HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oakland

$194+ 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — OAK
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Oakland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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
Mon 3/2312:35 pm
OAK
-
MSN
2 stops22h 06m
Delta
Deal found 1/27$444
This Delta deal was found by Cheapflights users on 1/27. 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 3/2212:35 pm
OAK
-
MSN
2 stops30h 31m
Delta
Deal found 1/27$575
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/122:45 pm
MSN
-
OAK
2 stops11h 01m
Delta
Tue 3/1712:35 pm
OAK
-
MSN
2 stops8h 23m
Delta
Deal found 1/28$692
This Delta deal was found by Cheapflights users on 1/27. 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 3/196:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Fri 3/2012:35 pm
OAK
-
MSN
2 stops8h 23m
Delta
Deal found 1/27$830
This Delta deal was found by Cheapflights users on 1/27. 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 2/1011:31 am
MSN
-
OAK
2 stops14h 22m
Delta
Sat 2/145:55 am
OAK
-
MSN
2 stops14h 53m
Delta
Deal found 1/27$868
This Delta deal was found by Cheapflights users on 1/27. 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 2/105:38 am
MSN
-
OAK
2 stops12h 36m
Delta
Fri 2/1312:40 pm
OAK
-
MSN
2 stops26h 24m
Delta
Deal found 1/27$869
This Delta deal was found by Cheapflights users on 1/27. 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 2/105:38 am
MSN
-
OAK
2 stops12h 36m
Delta
Sun 2/155:55 am
OAK
-
MSN
2 stops33h 10m
Delta
Deal found 1/27$927
This Delta deal was found by Cheapflights users on 1/26. 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.
Thu 4/26:04 pm
MSN
-
OAK
2 stops7h 42m
Delta
Sun 4/512:35 pm
OAK
-
MSN
2 stops8h 23m
Delta
Deal found 1/26$1,295
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/126:20 am
MSN
-
OAK
2 stops11h 52m
Delta
Mon 2/165:55 am
OAK
-
MSN
2 stops9h 19m
Delta
Deal found 1/28$1,348
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:31 pm
MSN
-
OAK
2 stops12h 22m
Delta
Sun 2/812:33 pm
OAK
-
MSN
2 stops8h 17m
Delta
Deal found 1/28$1,375
This Delta deal was found by Cheapflights users on 1/26. 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 5/162:40 pm
MSN
-
OAK
2 stops8h 54m
Delta
Wed 5/205:55 am
OAK
-
MSN
2 stops9h 09m
Delta
Deal found 1/26$1,450
This Delta deal was found by Cheapflights users on 1/27. 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.
Sun 2/81:55 pm
MSN
-
OAK
2 stops9h 43m
Delta
Sun 2/1512:40 pm
OAK
-
MSN
2 stops8h 08m
Delta
Deal found 1/27$1,660

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$444
(Delta)

One-way from

$194
(Delta)

Popular in

March

Cheapest in

August

Average price

$463
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. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
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 3/17

6:04 pm-11:46 pm

2 stops7h 42m

Oakland

Mon 3/23

12:35 pm-12:41 pm

2 stops22h 06m

$444

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 3/17

6:04 pm-11:46 pm

2 stops7h 42m

Oakland

Sun 3/22

12:35 pm-9:06 pm

2 stops30h 31m

$575

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 3/12

2:45 pm-11:46 pm

2 stops11h 01m

Oakland

Tue 3/17

12:35 pm-10:58 pm

2 stops8h 23m

$692

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 3/19

6:04 pm-11:46 pm

2 stops7h 42m

Oakland

Fri 3/20

12:35 pm-10:58 pm

2 stops8h 23m

$830

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 2/10

11:31 am-11:53 pm

2 stops14h 22m

Oakland

Sat 2/14

5:55 am-10:48 pm

2 stops14h 53m

$868

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 2/10

5:38 am-4:14 pm

2 stops12h 36m

Oakland

Fri 2/13

12:40 pm-5:04 pm

2 stops26h 24m

$869

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Tue 2/10

5:38 am-4:14 pm

2 stops12h 36m

Oakland

Sun 2/15

5:55 am-5:05 pm

2 stops33h 10m

$927

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 4/2

6:04 pm-11:46 pm

2 stops7h 42m

Oakland

Sun 4/5

12:35 pm-10:58 pm

2 stops8h 23m

$1,295

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Thu 2/12

6:20 am-4:12 pm

2 stops11h 52m

Oakland

Mon 2/16

5:55 am-5:14 pm

2 stops9h 19m

$1,348

MadisonOakland

MSN - OAK

MSNOAK

Madison Truax Field

Sat 5/16

2:40 pm-9:34 pm

2 stops8h 54m

Oakland

Wed 5/20

5:55 am-5:04 pm

2 stops9h 09m

$1,450

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 15 results
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 $172). Flying from Madison to Oakland, California in June is currently the most expensive (average of $256). 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 7h 42m. 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 $172). Flying from Madison to Oakland, California in June is currently the most expensive (average of $256). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Oakland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
Minneapolis to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to San Francisco flights
Minneapolis to San Diego flights
O'Hare Intl to Santa Ana flights
Minneapolis to Los Angeles flights
O'Hare Intl to San Diego flights
Milwaukee to Las Vegas flights
O'Hare Intl to Ontario flights
Minneapolis to San Francisco flights
O'Hare Intl to Palm Springs flights
Minneapolis to Palm Springs flights
O'Hare Intl to Burbank flights
Madison to Las Vegas flights
O'Hare Intl to Reno flights
Minneapolis to Ontario flights
O'Hare Intl to San Jose flights
O'Hare Intl to Sacramento flights
Minneapolis to Santa Ana flights
O'Hare Intl to Oakland flights
Appleton to Las Vegas flights
Milwaukee to Los Angeles flights
Minneapolis to Sacramento flights
Milwaukee to San Diego flights
Minneapolis to Reno flights
Minneapolis to San Jose flights
Milwaukee to San Francisco flights
Milwaukee to Palm Springs flights
Madison to San Diego flights
Madison to San Francisco flights
Madison to Los Angeles flights
Green Bay to Las Vegas flights
O'Hare Intl to Long Beach flights
Milwaukee to Reno flights
Milwaukee to Ontario flights
Minneapolis to Oakland flights
O'Hare Intl to Fresno flights
O'Hare Intl to Santa Barbara flights
Appleton to San Diego flights
Minneapolis to Fresno flights
Madison to Ontario flights
Minneapolis to Santa Barbara flights
Minneapolis to Burbank flights
Appleton to Los Angeles flights
Madison to Palm Springs flights
Madison to Santa Ana flights
Milwaukee to Sacramento flights
Milwaukee to San Jose flights
Minneapolis to Long Beach flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.