Helping travelers to find the best flight offers
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 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.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from San Jose to Chicago:
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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.
The San Jose — Chicago route is served by a wide range of airlines: 7 in total, including United Airlines, American Airlines, Southwest Airlines, Horizon Air, Frontier Airlines, Alaska Airlines, and Grumeti Air. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $57. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
San Francisco — Chicago
12/07/2025
Departure
Direct flight
UA2243
Starting at $595
San Francisco — Chicago
05/18/2026
Departure
Direct flight
UA1482
Starting at $270
San Francisco — Chicago
12/11/2025
Departure
Direct flight
AA2614
Starting at $459
San Francisco — Chicago
12/24/2025
Departure
Direct flight
AA2761
Starting at $453
San Francisco — Chicago
12/30/2025
Departure
Direct flight
UA2244
Starting at $234
San Francisco — Chicago
01/01/2026
Departure
Direct flight
UA2097
Starting at $234
San Francisco — Chicago
01/24/2026
Departure
Direct flight
UA1288
Starting at $201
San Francisco — Chicago
03/17/2026
Departure
Direct flight
AA2614
Starting at $183
San Jose — Chicago
12/15/2025
Departure
Direct flight
WN3730
Starting at $271
San Jose — Chicago
12/23/2025
Departure
Direct flight
UA2315
Starting at $494
Unable to find information about the schedule of direct flights from
The cheapest one-way flight from San Jose to Chicago departs on 01/07/2026, is operated by Horizon Air and costs $57
The cheapest roundtrip flight from San Jose to Chicago departs on 01/07/2026, is operated by Horizon Air and costs $169
Fastest flight from San Jose to Chicago takes 6h 55m
Starting at $201
Starting at $183
Starting at $186
Starting at $57
Starting at $70
Starting at $130
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RFD
Starting at $186
There are no direct flights on this route.
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 6:30 AM. The latest flight from San Jose departs at 10:40 AM
We couldn't find any special offers for flights from San Jose to Chicago
The cheapest flight ticket from San Jose to Chicago according to data for the last 48 hours costs $57
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: January, December.
The fastest flights from San Jose to Chicago start from 6 hours 55 minutes in the air.
The following airlines operate direct flights on the route San Jose — Chicago: United Airlines, American Airlines, Southwest Airlines
The minimum one-way ticket price from San Jose to Chicago is $135 (January 2026), while the maximum is $269 (December 2025). On average, a ticket costs $202–$269.