Cheap Flights from Chicago to Port Of Spain from CAD 185️ 2024

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Find Chicago to Port Of Spain flights starting at CAD 185.

Book one-way or return flights from Chicago to Port Of Spain from as little as CAD 185. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Chicago to Port Of Spain? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Port Of Spain. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from Chicago to Port Of Spain

View airlines operating flights from Chicago to Port Of Spain. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines

From CAD 185

United Airlines

From CAD 276

Delta Air Lines

From CAD 282

American Airlines

From CAD 301

Spirit Airlines

From CAD 330

Copa Airlines

From CAD 376

Jetblue Airways

From CAD 464

Porter Airlines

From CAD 576

Air Canada

From CAD 715

WestJet

From CAD 757

ANA airlines

Find more flights and airlines

Alternative Routes for Chicago to Port Of Spain Flights

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Port Of Spain.

Cheapest
MDW
19:17
22h 38m
1 transfer
POS
18:55
Midway International Airport - Piarco International Airport
Wed, May 1Frontier Airlines
CAD 185
ORD
07:10
10h 45m
1 transfer
POS
18:55
O'Hare International Airport - Piarco International Airport
Wed, May 1United Airlines
CAD 276
ORD
07:10
10h 45m
1 transfer
POS
18:55
O'Hare International Airport - Piarco International Airport
Wed, May 1United Airlines
CAD 276
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How do I find the cheapest flights?

When are flight tickets from Chicago (CHI) to Port Of Spain (POS) the cheapest?
Airlines adjust prices for flights from Chicago to Port Of Spain based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much are flights from Chicago (CHI) to Port Of Spain (POS) cost?
According to Trip.com's data, the lowest price is around CAD 748.
What is the transportation method from the main airport to downtown in Port Of Spain?
- The distance from Piarco International Airport to downtown is about 18km, by taxi about 30 minutes.
How many airports in Port Of Spain (POS)?
There are 1 airport(s) in Port Of Spain (POS): Piarco International Airport.

How to find a cheap flight from Chicago to Port Of Spain

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Port Of Spain. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

Save up to £10 per person when booking your flights on Trip.com