AirHint found the following cheapest return flights from Chicago (MDW) to San Jose (SJO) in November 2025 (see full year).

Return flights

14 Nov - 18 Nov	Southwest Airlines
01 Nov - 07 Nov	Southwest Airlines
08 Nov - 11 Nov	Southwest Airlines
13 Nov - 30 Nov	Frontier Airlines
21 Nov - 29 Nov	Porter Airlines (Canada) Ltd
22 Nov - 30 Nov	Porter Airlines (Canada) Ltd

Also check the deals for one-way flights from Chicago to San Jose in November.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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Cheapest return flights from Chicago to San Jose in November from 368€

Return flights