Skip to main content
Beginning of main content

POS (Port of Spain) to ORD (Chicago) Flights $319.08

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap POS to ORD Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Chicago

$3010.71

Interesting Facts About Flights from Port of Spain to Chicago (POS to ORD)

Question : What day in the next four weeks has the best fares?
Answer : Jul 24th has seen bookings (as of Jun 26th) as cheap as $411. That comes in 26% below the average price for this route. Saving now means you'll have more money to spend on your trip.

Question : How many days should you spend in Chicago?
Answer : Over the next two months, passengers from POS to ORD are planning on staying for 10 days on average.

Question : Is price more important than specific travel days for you?
Answer : For the month of July, the cheapest day to fly is Monday. Being flexible with your travel days garners even more savings during booking.

Question : Do prices fluctuate more for this route than others?
Answer : Flight prices are fluctuating less for this route than the majority of routes from Trinidad and Tobago, as they're ranging from $367 to $919. Prices tend to be lower the further out you book.

Question : What is the cheapest round-trip ticket you can get to Chicago?
Answer : Air Canada is offering the best deal at $367. Better snatch it up quickly because prices range all the way up to $919 over the next three months.