Cheapest return flights from Chicago to San Juan in December from 343€
AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU)
in December 2025 (see full year ).
Return flights
04 Dec
- 14 Dec
United
343 €
06 Dec
- 11 Dec
Southwest Airlines
368 €
14 Dec
- 21 Dec
United
409 €
13 Dec
- 21 Dec
United
418 €
12 Dec
- 19 Dec
United
437 €
direct
18 Dec
- 10 Jan
Southwest Airlines
605 €
25 Dec
- 05 Jan
Delta
612 €
24 Dec
- 10 Jan
Southwest Airlines
624 €
29 Dec
- 02 Jan
Southwest Airlines
649 €
27 Dec
- 02 Jan
Southwest Airlines
649 €
31 Dec
- 04 Jan
Southwest Airlines
675 €
25 Dec
- 31 Dec
Delta
705 €
29 Dec
- 03 Jan
Southwest Airlines
717 €
26 Dec
- 30 Dec
Sun Country Airlines
731 €
26 Dec
- 01 Jan
Southwest Airlines
802 €
24 Dec
- 04 Jan
Southwest Airlines
811 €
25 Dec
- 02 Jan
Southwest Airlines
811 €
26 Dec
- 31 Dec
Southwest Airlines
870 €
Also check the deals for one-way flights from Chicago to San Juan in December .
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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