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Oakland

$178+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — OAK
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$395
(Delta)

One-way from

$178
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$383
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. 8% potential increase in price ($40 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 September 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 10/76:00 amMSN - OAK
2 stops7h 50mDelta
Sat 10/255:55 amOAK - MSN
2 stops12h 26mDelta
Deal found 9/10$395
This Delta deal was found by Cheapflights users on 9/11. 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 10/117:00 amMSN - OAK
2 stops11h 11mDelta
Sat 11/85:55 amOAK - MSN
2 stops12h 56mDelta
Deal found 9/11$418
This Delta deal was found by Cheapflights users on 9/11. 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 10/117:00 amMSN - OAK
2 stops11h 11mDelta
Tue 11/45:55 amOAK - MSN
2 stops9h 17mDelta
Deal found 9/11$438
This Delta deal was found by Cheapflights users on 9/11. 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 10/117:00 amMSN - OAK
2 stops11h 11mDelta
Mon 11/34:51 pmOAK - MSN
2 stops25h 30mDelta
Deal found 9/11$446
This Delta deal was found by Cheapflights users on 9/10. 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.
Mon 10/65:52 pmMSN - OAK
2 stops19h 58mDelta
Sat 10/255:55 amOAK - MSN
2 stops14h 34mDelta
Deal found 9/10$486
This Delta deal was found by Cheapflights users on 9/10. 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 10/71:19 pmMSN - OAK
2 stops12h 34mDelta
Sun 10/2612:30 pmOAK - MSN
2 stops22h 04mDelta
Deal found 9/10$487
This Delta deal was found by Cheapflights users on 9/11. 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 10/117:00 amMSN - OAK
2 stops11h 11mDelta
Sun 11/25:55 amOAK - MSN
2 stops14h 34mDelta
Deal found 9/11$496
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 10/149:20 amMSN - OAK
2 stops28h 30mDelta
Wed 11/512:30 pmOAK - MSN
2 stops7h 59mDelta
Deal found 9/11$527
This Delta deal was found by Cheapflights users on 9/10. 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 10/71:19 pmMSN - OAK
2 stops12h 34mDelta
Fri 10/245:55 amOAK - MSN
2 stops32h 46mDelta
Deal found 9/10$531
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 10/149:20 amMSN - OAK
2 stops28h 30mDelta
Mon 11/35:55 amOAK - MSN
2 stops9h 17mDelta
Deal found 9/11$539
This Delta deal was found by Cheapflights users on 9/11. 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 10/117:00 amMSN - OAK
2 stops11h 11mDelta
Fri 11/74:51 pmOAK - MSN
2 stops27h 38mDelta
Deal found 9/11$562
This Delta deal was found by Cheapflights users on 9/11. 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 10/101:19 pmMSN - OAK
2 stops28h 52mDelta
Sat 11/812:30 pmOAK - MSN
2 stops7h 59mDelta
Deal found 9/11$572

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 September 11, 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 10/7

6:00 am-11:50 am

2 stops7h 50m

Oakland

Sat 10/25

5:55 am-8:21 pm

2 stops12h 26m

$395

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 10/11

7:00 am-4:11 pm

2 stops11h 11m

Oakland

Wed 11/5

5:55 am-5:12 pm

2 stops9h 17m

$438

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 10/11

7:00 am-4:11 pm

2 stops11h 11m

Oakland

Tue 11/4

5:55 am-5:12 pm

2 stops9h 17m

$438

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 10/11

7:00 am-4:11 pm

2 stops11h 11m

Oakland

Mon 11/3

4:51 pm-8:21 pm

2 stops25h 30m

$446

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 10/7

1:19 pm-11:53 pm

2 stops12h 34m

Oakland

Sun 10/26

12:30 pm-12:34 pm

2 stops22h 04m

$487

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 10/11

7:00 am-4:11 pm

2 stops11h 11m

Oakland

Sun 11/2

5:55 am-10:29 pm

2 stops14h 34m

$496

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 10/14

9:20 am-11:50 am

2 stops28h 30m

Oakland

Tue 11/4

5:55 am-5:12 pm

2 stops9h 17m

$527

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 10/7

1:19 pm-11:53 pm

2 stops12h 34m

Oakland

Fri 10/24

5:55 am-4:41 pm

2 stops32h 46m

$531

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 10/11

7:00 am-4:11 pm

2 stops11h 11m

Oakland

Fri 11/7

4:51 pm-10:29 pm

2 stops27h 38m

$562

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Fri 10/10

1:19 pm-4:11 pm

2 stops28h 52m

Oakland

Tue 11/4

5:55 am-5:12 pm

2 stops9h 17m

$572

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 18 results
1
2

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, April is the cheapest month in which you can book a flight from Madison to Oakland, California (average of $183). Flying from Madison to Oakland, California in November is currently the most expensive (average of $259). 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.

Reviews of airlines servicing Oakland

Get insights into the airlines that provide service to Oakland. 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 Oakland. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Delta from Madison to Oakland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 50m. Fly via Delta to get the fastest option. Madison and Oakland, California are separated by a distance of 1757 mi.

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

    Currently priced at $497, Delta will fly you from Madison to Oakland, California and back. In addition to Delta, many other airlines offer competitively priced options for your trip.

  • 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, April is the cheapest month in which you can book a flight from Madison to Oakland, California (average of $183). Flying from Madison to Oakland, California in November is currently the most expensive (average of $259). 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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Top airline flying from Madison to Oakland

Discover the top airline that operate flights from Madison to Oakland. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$497Average$573FlexibilityNo cancel feeOn-timeN/A

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