Helping travelers to find the best flight offers
Below you will find a list of airlines operating flights on the San Jose — Chicago route and the starting prices for flights of each specific airline on it.
San Jose — Chicago
05/04/2025
Departure date
Direct flight
UA374
Starting at $391
San Jose — Chicago
07/11/2025
Departure date
Direct flight
WN4508
Starting at $271
San Jose — Chicago
06/24/2025
Departure date
Direct flight
WN2773
Starting at $206
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from San Jose to Chicago:
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.
Starting at $92
The cheapest one-way flight from San Jose to Chicago departs on 06/24/2025, is operated by United Airlines and costs $195
The cheapest roundtrip flight from San Jose to Chicago departs on 07/10/2025, is operated by United Airlines and costs $525
Fastest flight from San Jose to Chicago takes 4h 10m
There are direct flights on this route 3 days a week: Su, Tu, and Th
The distance between San Jose and Chicago is 2958km (1834 miles). There are 10 direct flights from San Jose to Chicago. The time difference between San Jose and Chicago is 2h . Flights from San Jose begin at 6:40 AM. The latest flight from San Jose departs at 1:35 PM.
Unable to find information about the schedule of direct flights from
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 San Jose to Chicago. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
We carefully collect statistics on the search and pricing of airlines and, based on these data, we make an assumption about future prices. Thus, you can better understand which season is the cheapest to fly from San Jose to Chicago
A direct flight is the most convenient and comfortable way to fly from San Jose to Chicago, despite the fact that sometimes flights with transfers can cost significantly less.
The cheapest flight ticket from San Jose to Chicago according to data for the last 48 hours costs $195
Often the best time to buy tickets from San Jose to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from San Jose to Chicago can be found flying in these months: May.
The fastest flights from San Jose to Chicago start from 4 hours 10 minutes in the air.
The following airlines operate direct flights on the route San Jose — Chicago: United Airlines, Southwest Airlines
We couldn't find any special offers for flights from San Jose to Chicago
