$405+ Cheap flights from Trinidad and Tobago to Chicago (CHI)
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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Trinidad and Tobago to Chicago 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 Trinidad and Tobago to Chicago
Keep the following information in mind while searching for Trinidad and Tobago to Chicago flight deals. Data was last updated junio 12, 2025.
Round-trip from | $550 (Air Canada) |
|---|---|
One-way from | $405 (Mytrip) |
Find flight deals from Trinidad and Tobago to Chicago
Cheapest flights from Trinidad and Tobago to ChicagoExplore the most affordable flight options available from Trinidad and Tobago to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.
Explore the most affordable flight options available from Trinidad and Tobago to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 2025.
This Air Canada deal was found by Cheapflights users on 6/11. 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.
This Copa Airlines deal was found by Cheapflights users on 6/11. 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 Copa Airlines 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 6/12. 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 American Airlines deal was found by Cheapflights users on 6/11. 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 6/12. 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 JetBlue deal was found by Cheapflights users on 6/10. 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.
Cheapflights Fare Finder
Customize your flight search to find flights from Trinidad and Tobago to Chicago 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 junio 12, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
dom. 7/6
2:20 am-1:13 pm
1 stop11h 53m
Chicago O'Hare Intl
vie. 7/18
10:40 am-1:20 am
2 stops13h 40m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
mar. 8/5
3:48 am-1:42 pm
1 stop10h 54m
Chicago O'Hare Intl
lun. 8/11
3:07 pm-1:48 am
1 stop9h 41m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
mié. 7/9
12:30 am-11:12 pm
1 stop23h 42m
Chicago O'Hare Intl
dom. 7/13
6:00 am-11:23 pm
1 stop16h 23m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
mié. 10/8
8:00 am-9:25 pm
2 stops14h 25m
Chicago O'Hare Intl
lun. 10/20
6:00 am-9:25 pm
1 stop14h 25m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
vie. 7/11
11:10 am-7:04 am
2 stops20h 54m
Chicago O'Hare Intl
dom. 7/13
6:20 pm-1:20 am
1 stop30h 00m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
vie. 7/11
8:50 am-10:28 pm
1 stop14h 38m
Chicago O'Hare Intl
dom. 7/13
6:16 am-6:04 pm
1 stop10h 48m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
jue. 7/17
7:40 am-10:16 am
3 stops27h 36m
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
mié. 7/16
3:48 am-1:42 pm
1 stop10h 54m
Best time to book a flight from Trinidad and Tobago to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Trinidad and Tobago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Trinidad and Tobago to Chicago
What is the cheapest month to book a flight from Trinidad and Tobago to Chicago?
Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $245). Flying from Trinidad and Tobago to Chicago in March is currently the most expensive (average of $321). 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 TT to CHI?
Find hourly flight availability from Trinidad and Tobago to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 12, 2025.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Trinidad and Tobago to Chicago as you normally would.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated junio 12, 2025.
Read through reviews of airlines operating flights from Trinidad and Tobago to Chicago, such as Copa Airlines, United Airlines and JetBlue. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Paul,Jun 2025
PTY - MIA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Paul,Jun 2025
PTY - MIA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Paul,Jun 2025
PTY - MIA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Paul,Jun 2025
PTY - MIA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Paul,Jun 2025
PTY - MIA
Entertainment
Crew
Overall
Comfort
Boarding
Food
Reviews
Paul,Jun 2025
PTY - MIA
Related info for your journey
Find useful and relevant information for your journey from Trinidad and Tobago to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Trinidad and Tobago?
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Alternative routes for Trinidad and Tobago to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Trinidad and Tobago to Chicago
Discover the top 2 airlines that operate flights from Trinidad and Tobago to Chicago. 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 junio 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$493 | Average$610 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$561 | Average$662 | FlexibilityNo cancel fee | On-time71% |