$198 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.

Sat, Oct 18 - Mon, Oct 27
ORD
O'Hare Intl.
POS
Piarco Intl.
$448 Roundtrip, found 9 hours ago
$448
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Sat, Oct 18 from O'Hare Intl. to Piarco Intl., returning Mon, Oct 27, priced at $448 found 9 hours ago

Airfares from $198 One Way, $443 Round Trip from Chicago to Port of Spain

Prices starting at $443 for return flights and $198 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.

Sat, Mar 28 - Sat, Apr 4
ORD
Chicago
POS
Trinidad
$443 Roundtrip, found 1 hour ago
$443
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Sat, Mar 28 from Chicago to Trinidad, returning Sat, Apr 4, priced at $443 found 1 hour ago
Sun, Oct 19 - Tue, Oct 21
ORD
Chicago
POS
Trinidad
$448 Roundtrip, found 9 hours ago
$448
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Sun, Oct 19 from Chicago to Trinidad, returning Tue, Oct 21, priced at $448 found 9 hours ago
Sat, Jan 17 - Thu, Jan 22
ORD
Chicago
POS
Trinidad
$459 Roundtrip, found 12 hours ago
$459
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Sat, Jan 17 from Chicago to Trinidad, returning Thu, Jan 22, priced at $459 found 12 hours ago
Mon, Nov 3 - Fri, Nov 7
ORD
Chicago
POS
Trinidad
$465 Roundtrip, found 12 hours ago
$465
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Mon, Nov 3 from Chicago to Trinidad, returning Fri, Nov 7, priced at $465 found 12 hours ago
Tue, Oct 28 - Wed, Nov 19
ORD
Chicago
POS
Trinidad
$467 Roundtrip, found 5 days ago
$467
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Oct 28 from Chicago to Trinidad, returning Wed, Nov 19, priced at $467 found 5 days ago

Port of Spain economy flight packages

Price found within the past 48 hours. Click for updated prices.
Metro Hotel Couva
3.5-star property

Metro Hotel Couva

8.4/10 Very Good! (406 reviews)

Nov 22 - Nov 29

7 night stay

Chicago (ORD) to Port of Spain (POS)

Delta • Non-stop • Coach

Port of Spain (POS) to Chicago (ORD)

American Airlines • Non-stop • Coach
Price was $1,195, price is now $1,049 per person
$1,049
per person
found 11 hours ago
Rooms are huge. Don't expect 5 star quality but for the price it's hard to complain. The in the room they provided toothbrush with toothpaste, nail file, sewing kit, bedroom slippers, razors and more. There's complimentary tea and coffee in rhe lobby all day and the wifi worked well. If it's just a place to rest your head you cant go wrong.

Reviewed on Mar 10, 2023

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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

Low Cost Flights From Chicago to Port of Spain

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Frequently asked questions

What is the shortest flight from Chicago to Port of Spain?
The quickest flight from Chicago to Port of Spain is 7 hours and 15 minutes. Order your favorite tipple from the drink trolley, hone your travel itinerary or make friends with your seat mate — you'll have the time on this medium-haul trip.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.