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

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The best prices from Chicago to Port of Spain are usually found in May or September, booked 49 days in advance, depart on a Tuesday or Monday and return on a Wednesday

How to find the cheapest flight from
Chicago (CHI) to Port of Spain (POS)

CHI - POS
Price
$422 - $831
POS
Temperature
87.8 - 91.4 °F
POS
Rainfall
1.2 - 12.1 inches
Popular in December High demand for flights, 34% potential price rise
Cheapest in May Best time to find cheap flights, 24% potential price drop
Average price $550 Average for round-trip flights in August 2020
Round-trip from $422 From Chicago to Port of Spain
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Port of Spain?

Departing on a Monday is a good option for securing a great price. You can expect to save up to 32% when planning your travel around this day of the week.

What is the cheapest month to fly from Chicago to Port of Spain?

The best pricing can be found in the month of May. Prices to Port of Spain from Chicago average $638. You can even find prices in May for less than $638, as users have found deals to Port of Spain from as low as $444. The month of November appears to be one of the more expensive times to travel to Port of Spain from Chicago. Flying in the targeted month can save you up to 126%.

When is the cheapest time to fly from Chicago to Port of Spain (CHI - POS)?

One of the essential ways to save on airfare from Chicago to Port of Spain is to remain as flexible as possible. Flights that are in the noon tend to be the most expensive. If a flight is in the evening is possible it can save you up to 12% on airfare.

Cheap flights from Chicago to Port of Spain in August, September 2020

The best prices found for CHI to POS flights for August, September
25 Jul - 2 Aug
$1083pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Port of Spain 2020 flight deals

Cheap flights to Port of Spain from Chicago found for this year
11 Sep - 14 Sep
$373pp
ORD
Chicago O'Hare Intl
JetBlue
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl
13 Nov - 16 Nov
$440pp
ORD
Chicago O'Hare Intl
JetBlue
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl
14 Nov - 16 Nov
$797pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Port of Spain

Late deals on round-trip flights to Port of Spain from Chicago, departing today and this week
25 Jul - 2 Aug
$1083pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Related info for your journey

Useful info, stats and facts about Chicago to Port of Spain flights.

Flight FAQs

From Chicago to Port of Spain

Are flight prices decreasing from Chicago to Port of Spain due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Port of Spain for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago to Port of Spain for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Port of Spain for under $400. The cheapest flight booked recently is on JetBlue for just $373, but on average you can expect to pay $1497.

Are there nonstop flights from Chicago to Port of Spain for under $400 on Cheapflights?

There are no nonstop flights from Chicago to Port of Spain, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

Are there last-minute flights available from Chicago to Port of Spain for under $1100?

There are currently 1+ open flights from Chicago to Port of Spain within the next 7 days for less than $1100.

Is Chicago weather warmer or cooler than Port of Spain?

You can imagine temperatures to be in the 91 °F range in April. The weather in Port of Spain is generally hotter than Chicago's. As flight availability is subject to become more limited as peak season approaches it is ideal to book in a timely manner.

How long is the flight from Chicago to Port of Spain?

Airlines like JetBlue fly from Chicago to Port of Spain in about 7h 17m. The time it takes to get you to your destination can typically vary by up to .

What is the cheapest airline to fly from Chicago to Port of Spain round-trip?

Flying on JetBlue is currently your cheapest option to Port of Spain, with prices starting at $373. Users have found that JetBlue is 32% cheaper than the other options available to this destination.

Destination information for Port of Spain

Things to know before you go. Useful info for your trip from Chicago to Port of Spain
Today's exchange rate
$1 = $6.65
Average temperature for August in Port of Spain
91.4 °F
Avg rainfall for August in Port of Spain
11.2 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Port of Spain

Home Caribbean Trinidad and Tobago Port of Spain Cheap flights from Chicago to Port of Spain