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$569+ Cheap flights from Oakland, CA to Madison (OAK - MSN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MSN
oct. 25 — nov. 11
sáb. 10/25
sáb. 11/1
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 septiembre 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$478
(Delta)

Popular in

June

Cheapest in

February

Average price

$418
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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Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 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 septiembre 25, 2025.

This Delta deal was found by Cheapflights users on 9/24. 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.
jue. 10/25:05 pmOAK - MSN
2 stops14h 53mDelta
sáb. 10/410:55 amMSN - OAK
2 stops7h 29mDelta
Deal found 9/24$637
This Delta deal was found by Cheapflights users on 9/24. 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.
jue. 12/1812:30 pmOAK - MSN
2 stops18h 28mDelta
mié. 12/315:03 pmMSN - OAK
2 stops20h 51mDelta
Deal found 9/24$693
This Delta deal was found by Cheapflights users on 9/24. 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.
jue. 12/1812:30 pmOAK - MSN
2 stops8h 26mDelta
mar. 12/306:40 amMSN - OAK
2 stops19h 18mDelta
Deal found 9/24$758
This Delta deal was found by Cheapflights users on 9/24. 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.
jue. 12/1812:30 pmOAK - MSN
2 stops18h 28mDelta
jue. 1/15:03 pmMSN - OAK
2 stops20h 51mDelta
Deal found 9/24$813
This Delta deal was found by Cheapflights users on 9/24. 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.
mié. 10/2212:30 pmOAK - MSN
2 stops7h 59mDelta
lun. 10/275:30 amMSN - OAK
2 stops12h 41mDelta
Deal found 9/24$959
This Delta deal was found by Cheapflights users on 9/25. 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.
mié. 12/175:45 amOAK - MSN
2 stops9h 53mDelta
sáb. 12/2010:50 amMSN - OAK
2 stops12h 55mDelta
Deal found 9/25$985
This Delta deal was found by Cheapflights users on 9/25. 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.
jue. 10/25:05 pmOAK - MSN
2 stops14h 53mDelta
lun. 10/62:42 pmMSN - OAK
2 stops11h 11mDelta
Deal found 9/25$1,199
This Delta deal was found by Cheapflights users on 9/25. 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.
mié. 11/2612:28 pmOAK - MSN
2 stops8h 31mDelta
dom. 11/306:00 amMSN - OAK
2 stops7h 48mDelta
Deal found 9/25$1,208
This Delta deal was found by Cheapflights users on 9/24. 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.
vie. 12/195:45 amOAK - MSN
2 stops9h 03mDelta
mar. 12/306:40 amMSN - OAK
2 stops11h 37mDelta
Deal found 9/24$1,239
This Delta deal was found by Cheapflights users on 9/24. 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.
vie. 10/1012:30 pmOAK - MSN
2 stops7h 59mDelta
lun. 10/131:19 pmMSN - OAK
2 stops12h 34mDelta
Deal found 9/24$1,331
This Delta deal was found by Cheapflights users on 9/24. 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.
vie. 12/195:45 amOAK - MSN
2 stops9h 03mDelta
jue. 1/12:48 pmMSN - OAK
2 stops9h 59mDelta
Deal found 9/24$1,359
This Delta deal was found by Cheapflights users on 9/24. 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.
sáb. 12/205:53 amOAK - MSN
2 stops8h 30mDelta
mar. 12/306:40 amMSN - OAK
2 stops11h 37mDelta
Deal found 9/24$1,419

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 septiembre 25, 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

mar. 3/10

5:55 am-5:10 pm

2 stops9h 15m

Madison Truax Field

mié. 3/11

2:40 pm-11:53 pm

2 stops11h 13m

$569

OaklandMadison

OAK - MSN

OAKMSN

Oakland

jue. 12/18

12:30 pm-8:58 am

2 stops18h 28m

Madison Truax Field

mié. 12/31

5:03 pm-11:54 am

2 stops20h 51m

$693

OaklandMadison

OAK - MSN

OAKMSN

Oakland

jue. 12/18

12:30 pm-10:56 pm

2 stops8h 26m

Madison Truax Field

mar. 12/30

6:40 am-11:58 pm

2 stops19h 18m

$758

OaklandMadison

OAK - MSN

OAKMSN

Oakland

jue. 12/18

12:30 pm-8:58 am

2 stops18h 28m

Madison Truax Field

jue. 1/1

5:03 pm-11:54 am

2 stops20h 51m

$813

OaklandMadison

OAK - MSN

OAKMSN

Oakland

mié. 10/22

12:30 pm-10:29 pm

2 stops7h 59m

Madison Truax Field

lun. 10/27

5:30 am-4:11 pm

2 stops12h 41m

$959

OaklandMadison

OAK - MSN

OAKMSN

Oakland

mié. 12/17

5:45 am-5:38 pm

2 stops9h 53m

Madison Truax Field

sáb. 12/20

10:50 am-9:45 pm

2 stops12h 55m

$985

OaklandMadison

OAK - MSN

OAKMSN

Oakland

mié. 11/26

12:28 pm-10:59 pm

2 stops8h 31m

Madison Truax Field

dom. 11/30

6:00 am-11:48 am

2 stops7h 48m

$1,208

OaklandMadison

OAK - MSN

OAKMSN

Oakland

vie. 12/19

5:45 am-4:48 pm

2 stops9h 03m

Madison Truax Field

mar. 12/30

6:40 am-4:17 pm

2 stops11h 37m

$1,239

OaklandMadison

OAK - MSN

OAKMSN

Oakland

vie. 10/10

12:30 pm-10:29 pm

2 stops7h 59m

Madison Truax Field

lun. 10/13

1:19 pm-11:53 pm

2 stops12h 34m

$1,331

OaklandMadison

OAK - MSN

OAKMSN

Oakland

vie. 12/19

5:45 am-4:48 pm

2 stops9h 03m

Madison Truax Field

jue. 1/1

2:48 pm-10:47 pm

2 stops9h 59m

$1,359

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 13 results
1
2

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 September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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, January is the cheapest month in which you can book a flight from Oakland, California to Madison (average of $338). Flying from Oakland, California to Madison in March is currently the most expensive (average of $422). 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 septiembre 25, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Madison as you normally would.

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 septiembre 25, 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
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

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
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Overall

8.0

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, January is the cheapest month in which you can book a flight from Oakland, California to Madison (average of $338). Flying from Oakland, California to Madison in March is currently the most expensive (average of $422). 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 septiembre 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$654FlexibilityNo cancel feeOn-timeN/A

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