Cheap flights from Chicago to San José
A good round-trip price from Chicago to San José is under $438. Over the last 2 days the lowest fare we found each day was usually around $438, and the lowest of all was $438, for travel in January 2027. The cheapest month to fly is January 2027, at around $438.
Join to get alerts- Good price
- $438
- under this is a deal · round trip
- Typical price
- $438
- the middle of what we saw · round trip
- Lowest we saw
- $438
- for January 2027 · round trip
- Nonstop
- 0%
- of the cheapest fares
Cheapest months to fly
The cheapest round trip for each departure month, from fares seen on November 11, 2026.
- Dec 26$901
- Jan 27$438 (Cheapest)
- Mar 27$796
Price over the last 30 days
The lowest round-trip fare we found each day. Today: $438.
Deals on this route
Members get an alert when a fare on this route drops well under $438.
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Questions about this route
What is a good price to fly from Chicago to San José?
Under $438 round trip is a good price. Over the last 2 days the typical fare was $438 and the lowest was $438.
What is the cheapest month to fly from Chicago to San José?
January 2027, at $438 round trip, from the fares we found today. The most expensive month is December 2026, at $901.
Are there cheap nonstop flights from Chicago to San José?
None of the cheapest daily fares we found were nonstop. Expect one stop at the lowest prices.
How far ahead should I book flights from Chicago to San José?
The cheapest quarter of fares we found were for trips about 56 days ahead. Deals also appear at short notice, which is why members get alerts.
How long is the flight from Chicago to San José?
About 6 h 45 min one way on the cheapest fares we found, including any stops.
Fares like these don't wait
Members get an alert when a fare from their city drops far below normal, with the dates and a link to book.
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Based on 2 days of fares we checked between November 10, 2026 and November 11, 2026. Prices change fast, so always check the final price before you book.