Cheapest return flights from Chicago to San Juan in January from 221€

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

Return flights

24 Jan - 31 Jan Spirit Airlines direct
23 Jan - 24 Jan Spirit Airlines direct
24 Jan - 25 Jan Spirit Airlines direct
24 Jan - 26 Jan Spirit Airlines direct
17 Jan - 24 Jan Spirit Airlines direct
02 Jan - 21 Jan Spirit Airlines direct
23 Jan - 31 Jan Spirit Airlines direct
24 Jan - 30 Jan Spirit Airlines direct
01 Jan - 21 Jan Spirit Airlines direct
17 Jan - 31 Jan Spirit Airlines direct
24 Jan - 12 Feb Spirit Airlines direct
23 Jan - 12 Feb Spirit Airlines direct
24 Jan - 13 Feb Spirit Airlines direct
23 Jan - 13 Feb Spirit Airlines direct

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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