$267+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
abr. 8 — abr. 151
1 adult, Economy
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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 abril 3, 2025.
Round-trip from | $485 (Kiwi.com) |
|---|---|
One-way from | $267 (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 abril 3, 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 abril 3, 2025.
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
jue. 6/510:10 amPOS - ORD
1 stop14h 55mMultiple Airlines
sáb. 6/79:55 amORD - POS
1 stop32h 00mMultiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$485
This Air Canada deal was found by Cheapflights users on 4/1. 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.
lun. 6/22:25 amPOS - ORD
2 stops30h 34mAir Canada
mié. 6/46:15 pmORD - POS
2 stops54h 10mAir Canada
Deal found 4/1![Air Canada logo]()
$538
This United Airlines deal was found by Cheapflights users on 4/1. 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.
vie. 5/3012:30 amPOS - ORD
1 stop10h 25mUnited Airlines
mié. 6/49:40 pmORD - POS
1 stop24h 43mUnited Airlines
Deal found 4/1![United Airlines logo]()
$561
This American Airlines deal was found by Cheapflights users on 4/2. 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. 5/203:05 pmPOS - ORD
1 stop18h 55mAmerican Airlines
mar. 6/35:00 amORD - POS
1 stop8h 05mAmerican Airlines
Deal found 4/2![American Airlines logo]()
$563
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 abril 3, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.
Fly from
Trinidad and Tobago
Fly to
Chicago
Route
Depart
Return
Price
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
jue. 6/5
10:10 am-12:05 am
1 stop14h 55m
Chicago O'Hare Intl
sáb. 6/7
9:55 am-6:55 pm
1 stop32h 00m
$485
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
lun. 6/2
2:25 am-7:59 am
2 stops30h 34m
Chicago O'Hare Intl
mié. 6/4
6:15 pm-1:25 am
2 stops54h 10m
$538
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
vie. 5/30
12:30 am-9:55 am
1 stop10h 25m
Chicago O'Hare Intl
mar. 6/3
8:10 pm-11:23 pm
1 stop26h 13m
$561
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
mar. 5/20
3:05 pm-9:00 am
1 stop18h 55m
Chicago O'Hare Intl
mar. 6/3
5:00 am-2:05 pm
1 stop8h 05m
$563
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
vie. 5/2
10:10 am-9:24 am
1 stop24h 14m
$267
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
jue. 5/1
12:30 am-12:15 am
1 stop24h 45m
$308
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.
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.
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 abril 3, 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 abril 3, 2025.
Read through reviews of airlines operating flights from Trinidad and Tobago to Chicago, such as United Airlines, American Airlines and Air Canada. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Entertainment
7.0
Reviews
1 / 20
4.0
OkayPatti,Feb 2025
FCO - EWR
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Entertainment
7.0
Reviews
1 / 20
4.0
OkayPatti,Feb 2025
FCO - EWR
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Entertainment
7.0
Reviews
1 / 20
4.0
OkayPatti,Feb 2025
FCO - EWR
Food
6.6
Comfort
7.3
Crew
8.1
Boarding
7.7
Overall
7.4
Entertainment
7.0
Reviews
1 / 20
4.0
OkayPatti,Feb 2025
FCO - EWR
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?
Book flights to Trinidad and Tobago if you plan to visit one of these locationsMerrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton
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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 abril 3, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$493 | Average$603 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$561 | Average$663 | FlexibilityNo cancel fee | On-time71% |