Cheapest return flights from Chicago to San Juan in January from 220€

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

Return flights

27 Jan - 31 Jan Spirit Airlines direct
19 Jan - 31 Jan Spirit Airlines direct
18 Jan - 31 Jan Spirit Airlines direct
26 Jan - 31 Jan Spirit Airlines direct
27 Jan - 08 Feb Spirit Airlines direct
19 Jan - 23 Jan Spirit Airlines direct
19 Jan - 26 Jan Spirit Airlines direct
18 Jan - 23 Jan Spirit Airlines direct
18 Jan - 26 Jan Spirit Airlines direct
19 Jan - 08 Feb Spirit Airlines direct
18 Jan - 08 Feb Spirit Airlines direct
26 Jan - 08 Feb Spirit Airlines direct
16 Jan - 31 Jan Spirit Airlines direct
10 Jan - 18 Jan United

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

Skyscanner

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.