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$275+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — OAK
Apr 13 — Apr 201
Mon 4/13
Mon 4/20
1 adult, Economy
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Cheap 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 March 14, 2026.

This Delta deal was found by Cheapflights users on 3/12. 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 4/286:00 am
MSN
-
OAK
2 stops19h 54m
Delta
Fri 5/85:05 pm
OAK
-
MSN
2 stops18h 48m
Delta
Deal found 3/12$534
This Delta deal was found by Cheapflights users on 3/13. 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.
Sat 4/186:00 am
MSN
-
OAK
2 stops7h 53m
Delta
Tue 4/2112:34 pm
OAK
-
MSN
2 stops8h 17m
Delta
Deal found 3/13$558
This Delta deal was found by Cheapflights users on 3/12. 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 4/286:00 am
MSN
-
OAK
2 stops19h 54m
Delta
Thu 5/76:00 am
OAK
-
MSN
2 stops9h 33m
Delta
Deal found 3/12$581
This Delta deal was found by Cheapflights users on 3/11. 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 4/96:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Mon 4/135:55 am
OAK
-
MSN
2 stops14h 56m
Delta
Deal found 3/11$652
This Delta deal was found by Cheapflights users on 3/11. 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 4/96:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Sun 4/124:49 pm
OAK
-
MSN
2 stops15h 20m
Delta
Deal found 3/11$703
This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 3/176:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Tue 3/2412:35 pm
OAK
-
MSN
2 stops8h 23m
Delta
Deal found 3/10$713
This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 3/246:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Sun 3/2912:35 pm
OAK
-
MSN
2 stops18h 16m
Delta
Deal found 3/10$733
This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 3/176:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Wed 3/255:55 am
OAK
-
MSN
2 stops26h 10m
Delta
Deal found 3/10$747
This Delta deal was found by Cheapflights users on 3/11. 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 4/106:00 am
MSN
-
OAK
2 stops19h 46m
Delta
Mon 4/135:55 am
OAK
-
MSN
2 stops14h 56m
Delta
Deal found 3/11$749
This Delta deal was found by Cheapflights users on 3/11. 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.
Sat 4/117:00 am
MSN
-
OAK
2 stops11h 00m
Delta
Mon 4/135:55 am
OAK
-
MSN
2 stops14h 56m
Delta
Deal found 3/11$772
This Delta deal was found by Cheapflights users on 3/10. 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.
Tue 3/176:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Sun 3/2912:35 pm
OAK
-
MSN
2 stops18h 16m
Delta
Deal found 3/10$782

Find 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 March 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$534
(Delta)

One-way from

$275
(Delta)

Popular in

February

Cheapest in

August

Average price

$474
Provider with most accurate pricing for Madison Truax Field-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Oakland flights.
Search Deals
From Madison Truax Field to Oakland
Search Deals
One-way flight from Madison Truax Field to Oakland
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 14, 2026.
Use the filters below to find and compare flights from Madison to Oakland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 4/28

6:00 am-11:54 pm

2 stops19h 54m

Oakland

Fri 5/8

5:05 pm-1:53 pm

2 stops18h 48m

$534
Quickest round-trip

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 4/18

6:00 am-11:53 am

2 stops7h 53m

Oakland

Tue 4/21

5:55 am-5:36 pm

2 stops9h 41m

$630

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 3/24

6:04 pm-11:46 pm

2 stops7h 42m

Oakland

Sat 3/28

12:35 pm-12:41 pm

2 stops22h 06m

$733

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 4/11

7:00 am-4:00 pm

2 stops11h 00m

Oakland

Mon 4/13

5:55 am-10:51 pm

2 stops14h 56m

$772

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Mon 4/20

2:41 pm-11:54 pm

2 stops11h 13m

Oakland

Wed 4/22

5:55 am-5:36 pm

2 stops9h 41m

$804

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Fri 4/10

10:48 am-11:46 pm

2 stops14h 58m

Oakland

Sun 4/12

4:49 pm-2:00 pm

2 stops19h 11m

$806

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 4/11

7:00 am-4:00 pm

2 stops11h 00m

Oakland

Sun 4/12

4:49 pm-10:09 am

2 stops15h 20m

$823

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 3/26

7:00 am-4:00 pm

2 stops11h 00m

Oakland

Wed 4/8

12:35 pm-10:58 pm

2 stops8h 23m

$924

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 3/28

11:26 am-9:43 pm

2 stops12h 17m

Oakland

Wed 4/1

5:55 am-5:47 pm

2 stops9h 52m

$939

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 5/21

9:06 am-4:25 pm

2 stops9h 19m

Oakland

Thu 5/28

6:00 am-5:33 pm

2 stops9h 33m

$973

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/10

Showing 1-10 of 15 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Madison-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Oakland, California flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, May is the cheapest month in which you can book a flight from Madison to Oakland, California (average of $141). Flying from Madison to Oakland, California in October is currently the most expensive (average of $260). 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 19h 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, May is the cheapest month in which you can book a flight from Madison to Oakland, California (average of $141). Flying from Madison to Oakland, California in October is currently the most expensive (average of $260). 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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Alternative routes for Madison to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
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