- Fastest outbound flight
- Fastest inbound flight
- non-stop flights
- 23x / week
- Flight distance
- 2,974 km
- Time difference
- Airports in Chicago
- O'Hare International Airport, IL
- Midway International Airport, IL
- Rockford, IL
- Most popular airlines
- Southwest Airlines
- Southwest Airlines
Flight schedule from Oakland (OAK) to Chicago (CHI)
Select a travel date in the flight schedule for the route from Oakland (OAK) to Chicago (CHI) and compare affordable flight deals.
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Matching outbound flights12 of 12
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- September 20 – 26, 2026
- Sep 27 – Oct 3, 2026
- October 4 – 10, 2026
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Important flight information
Frequently Asked Questions (FAQ)
How long is the flight from Oakland to Chicago?
A nonstop flight from Oakland to Chicago typically takes around 4 hours. This makes the nonstop service the fastest and most convenient way to travel between Oakland and Chicago. It is worth checking flight times when searching, as they can vary by airline and travel date.
Are there nonstop flights from Oakland to Chicago?
Yes, there are nonstop flights from Oakland to Chicago, 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.
Which airlines fly from Oakland to Chicago?
Direct flights from Oakland to Chicago are operated by, among others, Southwest. These flights take you to Chicago 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.
On which days are there nonstop flights from Oakland to Chicago?
Nonstop flights from Oakland to Chicago 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.
How many flights are there per day from Oakland to Chicago?
On the route from Oakland to Chicago, 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.
How many flights per week are there from Oakland to Chicago?
From Oakland to Chicago, there are around 23 to 24 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.
When does the first flight from Oakland to Chicago depart?
The earliest nonstop flight from Oakland to Chicago usually departs at 5:10 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 Chicago.
When does the last flight from Oakland to Chicago depart?
The last nonstop flight from Oakland to Chicago usually departs at 11:55 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.