Oakland (OAK) → Chicago (ORD)
About Oakland to Chicago Flights
Discover the best flights from Oakland to Chicago, covering 2,947 km in approximately 4h 11m. Oakland (OAK) to Chicago (ORD) is one of the popular medium-haul routes within United States. With 4 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Oakland to Chicago.
12-Month Price History
Flight prices from Oakland to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $456, while July sees the highest prices, averaging $760. Savvy travelers can save up to 40% by choosing their travel dates wisely.
Best Time to Fly
Cheapest Month
February
Save up to 40% on average
Most Expensive
July
Peak season pricing
Book in Advance
32 days
For best prices
Booking Tips
For the best prices on Oakland to Chicago flights, we recommend booking 42 days in advance. Domestic flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.
Airlines Serving This Route
| Airline | Economy | Business | First |
|---|---|---|---|
Kalitta Air K4 | $760 | $2770 | $3960 |
United Airlines UA | $770 | $2420 | $3700 |
SkyWest Airlines OO | $810 | $2210 | $4470 |
American Airlines AA | $830 | $2180 | $3490 |
Kalitta Air
K4
Economy
$760
Business
$2770
First
$3960
United Airlines
UA
Economy
$770
Business
$2420
First
$3700
SkyWest Airlines
OO
Economy
$810
Business
$2210
First
$4470
American Airlines
AA
Economy
$830
Business
$2180
First
$3490
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
San Francisco → Chicago
San Francisco International (SFO) to O'Hare International (ORD)
Distance: 2,964 km
Average price: $545
San Jose → Chicago
San Jose International (SJC) to O'Hare International (ORD)
Distance: 2,937 km
Average price: $541
Sacramento → Chicago
Sacramento International (SMF) to O'Hare International (ORD)
Distance: 2,860 km
Average price: $529
San Jose → Chicago
San Jose International (SJC) to O'Hare International (ORD)
Distance: 2,937 km
Average price: $541
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Frequently Asked Questions
How long is the flight from Oakland to Chicago?
The flight time from Oakland (OAK) to Chicago (ORD) is approximately 4 hours and 11 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.
What is the distance between Oakland and Chicago?
The aerial distance between Oakland and Chicago is 2,947 kilometers (1,831 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from Oakland to Chicago?
Several airlines operate flights between Oakland and Chicago, including American Airlines, United Airlines, SkyWest Airlines and 1 more airlines. Direct flights are available on this route.
What is the cheapest month to fly from Oakland to Chicago?
Based on historical data, February typically offers the lowest airfares for flights from Oakland to Chicago. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.
How far in advance should I book my flight to Chicago?
For the best prices on Oakland to Chicago flights, we recommend booking 56 days in advance. Domestic flights can sometimes offer good last-minute deals, but advance booking is usually cheaper.
Do I need a visa to travel from Oakland to Chicago?
Visa requirements depend on your nationality and the purpose of your visit. Since this is a domestic flight, no visa is required for citizens.
What is the time difference between Oakland and Chicago?
Oakland operates on America/Los_Angeles time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.