$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.

Fri, Jul 10 - Fri, Jul 17
ORD
O'Hare Intl.
POS
Piarco Intl.
$653 Roundtrip, found 2 days ago
$653
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Jul 10 from O'Hare Intl. to Piarco Intl., returning Fri, Jul 17, priced at $653 found 2 days ago

Airfares from $246 One Way, $539 Round Trip from Chicago to Port of Spain

Prices starting at $539 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.

Fri, Sep 25 - Tue, Sep 29
ORD
Chicago
POS
Trinidad
$539 Roundtrip, found 5 days ago
$539
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Sep 25 from Chicago to Trinidad, returning Tue, Sep 29, priced at $539 found 5 days ago
Tue, Aug 4 - Sun, Aug 9
ORD
Chicago
POS
Trinidad
$585 Roundtrip, found 5 days ago
$585
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Chicago to Trinidad, returning Sun, Aug 9, priced at $585 found 5 days ago
Fri, Jan 15 - Mon, Jan 18
ORD
Chicago
POS
Trinidad
$585 Roundtrip, found 7 hours ago
$585
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Fri, Jan 15 from Chicago to Trinidad, returning Mon, Jan 18, priced at $585 found 7 hours ago
Mon, Dec 7 - Mon, Dec 14
ORD
Chicago
POS
Trinidad
$593 Roundtrip, found 6 days ago
$593
Roundtrip
found 6 days ago
Select Air Canada flight, departing Mon, Dec 7 from Chicago to Trinidad, returning Mon, Dec 14, priced at $593 found 6 days ago
Tue, Aug 4 - Sun, Aug 9
ORD
Chicago
POS
Trinidad
$595 Roundtrip, found 5 days ago
$595
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Chicago to Trinidad, returning Sun, Aug 9, priced at $595 found 5 days ago

Port of Spain economy flight packages

Price found within the past 48 hours. Click for updated prices.
Woodbrook on the Avenue
2.5-star property

Woodbrook on the Avenue

9/10 Wonderful! (85 reviews)

Aug 28 - Aug 31

3 night stay

Chicago (CHI) to Port of Spain (POS)

Copa • Non-stop roundtrip • Coach
Price was $832, price is now $683 per person
$683
per person
found 9 hours ago
Room was super clean and the staff was very courteous and helpful. The A/C worked just fine. I would stay here again

Reviewed on Jul 4, 2026

Airport Suites Hotel
3.0-star property

Airport Suites Hotel

6/10 (1,002 reviews)

Aug 28 - Aug 31

3 night stay

Chicago (CHI) to Port of Spain (POS)

Copa • Non-stop roundtrip • Coach
Price was $878, price is now $697 per person
$697
per person
found 9 hours ago
The hotel is a good stay for a one night layover.

Reviewed on Jul 5, 2026

The Chancellor Hotel
3.0-star property

The Chancellor Hotel

7/10 Good! (37 reviews)

Aug 28 - Aug 31

3 night stay

Chicago (CHI) to Port of Spain (POS)

Copa • Non-stop roundtrip • Coach
Price was $924, price is now $757 per person
$757
per person
found 9 hours ago
Shower was not properly functioning when asked to switch rooms front desk could not program room key - they gave me access to a second room so I can shower using the housekeeping key both rooms had 1 towel 1 face towel and no washcloths Bar onsite but no staff to serve drinks Ended up checking out early due to issues at property

Reviewed on Apr 8, 2026

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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

If it is not enough that we have guaranteed low prices for Chicago to Port of Spain flights, Orbitz can also integrate your hotel and car rental needs into the package. This ensures your trip goes smoothly and you get the best possible bargain.

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Plan A Spontaneous Trip Using Our Top Hotel and Flight Destinations

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Use Orbitz.com For Up To The Minute Hot Deals

Budget deals on flights from Chicago to Port of Spain are constantly changing. You can get up-to-the-minute updates on the hottest deals on discount tickets and hotels on our website.

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.