$240+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Sep 16 — Sep 231
Round-trip
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
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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 August 17, 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 August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:10 am -
1 stop30h 10m
Thu 9/177:11 am -
1 stop11h 49m
Deal found 8/12![Multiple Airlines logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
1 stop30h 10m
Mon 10/57:28 pm -
2 stops22h 27m
Deal found 8/12![Multiple Airlines logo]()
$554
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Fri 10/1610:10 am -
1 stop30h 26m
Tue 10/207:44 pm -
2 stops22h 11m
Deal found 8/15![Multiple Airlines logo]()
$637
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 August 17, 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 August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:10 am -
1 stop30h 10m
Thu 9/177:11 am -
1 stop11h 49m
Deal found 8/12![Multiple Airlines logo]()
$465
This Copa Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 10/13:50 am -
1 stop22h 07m
Mon 10/53:20 pm -
1 stop9h 27m
Deal found 8/13![Copa Airlines logo]()
$678
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Fri 10/163:08 pm -
1 stop19h 22m
Tue 10/207:29 pm -
1 stop17h 39m
Deal found 8/15![American Airlines logo]()
$690
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Wed 9/28:30 am -
1 stop15h 38m
Mon 9/712:44 am -
2 stops24h 03m
Deal found 8/14![Multiple Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Fri 10/23:06 pm -
2 stops19h 04m
Mon 10/59:30 pm -
2 stops15h 38m
Deal found 8/13![American Airlines logo]()
$695
Last-minute flights from Trinidad and Tobago to ChicagoDiscover last-minute flight deals from Trinidad and Tobago to Chicago. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad and Tobago to Chicago. Data last updated August 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Wed 9/28:30 am -
1 stop15h 38m
Mon 9/712:44 am -
2 stops24h 03m
Deal found 8/14![Multiple Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 8/14. 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.
Wed 9/27:00 am -
2 stops13h 46m
Tue 9/88:58 pm -
2 stops16h 08m
Deal found 8/14![American Airlines logo]()
$752
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 9/612:30 am -
1 stop15h 20m
Tue 9/157:30 am -
1 stop14h 53m
Deal found 8/12![United Airlines logo]()
$715
This American Airlines deal was found by Cheapflights users on 8/13. 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 9/73:15 pm -
1 stop10h 20m
Tue 9/158:55 pm -
2 stops16h 11m
Deal found 8/13![American Airlines logo]()
$753
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:10 am -
1 stop30h 10m
Thu 9/177:11 am -
1 stop11h 49m
Deal found 8/12![Multiple Airlines logo]()
$465
This American Airlines deal was found by Cheapflights users on 8/13. 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.
Thu 9/243:06 pm -
1 stop19h 23m
Sun 9/277:00 pm -
1 stop18h 06m
Deal found 8/13![American Airlines logo]()
$692
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 August 17, 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 August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:10 am -
1 stop30h 10m
Deal found 8/12![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Fri 10/210:10 am -
1 stop30h 10m
Deal found 8/14![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/1110:10 am -
1 stop30h 10m
Deal found 8/17![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Fri 8/282:19 pm -
2 stops34h 08m
Deal found 8/14![Multiple Airlines logo]()
$332
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 9/310:10 am -
2 stops54h 49m
Deal found 8/14![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 8/14. 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 8/3010:10 am -
2 stops46h 43m
Deal found 8/14![Multiple Airlines logo]()
$340
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 August 17, 2026.
Round-trip from | $465 (Kiwi.com) |
|---|---|
One-way from | $240 (Kiwi.com) |
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 August 17, 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
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Mon 9/14
10:10 am-3:20 pm
1 stop30h 10m
Chicago O'Hare Intl
Thu 9/17
7:11 am-8:00 pm
1 stop11h 49m
$465
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 9/2
8:30 am-11:08 pm
1 stop15h 38m
Chicago O'Hare Intl
Mon 9/7
12:44 am-1:47 am
2 stops24h 03m
$656
Quickest round-trip
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 10/1
3:50 am-12:57 am
1 stop22h 07m
Chicago O'Hare Intl
Mon 10/5
3:20 pm-1:47 am
1 stop9h 27m
$678
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 10/16
3:08 pm-9:30 am
1 stop19h 22m
Chicago O'Hare Intl
Tue 10/20
7:29 pm-2:08 pm
1 stop17h 39m
$690
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 10/2
3:06 pm-9:10 am
2 stops19h 04m
Chicago O'Hare Intl
Mon 10/5
9:30 pm-2:08 pm
2 stops15h 38m
$695
Cheapest one-way
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 10/2
10:10 am-3:20 pm
1 stop30h 10m
$260
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Mon 9/14
10:10 am-11:51 am
2 stops26h 41m
$262
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 9/11
9:10 am-2:17 pm
2 stops30h 07m
$294
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 10/2
3:06 pm-9:29 am
1 stop19h 23m
$383
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 9/3
10:10 am-12:50 pm
1 stop27h 40m
$385
Showing 1-10 of 11 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
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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 August 17, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Trinidad and Tobago and Chicago flights
Browse other Trinidad and Tobago and Chicago flight options. Last updated on August 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$304 | Average$563 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$573 | Average$825 | FlexibilityNo cancel fee | On-time71% |