Cheap flights from Madison to Oakland

One-way fares from $299 · MSN → OAK · prices found by travellers in the last 48 hours

Compare all dates Oakland → Madison
Cheapest fare
$299

Sun Country Airlines · Thu, Nov 12

Cheapest month
November

from $299

Direct flights
Not recently

Usually 1+ stop

Quickest trip
6h 33m

2,820 km

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Cheapest month to fly from Madison to Oakland

Lowest one-way fare per person in each month. Choose a month to see every date.

  1. November 2026 Cheapest $299

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About flights from Madison to Oakland

Madison (MSN) and Oakland (OAK) are about 2,820 km apart. We haven't seen direct fares on this route recently, so expect at least one stop; the quickest journey we've seen takes about 6h 33m. Over the next few months, one-way fares start from $299, and November 2026 is currently the cheapest month to fly.

These prices come from searches travellers made in the last 48 hours, so they move quickly. If you see a good fare, it's worth booking soon. FlightsExp is free to use: you book directly with our travel partner.

Frequently asked questions

How much is a flight from Madison to Oakland?

The cheapest one-way fare we've seen recently is $299 with Sun Country Airlines, departing Thursday, November 12, 2026.

What is the cheapest month to fly from Madison to Oakland?

November 2026 currently has the lowest fares, from $299 one way.

Are there direct flights from Madison to Oakland?

We haven't seen direct fares recently, so most journeys include at least one stop.

How long is the flight from Madison to Oakland?

The quickest journey we've seen takes about 6h 33m. Madison and Oakland are around 2,820 km apart.

Which airlines fly from Madison to Oakland?

Recent fares on this route were with Sun Country Airlines.

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