There are most likely no direct flights on the San Jose — Chicago route
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.
A non-stop 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.
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Answers to questions about the route that travelers are most interested in.
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There are most likely no direct flights on the San Jose — Chicago route
The minimum one-way ticket price from San Jose to Chicago is $149 (November 2026), while the maximum is $196 (March 2027). On average, a ticket costs $172–$196.
San Francisco — Chicago
11/12/2026
Departure
Direct flight
WN3849
starting at $275
San Francisco — Chicago
11/13/2026
Departure
Direct flight
WN3849
starting at $279
San Francisco — Chicago
11/14/2026
Departure
Direct flight
WN3849
starting at $281
starting at $275
starting at $194
The route San Jose — Chicago is served by several airlines: Southwest Airlines and Frontier Airlines. This gives passengers more freedom in choosing flights. You can consider not only the price but also schedules, baggage policies, and onboard service. Our service compares all offers so you can find tickets from $194 and choose the most convenient option. Thanks to airline competition, you may also find promotional fares or special offers, helping you save even more. Plan your trip in advance and choose the best flights without overpaying.
The cheapest flight ticket from San Jose to Chicago according to data for the last 48 hours costs $194
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: November, March.
The fastest flights from San Jose to Chicago start from 7 hours 37 minutes in the air.
The following airlines operate direct flights on the route San Jose — Chicago: Southwest Airlines
The cheapest one-way flight from San Jose to Chicago departs on 11/14/2026, is operated by Frontier Airlines and costs $194
The cheapest roundtrip flight from San Jose to Chicago departs on 12/07/2026, is operated by Frontier Airlines and costs $220
Fastest flight from San Jose to Chicago takes 7h 37m
There are direct flights on this route 3 days a week: Th, Fr, and Sa
The distance between San Jose and Chicago is 2958km (1834 miles). There are 27 direct flights from San Jose to Chicago. The time difference between San Jose and Chicago is 2h. Flights from San Jose begin at 6:00 AM. The latest flight from San Jose departs at 11:00 PM
We couldn't find any special offers for flights from San Jose to Chicago