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

Return flights

13 Nov - 16 Nov	Frontier Airlines
02 Nov - 09 Nov	Frontier Airlines
06 Nov - 12 Nov	Frontier Airlines
13 Nov - 17 Nov	Southwest Airlines
06 Nov - 11 Nov	Southwest Airlines
20 Nov - 25 Nov	Southwest Airlines
21 Nov - 26 Nov	Southwest Airlines
24 Nov - 28 Nov	Southwest Airlines
21 Nov - 27 Nov	Southwest Airlines
22 Nov - 28 Nov	Southwest Airlines

Also check the deals for one-way flights from Chicago to San Juan 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 Juan in November from 242€

Return flights