Compare Chicago to Puerto Rico flight deals starting at $302

Select journey type

Enter to select travel class and passengers

Find flights from Chicago (ORD) to Puerto Rico

Chicago (ORD) to San Juan (SJU)

Depart ** 28 01 19 **,
Return ** 12 02 19 **
from$ 306*Viewed: 1 hour ago

Chicago (ORD) to Aguadilla (BQN)

Depart ** 30 01 19 **,
Return ** 14 02 19 **
from$ 302*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.

Plan ahead for flights from Chicago to Puerto Rico

from
to
Type
Dates
Price*
Chicago (ORD)
to Aguadilla (BQN)
Roundtrip
Depart 01/30/2019
Return 02/14/2019
from$ 302*Viewed: 1 hour ago
Chicago (ORD)
to San Juan (SJU)
Roundtrip
Depart 01/30/2019
Return 02/14/2019
from$ 306*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.