Cheapest return flights from Chicago to San Juan in January from $116

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in January 2026 (see full year).

Return flights

10 Jan - 15 Jan Frontier Airlines
07 Jan - 15 Jan Frontier Airlines
12 Jan - 15 Jan Frontier Airlines
26 Jan - 29 Jan Frontier Airlines
08 Jan - 15 Jan Frontier Airlines
26 Jan - 05 Feb Frontier Airlines
07 Jan - 13 Jan Frontier Airlines
07 Jan - 12 Jan Frontier Airlines
24 Jan - 31 Jan Frontier Airlines
08 Jan - 12 Jan Frontier Airlines
05 Jan - 14 Jan Frontier Airlines
20 Jan - 04 Feb jetBlue
30 Jan - 07 Feb jetBlue
20 Jan - 04 Feb Spirit Airlines direct
31 Jan - 03 Feb Spirit Airlines direct
26 Jan - 05 Feb Spirit Airlines direct
26 Jan - 10 Feb Spirit Airlines direct
26 Jan - 04 Feb Spirit Airlines direct
26 Jan - 07 Feb Spirit Airlines direct
26 Jan - 03 Feb Spirit Airlines direct

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

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