Cheapest one-way flights from Chicago to San Juan in November from $136

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

One-Way flights

14 Nov Frontier Airlines
07 Nov Frontier Airlines
04 Nov Frontier Airlines
09 Nov Frontier Airlines
24 Nov Southwest Airlines
29 Nov Southwest Airlines
23 Nov Southwest Airlines
30 Nov Southwest Airlines
22 Nov Southwest Airlines
29 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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