Cheapest return flights from Chicago to San Juan in January from $153

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

Return flights

07 Jan - 15 Jan Frontier Airlines
07 Jan - 14 Jan Frontier Airlines
30 Jan - 02 Feb Frontier Airlines
09 Jan - 12 Jan Frontier Airlines
07 Jan - 12 Jan Frontier Airlines
31 Jan - 07 Feb Frontier Airlines
09 Jan - 17 Jan Frontier Airlines
07 Jan - 10 Jan Frontier Airlines
08 Jan - 15 Jan Frontier Airlines
23 Jan - 27 Jan Southwest Airlines
06 Jan - 12 Jan Frontier Airlines
22 Jan - 27 Jan Southwest Airlines
31 Jan - 01 Feb Southwest Airlines
31 Jan - 08 Feb Southwest Airlines
30 Jan - 01 Feb Frontier Airlines

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.