$241+ 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.
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 January 21, 2025.
Round-trip from | $493 (FlightHub) |
|---|---|
One-way from | $241 (American Airlines) |
Find flight deals from Chicago to Trinidad and Tobago
Cheapest flights from Chicago to Trinidad and TobagoExplore 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 January 21, 2025.
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 January 21, 2025.
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This United Airlines deal was found by Cheapflights users on 1/21. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 1/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Air Canada deal was found by Cheapflights users on 1/21. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 2,558,603 searches. Data last updated January 21, 2025.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 3/7
8:46 pm-1:15 pm
2 stops14h 29m
Port of Spain Piarco Intl
Thu 3/13
6:01 pm-10:36 am
1 stop17h 35m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 3/19
10:10 am-4:41 pm
2 stops29h 31m
Port of Spain Piarco Intl
Thu 3/27
6:01 pm-1:43 pm
2 stops44h 42m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 5/8
6:45 pm-2:00 pm
1 stop18h 15m
Port of Spain Piarco Intl
Thu 5/15
3:15 pm-9:07 am
1 stop18h 52m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 3/7
6:55 am-1:37 am
1 stop16h 42m
Port of Spain Piarco Intl
Wed 3/12
3:39 am-12:27 am
1 stop21h 48m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 2/12
12:45 pm-12:23 am
1 stop9h 38m
Port of Spain Piarco Intl
Fri 2/21
1:30 am-5:06 pm
1 stop17h 36m
ChicagoScarborough
ORD - TAB
ORDTAB
Chicago O'Hare Intl
Fri 3/7
5:10 am-6:50 am
2 stops23h 40m
Scarborough ANR Robinson Intl
Fri 3/14
9:15 am-9:33 pm
3 stops37h 18m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 6/1
8:25 pm-1:35 am
1 stop28h 10m
Port of Spain Piarco Intl
Fri 6/6
2:35 am-7:38 am
2 stops30h 03m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 1/30
10:28 am-11:14 pm
2 stops10h 46m
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 1/30
11:55 am-1:33 am
3 stops35h 38m
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.
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 December is currently the most expensive (average of $710). 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 January 21, 2025.
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 January 21, 2025.
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
Comfort
Crew
Food
Overall
Boarding
Entertainment
Reviews
United Airlines flights seem to always use a bus to/from the boarding gate to the plane. Can they not get their own gate? This time there was no lift when leaving the plane and people in wheelchairs somehow had to climb down the steps to the ground to get to the bus. I udon’t know how some managed that!
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.
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Alternative routes for Chicago to Trinidad and Tobago
See prices for flight routes from nearby airports that may be better suited for you.
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 2,558,603 searches. Data last updated January 21, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$426 | Average$653 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$430 | Average$529 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$478 | Average$632 | FlexibilityNo cancel fee | On-time69% |