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$285+ Cheap flights from Madison to Oakland, CA (MSN - OAK)

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — OAK
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Madison to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Oakland (OAK). 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$569
(Delta)

One-way from

$285
(Delta)

Popular in

December

Cheapest in

August

Average price

$443
Provider with most accurate pricing for Madison Truax Field-Oakland flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Oakland flights.
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From Madison Truax Field to Oakland
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One-way flight from Madison Truax Field to Oakland
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Highest demand for flights based on searches. 5% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Madison to Oakland

Cheapest flights from Madison to Oakland
Explore the most affordable flight options available from Madison to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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 11/216:00 amMSN - OAK
2 stops20h 03mDelta
Mon 12/14:51 pmOAK - MSN
2 stops17h 59mDelta
Deal found 10/30$696
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:00 amMSN - OAK
2 stops7h 48mDelta
Mon 11/175:55 amOAK - MSN
2 stops9h 27mDelta
Deal found 10/29$768
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amMSN - OAK
2 stops7h 48mDelta
Sat 11/2912:28 pmOAK - MSN
2 stops8h 31mDelta
Deal found 10/28$1,264
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/256:00 amMSN - OAK
2 stops7h 48mDelta
Sat 11/2912:28 pmOAK - MSN
2 stops8h 31mDelta
Deal found 10/28$1,382
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/261:30 pmMSN - OAK
2 stops12h 33mDelta
Sat 11/2912:28 pmOAK - MSN
2 stops8h 31mDelta
Deal found 10/28$1,439
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:00 amMSN - OAK
2 stops7h 48mDelta
Sun 11/305:55 amOAK - MSN
2 stops9h 27mDelta
Deal found 10/28$1,704
This Delta deal was found by Cheapflights users on 10/30. 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 11/216:00 amMSN - OAK
2 stops7h 48mDelta
Sun 11/305:55 amOAK - MSN
2 stops8h 55mDelta
Deal found 10/30$1,769
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/256:00 amMSN - OAK
2 stops7h 48mDelta
Sun 11/3012:28 pmOAK - MSN
2 stops8h 31mDelta
Deal found 10/28$1,879

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Oakland 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 October 30, 2025.
Use the filters below to find and compare flights from Madison to Oakland that are best for you.

Fly from

Madison

Fly to

Oakland

Route

Depart

Return

Price

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 4/14

5:55 pm-11:49 pm

2 stops7h 54m

Oakland

Wed 4/15

5:55 am-12:54 pm

2 stops28h 59m

$602

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Fri 11/21

6:00 am-12:03 am

2 stops20h 03m

Oakland

Mon 12/1

4:51 pm-12:50 pm

2 stops17h 59m

$696

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 11/13

6:00 am-11:48 am

2 stops7h 48m

Oakland

Mon 11/17

5:55 am-5:22 pm

2 stops9h 27m

$768

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 11/25

6:00 am-11:48 am

2 stops7h 48m

Oakland

Sat 11/29

12:28 pm-10:59 pm

2 stops8h 31m

$1,382

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Wed 11/26

1:30 pm-12:03 am

2 stops12h 33m

Oakland

Sat 11/29

12:28 pm-10:59 pm

2 stops8h 31m

$1,439

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Mon 11/24

6:00 am-11:48 am

2 stops7h 48m

Oakland

Sun 11/30

5:55 am-5:22 pm

2 stops9h 27m

$1,704

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Fri 11/21

6:00 am-11:48 am

2 stops7h 48m

Oakland

Sun 11/30

5:55 am-4:50 pm

2 stops8h 55m

$1,769

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 11/25

6:00 am-11:48 am

2 stops7h 48m

Oakland

Sun 11/30

12:28 pm-10:59 pm

2 stops8h 31m

$1,879

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 12/4

6:59 am-4:04 pm

2 stops11h 05m

$285

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sun 11/16

6:59 am-4:11 pm

2 stops11h 12m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 16 results
1
2

Compare providers for flights from Madison to Oakland

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

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

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

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

Currently, February is the cheapest month in which you can book a flight from Madison to Oakland, California (average of $189). Flying from Madison to Oakland, California in June is currently the most expensive (average of $256). 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.

Related info for your journey

Find useful and relevant information for your journey from Madison to Oakland. 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 Madison to Oakland, California?

    There are many flights that can get you from Madison to Oakland, California in 7h 54m. Fly via Delta to get the fastest option. Madison and Oakland, California are separated by a distance of 1757 mi.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Madison to Oakland, California (average of $189). Flying from Madison to Oakland, California in June is currently the most expensive (average of $256). 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

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