$185+ 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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
mai 23 — mai 301
Round-trip
1 adult, Economy
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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 aprilie 23, 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 aprilie 23, 2026.
This Travelocity deal was found by Cheapflights users on 4/21. 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.
Vi 4/247:55 am
ORD
- POS
1 stop15h 25m
Air Canada
Ma 4/281:20 am
POS
- ORD
1 stop17h 30m
Air Canada
Deal found 4/21![Air Canada logo]()
$428
This Travelocity deal was found by Cheapflights users on 4/22. 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.
Du 4/267:55 am
ORD
- POS
1 stop15h 25m
Air Canada
Du 5/31:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 4/22![Air Canada logo]()
$517
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Jo 5/215:05 am
ORD
- POS
1 stop13h 55m
Multiple Airlines
Jo 5/2810:10 am
POS
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$523
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Ma 4/2810:00 am
ORD
- POS
2 stops26h 10m
Multiple Airlines
Sâ 5/29:10 am
POS
- ORD
1 stop15h 49m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Sâ 4/256:40 am
ORD
- POS
1 stop11h 15m
Multiple Airlines
Sâ 5/29:10 am
POS
- ORD
1 stop15h 49m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Ma 4/2810:00 am
ORD
- POS
2 stops26h 10m
Multiple Airlines
Vi 5/110:10 am
POS
- ORD
1 stop14h 44m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$579
This Justfly.com deal was found by Cheapflights users on 4/20. 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.
Vi 9/47:25 am
ORD
- POS
1 stop15h 50m
Air Canada
Lu 9/71:20 am
POS
- ORD
2 stops18h 26m
Air Canada
Deal found 4/20![Air Canada logo]()
$580
This Orbitz deal was found by Cheapflights users on 4/20. 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.
Vi 9/48:55 am
STL
- POS
1 stop14h 20m
Air Canada
Lu 9/71:20 am
POS
- STL
1 stop19h 40m
Air Canada
Deal found 4/20![Air Canada logo]()
$619
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/196:00 am
STL
- POS
1 stop16h 23m
United Airlines
Lu 5/2512:30 am
POS
- STL
1 stop10h 37m
United Airlines
Deal found 4/21![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/193:24 pm
STL
- POS
2 stops22h 08m
American Airlines
Ma 5/267:00 am
POS
- STL
2 stops17h 44m
American Airlines
Deal found 4/21![American Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/126:00 am
STL
- POS
1 stop16h 23m
United Airlines
Lu 5/1812:30 am
POS
- STL
1 stop10h 00m
United Airlines
Deal found 4/21![United Airlines logo]()
$675
This American Airlines deal was found by Cheapflights users on 4/18. 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.
Jo 12/246:00 pm
STL
- POS
1 stop19h 46m
American Airlines
Jo 12/316:02 am
POS
- STL
1 stop13h 49m
American Airlines
Deal found 4/18![American Airlines logo]()
$742
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 aprilie 23, 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 aprilie 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Jo 5/215:05 am
ORD
- POS
1 stop13h 55m
Multiple Airlines
Jo 5/289:10 am
POS
- ORD
2 stops23h 45m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$550
This Orbitz deal was found by Cheapflights users on 4/22. 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.
Ma 8/258:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Lu 8/311:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 4/22![Air Canada logo]()
$576
This United Airlines deal was found by Cheapflights users on 4/19. 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.
Ma 7/2111:25 am
STL
- POS
2 stops12h 25m
United Airlines
Lu 7/2712:30 am
POS
- STL
1 stop10h 37m
United Airlines
Deal found 4/19![United Airlines logo]()
$630
This Copa Airlines deal was found by Cheapflights users on 4/23. 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.
Jo 6/183:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Sâ 6/203:49 am
POS
- ORD
1 stop11h 17m
Copa Airlines
Deal found 4/23![Copa Airlines logo]()
$633
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Mi 8/2610:42 am
ORD
- POS
2 stops11h 36m
American Airlines
Mi 9/27:00 am
POS
- ORD
2 stops13h 46m
American Airlines
Deal found 4/22![American Airlines logo]()
$634
This Expedia deal was found by Cheapflights users on 4/20. 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.
Vi 9/49:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Lu 9/71:20 am
POS
- ORD
1 stop13h 03m
Air Canada
Deal found 4/20![Air Canada logo]()
$579
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/196:00 am
STL
- POS
1 stop16h 23m
United Airlines
Lu 5/2512:30 am
POS
- STL
1 stop10h 37m
United Airlines
Deal found 4/21![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Jo 5/216:55 am
ORD
- POS
2 stops15h 04m
American Airlines
Ma 5/267:00 am
POS
- ORD
2 stops14h 21m
American Airlines
Deal found 4/22![American Airlines logo]()
$659
This Air Canada deal was found by Cheapflights users on 4/19. 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.
Mi 7/19:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Lu 7/131:25 am
POS
- ORD
2 stops14h 30m
Air Canada
Deal found 4/19![Air Canada logo]()
$609
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/1210:25 am
STL
- POS
2 stops11h 58m
United Airlines
Lu 5/1812:30 am
POS
- STL
1 stop16h 31m
United Airlines
Deal found 4/21![United Airlines logo]()
$675
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Jo 6/185:00 am
ORD
- POS
1 stop17h 01m
American Airlines
Du 6/217:00 am
POS
- ORD
1 stop16h 26m
American Airlines
Deal found 4/21![American Airlines logo]()
$675
This Orbitz deal was found by Cheapflights users on 4/20. 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.
Vi 9/48:55 am
STL
- POS
1 stop14h 20m
Air Canada
Lu 9/71:20 am
POS
- STL
1 stop19h 40m
Air Canada
Deal found 4/20![Air Canada logo]()
$619
This FlightHub deal was found by Cheapflights users on 4/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Lu 6/222:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Du 6/281:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 4/21![Air Canada logo]()
$624
This United Airlines deal was found by Cheapflights users on 4/18. 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.
Sâ 6/66:14 am
STL
- POS
1 stop16h 09m
United Airlines
Ma 6/912:30 am
POS
- STL
1 stop14h 46m
United Airlines
Deal found 4/18![United Airlines logo]()
$890
This Mytrip deal was found by Cheapflights users on 4/18. 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.
Mi 6/38:45 am
ORD
- TAB
3 stops35h 55m
Multiple Airlines
Ma 6/912:30 am
TAB
- ORD
3 stops34h 48m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$1,932
Last-minute flights from Illinois to Trinidad and TobagoDiscover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated aprilie 23, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated aprilie 23, 2026 and is based on user searches.
This Travelocity deal was found by Cheapflights users on 4/21. 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.
Vi 4/247:55 am
ORD
- POS
1 stop15h 25m
Air Canada
Ma 4/281:20 am
POS
- ORD
1 stop17h 30m
Air Canada
Deal found 4/21![Air Canada logo]()
$428
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Sâ 4/256:40 am
ORD
- POS
1 stop11h 15m
Multiple Airlines
Sâ 5/29:10 am
POS
- ORD
1 stop15h 49m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$576
This Travelocity deal was found by Cheapflights users on 4/22. 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.
Du 4/267:55 am
ORD
- POS
1 stop15h 25m
Air Canada
Du 5/31:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 4/22![Air Canada logo]()
$517
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Ma 4/2810:00 am
ORD
- POS
2 stops26h 10m
Multiple Airlines
Sâ 5/29:10 am
POS
- ORD
1 stop15h 49m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
Ma 4/2810:00 am
ORD
- POS
2 stops26h 10m
Multiple Airlines
Vi 5/110:10 am
POS
- ORD
1 stop14h 44m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$579
This United Airlines deal was found by Cheapflights users on 4/20. 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.
Vi 5/16:00 am
STL
- POS
1 stop16h 23m
United Airlines
Lu 5/1112:30 am
POS
- STL
1 stop10h 00m
United Airlines
Deal found 4/20![United Airlines logo]()
$830
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/1210:25 am
STL
- POS
2 stops11h 58m
United Airlines
Lu 5/1812:30 am
POS
- STL
1 stop16h 31m
United Airlines
Deal found 4/21![United Airlines logo]()
$675
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Ma 5/121:05 pm
STL
- POS
3 stops31h 25m
Multiple Airlines
Ma 5/199:00 am
POS
- STL
2 stops28h 06m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$997
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/196:00 am
STL
- POS
1 stop16h 23m
United Airlines
Lu 5/2512:30 am
POS
- STL
1 stop10h 37m
United Airlines
Deal found 4/21![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 4/21. 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.
Ma 5/193:24 pm
STL
- POS
2 stops22h 08m
American Airlines
Ma 5/267:00 am
POS
- STL
2 stops17h 44m
American Airlines
Deal found 4/21![American Airlines logo]()
$634
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Jo 5/215:05 am
ORD
- POS
1 stop13h 55m
Multiple Airlines
Jo 5/2810:10 am
POS
- ORD
1 stop14h 05m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$523
This FlightHub deal was found by Cheapflights users on 4/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Jo 5/216:22 pm
ORD
- POS
2 stops28h 53m
Air Canada
Lu 5/251:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 4/19![Air Canada logo]()
$583
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 aprilie 23, 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 aprilie 23, 2026.
This Gotogate deal was found by Cheapflights users on 4/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Jo 4/302:00 pm
ORD
- POS
1 stop9h 20m
Air Canada
Deal found 4/18![Air Canada logo]()
$185
This Expedia deal was found by Cheapflights users on 4/20. 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.
Du 7/262:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Deal found 4/20![Air Canada logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Jo 4/3011:28 am
ORD
- POS
2 stops30h 27m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Du 7/269:34 pm
ORD
- POS
3 stops20h 21m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$438
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 aprilie 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $523 (Mytrip) |
One-way from | $185 (Gotogate) |
Popular in | December |
Cheapest in | February |
Average price | $482 |
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 aprilie 23, 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
Jo 5/21
5:05 am-8:00 pm
1 stop13h 55m
Port of Spain Piarco Intl
Jo 5/28
9:10 am-7:55 am
2 stops23h 45m
$550
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Ma 8/25
8:40 pm-12:15 am
1 stop26h 35m
Port of Spain Piarco Intl
Lu 8/31
1:25 am-1:22 pm
1 stop12h 57m
$576
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Vi 9/4
9:50 am-12:15 am
1 stop13h 25m
Port of Spain Piarco Intl
Lu 9/7
1:20 am-1:23 pm
1 stop13h 03m
$579
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mi 7/1
9:50 am-12:15 am
1 stop13h 25m
Port of Spain Piarco Intl
Lu 7/13
1:25 am-2:55 pm
2 stops14h 30m
$609
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Vi 9/4
8:55 am-12:15 am
1 stop14h 20m
Port of Spain Piarco Intl
Lu 9/7
1:20 am-8:00 pm
1 stop19h 40m
$619
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Lu 6/22
2:15 pm-12:15 am
1 stop9h 00m
Port of Spain Piarco Intl
Du 6/28
1:25 am-2:55 pm
1 stop14h 30m
$624
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Ma 7/21
11:25 am-12:50 am
2 stops12h 25m
Port of Spain Piarco Intl
Lu 7/27
12:30 am-10:07 am
1 stop10h 37m
$630
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Ma 5/19
6:00 am-11:23 pm
1 stop16h 23m
Port of Spain Piarco Intl
Lu 5/25
12:30 am-10:07 am
1 stop10h 37m
$630
Quickest round-trip
ChicagoPort of Spain
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Chicago O'Hare Intl
Jo 6/18
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Sâ 6/20
3:49 am-2:06 pm
1 stop11h 17m
$633
ChicagoPort of Spain
ORD - POS
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Chicago O'Hare Intl
Mi 8/26
10:42 am-11:18 pm
2 stops11h 36m
Port of Spain Piarco Intl
Mi 9/2
7:00 am-7:46 pm
2 stops13h 46m
$634
Showing 1-10 of 19 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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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
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What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?
Currently, June is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $317). Flying from Illinois to Trinidad and Tobago in January is currently the most expensive (average of $638). 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
Find flights from Illinois to Trinidad and Tobago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Trinidad and Tobago flights
Browse other Illinois and Trinidad and Tobago flight options. Last updated on aprilie 23, 2026.
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Illinois to Trinidad and Tobago flights
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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 aprilie 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$392 | Average$516 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$472 | Average$597 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$548 | Average$688 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$629 | FlexibilityNo cancel fee | On-time69% |