Port of Spain (POS) → Chicago (ORD)
About Port of Spain to Chicago Flights
Discover the best flights from Port of Spain to Chicago, covering 4,342 km in approximately 5h 56m. Port of Spain (POS) to Chicago (ORD) is one of the popular medium-haul routes connecting Trinidad and Tobago and United States. With 7 major airlines operating this route including direct flights, travelers have plenty of options to choose from. Whether you're traveling for business or leisure, our comprehensive guide helps you find the best deals, understand seasonal price variations, and choose the right airline for your journey from Port of Spain to Chicago.
12-Month Price History
Flight prices from Port of Spain to Chicago vary significantly throughout the year. February typically offers the best deals with average prices around $834, while July sees the highest prices, averaging $1437. Savvy travelers can save up to 42% by choosing their travel dates wisely.
Best Time to Fly
Cheapest Month
February
Save up to 40% on average
Most Expensive
July
Peak season pricing
Book in Advance
175 days
For best prices
Booking Tips
For the best prices on Port of Spain to Chicago flights, we recommend booking 69 days in advance. International flights typically see price increases as the departure date approaches, so early booking is advisable. Tuesday and Wednesday departures often offer the lowest fares, while Friday and Sunday flights tend to be more expensive due to business and leisure travel demand. Consider flying early morning or late evening for additional savings, as these off-peak times usually have lower demand.
Airlines Serving This Route
| Airline | Economy | Business | First |
|---|---|---|---|
Caribbean Airlines BW | $1380 | $5500 | $9500 |
Kalitta Air K4 | $1490 | $5370 | $9510 |
American Airlines AA | $1590 | $5330 | $8940 |
SkyWest Airlines OO | $1630 | $5680 | $9070 |
United Airlines UA | $1670 | $4990 | $7500 |
British Airways BA | $1750 | $6310 | $9860 |
Delta Air Lines DL | $1760 | $6540 | $9000 |
Caribbean Airlines
BW
Economy
$1380
Business
$5500
First
$9500
Kalitta Air
K4
Economy
$1490
Business
$5370
First
$9510
American Airlines
AA
Economy
$1590
Business
$5330
First
$8940
SkyWest Airlines
OO
Economy
$1630
Business
$5680
First
$9070
United Airlines
UA
Economy
$1670
Business
$4990
First
$7500
British Airways
BA
Economy
$1750
Business
$6310
First
$9860
Delta Air Lines
DL
Economy
$1760
Business
$6540
First
$9000
Prices shown are estimates based on historical data. Actual prices may vary based on dates, availability, and current promotions.
Alternative Flight Options
Port of Spain → Milwaukee
Piarco International (POS) to Milwaukee Mitchell International (MKE)
Distance: 4,420 km
Average price: $992
Port of Spain → Chicago
Piarco International (POS) to Chicago Midway International (MDW)
Distance: 4,319 km
Average price: $972
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Frequently Asked Questions
How long is the flight from Port of Spain to Chicago?
The flight time from Port of Spain (POS) to Chicago (ORD) is approximately 5 hours and 56 minutes. This duration is for direct flights and may vary depending on aircraft type, weather conditions, and air traffic.
What is the distance between Port of Spain and Chicago?
The aerial distance between Port of Spain and Chicago is 4,342 kilometers (2,698 miles). This is the straight-line distance, which is used to calculate flight times.
Which airlines fly from Port of Spain to Chicago?
Several airlines operate flights between Port of Spain and Chicago, including American Airlines, United Airlines, Caribbean Airlines and 4 more airlines. Direct flights are available on this route.
What is the cheapest month to fly from Port of Spain to Chicago?
Based on historical data, February typically offers the lowest airfares for flights from Port of Spain to Chicago. However, prices can vary based on holidays, events, and airline promotions. We recommend checking our price calendar for the most up-to-date information.
How far in advance should I book my flight to Chicago?
For the best prices on Port of Spain to Chicago flights, we recommend booking 120 days in advance. International flights generally require earlier booking than domestic routes.
Do I need a visa to travel from Port of Spain to Chicago?
Visa requirements depend on your nationality and the purpose of your visit. Citizens of Trinidad and Tobago traveling to United States should check the latest visa requirements. Visit our partner site visarequirements.io for detailed visa information.
What is the time difference between Port of Spain and Chicago?
Port of Spain operates on America/Port_of_Spain time zone, while Chicago is in the America/Chicago time zone. For current time differences and to plan your schedule, visit our partner site timezig.com for accurate timezone conversions.