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Fares from $29 One Way, $58 Round Trip from Chicago to Oakland

Prices starting at $58 for return flights and $29 for one-way flights to Oakland were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

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More About Flying To Oakland from Chicago

Route Information for Flights from Chicago to Oakland

Origin Airport IATA CodeCHI
Destination Airport IATA CodeSJC
Distance1842 mi
Direct Flight AirlinesAmerican Airlines, JAL, Air Canada, Austrian, Aer Lingus, Air New Zealand, United Airlines, Alaska Airlines, Qantas, ANA, Lufthansa, Singapore Airlines, Air China LTD, Gulf Air, British Airways
Earliest Flight Arrival4:36PM UTC
Latest Flight Arrival5:25AM UTC

Flights Review

Jan 30, 2020

Had to pay $10.75 to change to a window seat near the back on a not full flight....

Jan 19, 2020

Our flight was rebooked to a different plane due to de-icing fluid d in the first plane"s ventilation system...

Dec 24, 2019

I thought the seats were a little uncomfortable

Oct 11, 2019

Late takeoff annoying but it happens..

Jul 5, 2019

My cat ripped through his carrier and the staff was wonderful and helpful about it

Sep 27, 2018

For Flight over 4 hrs ( especially around lunch Time) a FREE sandwich or salad or...would be appreciated. Price of ticket high enough to include this. I took 3 planes from Portland , Me to San Jose , Ca - ( my choice , I accepted a voucher to give my place in Portland) and wondered if my suitcase was going to follow. Actually, it was at the carousel waiting for me. Excellent work. Thank you.

May 9, 2018

Missed some kind of entertainment from Chicago to San Jose - more than 4 hour flight. There was nothing.

Feb 5, 2018

Thank you very much.

Cheap Flights from Chicago to Oakland

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Flights to Oakland

If you're looking for cheap flights to Oakland, using Orbitz.com makes it easy to find what you need. The website searches available flights landing at the Oakland International Airport to find you tickets with a low fare.

Oakland International Airport

The Oakland International Airport is located on Airport Drive, approximately 10 miles from downtown Oakland and 25 miles from downtown San Francisco. The airport has hubs for 11 different airlines, including JetBlue, US Airways, Hawaiian Airlines and Delta. When you use Orbitz.com to book your flight, you'll find flight options from all of the airlines. This makes it easy for you to choose the option that fits your travel needs.

Transportation from the Airport

The Bay Area Rapid Transit (BART) train services the Oakland International Airport. The fare between the airport and downtown Oakland is $1.75. You can also take the bus from the airport into Oakland. The bus costs $2 for adults and $1 for children. It runs every 15 minutes from 4:56 a.m. to 12:06 a.m. and every hour from 12:35 a.m. to 4:30 a.m. If you want access to your own vehicle, you can reserve a rental car using Orbitz.com.

Weather in Oakland

Oakland has moderate weather. Temperatures range from 44 degrees Fahrenheit to 57 degrees Fahrenheit during the winter months. During the summer, the temperatures range from 55 degrees Fahrenheit to 75 degrees Fahrenheit. The winter months are Oakland's off-peak travel season. If you use Orbitz.com to plan your trip during this time, it will be easy to find cheap flights to Oakland.

Highlights and Attractions

Popular attractions in Oakland include the Oakland Zoo, Old Oakland and the Oakland Museum of California. Orbitz.com does more than book cheap flights to Oakland. You can also use the website to purchase tickets to area attractions.

Flights from Chicago to Oakland - Frequently Asked Questions

Are there non-stop flights from Chicago to Oakland?

There is. Southwest Airlines offers nonstop flights from Chicago, IL Airport (MDW-Midway Intl.) to Oakland, CA Airport (OAK-Oakland Intl.), which makes traveling from Chicago to Oakland a snap.

What is the shortest flight from Chicago to Oakland?

Jetting from Chicago, IL Airport (ORD-O'Hare Intl.) to Oakland, CA Airport (OAK-Oakland Intl.) will take a minimum of 4 hours and 29 minutes. Indulge in a tipple and watch a movie or two — this is the perfect opportunity to sit back and relax.

What airlines fly from Chicago to Oakland most frequently?

If you're looking for the airline with the most flights from Chicago to Oakland, Southwest Airlines is the top pick. This respected airline operates 76 flights along this route per month.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.