Find Flights Tickets and Deals on JetBlue from United States to Puerto Rico from $198

Our Most Popular Flights from Chicago to Puerto Rico

$

Chicago (ORD)to

San Juan (SJU)
Depart 02/25/2026
from
$158
Seen: 2 hrs ago
one-way
Core

Chicago (ORD)to

Aguadilla (BQN)
Depart 02/11/2026
from
$708
Seen: 20 hrs ago
one-way
Core

*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.

Tickets for Cheap Flights from Chicago to Puerto Rico

$
Tickets for Cheap Flights from Chicago to Puerto Rico
From
To
Fare Type
Dates
Price
Chicago (ORD)San Juan (SJU)one-way
/
Core		Depart 05/06/2026

from

$198

Seen: 6 hrs ago

Chicago (ORD)Aguadilla (BQN)one-way
/
Core		Depart 08/31/2026

from

$393

Seen: 18 hrs ago

*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.

Book flights from Chicago to Puerto Rico

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