Compare Chicago to Puerto Rico flight deals starting at $353

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Find flights from Chicago (ORD) to Puerto Rico

Chicago (ORD) to San Juan (SJU)

Depart Sun 14 Oct 2018,
Return Mon 29 Oct 2018
from$ 353*Viewed: 1 hour ago

Chicago (ORD) to Aguadilla (BQN)

Depart Mon 17 Sep 2018,
Return Tue 2 Oct 2018
from$ 358*Viewed: 1 hour ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.
Stone fortress next to the water in Puerto Rico

Plan ahead for flights from Chicago to Puerto Rico

from
to
Type
Dates
Price*
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart Tue 16 Oct 2018
Return Wed 31 Oct 2018
from$ 353*Viewed: 1 hour ago
Chicago (ORD)
to Aguadilla (BQN)
Roundtrip
Depart Tue 2 Oct 2018
Return Wed 17 Oct 2018
from$ 358*Viewed: 1 hour ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.