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Cheap flights from Chicago (CHI) to Trinidad and Tobago

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How to find the cheapest flight from
Chicago (CHI) to Trinidad and Tobago

What is the cheapest month to fly from Chicago to Trinidad and Tobago?

The best pricing can be found in the month of May. Prices to Trinidad and Tobago from Chicago average $492. You can even find prices in May for less than $492, as users have found deals to Trinidad and Tobago from as low as $342. The month of December appears to be one of the more expensive times to travel to Trinidad and Tobago from Chicago. Flying in the targeted month can save you up to 53%.

Cheap flights from Chicago to Trinidad and Tobago in November, December 2020

The best prices found for CHI to Trinidad and Tobago flights for November, December
26 Dec - 2 Jan
$439pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
26 Dec - 2 Jan
$455pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
26 Dec - 2 Jan
$469pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Trinidad and Tobago 2021 flight deals

Cheap flights to Trinidad and Tobago from Chicago found for next year
26 Dec - 2 Jan
$439pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
26 Dec - 2 Jan
$455pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
26 Dec - 2 Jan
$469pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
JetBlue
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Trinidad and Tobago

Late deals on round-trip flights to Trinidad and Tobago from Chicago, departing today and this week
7 Dec - 17 Dec
$4,464pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
7 Dec - 17 Dec
$4,660pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
POS
Port of Spain Piarco Intl
POS
Port of Spain Piarco Intl
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl

One-way flights to Trinidad and Tobago from Chicago

The cheapest one-way flights from Chicago to Trinidad and Tobago
12:30 am - 11:41 am
American Airlines
2 Stops
9h 11m
ORD - POS
American Airlines
3:10 pm - 8:58 pm
Multiple Airlines
3 Stops
27h 48m
ORD - POS
Multiple Airlines
$282
Kiwi.com

Related info for your journey

Useful info, stats and facts about Chicago to Trinidad and Tobago flights.

Flight FAQs

From Chicago to Trinidad and Tobago

Are flight prices decreasing from Chicago to Trinidad and Tobago 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 Trinidad and Tobago 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.

Which airlines flying from Chicago to Trinidad and Tobago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Chicago to Trinidad and Tobago have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and Air Canada are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

Can I find flights from Chicago to Trinidad and Tobago for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Trinidad and Tobago for under $300. The cheapest flight booked recently is on Multiple Airlines for just $300, but on average you can expect to pay $373.

Are there nonstop flights from Chicago to Trinidad and Tobago for under $300 on Cheapflights?

There are no nonstop flights from Chicago to Trinidad and Tobago, 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 Trinidad and Tobago for under $4,500?

There are currently 2+ open flights from Chicago to Trinidad and Tobago within the next 7 days for less than $4,500.

What are the most popular airlines that fly from Chicago to Trinidad and Tobago?

Consider Major Airline, American Airlines or Air Canada when booking your flight. These represent the most popular airlines when flying from Chicago to Trinidad and Tobago.

What are the cheapest Flights from Chicago to Trinidad and Tobago?

Looking at all options, your cheapest flight can be booked for $236. While the most popular route (Chicago O'Hare Intl - Port of Spain Piarco Intl) can be booked for $341 on average our data indicates $493 when flying from Chicago to Trinidad and Tobago

How long is the flight from Chicago to Trinidad and Tobago?

United Airlines and Copa Airlines can get you from Chicago to Trinidad and Tobago in just under 10h. Your travel time can differ by up to 3h 35m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines to fly from Chicago to Trinidad and Tobago one-way?

$239 is the cheapest one-way deal found within the past few days, from American Airlines.

Arrival points for flights from Chicago to Trinidad and Tobago

Destination information for Trinidad and Tobago

Things to know before you go. Useful info for your trip from Chicago to Trinidad and Tobago
Today's exchange rate
$1 = $6.66

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing

Scarborough (TAB)

Top 3 airlines from Chicago to Trinidad and Tobago

The chart below displays the airlines Cheapflights users traveling from Chicago to Trinidad and Tobago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Air Canada
$276 $465 No cancel fee 67%
United Airlines
$237 $525 No cancel fee 69%
American Airlines
$239 $558 No cancel fee 71%
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