Cheap Flights from San Jose to Chicago Starting at $195

Helping travelers to find the best flight offers

Cheapest flights from San Jose to Chicago

Airfare from San Jose to Chicago by month

May 2025
Lowest price
on average:
$127
  • Avg Price

Airlines operating on route

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.

Direct Flights from San Jose to Chicago

Chicago city image

San JoseChicago

SJCCHI

05/04/2025

Departure date

Direct flight

United Airlines

UA374

Starting at $391

Chicago city image

San JoseChicago

SJCCHI

07/11/2025

Departure date

Direct flight

Southwest Airlines

WN4508

Starting at $271

Chicago city image

San JoseChicago

SJCCHI

06/24/2025

Departure date

Direct flight

Southwest Airlines

WN2773

Starting at $206

Schedule of direct flights from San Jose to Chicago

A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from San Jose to Chicago:

San Jose airports overview

Chicago airports overview

Frequently asked questions (FAQ)

Answers to questions about the route that travelers are most interested in.

Special offers and sales on air tickets 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.

Alternative routes