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Madison

$335+ 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 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MSN
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap 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 February 11, 2026.

This Delta deal was found by Cheapflights users on 2/7. 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 3/175:55 am
OAK
-
MSN
2 stops9h 52m
Delta
Tue 3/246:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/7$387
This Delta deal was found by Cheapflights users on 2/8. 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 3/1012:35 pm
OAK
-
MSN
2 stops22h 06m
Delta
Tue 3/176:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/8$397
This Delta deal was found by Cheapflights users on 2/7. 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 3/175:55 am
OAK
-
MSN
2 stops9h 52m
Delta
Mon 3/236:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/7$430
This Delta deal was found by Cheapflights users on 2/7. 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 3/185:55 am
OAK
-
MSN
2 stops15h 03m
Delta
Mon 3/236:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/7$440
This Delta deal was found by Cheapflights users on 2/8. 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 4/185:55 am
OAK
-
MSN
2 stops9h 39m
Delta
Tue 4/212:41 pm
MSN
-
OAK
2 stops11h 13m
Delta
Deal found 2/8$448
This Delta deal was found by Cheapflights users on 2/10. 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 3/212:40 pm
OAK
-
MSN
2 stops8h 08m
Delta
Mon 3/96:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/10$518
This Delta deal was found by Cheapflights users on 2/8. 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 5/65:04 pm
OAK
-
MSN
2 stops13h 22m
Delta
Mon 5/189:06 am
MSN
-
OAK
2 stops16h 51m
Delta
Deal found 2/8$527
This Delta deal was found by Cheapflights users on 2/8. 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 3/1012:35 pm
OAK
-
MSN
2 stops22h 06m
Delta
Wed 3/186:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/8$538
This Delta deal was found by Cheapflights users on 2/8. 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 5/115:06 pm
OAK
-
MSN
2 stops17h 39m
Delta
Mon 5/186:12 pm
MSN
-
OAK
2 stops24h 14m
Delta
Deal found 2/8$565
This Delta deal was found by Cheapflights users on 2/8. 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 3/1612:35 pm
OAK
-
MSN
2 stops8h 23m
Delta
Mon 3/236:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Deal found 2/8$571
This Delta deal was found by Cheapflights users on 2/8. 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 5/65:04 pm
OAK
-
MSN
2 stops13h 22m
Delta
Tue 5/129:06 am
MSN
-
OAK
2 stops16h 51m
Delta
Deal found 2/8$592
This Delta deal was found by Cheapflights users on 2/8. 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 5/95:55 pm
OAK
-
MSN
2 stops16h 50m
Delta
Mon 5/186:12 pm
MSN
-
OAK
2 stops24h 14m
Delta
Deal found 2/8$599

Find 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 February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$387
(Delta)

One-way from

$335
(Delta)

Popular in

December

Cheapest in

September

Average price

$463
Provider with most accurate pricing for Oakland-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Madison Truax Field flights.
Search Deals
From Oakland to Madison Truax Field
Search Deals
One-way flight from Oakland to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 11, 2026.
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 3/17

5:55 am-5:47 pm

2 stops9h 52m

Madison Truax Field

Tue 3/24

6:04 pm-11:46 pm

2 stops7h 42m

$387

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 3/10

12:35 pm-12:41 pm

2 stops22h 06m

Madison Truax Field

Tue 3/17

6:04 pm-11:46 pm

2 stops7h 42m

$397

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Wed 3/18

5:55 am-10:58 pm

2 stops15h 03m

Madison Truax Field

Tue 3/24

6:04 pm-11:46 pm

2 stops7h 42m

$397

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Wed 3/18

5:55 am-10:58 pm

2 stops15h 03m

Madison Truax Field

Mon 3/23

6:04 pm-11:46 pm

2 stops7h 42m

$440

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Sat 4/18

5:55 am-5:34 pm

2 stops9h 39m

Madison Truax Field

Tue 4/21

2:41 pm-11:54 pm

2 stops11h 13m

$448

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Mon 3/2

12:40 pm-10:48 pm

2 stops8h 08m

Madison Truax Field

Mon 3/9

6:04 pm-11:46 pm

2 stops7h 42m

$518

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Fri 5/8

5:06 pm-9:27 pm

2 stops26h 21m

Madison Truax Field

Mon 5/18

9:06 am-11:57 pm

2 stops16h 51m

$527

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Wed 5/6

5:04 pm-8:26 am

2 stops13h 22m

Madison Truax Field

Mon 5/18

9:06 am-11:57 pm

2 stops16h 51m

$527

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 5/12

5:06 pm-8:26 am

2 stops13h 20m

Madison Truax Field

Mon 5/18

9:06 am-11:57 pm

2 stops16h 51m

$527

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 3/10

12:35 pm-12:41 pm

2 stops22h 06m

Madison Truax Field

Wed 3/18

6:04 pm-11:46 pm

2 stops7h 42m

$538

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Showing 1-10 of 21 results
1
2
3
  • Most accurate provider: When it comes to deals on Oakland, California-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Madison flight deals on Cheapflights vs. FlightHub >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 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 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 January is currently the most expensive (average of $268). 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 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 February 11, 2026.
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
8,179 reviews

Comfort

7.9

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

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
8,179 reviews
Delta
7.9
Good
8,179 reviews

Comfort

7.9

Crew

8.5

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

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 52m. 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 January is currently the most expensive (average of $268). 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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Alternative routes for Oakland to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$519FlexibilityNo cancel feeOn-timeN/A

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