Cheapest return flights from Chicago to San Juan in December from 341€

Best time to book flights for Chicago (ORD) to San Juan (SJU) flights at AirHint

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in December 2025 (see full year).

Return flights

03 Dec - 10 Dec United direct
17 Dec - 17 Jan United
17 Dec - 07 Jan United
17 Dec - 11 Jan United
31 Dec - 03 Jan United
30 Dec - 03 Jan United
17 Dec - 03 Jan United
23 Dec - 03 Jan Delta
27 Dec - 03 Jan Delta

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

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.

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