San Jose to Chicago flights

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Airlines seen: Aeromexico, Air Canada, Allegiant Air, American Airlines, Avianca, Breeze Airways +9 more
Typical journey time: 16h 42m

Fare seen

€284Seen on 9 Sep 2026

Last checked

7 Oct 2026

Observed fares. Prices may change.

Your next trip, last seen at €178

Lowest observed

6 Nov 2026

Viva Aerobus · 1 stop · One way

Cheapest observed day · Last checked: 9 Sep 2026

Departure

02:40

When to fly

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The lowest fare we observed for each month. Open a month to see its days, then pick your outbound and return. A day with no price is one we will search for you.

Prices are for observed departure and return date pairs. No data does not mean no flights.

Short answer

These are prices our searches returned on the dates shown, not quotes; run a live search for today's fare. Fare seen: €284 on 9 Sep 2026.

Short answer

These are prices our searches returned on the dates shown, not quotes; run a live search for today's fare. Fare seen: €284 on 9 Sep 2026.

About this route

Explore the fares we observed from San Jose to Chicago. Prices move often, so pick your dates to see the latest options.

Route distance: 3,569 km
Typical journey time: 16h 42m
Airlines seen: Aeromexico, Air Canada, Allegiant Air, American Airlines, Avianca, Breeze Airways +9 more
Seen on fares with a connection: JetBlue, Viva Aerobus, Air Canada, Volaris Costa Rica, Breeze Airways, SANSA +3 more
Alternative airports: CGX, DPA, MDW, PWK, RFD

Route-level information; individual journeys vary.
We have not observed non-stop service on this route; the fares shown include at least one stop.

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Observed, not guaranteed

Every price is a fare we actually saw, and it may change at any time.

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How our prices work

Frequently asked

How much was a flight from San Jose to Chicago?

A fare of €284 was seen on 9 Sep 2026. Fares change, so search your dates for the current price.

Are there direct flights from San Jose to Chicago?

Our data holds no non-stop flight from San Jose to Chicago. The fares on this page include at least one stop.

How long does the flight from San Jose to Chicago take?

The average journey time across the 70 fares we observed is 16h 54m, including any stops. Individual departures vary; the fastest observed flight is listed in the route facts above.

How observed prices work, what "No data" means and what a fare includes: Read the flight price guide