HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$414+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — MSN
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Madison 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 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 August 14, 2025.

Round-trip from

$652
(Delta)

One-way from

$414
(Delta)

Popular in

December

Cheapest in

February

Average price

$450
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. 3% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 14, 2025.

This Delta deal was found by Cheapflights users on 8/13. 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 8/216:00 amOAK - MSN
1 stop5h 08mDelta
Tue 8/265:40 amMSN - OAK
2 stops12h 36mDelta
Deal found 8/13$612
This Delta deal was found by Cheapflights users on 8/13. 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 10/255:55 amOAK - MSN
2 stops8h 35mDelta
Sun 11/25:00 amMSN - OAK
2 stops7h 50mDelta
Deal found 8/13$652
This Delta deal was found by Cheapflights users on 8/13. 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 8/2012:35 pmOAK - MSN
2 stops8h 15mDelta
Tue 8/266:05 amMSN - OAK
2 stops7h 50mDelta
Deal found 8/13$663
This Delta deal was found by Cheapflights users on 8/12. 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 8/216:00 amOAK - MSN
1 stop5h 08mDelta
Sat 8/2310:59 amMSN - OAK
2 stops7h 17mDelta
Deal found 8/12$742
This Trip.com deal was found by Cheapflights users on 8/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:40 amOAK - MSN
2 stops26h 45mMultiple Airlines
Mon 10/2011:55 amMSN - OAK
2 stops14h 08mMultiple Airlines
Deal found 8/11$749
This Delta deal was found by Cheapflights users on 8/13. 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 8/226:00 amOAK - MSN
2 stops14h 50mDelta
Tue 8/266:05 amMSN - OAK
2 stops18h 41mDelta
Deal found 8/13$790
This Delta deal was found by Cheapflights users on 8/13. 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 8/216:00 amOAK - MSN
1 stop5h 08mDelta
Mon 8/256:05 amMSN - OAK
2 stops18h 41mDelta
Deal found 8/13$802
This Delta deal was found by Cheapflights users on 8/13. 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 8/216:00 amOAK - MSN
1 stop5h 08mDelta
Sun 8/246:37 pmMSN - OAK
2 stops19h 18mDelta
Deal found 8/13$842
This Delta deal was found by Cheapflights users on 8/13. 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 8/2012:35 pmOAK - MSN
2 stops8h 15mDelta
Mon 8/256:05 amMSN - OAK
2 stops18h 41mDelta
Deal found 8/13$853
This Delta deal was found by Cheapflights users on 8/13. 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 8/2012:35 pmOAK - MSN
2 stops8h 15mDelta
Sun 8/246:37 pmMSN - OAK
2 stops19h 18mDelta
Deal found 8/13$893
This Delta deal was found by Cheapflights users on 8/11. 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.
Wed 8/1312:35 pmOAK - MSN
2 stops8h 13mDelta
Sat 8/232:44 pmMSN - OAK
2 stops10h 02mDelta
Deal found 8/11$973

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 August 14, 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 10/25

5:55 am-4:30 pm

2 stops8h 35m

Madison Truax Field

Sun 11/2

5:00 am-10:50 am

2 stops7h 50m

$652

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Sat 10/25

5:55 am-4:30 pm

2 stops8h 35m

Madison Truax Field

Mon 11/3

2:42 pm-11:53 pm

2 stops11h 11m

$652

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Fri 10/17

6:40 am-11:25 am

2 stops26h 45m

Madison Truax Field

Mon 10/20

11:55 am-12:03 am

2 stops14h 08m

$749

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Thu 9/18

6:00 am-4:09 pm

2 stops8h 09m

Madison Truax Field

Sun 9/21

6:00 am-11:56 am

2 stops7h 56m

$1,058

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Sun 10/5

12:37 pm-10:34 pm

2 stops7h 57m

Madison Truax Field

Thu 10/9

1:19 pm-11:53 pm

2 stops12h 34m

$1,159

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Thu 8/28

4:58 pm-9:56 am

2 stops14h 58m

Madison Truax Field

Mon 9/1

6:05 am-11:55 am

2 stops7h 50m

$1,489

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Thu 10/9

5:55 am-5:12 pm

2 stops9h 17m

Madison Truax Field

Mon 10/13

9:34 am-4:11 pm

2 stops8h 37m

$1,512

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Thu 9/11

5:05 pm-9:54 am

2 stops14h 49m

$414

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Sun 8/24

4:58 pm-9:48 am

2 stops14h 50m

$455

OaklandMadison

OAK - MSN

OAKMSN

Oakland

Wed 9/17

12:37 pm-10:34 pm

2 stops7h 57m

$515

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 11 results
1
2

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 August 14, 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 August 14, 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
7,984 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

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
7,984 reviews
Delta
8.0
Very good
7,984 reviews

Boarding

8.2

Overall

8.0

Food

7.3

Comfort

7.9

Crew

8.5

Entertainment

7.9

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 $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

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 Oakland to Madison

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

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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$654FlexibilityNo cancel feeOn-timeN/A

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.