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$191+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MSN
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$533
(Delta)

One-way from

$191
(Delta)

Popular in

November

Cheapest in

February

Average price

$453
From Oakland to Madison Truax Field
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One-way flight from Oakland to Madison Truax Field
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Highest demand for flights based on searches. 9% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/26. 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 9/275:05 pmOAK - MSN
2 stops14h 53mDelta
Tue 9/306:00 amMSN - OAK
2 stops7h 56mDelta
Deal found 7/26$533
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/126:00 amOAK - MSN
3 stops24h 01mMultiple Airlines
Sat 8/168:46 amMSN - OAK
2 stops24h 32mMultiple Airlines
Deal found 7/28$594

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 July 29, 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

Sat 9/27

5:05 pm-9:58 am

2 stops14h 53m

Madison Truax Field

Tue 9/30

6:00 am-11:56 am

2 stops7h 56m

$533

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Tue 8/12

6:00 am-8:01 am

3 stops24h 01m

Madison Truax Field

Sat 8/16

8:46 am-7:18 am

2 stops24h 32m

$594

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Thu 8/21

6:00 am-1:08 pm

1 stop5h 08m

$191

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Sat 8/9

6:00 am-6:33 pm

2 stops34h 33m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 29, 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 July 29, 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
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

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
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Crew

8.5

Overall

8.0

Food

7.3

Comfort

7.9

Entertainment

7.9

Boarding

8.2

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.

  • 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 $533.

  • 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

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$654FlexibilityNo cancel feeOn-timeN/A

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