Price observed over the last 3 months for a round trip.
Compare all flight tickets and find cheap flights from Chicago to Oakland
The cheapest flights right now
Chicago – Oakland
Outbound – Nov 5, 2026
1 stop
7h 17m SAN
Return – Nov 11, 2026
1 stop
7h 20m SAN
$368
yesterday
Chicago – Oakland
Outbound – Nov 5, 2026
1 stop
7h 39m PDX
Return – Nov 11, 2026
1 stop
6h 59m SAN
$366
yesterday
Chicago – Oakland
Outbound – Nov 5, 2026
1 stop
7h 17m SAN
Return – Nov 11, 2026
1 stop
6h 59m SAN
$364
yesterday
* Prices are in USD per passenger, including taxes, for a round trip. Prices are based on searches carried out within the last 72 hours. Please note that availability and ticket prices are subject to change and should not be considered as the final price quoted.
Cheapest flight tickets
$259
Average price of a round trip
$318
Average flight ticket price recorded over the last 3 months for a round trip.
Flight duration
15h8
A flight from Chicago to Oakland takes on average 15h8.
Best time
July
According to user searches, the ideal month to go to Oakland is July.
Tips for finding a cheap flight from Chicago to Oakland
Check out our tips for booking your flight to Oakland (USA) from Chicago (USA) at the cheapest possible price.
Usually, the cheapest month to pick up a ticket on this route is August, with an average flight ticket price of $94 (calculation over the last two years). The most touristic season corresponds to the months of December, October and November.
For the cheapest flights, it is advisable to buy your ticket at least 22 days before the departure date.
The airline offering the cheapest flight tickets is Frontier Airlines. A ticket from the airline Frontier Airlines to Oakland costs on average $273.
The airlines that offer the most flights are .
Price of flight tickets from Chicago to Oakland
Here is some information and tips to know before booking your flight:
- Flight ticket prices range from $259 to $527
- The average price of a flight ticket is about $318
- Prices are lowest for stays in the month of August
- The month in which booking a ticket is cheaper is: October
info departure city :
Chicago, USA
airports :
Chicago-Merrill C. Meigs Field Airport (CGX)
Chicago FSS (CHI)
Chicago-Midway International Airport (MDW)
Chicago-O'Hare International Airport (ORD)
local time :
Chicago is a city in the country USA, the time zone is [[timezone]]. In Chicago, it is currently {fromLocalTime}, the temperature is on average 16°C, with a minimum of 15°C and a maximum of 18°C.
The city of Chicago (CHI) has 4 airport(s): Chicago-Merrill C. Meigs Field, Chicago FSS, Chicago-Midway and Chicago-O'Hare
destination info :
Oakland, USA
airport :
Oakland International Airport (OAK)
local time :
Oakland is in the country USA, the time zone is [[timezone]]. In Oakland, it is currently {toLocalTime}, the temperature is on average 19°C, with a minimum of 14°C and a maximum of 27°C.
The city of Oakland has 1 airport(s): Oakland
Useful info about Oakland
What is the least touristic period to go to Oakland?
If you want to visit Oakland during the least touristic period, choose the month of July.
What is the most popular time to travel to Oakland?
In Oakland, the most popular month is December. It is during this period that the prices offered by airlines are also the highest.
When should I book my flight from Chicago to Oakland?
According to our data, it is recommended to book your flight 22 days before your departure. If you book your flight ticket 4 weeks before your departure, you may find a price below average. You can also choose morning flights that are 100% cheaper than afternoon and evening flights. The cheapest day to book a flight from Chicago to Oakland is Thursday.
What are the arrival and destination airports when traveling between Chicago and Oakland?
When you leave, you can leave from Chicago-O'Hare, and you will arrive at Oakland, San Francisco or San Jose-Norman Y. Mineta.
How to reach Chicago airport from the city centre?
The airport Chicago-Merrill C. Meigs Field is located 4 km, Chicago FSS is located 29 km, Chicago-Midway is located 12 km or Chicago-O'Hare is located 29 km from the city centre. You can access it by using public transportation, taking a taxi, or renting a car.
Are there other means of transportation to go from Chicago to Oakland?
Airplane is the only means of transportation listed on Liligo for this journey.
Are there big differences in weather between Chicago and Oakland?
In summer, the average temperature is 17°C in Oakland and 22°C in Chicago. The average rainfall in summer is 2 mm in Oakland and 145 mm in Chicago. In summer, it is warmer in Chicago and it rains less in Oakland. In winter, it is colder in Oakland and it rains more in Oakland.
