Cheap flights from Chicago (CHI) to Port of Spain (POS)

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Lowest round trip fares by airline from Chicago and Port of Spain

Cheapest prices ($220 One Way, $645 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Port of Spain

Kapok Hotel

Kapok Hotel

4 out of 5
16-18 Cotton Hill St Clair, Port of Spain, Trinidad
The price is $198 per night from Nov 26 to Nov 27
$198
includes taxes & fees
$181 per night
Nov 26 - Nov 27
Book a stay at this spa resort in Port of Spain. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the room service ...
8/10 Very Good! (930 reviews)
Noisy Room
"Kapok is always been my first choice since 2019 ,This time I do had little discomfort,since I do not use AC I always leave the windows open but the room i was right on top of generator so whole trip slept in noise even if I close the window couldn't escape the noise hope next time plzz consider my ..."

Reviewed on Nov 19, 2024

Kapok Hotel
Hyatt Regency Trinidad

Hyatt Regency Trinidad

4.5 out of 5
No 1 Wrighton Road, Port of Spain, Trinidad
The price is $204 per night from Dec 8 to Dec 9
$204
includes taxes & fees
$187 per night
Dec 8 - Dec 9
Stay at this 4.5-star luxury resort in Port of Spain. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,002 reviews)
Not worth the hype
"Breakfast buffet didn’t have an omelet station which would have been nice. Variety of local as well as American cuisine. Some dishes were not warm enough. The wait staff was not receptive to feedback when i mentioned one of the handles on the trays was too hot and could possibly cause a burn. The ..."

Reviewed on Nov 21, 2024

Hyatt Regency Trinidad
Melbourne Inn Trinidad

Melbourne Inn Trinidad

2 out of 5
7 French Street, Woodbrook, Port of Spain
The price is $69 per night from Dec 18 to Dec 19
$69
includes taxes & fees
$63 per night
Dec 18 - Dec 19
Stay at this guesthouse in Port of Spain. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Adam Smith Square and Ariapita Avenue are located ...
6.8/10 (48 reviews)
"Very quiet, friendly and helpful staff. Transportation to city and surrounding areas easily accessable"

Reviewed on Jul 1, 2024

Melbourne Inn Trinidad
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Port of Spain

Origin
Chicago
Destination
Port of Spain
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Chicago to Port of Spain

Cheap flights from Chicago to Port of Spain

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.