
$47 Cheap flight deals from Oakland (SJC) to Chicago (CHI)
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This Weekend's Flight Deals from Oakland to Chicago
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 $47 One Way, $171 Round Trip from Oakland to Chicago
Prices starting at $171 for return flights and $47 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages

Embassy Suites by Hilton Chicago Downtown River North
Jun 17 - Jun 20
Oakland (OAK) to Chicago (ORD)
Chicago (ORD) to Oakland (OAK)
Reviewed on Apr 18, 2025

Arlo Chicago
Jun 17 - Jun 20
Oakland (OAK) to Chicago (ORD)
Chicago (ORD) to Oakland (OAK)
Reviewed on Oct 13, 2024
More About Flying To Chicago from Oakland
Route Information for Flights from Oakland to Chicago
Origin Airport IATA Code | SJC |
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Destination Airport IATA Code | CHI |
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Flights from Oakland to Chicago
Oakland Airport Information
If you are searching for cheap flights from Oakland, Orbitz.com can help. The Oakland International Airport provides air service to the Oakland area and is located on Airport Drive, about 10 miles from downtown Oakland. Several major airlines provide service to the airport, including Alaska, Allegiant, ArkeFly, Delta, Hawaiian, JetBlue, Sata, Southwest, Spirit, US Airways, and Volaris. Orbitz.com can compare the rates on most of these carriers, so you can choose the best bargain before you purchase your tickets.
Parking Options Located at the Airport
The airport has several parking lots for you to choose from. Long-term parking is $22 a day, Short-term rates are $2 for 30 minutes with a daily rate of $32, economy parking is $16 per day, and premier parking, located right near the terminal, is $3 every 30 minutes with a daily maximum of $36.
Transportation to the Airport
Transportation to and from the airport is provided by shuttles, limos, taxis, car rentals, and the BART. Taxi service from downtown Oakland to the airport will cost around $28. Car rentals are a convenient way of getting to the airport, and Orbitz.com can find you the best rates from among the several different carriers.
Restaurants Located at the Airport
Restaurants located in the airport include Mua, Caffee Trieste, Marica, The Grand Tavern, Toast, Café Dejena, Yayu Ethiopian, and 360 Degrees Gourmet Burritos. These restaurants provide a wide variety of snack, dining, and breakfast options for travelers. Orbitz.com can find deals on transportation to the airport and cheap flights from Oakland when you are planning your next vacation.
Airports in Chicago
Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.
Transportation from the Airport
Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.
Weather in Chicago
Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.
Highlights and Attractions
Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.
Frequently asked questions
Flights to Chicago
- New York to Chicago
- Houston to Chicago
- Dallas to Chicago
- Toronto to Chicago
- Phoenix to Chicago
- Los Angeles to Chicago
- Orlando to Chicago
- Las Vegas to Chicago
- San Francisco to Chicago
- Detroit to Chicago
- Washington to Chicago
- New Orleans to Chicago
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- Hartford to Chicago
- London to Chicago
- Paris to Chicago
- Harrisburg - Hershey to Chicago
- Rome to Chicago
Oakland Airports
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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.