$245 Cheap flight deals from Chicago (CHI) to Port of Spain (POS)
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Airfares from $245 One Way, $538 Round Trip from Chicago to Port of Spain
Prices starting at $538 for return flights and $245 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
Woodbrook on the Avenue
Jun 18 - Jun 21
Chicago (CHI) to Port of Spain (POS)
Reviewed on Nov 27, 2018
Hilton Trinidad & Conference Centre
Jun 18 - Jun 21
Chicago (CHI) to Port of Spain (POS)
Reviewed on Sep 10, 2025
Mt. Plaisir Estate Hotel
Jun 15 - Jun 19
Chicago (ORD) to Port of Spain (POS)
Port of Spain (POS) to Chicago (ORD)
Port of Spain business class flight packages
Hilton Trinidad & Conference Centre
Jun 16 - Jun 21
Chicago (ORD) to Port of Spain (POS)
Port of Spain (POS) to Chicago (ORD)
Reviewed on Sep 10, 2025
HADCO Experiences at AWNC
Jun 16 - Jun 21
Chicago (ORD) to Port of Spain (POS)
Port of Spain (POS) to Chicago (ORD)
Hyatt Regency Trinidad
Jun 16 - Jun 21
Chicago (ORD) to Port of Spain (POS)
Port of Spain (POS) to Chicago (ORD)
Reviewed on Apr 3, 2026
More About Flying To Port of Spain from Chicago
Route Information for Flights from Chicago to Port of Spain
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | POS |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Port of Spain
For the best travel experience from Chicago to Port of Spain domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.
Convenient Low-Cost Travel
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Earn Rewards on Your Chicago to Port of Spain Flights
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Frequently asked questions
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Port of Spain Airports
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.