Cheapest return flights from Chicago to San Juan in November from $239

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

Return flights

03 Nov - 08 Nov Frontier Airlines
14 Nov - 16 Nov Frontier Airlines
06 Nov - 10 Nov Frontier Airlines
10 Nov - 14 Nov Southwest Airlines
25 Nov - 01 Dec Southwest Airlines
22 Nov - 30 Nov Air Transat
26 Nov - 30 Nov Southwest Airlines
25 Nov - 30 Nov Southwest Airlines

Also check the deals for one-way 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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