Cheap Flight Deals From Chicago (CHI) to Oakland (SJC) Starting at $71

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This Weekend's Flight Deals from Chicago to Oakland

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Airfares from $71 One Way, $142 Round Trip from Chicago to Oakland

Prices starting at $142 for return flights and $71 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.

Oakland economy flight packages

River Terrace Inn - A Noble House Hotel
Villagio at The Estate Yountville
Vintage House at The Estate Yountville
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More About Flying To Oakland from Chicago

Route Information for Flights from Chicago to Oakland

Origin Airport IATA Code CHI
Destination Airport IATA Code SJC
Distance 1842 mi
Direct Flight Airlines American Airlines, Qatar Airways, JAL, Air Canada, LOT - Polish Airlines, Azul, Aer Lingus, Austrian, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Finnair, SAS, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, British Airways, Gulf Air
Earliest Flight Arrival 3:41PM UTC
Latest Flight Arrival 5:24AM UTC

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.

Frequently asked questions

Am I able to catch a flight from Chicago to Oakland now?
Check out the Covid-19 Travel Advisor for the most up-to-date info on quarantine requirements and travel restrictions when catching a flight from Chicago to Oakland.
Are there non-stop flights from Chicago to Oakland?
Yep, your fun-filled getaway is just one simple flight away. Great news, isn’t it? Book your favorite seat with one of the 3 carriers that fly direct from O’Hare Airport to SFO. Popular choices include:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from Chicago to Oakland?
The shortest flight from ORD to Norman Y. Mineta San Jose Intl. Airport (SJC) is 5 hours and 5 minutes. Bring something on board to keep you occupied, like the latest edition of your favorite magazine or some Sudoku puzzles.
What airlines fly from Chicago to Oakland most frequently?
Consider booking a flight with United Airlines (UA), which flies frequently along this route. This airline operates 243 flights every month between Chicago, IL (ORD-O’Hare Intl.) and San Francisco, CA (SFO-San Francisco Intl.). Also investigate the great fares from American Airlines (AA). Offering 126 monthly flights between Chicago and Oakland, they’ll ensure your journey is just as delightful as the destination.
If I am not able to travel due to COVID-19, can I cancel my flight to Oakland?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Oakland have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Oakland with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Oakland without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.