Flight schedule from Chicago (CHI) to Oakland (OAK)
Select a travel date in the flight schedule for the route from Chicago (CHI) to Oakland (OAK) and compare affordable flight deals.
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- August 23 – 29, 2026
- Aug 30 – Sep 5, 2026
- September 6 – 12, 2026
- ORDOAK1 stopover
- MDWOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
- ORDOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
- MDWOAKnonstop
Important flight information
Frequently Asked Questions (FAQ)
A nonstop flight from Chicago to Oakland typically takes around 4 hours 40 minutes. This makes the nonstop service the fastest and most convenient way to travel between Chicago and Oakland. It is worth checking flight times when searching, as they can vary by airline and travel date.
Yes, there are nonstop flights from Chicago to Oakland, averaging around 3 to 4 flights per day, operated by, among others, Southwest. If you want to fly without a layover, it is worth filtering specifically for nonstop flights when searching.
Direct flights from Chicago to Oakland are operated by, among others, Southwest. These flights take you to Oakland nonstop, making them especially practical for short trips or weekend getaways. It is still worth comparing departure times and airline policies, as baggage rules and fees can vary.
Nonstop flights from Chicago to Oakland operate daily. The schedule may vary by season, so it is worth comparing several travel dates. If your preferred day does not have a nonstop flight, nearby departure days or short connecting flights may be a good alternative.
On the route from Chicago to Oakland, there are on average around 3 to 4 flights per day. The number of flights can vary by day of the week and season. If you are flexible with your dates, it is worth comparing several departure days.
From Chicago to Oakland, there are around 21 to 22 flights per week. This means you usually have connections available on several days and at various times. Beyond the price, it is worth comparing flight duration, airline, and any potential additional fees.
The earliest nonstop flight from Chicago to Oakland usually departs at 9:35 AM. The exact departure time may vary by day of the week and airline. Early flights are especially useful if you want to make the most of your arrival day in Oakland.
The last nonstop flight from Chicago to Oakland usually departs at 11:05 PM. Late flights can be convenient if you want to travel after work or in the evening. Do check whether it is a nonstop flight, as a connecting itinerary could push the arrival time significantly later.