2:45 pm-10:53 pm

2 stops10h 08m

$829

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Fri 12/19

12:30 pm-11:02 pm

2 stops8h 32m

Madison Truax Field

Wed 12/24

2:56 pm-10:47 pm

2 stops9h 51m

$838

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Wed 12/17

12:30 pm-10:57 pm

2 stops8h 27m

Madison Truax Field

Tue 12/30

7:00 am-4:04 pm

2 stops11h 04m

$859

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Mon 3/23

5:55 am-5:10 pm

2 stops9h 15m

Madison Truax Field

Wed 3/25

2:40 pm-11:53 pm

2 stops11h 13m

$889

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 12/16

12:30 pm-10:57 pm

2 stops8h 27m

Madison Truax Field

Wed 12/31

2:56 pm-10:47 pm

2 stops9h 51m

$973

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 12/16

12:30 pm-10:57 pm

2 stops8h 27m

Madison Truax Field

Thu 1/1

2:56 pm-10:47 pm

2 stops9h 51m

$973

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 22 results
1
2
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Compare providers for flights from Oakland to Madison

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 Oakland to Madison in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Oakland, California-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Oakland, California-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Madison flights, Cheapflights users trust eDreams the most. eDreams 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 Oakland, California-Madison 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 Oakland to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Oakland 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 Oakland to Madison

What is the cheapest month to book a flight from Oakland, California to Madison?

Currently, October is the cheapest month in which you can book a flight from Oakland, California to Madison (average of $140). Flying from Oakland, California to Madison in December is currently the most expensive (average of $297). 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 OAK to MSN?

Find hourly flight availability from Oakland 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 November 12, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 74% on flights from Oakland, California to Madison by exploring options for tickets in the afternoon.

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 November 12, 2025.
Read through reviews of airlines operating flights from Oakland to Madison, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,009 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Michael,Sep 2023

SMF - ATL

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin
Delta
7.9
Good
8,009 reviews
Delta
7.9
Good
8,009 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Michael,Sep 2023

SMF - ATL

Not sufficient leg room and three seats are very tigh.t on 737 in economy main cabin

Related info for your journey

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

  • How long is the flight from Oakland, California to Madison?

    Departing from Oakland, California to Madison will take you 9h 15m. There are 1757 mi between Oakland, California and Madison.

  • What is the cheapest airline to fly from Oakland, California to Madison round-trip?

    Cheapflights users have booked flights from Oakland, California to Madison round-trip from $264.

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

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

  • How can I find direct flights from Oakland to Madison?

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

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

    Yes. Cheapflights offers flight deals from Oakland 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 Oakland, California to Madison?

    Currently, October is the cheapest month in which you can book a flight from Oakland, California to Madison (average of $140). Flying from Oakland, California to Madison in December is currently the most expensive (average of $297). 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 airline flying from Oakland to Madison

Discover the top airline that operate flights from Oakland 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$654FlexibilityNo cancel feeOn-timeN/A

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