Flights from Chicago to Oakland
CHI
Chicago
15h 25m avg
OAK
Oakland
Flights from
$299
Compare 1 options across 1 airline
Updated 3 months ago
$299
Cheapest Flight
$299
Average Price
0
Direct Flights
1
Airlines
Compare All CHI to OAK Flights
Prices are per person for one-way travel. Click “Book” to complete your reservation on the partner site.
1 of 1 flight
| Airline | Schedule | Stops | Duration | Price | |
|---|---|---|---|---|---|
AS
AS · 413
|
07:00
CHI
22:25
OAK
|
0 stop(s) | 15h 25m | $299 Best | Book → |
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Airport Information
Key details about departure and arrival airports for this route
OAK
San Francisco Bay Oakland International Airport
City: Oakland
Country: US
Type: Large Airport
Elevation: 9 ft
OAK Airport Guide →
Country: US
Type: Large Airport
Elevation: 9 ft
Tips for Chicago to Oakland Flights
Save money and travel smarter with these route-specific tips
When to Book
Book CHI–OAK flights 6–8 weeks in advance for the best prices. Last-minute fares are typically 40–60% more expensive on this route.
Price Trends
The average fare is $299, but prices as low as $299 are available.
Direct vs Connecting
No direct flights currently listed. Consider flexible dates or nearby airports for better connections.
Flexible Dates
Flying midweek (Tuesday–Thursday) on CHI–OAK is typically 15–30% cheaper. Use our price comparison to spot the best day to fly.
Frequently Asked Questions
Everything you need to know about flying CHI to OAK
What is the cheapest flight from Chicago to Oakland?
The cheapest flight from Chicago (CHI) to Oakland (OAK) currently starts at $299 with AS. Prices are updated regularly and may vary by date and availability.
How many airlines fly from CHI to OAK?
We found 1 airline(s) operating on the CHI–OAK route, including AS.
Are there direct flights from Chicago to Oakland?
No direct flights are currently listed on this route. All available options involve at least one stop. Consider flexible dates or nearby airports for better connection options.
What is the average flight price on this route?
The average flight price from Chicago to Oakland is approximately $299. Prices range from $299 to $299 depending on airline, time, and class.
How long is the flight from CHI to OAK?
The average flight duration from Chicago to Oakland is approximately 15 hours 25 minutes. Direct flights are typically shorter than connecting options.
What is the baggage allowance on CHI–OAK flights?
Baggage allowance varies by airline and fare class. Most economy fares on this route include 1 carry-on (7–8 kg) and 1 checked bag (20–23 kg). Always confirm baggage rules on the airline's site at booking — low-cost carriers may charge for checked bags.
From
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