Direct (nonstop) flights from Chicago to Oakland
1 airline flys nonstop from Chicago Midway International (MDW) to Metropolitan Oakland International (OAK). It's 1,844 miles (2,968 km), about 4h 35m in the air. Operated by Southwest Airlines.
Southwest Airlines
Route data last updated: May 26, 2026
Airlines with non-stop flights
WN
Southwest Airlines
Alternative Routes
Other ways to fly from Chicago to Oakland with one stop · direct emits 312 kg CO₂ per passenger
Looking for the return flight?
OAK → MDW: Flights from Oakland to ChicagoOther direct flights from Chicago
Direct flights from Oakland (OAK)
Frequently Asked Questions
How long is the direct flight from Chicago to Oakland?
A nonstop flight from Chicago (MDW) to Oakland (OAK) takes approximately 4 hours and 35 minutes. The distance is 1,844 miles (2,968 km).
Which airlines fly nonstop from Chicago to Oakland?
Just Southwest Airlines.
Is there a nonstop flight from Chicago to Oakland?
Yes. 1 airline: Southwest Airlines.
How far is Chicago from Oakland?
The flight distance from Chicago to Oakland is 1,844 miles (2,968 km), measured as the great-circle (shortest air) distance.
What type of aircraft flies from Chicago to Oakland?
At 4h 35m, this route typically uses narrow-body or mid-range jets — Boeing 737 MAX or Airbus A320neo. Varies by airline.
What is the carbon footprint of a flight from Chicago to Oakland?
Roughly 312 kg CO2 per passenger one-way. That's about the same as driving 1,560 km.
Is the return flight from Oakland to Chicago also nonstop?
Yes — nonstop flights run both ways. Flight time may differ slightly due to wind patterns.
When is the cheapest time to fly from Chicago to Oakland?
Midweek flights (Tue/Wed) outside holiday peaks are usually cheapest. 3-6 weeks ahead is a good window for this route. Use "Check Prices" above to compare.
How early should I arrive at Chicago Midway International for this flight?
1.5-2 hours for domestic. Add more time during holidays or busy travel weekends.