Cheap Flights from Chicago to San Jose Starting at $141

Helping travelers to find the best flight offers

Cheapest flights from Chicago to San Jose

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.

Cheapest one way flight

$141

Spirit Airlines
Spirit Airlines
1 transfer
18h 52m
05/10/2025

The cheapest one-way flight from Chicago to San Jose departs on 05/10/2025, is operated by Spirit Airlines and costs $141

Cheapest round trip flight

$293

Spirit Airlines
Spirit Airlines
1 transfer
1d 14h 40m
05/14/2025

The cheapest roundtrip flight from Chicago to San Jose departs on 05/14/2025, is operated by Spirit Airlines and costs $293

The fastest flight

18h 52m

Fastest flight from Chicago to San Jose takes 18h 52m

Direct flights

No direct flights

There are no direct flights on this route.

Earliest flight

7:35 AM

Latest flight

7:35 AM

Direct flights count

2

Distance

3560km

Timezone difference

0h

The distance between Chicago and San Jose is 3560km (2207 miles). There are 2 direct flights from Chicago to San Jose. Chicago and San Jose are in the same time zone. Flights from Chicago begin at 7:35 AM. The latest flight from Chicago departs at 7:35 AM.

Airfare from Chicago to San Jose by month

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 Chicago to San Jose

May 2025
Lowest price
on average:
$141

Airlines operating on route

Starting at $155

Starting at $164

Direct Flights from Chicago to San Jose

A direct 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.

San Jose city image

ChicagoSan Jose

CHISJO

05/10/2025

Departure date

Direct flight

United Airlines

UA1135

Starting at $412

Schedule of direct flights from Chicago to San Jose

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

Chicago airports overview

ORD
United Airlines
Spirit Airlines
Frontier Airlines
Airlines flying to this airport
$155
Starting at
$216
on average

San Jose airports overview

SJO
United Airlines
Spirit Airlines
Frontier Airlines
Airlines flying to this airport
$155
Starting at
$216
on average

Frequently asked questions (FAQ)

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

How much is the cheapest flight ticket from Chicago to San Jose?

The cheapest flight ticket from Chicago to San Jose according to data for the last 48 hours costs $141

When is the best time to buy air tickets on the route Chicago — San Jose?

Often the best time to buy tickets from Chicago to San Jose is 2 months before departure.

When is the cheapest time of year to fly from Chicago to San Jose?

Based on statistics over the past years, the lowest prices for flights from Chicago to San Jose can be found flying in these months: May.

How long does it take to fly from Chicago to San Jose?

The fastest flights from Chicago to San Jose start from 18 hours 52 minutes in the air.

Which airline can fly direct from Chicago to San Jose?

The following airlines operate direct flights on the route Chicago — San Jose: United Airlines

Special offers and sales on air tickets from Chicago to San Jose

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

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