Cheapest return flights from Chicago to San Juan in January from $198

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

Return flights

12 Jan - 21 Jan Frontier Airlines
31 Jan - 11 Feb Spirit Airlines
31 Jan - 07 Feb Spirit Airlines direct
29 Jan - 02 Feb Spirit Airlines direct
31 Jan - 11 Feb Spirit Airlines direct
21 Jan - 26 Jan Spirit Airlines direct
06 Jan - 13 Jan Spirit Airlines direct
21 Jan - 27 Jan Spirit Airlines direct
22 Jan - 29 Jan Spirit Airlines direct
12 Jan - 21 Jan Spirit Airlines direct
22 Jan - 26 Jan Spirit Airlines direct
21 Jan - 28 Jan Spirit Airlines direct
24 Jan - 31 Jan Spirit Airlines direct
08 Jan - 13 Jan Spirit Airlines direct
31 Jan - 04 Feb Spirit Airlines direct
31 Jan - 05 Feb Spirit Airlines direct
31 Jan - 10 Feb Spirit Airlines direct
14 Jan - 04 Feb Spirit Airlines direct
21 Jan - 07 Feb Spirit Airlines direct
21 Jan - 04 Feb Spirit Airlines direct

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

Powered by

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.