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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 Chicago to San Jose. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
A non-stop flight is the most convenient and comfortable way to fly from Chicago to San Jose, despite the fact that sometimes flights with transfers can cost significantly less.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Chicago to San Jose:
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Answers to questions about the route that travelers are most interested in.
We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
Unable to find information about the schedule of direct flights from
Chicago — San Francisco
03/27/2026
Departure
Direct flight
AA2969
starting at $268
starting at $195
You can fly from Chicago to San Jose with American Airlines. It is the only carrier on this route, which makes the choice straightforward. Despite the lack of competition, ticket prices remain affordable: fares start from $195. Our service helps you track price changes, compare by dates, and select the most suitable flight. If you value stability and predictability, flying with American Airlines is a convenient solution. We make it easy to find good deals and ensure a comfortable booking process.
The cheapest one-way flight from Chicago to San Jose departs on 03/28/2026, is operated by American Airlines and costs $195
There is no information about the cheapest roundtrip flight from Chicago to San Jose
Fastest flight from Chicago to San Jose takes 4h 59m
There are direct flights on this route 1 day a week: Fr
The distance between Chicago and San Jose is 2958km (1834 miles). There are 8 direct flights from Chicago to San Jose. The time difference between Chicago and San Jose is 2h. Flights from Chicago begin at 7:50 AM. The latest flight from Chicago departs at 7:35 PM
We couldn't find any special offers for flights from Chicago to San Jose
The cheapest flight ticket from Chicago to San Jose according to data for the last 48 hours costs $195
Often the best time to buy tickets from Chicago to San Jose is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Chicago to San Jose can be found flying in these months: March, February, June.
The fastest flights from Chicago to San Jose start from 4 hours 59 minutes in the air.
The following airlines operate direct flights on the route Chicago — San Jose: American Airlines
In different months, ticket prices from Chicago to San Jose vary: minimum — $110 (March 2026), maximum — $187 (June 2026). Typically, the flight costs $151–$341.