Cheapest one-way flights from Chicago to San Juan in November from 287€

AirHint found the following cheapest one-way flights from Chicago (MDW) to San Juan (SJU) in November 2025 (see full year).

One-Way flights

22 Nov Southwest Airlines
21 Nov Southwest Airlines
22 Nov Southwest Airlines direct

Also check the deals for return flights from Chicago to San Juan in November.

Skyscanner

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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