Cheap flights from Chicago to Oakland from $99

Travelers frequently search for route combinations, such as Chicago and Mexico City, Guadalajara, Orlando, Atlanta, Dallas, Miami, Phoenix, Las Vegas, Denver, Fort Lauderdale, León, Tampa, Cancún, New York, Los Angeles, Morelia, San Francisco, Houston, Philadelphia, San Juan.

Travelers frequently search for route combinations, such as Oakland and Mexico City, Guadalajara, Las Vegas, Dallas, Los Angeles, New York, San Diego, Morelia, León, Santa Ana, Houston, Detroit, Denver, Seattle, Burbank, Oaxaca, San Salvador, Portland, Monterrey, Phoenix.

Chicago is mainly served by O Hare International. But there are other airports nearby, including Chicago Midway International, Chicago Rockford International.

The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, South Bend International, Dane County Regional, Fort Wayne International, General Wayne A. Downing Peoria International, Central Illinois Regional, Quad City International, Muskegon County, University of Illinois Willard.

The main airport in Oakland is Oakland International. It is also served by San Francisco International, Sacramento International, Oakland International, San Jose International, Charles M. Schulz–Sonoma County, Stockton Metropolitan, Monterey Regional, Merced Regional.

Currently, you can fly between Chicago and Oakland with Hawaiian Airlines, Alaska Airlines, Spirit Airlines, United Airlines.

If you don’t have specific dates for your trip between Chicago and Oakland, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Traveling between Chicago and Oakland, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, General Mitchell International, South Bend International, Dane County Regional, Fort Wayne International, General Wayne A. Downing Peoria International, Central Illinois Regional, Quad City International, Muskegon County, University of Illinois Willard