$273+ Cheap flights from Illinois to Trinidad and Tobago
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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Oct 20 — Oct 271
Round-trip
1 adult, Economy
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Find cheap flights from Illinois 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
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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 Illinois to Trinidad and Tobago
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Cheapest flights from Illinois to Trinidad and TobagoExplore the most affordable flight options available from Illinois to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 20, 2026.
Explore the most affordable flight options available from Illinois to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 20, 2026.
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Sat 10/38:40 pm -
1 stop26h 35m
Sat 10/109:10 am -
2 stops25h 11m
Deal found 9/16![Multiple Airlines logo]()
$592
This Orbitz deal was found by Cheapflights users on 9/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:15 pm -
1 stop9h 00m
Fri 10/231:20 am -
1 stop19h 28m
Deal found 9/18![Air Canada logo]()
$593
This Trip.com deal was found by Cheapflights users on 9/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:40 pm -
1 stop26h 35m
Fri 10/161:20 am -
1 stop14h 35m
Deal found 9/19![Air Canada logo]()
$603
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 10/198:04 am -
1 stop10h 56m
Sun 10/259:10 am -
2 stops25h 11m
Deal found 9/15![Multiple Airlines logo]()
$620
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Mon 11/28:40 pm -
1 stop26h 20m
Sun 11/82:15 am -
1 stop12h 58m
Deal found 9/18![Air Canada logo]()
$621
This Copa Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/233:20 pm -
1 stop9h 27m
Fri 10/302:26 pm -
1 stop24h 20m
Deal found 9/18![Copa Airlines logo]()
$638
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/226:15 am -
1 stop16h 08m
Wed 11/181:25 am -
1 stop10h 37m
Deal found 9/16![United Airlines logo]()
$650
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:45 am -
1 stop13h 38m
Sat 10/2412:30 am -
1 stop11h 47m
Deal found 9/15![United Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/225:08 pm -
2 stops20h 00m
Thu 11/194:42 pm -
1 stop19h 25m
Deal found 9/16![American Airlines logo]()
$654
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/239:00 pm -
2 stops16h 08m
Fri 10/303:08 pm -
2 stops19h 03m
Deal found 9/18![American Airlines logo]()
$654
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/186:15 am -
1 stop16h 08m
Sat 11/141:25 am -
1 stop10h 37m
Deal found 9/18![United Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/225:08 pm -
2 stops20h 00m
Mon 10/263:08 pm -
2 stops20h 42m
Deal found 9/18![American Airlines logo]()
$674
Best flights from Illinois to Trinidad and TobagoDiscover carefully curated flight deals from Illinois to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
Discover carefully curated flight deals from Illinois to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 10/198:04 am -
1 stop10h 56m
Sun 10/259:10 am -
2 stops25h 11m
Deal found 9/15![Multiple Airlines logo]()
$620
This Copa Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/233:20 pm -
1 stop9h 27m
Fri 10/302:26 pm -
1 stop24h 20m
Deal found 9/18![Copa Airlines logo]()
$638
This United Airlines deal was found by Cheapflights users on 9/19. 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.
Tue 11/38:30 am -
1 stop13h 48m
Mon 11/91:25 am -
1 stop14h 48m
Deal found 9/19![United Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/19. 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 11/35:00 am -
1 stop8h 37m
Tue 11/104:42 pm -
2 stops23h 22m
Deal found 9/19![American Airlines logo]()
$654
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/24:30 pm -
1 stop30h 30m
Sun 11/82:15 am -
2 stops42h 15m
Deal found 9/18![Air Canada logo]()
$771
This Copa Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 1/127:35 am -
1 stop16h 20m
Sat 1/163:26 am -
1 stop11h 20m
Deal found 9/16![Copa Airlines logo]()
$648
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/226:15 am -
1 stop16h 08m
Wed 11/181:25 am -
1 stop10h 37m
Deal found 9/16![United Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/15. 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 1/228:55 pm -
2 stops16h 37m
Mon 2/14:37 pm -
1 stop18h 53m
Deal found 9/15![American Airlines logo]()
$654
This Copa Airlines deal was found by Cheapflights users on 9/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/82:13 pm -
1 stop9h 42m
Fri 1/223:26 am -
1 stop22h 41m
Deal found 9/15![Copa Airlines logo]()
$648
This United Airlines deal was found by Cheapflights users on 9/19. 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 11/209:21 am -
1 stop12h 57m
Fri 11/271:25 am -
1 stop10h 46m
Deal found 9/19![United Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/226:40 pm -
2 stops16h 50m
Wed 3/34:47 pm -
2 stops16h 48m
Deal found 9/17![American Airlines logo]()
$654
This Mytrip deal was found by Cheapflights users on 9/18. 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.
Sun 10/1812:10 pm -
2 stops35h 05m
Sun 11/159:10 am -
3 stops28h 09m
Deal found 9/18![Multiple Airlines logo]()
$761
This Copa Airlines deal was found by Cheapflights users on 9/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/222:13 pm -
1 stop9h 42m
Mon 2/12:12 pm -
1 stop24h 34m
Deal found 9/15![Copa Airlines logo]()
$648
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/186:15 am -
1 stop16h 08m
Sat 11/141:25 am -
1 stop10h 37m
Deal found 9/18![United Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/185:08 pm -
2 stops20h 00m
Sun 11/154:42 pm -
2 stops20h 11m
Deal found 9/18![American Airlines logo]()
$699
This KAYAK deal was found by Cheapflights users on 9/18. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:13 pm -
1 stop9h 41m
Sun 11/83:40 am -
1 stop22h 31m
Deal found 9/18![Copa Airlines logo]()
$688
This United Airlines deal was found by Cheapflights users on 9/16. 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 12/2612:40 pm -
1 stop9h 38m
Tue 12/292:20 am -
1 stop10h 29m
Deal found 9/16![United Airlines logo]()
$756
This United Airlines deal was found by Cheapflights users on 9/16. 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 12/2510:33 am -
1 stop11h 45m
Tue 12/292:20 am -
1 stop10h 29m
Deal found 9/16![United Airlines logo]()
$771
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:15 am -
1 stop16h 08m
Sun 10/2512:25 am -
1 stop23h 01m
Deal found 9/15![United Airlines logo]()
$780
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/53:43 pm -
2 stops21h 49m
Sun 2/144:47 pm -
2 stops21h 48m
Deal found 9/17![American Airlines logo]()
$1,217
This United Airlines deal was found by Cheapflights users on 9/18. 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 12/216:04 am -
1 stop17h 01m
Tue 12/292:20 am -
1 stop22h 39m
Deal found 9/18![United Airlines logo]()
$1,090
This Orbitz deal was found by Cheapflights users on 9/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/48:45 am -
3 stops32h 20m
Mon 2/810:20 pm -
2 stops37h 25m
Deal found 9/17![Multiple Airlines logo]()
$4,173
Last-minute flights from Illinois to Trinidad and TobagoDiscover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated September 20, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Sat 10/38:40 pm -
1 stop26h 35m
Sat 10/109:10 am -
2 stops25h 11m
Deal found 9/16![Multiple Airlines logo]()
$592
This Trip.com deal was found by Cheapflights users on 9/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:40 pm -
1 stop26h 35m
Fri 10/161:20 am -
1 stop14h 35m
Deal found 9/19![Air Canada logo]()
$603
This Air Canada deal was found by Cheapflights users on 9/19. 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.
Sat 10/38:40 pm -
2 stops22h 00m
Fri 10/161:20 am -
2 stops18h 26m
Deal found 9/19![Multiple Airlines logo]()
$674
This United Airlines deal was found by Cheapflights users on 9/18. 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 10/186:15 am -
1 stop16h 08m
Sat 11/141:25 am -
1 stop10h 37m
Deal found 9/18![United Airlines logo]()
$670
This Orbitz deal was found by Cheapflights users on 9/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/192:15 pm -
1 stop9h 00m
Fri 10/231:20 am -
1 stop19h 28m
Deal found 9/18![Air Canada logo]()
$593
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Mon 10/198:04 am -
1 stop10h 56m
Sun 10/259:10 am -
2 stops25h 11m
Deal found 9/15![Multiple Airlines logo]()
$620
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:45 am -
1 stop13h 38m
Sat 10/2412:30 am -
1 stop11h 47m
Deal found 9/15![United Airlines logo]()
$650
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/226:15 am -
1 stop16h 08m
Wed 11/181:25 am -
1 stop10h 37m
Deal found 9/16![United Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/225:08 pm -
2 stops20h 00m
Thu 11/194:42 pm -
2 stops22h 02m
Deal found 9/16![American Airlines logo]()
$654
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/225:08 pm -
2 stops20h 00m
Mon 10/263:08 pm -
2 stops20h 42m
Deal found 9/18![American Airlines logo]()
$674
This Copa Airlines deal was found by Cheapflights users on 9/18. 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.
Fri 10/233:20 pm -
1 stop9h 27m
Fri 10/302:26 pm -
1 stop24h 20m
Deal found 9/18![Copa Airlines logo]()
$638
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/239:00 pm -
2 stops16h 08m
Fri 10/303:08 pm -
2 stops19h 03m
Deal found 9/18![American Airlines logo]()
$654
One-way flights from Illinois to Trinidad and TobagoSearch for one-way flight options from Illinois to Trinidad and Tobago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
Search for one-way flight options from Illinois to Trinidad and Tobago. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
This Travelocity deal was found by Cheapflights users on 9/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:45 pm -
1 stop31h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$273
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Mon 10/122:15 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$278
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Sun 9/273:40 pm -
2 stops31h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/308:00 am -
1 stop11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Sat 10/174:41 pm -
3 stops43h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$295
This Travelocity deal was found by Cheapflights users on 9/16. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/88:45 am -
1 stop14h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Air Canada logo]()
$301
This Expedia deal was found by Cheapflights users on 9/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:21 pm -
2 stops52h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$302
This Air Canada deal was found by Cheapflights users on 9/18. 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.
Mon 9/288:45 am -
2 stops14h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$305
This Travelocity deal was found by Cheapflights users on 9/19. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:58 pm -
2 stops54h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Air Canada logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 9/18. 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.
Sat 10/104:41 pm -
3 stops43h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/277:50 pm -
2 stops22h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$313
This United Airlines deal was found by Cheapflights users on 9/19. 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 11/56:15 am -
1 stop16h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![United Airlines logo]()
$538
Find flight deals from Illinois to Trinidad and Tobago
Keep the following information in mind while searching for Illinois to Trinidad and Tobago flight deals. Data was last updated September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $592 (Mytrip) |
One-way from | $273 (Expedia) |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois 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 7,457,451 searches. Data last updated September 20, 2026.
Use the filters below to find and compare flights from Illinois to Trinidad and Tobago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sun 9/27
8:40 pm-12:15 am
1 stop26h 35m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$278
Quickest round-trip
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 10/5
2:15 pm-12:15 am
1 stop9h 00m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$278
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 10/26
4:41 pm-1:54 am
3 stops32h 13m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$304
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 1/8
7:05 am-1:00 am
2 stops15h 55m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$304
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 10/27
7:50 pm-7:30 pm
2 stops22h 40m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$313
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sun 1/17
8:45 am-1:00 am
1 stop14h 15m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$325
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 1/16
4:30 pm-1:00 am
1 stop30h 30m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$330
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sun 1/17
6:50 am-12:20 am
1 stop15h 30m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$339
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 10/3
3:50 pm-1:17 pm
3 stops44h 27m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$344
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 10/5
3:50 pm-1:47 am
3 stops32h 57m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$356
Showing 1-10 of 39 resultsSorted by cheapest first
Best time to book a flight from Illinois to Trinidad and Tobago
Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from Illinois with our price prediction graph.
ORD-POS
STL-POS
ORD-TAB
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 Illinois to Trinidad and Tobago
USIL-TT0
ORD-POS
STL-POS
ORD-TAB
What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?
Currently, October is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $432). Flying from Illinois to Trinidad and Tobago in February is currently the most expensive (average of $948). 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.
Related info for your journey
Find useful and relevant information for your journey from Illinois 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 Illinois to Trinidad and Tobago
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Complete your trip
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Search flights from Illinois to Trinidad and Tobago by cabin class
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Illinois and Trinidad and Tobago flights
Browse other Illinois and Trinidad and Tobago flight options. Last updated on September 20, 2026.
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Illinois to Trinidad and Tobago flights
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Top 3 airlines flying from Illinois to Trinidad and Tobago
Discover the top 3 airlines that operate flights from Illinois 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 7,457,451 searches. Data last updated September 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$317 | Average$443 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$578 | Average$759 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$596 | Average$739 | FlexibilityNo cancel fee | On-time71% |