Cheap Flights from Oakland to Chicago Starting at $102

The Oakland — Chicago route is served by multiple airlines, including United Airlines, American Airlines, and Frontier Airlines. This is convenient for those who want the best balance of price, schedule, and travel conditions. Tickets start from $102, and depending on season and promotions, even better deals may appear. With our service, you can easily compare available options and book tickets that match your plans. The variety of carriers allows flexible choices and comfortable travel without overpaying.

Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Oakland to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.

In different months, ticket prices from Oakland to Chicago vary: minimum — $138 (October 2025), maximum — $169 (November 2025). Typically, the flight costs $154–$169.