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Fares from $61 One Way, $121 Round Trip from Oakland to Chicago

Prices starting at $121 for return flights and $61 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.

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More About Flying To Chicago from Oakland

Flights from Oakland to Chicago - Frequently Asked Questions

Are there non-stop flights from Oakland to Chicago?

There sure is. You can fly directly from Oakland to Chicago with Southwest Airlines. It's the only carrier with nonstop services from Oakland, CA Airport (OAK-Oakland Intl.) to Chicago, IL Airport (MDW-Midway Intl.).

What is the shortest flight from Oakland to Chicago?

The shortest flight time from Oakland, CA Airport (OAK-Oakland Intl.) to Chicago, IL Airport (ORD-O'Hare Intl.) is 4 hours and 15 minutes, which gives you plenty of time to enjoy a wine or lose yourself in a gripping novel.

What airlines fly from Oakland to Chicago most frequently?

Southwest Airlines is the most frequent airline operating on the Oakland to Chicago route. You can choose from 52 flights each month with this carrier.

Route Information for Flights from Oakland to Chicago

Origin Airport IATA CodeSJC
Destination Airport IATA CodeCHI
Distance1842 mi
Direct Flight AirlinesAmerican Airlines, Qatar Airways, Air Canada, Austrian, Aer Lingus, Asiana Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, SAS, ANA, Lufthansa, Singapore Airlines, Air China LTD, Gulf Air
Earliest Flight Arrival2:00PM UTC
Latest Flight Arrival6:40AM UTC

Flights Review

Aug 18, 2019

The flight attendants really helped my husband and I the ladies in the back of the plane were wonderful. My husband has a tumor in his spine we used your wheelchair service everyone was awesome to us. We are now here at Mayo in Rochester. Thank to all your crew from SJC to Rochester Minn

Aug 13, 2019

Too expensive!

Aug 11, 2019

Good experience

Jul 12, 2019

Good customer service

Jul 22, 2018

Seat spacing is so tight my knees are constantly jammed into the seat ahead of me. Tall is a handicap at Times.

Jun 12, 2018

Very long line to drop off bag.

May 29, 2018

Serving extra water is a great idea.

Feb 2, 2018

Great seats! Seemed very roomy in coach class.

Flights from Oakland to Chicago

Oakland Airport Information

If you are searching for cheap flights from Oakland, 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. 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 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. 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. 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, 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 and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions 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.

^Savings based on all package bookings with Flight + Hotel made on 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.