Cheapest return flights from Chicago to San Juan in January from 313€

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

Return flights

14 Jan - 26 Jan Delta
13 Jan - 17 Jan United
14 Jan - 26 Jan United direct
30 Jan - 04 Feb Delta
10 Jan - 25 Jan Southwest Airlines
04 Jan - 11 Jan United direct
01 Jan - 03 Jan United

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

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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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