Cheapest return flights from Chicago to San Juan in November from $270

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

Return flights

03 Nov - 06 Nov Frontier Airlines
02 Nov - 07 Nov Frontier Airlines
03 Nov - 10 Nov Frontier Airlines
07 Nov - 09 Nov Frontier Airlines
01 Nov - 09 Nov Frontier Airlines
13 Nov - 16 Nov Frontier Airlines
13 Nov - 17 Nov Frontier Airlines
27 Nov - 04 Dec Frontier Airlines
20 Nov - 27 Nov Frontier Airlines
03 Nov - 08 Nov Frontier Airlines
06 Nov - 09 Nov Frontier Airlines
26 Nov - 02 Dec Southwest Airlines
25 Nov - 02 Dec Southwest Airlines
26 Nov - 01 Dec Southwest Airlines
25 Nov - 01 Dec Southwest Airlines
27 Nov - 01 Dec Southwest Airlines
25 Nov - 03 Dec Frontier Airlines

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

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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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