
$246 Cheap flight deals from Chicago (CHI) to Port of Spain (POS)
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This Weekend's Flight Deals from Chicago to Port of Spain
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $246 One Way, $538 Round Trip from Chicago to Port of Spain
Prices starting at $538 for return flights and $246 for one-way flights to Port of Spain were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Port of Spain economy flight packages


Hyatt Regency Trinidad
Aug 22 - Aug 25
Chicago (CHI) to Port of Spain (POS)
Port of Spain (POS) to Chicago (CHI)
Reviewed on May 20, 2025

Hilton Trinidad & Conference Centre
Aug 22 - Aug 25
Chicago (CHI) to Port of Spain (POS)
Port of Spain (POS) to Chicago (CHI)
Reviewed on Jan 28, 2025
More About Flying To Port of Spain from Chicago
Route Information for Flights from Chicago to Port of Spain
Origin Airport IATA Code | CHI |
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Destination Airport IATA Code | POS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Port of Spain
Orbitz assures that you will receive cheap air fares on flights from Chicago to Port of Spain and special deals that give you guaranteed low prices on hotels, cruises, car rentals, and anything else you need on your trip.
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Low fares on Chicago to Port of Spain flights
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.