$411+ Cheap flights from Trinidad and Tobago to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
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 October 1, 2026.
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 October 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Thu 10/2210:10 am -
1 stop30h 20m
Tue 10/277:15 am -
2 stops35h 15m
Deal found 9/29![Multiple Airlines logo]()
$661
This Copa Airlines deal was found by Cheapflights users on 9/26. 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.
Wed 12/163:23 am -
1 stop21h 40m
Wed 12/302:13 pm -
1 stop9h 48m
Deal found 9/26![Copa Airlines logo]()
$700
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/2112:30 am -
1 stop15h 20m
Tue 10/2712:40 pm -
1 stop9h 38m
Deal found 9/29![United Airlines logo]()
$715
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Sat 10/2412:30 am -
1 stop11h 47m
Sun 11/16:55 am -
1 stop15h 23m
Deal found 9/26![United Airlines logo]()
$718
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/243:08 pm -
2 stops17h 19m
Sat 10/318:58 pm -
2 stops17h 39m
Deal found 9/27![American Airlines logo]()
$719
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Mon 12/710:10 am -
2 stops23h 10m
Sat 12/125:24 pm -
1 stop24h 06m
Deal found 9/27![Multiple Airlines logo]()
$728
Best flights from Trinidad and Tobago to ChicagoDiscover carefully curated flight deals from Trinidad and Tobago to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
Discover carefully curated flight deals from Trinidad and Tobago to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Thu 10/2210:10 am -
1 stop30h 20m
Tue 10/277:15 am -
2 stops35h 15m
Deal found 9/29![Multiple Airlines logo]()
$661
This Copa Airlines deal was found by Cheapflights users on 9/26. 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.
Wed 12/163:23 am -
1 stop21h 40m
Wed 12/302:13 pm -
1 stop9h 48m
Deal found 9/26![Copa Airlines logo]()
$700
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/2112:30 am -
1 stop15h 20m
Tue 10/2712:40 pm -
1 stop9h 38m
Deal found 9/29![United Airlines logo]()
$715
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 12/171:25 am -
1 stop25h 19m
Wed 12/309:43 pm -
1 stop24h 35m
Deal found 9/30![United Airlines logo]()
$715
This United Airlines deal was found by Cheapflights users on 9/27. 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.
Fri 10/2312:30 am -
1 stop12h 55m
Sat 10/3112:40 pm -
1 stop10h 50m
Deal found 9/27![United Airlines logo]()
$715
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Wed 12/161:25 am -
1 stop17h 00m
Wed 12/306:29 pm -
1 stop27h 49m
Deal found 9/26![United Airlines logo]()
$715
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 12/242:20 am -
1 stop10h 29m
Sun 1/35:50 pm -
1 stop28h 28m
Deal found 9/29![United Airlines logo]()
$715
Last-minute flights from Trinidad and Tobago to ChicagoDiscover last-minute flight deals from Trinidad and Tobago to Chicago. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad and Tobago to Chicago. Data last updated October 1, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/2112:30 am -
1 stop15h 20m
Tue 10/2712:40 pm -
1 stop9h 38m
Deal found 9/29![United Airlines logo]()
$715
This Booking.com deal was found by Cheapflights users on 9/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:20 am -
2 stops19h 52m
Tue 10/2710:15 am -
1 stop12h 46m
Deal found 9/28![Air Canada logo]()
$743
This Kiwi.com deal was found by Cheapflights users on 9/29. 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.
Thu 10/2210:10 am -
1 stop30h 20m
Tue 10/277:15 am -
2 stops35h 15m
Deal found 9/29![Multiple Airlines logo]()
$661
This United Airlines deal was found by Cheapflights users on 9/26. 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.
Sat 10/2412:30 am -
1 stop11h 47m
Sun 11/16:55 am -
1 stop15h 23m
Deal found 9/26![United Airlines logo]()
$718
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/243:08 pm -
2 stops17h 19m
Sat 10/318:58 pm -
2 stops17h 39m
Deal found 9/27![American Airlines logo]()
$719
One-way flights from Trinidad and Tobago to ChicagoSearch for one-way flight options from Trinidad and Tobago to Chicago. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
Search for one-way flight options from Trinidad and Tobago to Chicago. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 3/2912:30 am -
1 stop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 3/293:38 pm -
1 stop17h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$469
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Tue 3/303:38 pm -
2 stops23h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$483
This Air Canada deal was found by Cheapflights users on 9/30. 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.
Fri 3/261:15 am -
2 stops42h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Air Canada logo]()
$507
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Sun 3/289:10 am -
2 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$609
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 3/283:38 pm -
2 stops21h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Mon 3/299:55 pm -
3 stops38h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$835
This Kiwi.com deal was found by Cheapflights users on 9/30. 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.
Tue 3/309:30 am -
3 stops18h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$917
Find 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 October 1, 2026.
Round-trip from | $661 (Kiwi.com) |
|---|---|
One-way from | $469 (American Airlines) |
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 7,457,451 searches. Data last updated October 1, 2026.
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
Cheapest round-trip
Quickest round-trip
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Mon 3/29
12:30 am-9:25 am
1 stop9h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$411
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 3/26
1:15 am-6:55 pm
2 stops42h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$507
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Sun 3/28
9:10 am-11:50 am
2 stops27h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$609
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 10/22
10:10 am-3:30 pm
1 stop30h 20m
Chicago O'Hare Intl
Tue 10/27
7:15 am-7:30 pm
2 stops35h 15m
$661
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 12/16
3:23 am-11:03 pm
1 stop21h 40m
Chicago O'Hare Intl
Wed 12/30
2:13 pm-2:01 am
1 stop9h 48m
$700
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 10/21
12:30 am-2:50 pm
1 stop15h 20m
Chicago O'Hare Intl
Tue 10/27
12:40 pm-11:18 pm
1 stop9h 38m
$715
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 12/17
1:25 am-12:44 am
1 stop25h 19m
Chicago O'Hare Intl
Wed 12/30
9:43 pm-12:18 am
1 stop24h 35m
$715
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 10/23
12:30 am-12:25 pm
1 stop12h 55m
Chicago O'Hare Intl
Sat 10/31
12:40 pm-12:30 am
1 stop10h 50m
$715
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 12/16
1:25 am-4:25 pm
1 stop17h 00m
Chicago O'Hare Intl
Wed 12/30
6:29 pm-12:18 am
1 stop27h 49m
$715
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 12/24
2:20 am-10:49 am
1 stop10h 29m
Chicago O'Hare Intl
Sun 1/3
5:50 pm-12:18 am
1 stop28h 28m
$715
Showing 1-10 of 12 resultsSorted by cheapest first
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.
POS-ORD
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
TT0-CHI
POS-ORD
No data available for this route at this time. Please check back soon.
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 Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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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.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 1, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Trinidad and Tobago to Chicago by cabin class
Find flights from Trinidad and Tobago to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Trinidad and Tobago and Chicago flights
Browse other Trinidad and Tobago and Chicago flight options. Last updated on October 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Trinidad and Tobago to Chicago
Discover the top airline 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 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$574 | Average$824 | FlexibilityNo cancel fee | On-time71% |