HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad and Tobago

$220+ Cheap flights from Chicago (CHI) to Trinidad and Tobago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
nov. 26 — dic. 31
mar. 11/26
mar. 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Trinidad and Tobago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Trinidad and Tobago

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Trinidad and Tobago (TT0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated noviembre 21, 2024.

Find flight deals from Chicago to Trinidad and Tobago

Cheapest flights from Chicago to Trinidad and Tobago
Explore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/247:39 pmORD - POS
1 stop22h 21mMultiple Airlines
mar. 11/2610:50 amPOS - ORD
1 stop24h 14mMultiple Airlines
Deal found 11/20$629
This JetBlue deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/1010:14 amORD - POS
1 stop14h 27mJetBlue
mar. 12/1710:05 pmPOS - ORD
1 stop13h 13mJetBlue
Deal found 11/20$645
This American Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/106:31 amORD - POS
2 stops14h 14mAmerican Airlines
mar. 12/174:09 pmPOS - ORD
1 stop18h 55mAmerican Airlines
Deal found 11/20$660
This United deal was found by Cheapflights users on 11/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/67:35 amORD - POS
1 stop14h 48mUnited Airlines
dom. 12/291:30 amPOS - ORD
1 stop10h 38mUnited Airlines
Deal found 11/21$695
This business-class.com deal was found by Cheapflights users on 11/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure business-class.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/196:54 amORD - POS
1 stop16h 49mCopa Airlines
vie. 1/32:25 pmPOS - ORD
1 stop11h 02mCopa Airlines
Deal found 11/21$3,836

Find flights from Chicago to Trinidad and Tobago within your budget

Customize your flight search to find flights from Chicago to Trinidad and Tobago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,612,795 searches. Data last updated noviembre 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 1/16

8:50 am-12:23 am

1 stop13h 33m

Port of Spain Piarco Intl

sáb. 1/18

1:30 am-11:25 am

1 stop11h 55m

$487

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 1/16

7:00 am-11:14 pm

2 stops14h 14m

Port of Spain Piarco Intl

dom. 1/19

4:35 pm-12:27 am

1 stop9h 52m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 4/11

7:56 am-1:43 am

1 stop16h 47m

Port of Spain Piarco Intl

sáb. 4/19

2:16 pm-12:21 am

1 stop11h 05m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 1/16

3:22 pm-8:00 pm

1 stop26h 38m

Port of Spain Piarco Intl

sáb. 1/18

3:36 am-10:27 pm

2 stops20h 51m

$557

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 12/10

10:14 am-2:41 am

1 stop14h 27m

Port of Spain Piarco Intl

mar. 12/17

10:05 pm-9:18 am

1 stop13h 13m

$645

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

jue. 1/30

11:55 am-11:14 pm

1 stop9h 19m

$220

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dom. 3/9

3:04 pm-1:41 am

1 stop9h 37m

$262

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 3/8

9:15 am-12:23 am

1 stop13h 08m

$265

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 12/28

1:00 pm-2:09 pm

1 stop23h 09m

$276

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb. 3/8

11:55 am-1:41 am

3 stops35h 46m

$1,461

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 11 results
1
2

Best time to book a flight from Chicago to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Trinidad and Tobago

Get recent, data-driven insights about flights from Chicago to Trinidad and Tobago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Trinidad and Tobago?

Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $435). Flying from Chicago to Trinidad and Tobago in February is currently the most expensive (average of $621). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to TT?

Find hourly flight availability from Chicago to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated noviembre 21, 2024.

When flying from Chicago to Trinidad and Tobago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Trinidad and Tobago ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Trinidad and Tobago when rainfall is around 1.2 in.

Temperature in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Trinidad and Tobago, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Trinidad and Tobago. Reviews last updated noviembre 21, 2024.
Copa Airlines
7.8
Good
1,779 reviews

Boarding

7.9

Crew

8.2

Comfort

7.5

Food

7.1

Overall

7.8

Entertainment

7.0

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Copa Airlines
7.8
Good
1,779 reviews
Copa Airlines
7.8
Good
1,779 reviews

Boarding

7.9

Crew

8.2

Comfort

7.5

Food

7.1

Overall

7.8

Entertainment

7.0

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

JetBlue
7.5
Good
3,389 reviews
Copa Airlines
7.8
Good
1,779 reviews

Boarding

7.9

Crew

8.2

Comfort

7.5

Food

7.1

Overall

7.8

Entertainment

7.0

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Turkish Airlines
7.4
Good
3,920 reviews
Copa Airlines
7.8
Good
1,779 reviews

Boarding

7.9

Crew

8.2

Comfort

7.5

Food

7.1

Overall

7.8

Entertainment

7.0

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

United Airlines
7.4
Good
9,172 reviews
Copa Airlines
7.8
Good
1,779 reviews

Boarding

7.9

Crew

8.2

Comfort

7.5

Food

7.1

Overall

7.8

Entertainment

7.0

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.8
Good
1,779 reviews

Boarding

7.9

Crew

8.2

Comfort

7.5

Food

7.1

Overall

7.8

Entertainment

7.0

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Trinidad and Tobago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $220. Users have also found prices from $262 and $265 on Copa Airlines and United Airlines, respectively.

  • Can I find deals for flights from Chicago to Trinidad and Tobago that include hotel bookings?

    Yes. In addition to deals on Chicago to Trinidad and Tobago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Trinidad and Tobago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Trinidad and Tobago.

  • Can I find deals for business class flights from Chicago to Trinidad and Tobago?

    Yes. Cheapflights offers flight deals from Chicago to Trinidad and Tobago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Trinidad and Tobago?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $435). Flying from Chicago to Trinidad and Tobago in February is currently the most expensive (average of $621). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Nassau flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
Midway to Punta Cana flights
O'Hare Intl to George Town flights
O'Hare Intl to Providenciales flights
Midway to Montego Bay flights
O'Hare Intl to Simpson Bay flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Castries flights
Midway to Nassau flights
O'Hare Intl to Puerto Plata flights
Midway to Oranjestad flights
O'Hare Intl to Willemstad flights
Midway to Saint Thomas Island flights
St. Louis to Punta Cana flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Bridgetown flights
Midway to Providenciales flights
O'Hare Intl to Christiansted flights
St. Louis to Montego Bay flights
Midway to George Town flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to St. John's flights
O'Hare Intl to Kingston flights
Midway to Simpson Bay flights
St. Louis to George Town flights
St. Louis to Christiansted flights
O'Hare Intl to Basseterre flights
Midway to Santo Domingo flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Gregory Town flights
St. Louis to Oranjestad flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Port of Spain flights
Moline to Montego Bay flights
St. Louis to Simpson Bay flights
St. Louis to Castries flights
O'Hare Intl to St. George's flights
St. Louis to Willemstad flights
Midway to Castries flights
St. Louis to Nassau flights
St. Louis to Providenciales flights
O'Hare Intl to Road Town flights
O'Hare Intl to Freeport flights

Top 3 airlines flying from Chicago to Trinidad and Tobago

Discover the top 3 airlines that operate flights from Chicago to Trinidad and Tobago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,612,795 searches. Data last updated noviembre 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$426Average$676FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$430Average$555FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$478Average$637FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines