Direct flights from Oakland to Chicago

  • 13 flights a week
  • Southwest Airlines

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When the nonstops leave

Typical weekly schedule · 13 flights per week (~2 per day) · Updated 82d ago

Most leave in the evening.

Morning before noon 6 a week

Arrive the same day

5:05 AMSun 5:10 AMMon, Thu, Fri 5:55 AMTue, Wed
Afternoon noon – 6 PM 0 a week

No nonstop leaves between noon and 6 PM.

Evening after 6 PM 7 a week

Arrive the next morning

11:55 PM
Southwest Airlines Departs Terminal 2

More nonstops from Oakland

OAK → LAS Las Vegas OAK → LGB Long Beach OAK → ONT Ontario OAK → SNA Santa Ana OAK → ABQ Albuquerque OAK → BUR Burbank OAK → DAL Dallas OAK → HOU Houston MDW → OAK The return trip OAK All nonstops from Oakland MDW All nonstops from Chicago

Frequently asked questions

Is there a direct flight from Oakland to Chicago?

Yes. Southwest Airlines flies nonstop from Oakland (OAK) to Chicago (MDW), daily. The flight takes about 4h 18m and covers 1,840 miles (2,961 km). Schedule data from 28 July 2026.

Which airlines fly direct from Oakland to Chicago?

Southwest Airlines operates nonstop flights from Oakland to Chicago.

How long is the flight from Oakland to Chicago?

The nonstop flight from Oakland to Chicago takes ~4h 18m (approximately 2961 km).

How often do direct flights operate from Oakland to Chicago?

Nonstop flights from Oakland to Chicago operate daily — 13 flights per week (~2 per day).

What days of the week are there direct flights from Oakland to Chicago?

Direct flights from Oakland to Chicago operate every day of the week.