Cheap flights from Oakland to Chicago from $157

Travelers frequently search for route combinations, such as Oakland and Mexico City, Guadalajara, Monterrey, Morelia, Oaxaca, León, San José del Cabo, Las Vegas, Honolulu, Cancún, San Diego, Puerto Escondido, Oaxaca, Burbank, Santa Ana, Santiago de Querétaro, Puerto Vallarta, Los Angeles, Villahermosa, Veracruz, Ciudad Juárez.

Travelers frequently search for route combinations, such as Chicago and Mexico City, New York, Guadalajara, Dallas, Houston, Atlanta, Los Angeles, Morelia, Orlando, Philadelphia, León, Tampa, San Francisco, Miami, Denver, Phoenix, Seattle, Monterrey, Las Vegas, Washington, D.C..

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

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

Currently, you can fly between Oakland and Chicago with Volaris, VivaAerobus, Alaska Airlines, Frontier Airlines, Hawaiian Airlines.

If you don’t have specific dates for your trip between Oakland and Chicago, 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 Oakland and Chicago, 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 Oakland. The main one is Oakland International and other nearby airports include San Francisco International, Sacramento International, San Jose International, Oakland International, Stockton Metropolitan, Monterey Regional, Charles M. Schulz–Sonoma County, Merced Regional

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, South Bend International, General Mitchell International, Fort Wayne International, Dane County Regional, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, University of Illinois Willard.