$265+ Cheap flights from Illinois to Trinidad and Tobago
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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Aug 17 — Aug 241
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Trinidad and Tobago with Cheapflights
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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 July 18, 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 July 18, 2026.
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Wed 9/21:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 7/13![Air Canada logo]()
$545
This Orbitz deal was found by Cheapflights users on 7/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:35 pm
ORD
- POS
1 stop29h 40m
Air Canada
Fri 9/181:20 am
POS
- ORD
1 stop16h 38m
Air Canada
Deal found 7/14![Air Canada logo]()
$555
This Kiwi.com deal was found by Cheapflights users on 7/14. 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 11/57:50 am
ORD
- POS
1 stop10h 10m
Multiple Airlines
Tue 11/179:10 am
POS
- ORD
2 stops36h 34m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$564
This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Mon 8/248:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Mon 8/3110:10 am
POS
- ORD
1 stop27h 40m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$568
This Air Canada deal was found by Cheapflights users on 7/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Fri 9/41:25 am
POS
- ORD
1 stop19h 28m
Air Canada
Deal found 7/13![Air Canada logo]()
$583
This Kiwi.com deal was found by Cheapflights users on 7/15. 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.
Thu 11/57:50 am
ORD
- POS
1 stop10h 10m
Multiple Airlines
Fri 11/139:10 am
POS
- ORD
2 stops28h 52m
Multiple Airlines
Deal found 7/15![Multiple Airlines logo]()
$591
This Air Canada deal was found by Cheapflights users on 7/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/110:15 am
ORD
- POS
1 stop12h 45m
Air Canada
Sun 11/82:05 am
POS
- ORD
1 stop19h 53m
Air Canada
Deal found 7/15![Air Canada logo]()
$595
This Air Canada deal was found by Cheapflights users on 7/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:50 pm
ORD
- POS
1 stop26h 25m
Air Canada
Sun 8/301:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 7/13![Air Canada logo]()
$600
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:10 pm
STL
- POS
2 stops35h 05m
Air Canada
Wed 9/21:25 am
POS
- STL
1 stop13h 37m
Air Canada
Deal found 7/13![Air Canada logo]()
$626
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/2711:35 am
STL
- POS
1 stop10h 43m
American Airlines
Thu 9/37:00 am
POS
- STL
1 stop16h 40m
American Airlines
Deal found 7/13![American Airlines logo]()
$630
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/1112:27 pm
STL
- POS
1 stop11h 23m
United Airlines
Sat 8/152:00 am
POS
- STL
1 stop10h 16m
United Airlines
Deal found 7/18![United Airlines logo]()
$695
This American Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/116:00 am
STL
- POS
2 stops16h 18m
American Airlines
Sun 8/167:00 am
POS
- STL
2 stops17h 34m
American Airlines
Deal found 7/18![American Airlines logo]()
$749
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 July 18, 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 July 18, 2026.
This Air Canada deal was found by Cheapflights users on 7/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Fri 9/181:20 am
POS
- ORD
2 stops14h 32m
Air Canada
Deal found 7/14![Air Canada logo]()
$558
This Copa Airlines deal was found by Cheapflights users on 7/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:02 am
ORD
- POS
1 stop28h 15m
Copa Airlines
Mon 8/312:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 7/17![Copa Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/2711:35 am
STL
- POS
1 stop10h 43m
American Airlines
Thu 9/37:00 am
POS
- STL
1 stop16h 40m
American Airlines
Deal found 7/13![American Airlines logo]()
$630
This JetBlue deal was found by Cheapflights users on 7/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Mon 8/178:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/13![JetBlue logo]()
$632
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:40 am
ORD
- POS
1 stop14h 38m
United Airlines
Tue 11/101:25 am
POS
- ORD
1 stop10h 46m
United Airlines
Deal found 7/14![United Airlines logo]()
$650
This Copa Airlines deal was found by Cheapflights users on 7/15. 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 11/132:13 pm
ORD
- POS
1 stop9h 41m
Copa Airlines
Wed 11/182:19 pm
POS
- ORD
1 stop11h 52m
Copa Airlines
Deal found 7/15![Copa Airlines logo]()
$618
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:10 pm
STL
- POS
2 stops35h 05m
Air Canada
Wed 9/21:25 am
POS
- STL
1 stop13h 37m
Air Canada
Deal found 7/13![Air Canada logo]()
$626
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Sun 8/238:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/15![JetBlue logo]()
$633
This American Airlines deal was found by Cheapflights users on 7/17. 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.
Sat 8/228:00 am
ORD
- POS
2 stops14h 18m
American Airlines
Mon 8/313:15 pm
POS
- ORD
1 stop17h 19m
American Airlines
Deal found 7/17![American Airlines logo]()
$634
This Copa Airlines deal was found by Cheapflights users on 7/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:13 pm
ORD
- POS
1 stop21h 04m
Copa Airlines
Mon 11/163:40 am
POS
- ORD
1 stop11h 06m
Copa Airlines
Deal found 7/14![Copa Airlines logo]()
$618
This Mytrip deal was found by Cheapflights users on 7/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:12 pm
ORD
- TAB
3 stops46h 23m
Multiple Airlines
Thu 9/311:45 am
TAB
- ORD
3 stops25h 15m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$1,387
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/118:50 am
STL
- POS
2 stops15h 00m
United Airlines
Sat 8/1512:30 am
POS
- STL
1 stop10h 40m
United Airlines
Deal found 7/18![United Airlines logo]()
$695
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Fri 8/218:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/15![JetBlue logo]()
$674
This Air Canada deal was found by Cheapflights users on 7/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/299:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Sun 8/21:25 am
POS
- ORD
2 stops14h 19m
Air Canada
Deal found 7/14![Air Canada logo]()
$676
This Copa Airlines deal was found by Cheapflights users on 7/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:35 am
ORD
- POS
1 stop16h 19m
Copa Airlines
Mon 11/163:40 am
POS
- ORD
1 stop22h 31m
Copa Airlines
Deal found 7/14![Copa Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/116:00 am
STL
- POS
2 stops16h 18m
American Airlines
Sun 8/167:00 am
POS
- STL
2 stops17h 34m
American Airlines
Deal found 7/18![American Airlines logo]()
$749
This JetBlue deal was found by Cheapflights users on 7/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Thu 9/38:00 pm
POS
- ORD
1 stop13h 52m
JetBlue
Deal found 7/13![JetBlue logo]()
$682
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
STL
- POS
1 stop16h 50m
United Airlines
Tue 9/12:00 am
POS
- STL
1 stop10h 17m
United Airlines
Deal found 7/14![United Airlines logo]()
$790
This American Airlines deal was found by Cheapflights users on 7/14. 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 12/236:44 pm
STL
- POS
2 stops19h 02m
American Airlines
Wed 1/136:30 am
POS
- STL
2 stops12h 53m
American Airlines
Deal found 7/14![American Airlines logo]()
$964
This Flightnetwork deal was found by Cheapflights users on 7/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/288:50 pm
ORD
- TAB
2 stops37h 30m
Multiple Airlines
Fri 9/41:10 pm
TAB
- ORD
2 stops20h 50m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$1,419
This Mytrip deal was found by Cheapflights users on 7/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:45 pm
ORD
- TAB
2 stops15h 45m
Multiple Airlines
Thu 10/159:55 am
TAB
- ORD
2 stops24h 05m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$3,485
Last-minute flights from Illinois to Trinidad and TobagoDiscover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated July 18, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated July 18, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 7/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Mon 8/171:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 7/15![Air Canada logo]()
$615
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/118:50 am
STL
- POS
2 stops15h 00m
United Airlines
Sat 8/1512:30 am
POS
- STL
1 stop10h 40m
United Airlines
Deal found 7/18![United Airlines logo]()
$695
This American Airlines deal was found by Cheapflights users on 7/18. 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.
Tue 8/116:00 am
STL
- POS
2 stops16h 18m
American Airlines
Sun 8/167:00 am
POS
- STL
2 stops17h 34m
American Airlines
Deal found 7/18![American Airlines logo]()
$749
This Air Canada deal was found by Cheapflights users on 7/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:50 pm
ORD
- POS
1 stop26h 25m
Air Canada
Sun 8/301:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 7/13![Air Canada logo]()
$600
This Copa Airlines deal was found by Cheapflights users on 7/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:02 am
ORD
- POS
1 stop28h 15m
Copa Airlines
Sun 8/303:50 am
POS
- ORD
1 stop22h 12m
Copa Airlines
Deal found 7/14![Copa Airlines logo]()
$618
This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Mon 8/248:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Mon 8/3110:10 am
POS
- ORD
1 stop27h 40m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$568
This Air Canada deal was found by Cheapflights users on 7/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:40 am
ORD
- POS
2 stops14h 35m
Air Canada
Sun 8/301:25 am
POS
- ORD
2 stops14h 19m
Air Canada
Deal found 7/14![Air Canada logo]()
$619
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Wed 9/21:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 7/13![Air Canada logo]()
$545
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:10 pm
STL
- POS
2 stops35h 05m
Air Canada
Wed 9/21:25 am
POS
- STL
1 stop13h 37m
Air Canada
Deal found 7/13![Air Canada logo]()
$626
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/2711:35 am
STL
- POS
1 stop10h 43m
American Airlines
Thu 9/37:00 am
POS
- STL
1 stop16h 40m
American Airlines
Deal found 7/13![American Airlines logo]()
$630
This JetBlue deal was found by Cheapflights users on 7/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Fri 9/48:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/14![JetBlue logo]()
$624
This Travelocity deal was found by Cheapflights users on 7/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:15 pm
ORD
- POS
1 stop9h 00m
Multiple Airlines
Fri 9/43:14 pm
POS
- ORD
1 stop18h 29m
Multiple Airlines
Deal found 7/14![Multiple Airlines logo]()
$617
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 July 18, 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 July 18, 2026.
This Air Canada deal was found by Cheapflights users on 7/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/269:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 7/13![Air Canada logo]()
$265
This Orbitz deal was found by Cheapflights users on 7/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:30 pm
ORD
- POS
1 stop31h 30m
Air Canada
Deal found 7/14![Air Canada logo]()
$284
This Expedia deal was found by Cheapflights users on 7/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 7/15![Air Canada logo]()
$285
This Air Canada deal was found by Cheapflights users on 7/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:50 pm
ORD
- POS
1 stop26h 25m
Air Canada
Deal found 7/15![Air Canada logo]()
$290
This Justfly.com deal was found by Cheapflights users on 7/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/301:00 pm
ORD
- POS
1 stop24h 20m
JetBlue
Deal found 7/14![JetBlue logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 7/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:57 pm
STL
- POS
2 stops24h 58m
Multiple Airlines
Deal found 7/13![Multiple Airlines logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2912:23 pm
STL
- POS
1 stop11h 27m
United Airlines
Deal found 7/13![United Airlines logo]()
$408
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 July 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $545 (Gotogate) |
One-way from | $265 (Air Canada) |
Popular in | December |
Cheapest in | May |
Average price | $624 |
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 2,558,603 searches. Data last updated July 18, 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 - POS
ORDPOS
Chicago O'Hare Intl
Sat 9/5
8:40 pm-12:15 am
1 stop26h 35m
Port of Spain Piarco Intl
Fri 9/18
1:20 am-2:52 pm
2 stops14h 32m
$558
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 8/22
8:02 am-1:17 pm
1 stop28h 15m
Port of Spain Piarco Intl
Mon 8/31
2:19 pm-1:02 am
1 stop11h 43m
$618
Quickest round-trip
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 11/13
2:13 pm-1:54 am
1 stop9h 41m
Port of Spain Piarco Intl
Wed 11/18
2:19 pm-12:11 am
1 stop11h 52m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 11/5
2:13 pm-1:17 pm
1 stop21h 04m
Port of Spain Piarco Intl
Mon 11/16
3:40 am-12:46 pm
1 stop11h 06m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 11/4
7:35 am-1:54 am
1 stop16h 19m
Port of Spain Piarco Intl
Mon 11/16
3:40 am-12:11 am
1 stop22h 31m
$618
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Thu 8/27
12:10 pm-12:15 am
2 stops35h 05m
Port of Spain Piarco Intl
Wed 9/2
1:25 am-2:02 pm
1 stop13h 37m
$626
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Thu 8/27
11:35 am-11:18 pm
1 stop10h 43m
Port of Spain Piarco Intl
Thu 9/3
7:00 am-10:40 pm
1 stop16h 40m
$630
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 8/10
6:00 am-6:35 pm
1 stop11h 35m
Port of Spain Piarco Intl
Mon 8/17
8:00 pm-8:43 am
1 stop13h 43m
$632
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 8/14
6:00 am-6:35 pm
1 stop11h 35m
Port of Spain Piarco Intl
Sun 8/23
8:00 pm-8:43 am
1 stop13h 43m
$633
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 8/22
8:00 am-11:18 pm
2 stops14h 18m
Port of Spain Piarco Intl
Mon 8/31
3:15 pm-7:34 am
1 stop17h 19m
$634
Showing 1-10 of 27 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.
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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
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What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?
Currently, November is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $443). Flying from Illinois to Trinidad and Tobago in February is currently the most expensive (average of $836). 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 July 18, 2026.
Popular flight searches
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Illinois to Trinidad and Tobago flights
Consider these flights traveling from Illinois to Trinidad and Tobago.
Fly to Trinidad and Tobago regions
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Top 4 airlines flying from Illinois to Trinidad and Tobago
Discover the top 4 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 2,558,603 searches. Data last updated July 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$285 | Average$627 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$317 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$548 | Average$739 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$706 | FlexibilityNo cancel fee | On-time69% |