Direct (nonstop) flights from Oakland to Chicago
1 airline flys nonstop from Metropolitan Oakland International (OAK) to Chicago Midway International (MDW). It's 1,844 miles (2,968 km), about 4h 5m in the air. Operated by Southwest Airlines.
Southwest Airlines
Route data last updated: May 28, 2026
Airlines with non-stop flights
WN
Southwest Airlines
Alternative Routes
Other ways to fly from Oakland to Chicago with one stop · direct emits 312 kg CO₂ per passenger
Looking for the return flight?
MDW → OAK: Flights from Chicago to OaklandOther direct flights from Oakland
Direct flights from Chicago (MDW)
Frequently Asked Questions
How long is the direct flight from Oakland to Chicago?
A nonstop flight from Oakland (OAK) to Chicago (MDW) takes approximately 4 hours and 5 minutes. The distance is 1,844 miles (2,968 km).
Which airlines fly nonstop from Oakland to Chicago?
Just Southwest Airlines.
Is there a nonstop flight from Oakland to Chicago?
Yes. 1 airline: Southwest Airlines.
How far is Oakland from Chicago?
The flight distance from Oakland to Chicago is 1,844 miles (2,968 km), measured as the great-circle (shortest air) distance.
What type of aircraft flies from Oakland to Chicago?
At 4h 5m, 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 Oakland to Chicago?
Roughly 312 kg CO2 per passenger one-way. That's about the same as driving 1,560 km.
Is the return flight from Chicago to Oakland 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 Oakland to Chicago?
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 Metropolitan Oakland International for this flight?
1.5-2 hours for domestic. Add more time during holidays or busy travel weekends.