$317+ Cheap flights from Trinidad and Tobago to Illinois
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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from Trinidad and Tobago to Illinois with Cheapflights
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Trinidad and Tobago to Illinois
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Cheapest flights from Trinidad and Tobago to IllinoisExplore the most affordable flight options available from Trinidad and Tobago to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
Explore the most affordable flight options available from Trinidad and Tobago to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/51:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Thu 6/118:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Deal found 4/30![Air Canada logo]()
$582
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/151:25 am
POS
- ORD
2 stops18h 27m
Multiple Airlines
Tue 6/236:27 pm
ORD
- POS
1 stop17h 59m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$609
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/141:25 am
POS
- ORD
1 stop12h 56m
Air Canada
Mon 6/222:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Deal found 5/1![Air Canada logo]()
$616
This Priceline deal was found by Cheapflights users on 5/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:25 am
POS
- ORD
2 stops18h 21m
Air Canada
Mon 8/318:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Deal found 5/3![Air Canada logo]()
$619
This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2210:10 am
POS
- ORD
1 stop14h 05m
Multiple Airlines
Tue 6/308:40 pm
ORD
- POS
1 stop26h 35m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$627
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Tue 6/308:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Deal found 4/30![Air Canada logo]()
$646
This Mytrip deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/191:25 am
POS
- STL
1 stop11h 56m
Air Canada
Sun 6/288:40 am
STL
- POS
1 stop14h 35m
Air Canada
Deal found 4/30![Air Canada logo]()
$655
This Expedia deal was found by Cheapflights users on 5/1. 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.
Mon 5/251:25 am
POS
- ORD
1 stop13h 00m
Multiple Airlines
Wed 6/33:27 pm
ORD
- POS
1 stop21h 54m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$663
This Air Canada deal was found by Cheapflights users on 5/3. 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 7/221:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Sun 7/269:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 5/3![Air Canada logo]()
$665
This Air Canada deal was found by Cheapflights users on 5/3. 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 7/221:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Mon 7/278:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Deal found 5/3![Air Canada logo]()
$668
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:30 am
POS
- STL
1 stop18h 12m
United Airlines
Thu 6/1111:10 am
STL
- POS
1 stop11h 13m
United Airlines
Deal found 4/29![United Airlines logo]()
$692
This United Airlines deal was found by Cheapflights users on 5/2. 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 5/3112:30 am
POS
- STL
2 stops21h 51m
United Airlines
Wed 6/109:14 am
STL
- POS
2 stops37h 09m
United Airlines
Deal found 5/2![United Airlines logo]()
$693
Best flights from Trinidad and Tobago to IllinoisDiscover carefully curated flight deals from Trinidad and Tobago to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
Discover carefully curated flight deals from Trinidad and Tobago to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 4, 2026.
This Mytrip deal was found by Cheapflights users on 5/2. 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.
Fri 6/51:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Fri 6/129:55 am
ORD
- POS
1 stop13h 20m
Air Canada
Deal found 5/2![Air Canada logo]()
$582
This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2210:10 am
POS
- ORD
1 stop14h 05m
Multiple Airlines
Tue 6/308:40 pm
ORD
- POS
1 stop26h 35m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$627
This Justfly.com deal was found by Cheapflights users on 5/3. 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 6/197:45 pm
POS
- ORD
1 stop14h 00m
JetBlue
Wed 6/246:27 pm
ORD
- POS
1 stop18h 08m
JetBlue
Deal found 5/3![JetBlue logo]()
$688
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:30 am
POS
- STL
1 stop18h 12m
United Airlines
Thu 6/1111:10 am
STL
- POS
1 stop11h 13m
United Airlines
Deal found 4/29![United Airlines logo]()
$692
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:00 am
POS
- STL
1 stop16h 58m
American Airlines
Wed 6/105:16 am
STL
- POS
1 stop7h 55m
American Airlines
Deal found 4/29![American Airlines logo]()
$692
This Copa Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/33:50 am
POS
- ORD
1 stop11h 07m
Copa Airlines
Thu 7/93:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Deal found 4/29![Copa Airlines logo]()
$695
This Priceline deal was found by Cheapflights users on 5/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/141:25 am
POS
- ORD
2 stops14h 25m
Air Canada
Mon 6/228:35 am
ORD
- POS
2 stops14h 40m
Air Canada
Deal found 5/1![Air Canada logo]()
$623
This United Airlines deal was found by Cheapflights users on 5/2. 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 5/3112:30 am
POS
- ORD
1 stop10h 50m
United Airlines
Sun 6/79:36 pm
ORD
- POS
1 stop24h 47m
United Airlines
Deal found 5/2![United Airlines logo]()
$693
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/197:01 am
POS
- ORD
2 stops14h 49m
American Airlines
Wed 6/248:30 am
ORD
- POS
1 stop13h 30m
American Airlines
Deal found 4/29![American Airlines logo]()
$694
This Copa Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:22 pm
POS
- ORD
1 stop11h 53m
Copa Airlines
Tue 6/303:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Deal found 4/30![Copa Airlines logo]()
$697
This Mytrip deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/191:25 am
POS
- STL
1 stop11h 56m
Air Canada
Sun 6/281:20 pm
STL
- POS
2 stops34h 10m
Air Canada
Deal found 4/30![Air Canada logo]()
$658
This United Airlines deal was found by Cheapflights users on 5/2. 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 5/3112:30 am
POS
- STL
1 stop23h 15m
United Airlines
Wed 6/106:00 am
STL
- POS
2 stops40h 23m
United Airlines
Deal found 5/2![United Airlines logo]()
$693
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
POS
- STL
2 stops17h 59m
American Airlines
Thu 6/117:04 am
STL
- POS
2 stops14h 56m
American Airlines
Deal found 4/29![American Airlines logo]()
$697
This Air Canada deal was found by Cheapflights users on 5/3. 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 7/221:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Sun 7/268:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Deal found 5/3![Air Canada logo]()
$668
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:30 am
POS
- STL
2 stops21h 46m
United Airlines
Sun 6/287:22 am
STL
- POS
2 stops16h 28m
United Airlines
Deal found 4/30![United Airlines logo]()
$716
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/267:00 am
POS
- STL
1 stop16h 58m
American Airlines
Wed 6/105:16 am
STL
- POS
1 stop7h 55m
American Airlines
Deal found 5/2![American Airlines logo]()
$743
Last-minute flights from Trinidad and Tobago to IllinoisDiscover last-minute flight deals from Trinidad and Tobago to Illinois. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad and Tobago to Illinois. Data last updated May 4, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2210:10 am
POS
- ORD
1 stop14h 05m
Multiple Airlines
Tue 6/308:40 pm
ORD
- POS
1 stop26h 35m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$627
This Priceline deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:25 am
POS
- ORD
2 stops18h 27m
Air Canada
Tue 6/308:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Deal found 4/30![Air Canada logo]()
$646
This Mytrip deal was found by Cheapflights users on 5/1. 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.
Fri 5/221:25 am
POS
- ORD
3 stops31h 57m
Multiple Airlines
Tue 6/305:35 pm
ORD
- POS
1 stop29h 40m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$674
This Priceline deal was found by Cheapflights users on 5/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:25 am
POS
- ORD
2 stops18h 27m
Air Canada
Fri 7/38:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Deal found 5/2![Air Canada logo]()
$683
This Copa Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:22 pm
POS
- ORD
1 stop11h 53m
Copa Airlines
Tue 6/308:02 am
ORD
- POS
1 stop16h 44m
Copa Airlines
Deal found 4/29![Copa Airlines logo]()
$697
This Expedia deal was found by Cheapflights users on 5/1. 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.
Mon 5/251:25 am
POS
- ORD
1 stop13h 00m
Multiple Airlines
Wed 6/33:27 pm
ORD
- POS
1 stop21h 54m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$663
This United Airlines deal was found by Cheapflights users on 5/2. 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 5/2512:30 am
POS
- STL
2 stops33h 09m
United Airlines
Wed 6/108:35 am
STL
- POS
1 stop13h 48m
United Airlines
Deal found 5/2![United Airlines logo]()
$745
This Mytrip deal was found by Cheapflights users on 5/2. 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.
Tue 5/261:05 pm
POS
- STL
3 stops32h 20m
Multiple Airlines
Wed 6/108:10 am
STL
- POS
2 stops20h 20m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$1,683
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:30 am
POS
- STL
1 stop18h 12m
United Airlines
Thu 6/1111:10 am
STL
- POS
1 stop11h 13m
United Airlines
Deal found 4/29![United Airlines logo]()
$692
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:00 am
POS
- STL
1 stop16h 58m
American Airlines
Wed 6/105:16 am
STL
- POS
1 stop7h 55m
American Airlines
Deal found 4/30![American Airlines logo]()
$743
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:00 am
POS
- STL
2 stops17h 59m
American Airlines
Thu 6/118:36 am
STL
- POS
2 stops13h 24m
American Airlines
Deal found 4/30![American Airlines logo]()
$697
One-way flights from Trinidad and Tobago to IllinoisSearch for one-way flight options from Trinidad and Tobago to Illinois. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
Search for one-way flight options from Trinidad and Tobago to Illinois. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/223:49 am
POS
- ORD
2 stops20h 37m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$317
This Travelocity deal was found by Cheapflights users on 5/2. 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 9/141:20 am
POS
- ORD
1 stop13h 03m
Air Canada
Deal found 5/2![Air Canada logo]()
$323
This Orbitz deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/221:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 4/30![Air Canada logo]()
$356
This Air Canada deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:25 am
POS
- ORD
2 stops14h 28m
Air Canada
Deal found 5/1![Air Canada logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/152:22 pm
POS
- ORD
3 stops29h 22m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
POS
- ORD
1 stop17h 30m
American Airlines
Deal found 4/30![American Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 6/179:10 am
POS
- ORD
2 stops40h 38m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 5/2. 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 6/1612:30 am
POS
- ORD
1 stop17h 09m
United Airlines
Deal found 5/2![United Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/229:10 am
POS
- ORD
3 stops28h 15m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$451
Find flight deals from Trinidad and Tobago to Illinois
Keep the following information in mind while searching for Trinidad and Tobago to Illinois flight deals. Data was last updated May 4, 2026.
Round-trip from | $582 (Priceline) |
|---|---|
One-way from | $317 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Trinidad and Tobago to Illinois 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 May 4, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Fri 6/5
1:25 am-2:55 pm
1 stop14h 30m
Chicago O'Hare Intl
Fri 6/12
9:55 am-12:15 am
1 stop13h 20m
$582
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Sun 6/14
1:25 am-2:50 pm
2 stops14h 25m
Chicago O'Hare Intl
Mon 6/22
8:35 am-12:15 am
2 stops14h 40m
$623
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Fri 5/22
10:10 am-11:15 pm
1 stop14h 05m
Chicago O'Hare Intl
Tue 6/30
8:40 pm-12:15 am
1 stop26h 35m
$627
Port of SpainSt. Louis
POS - STL
POSSTL
Port of Spain Piarco Intl
Fri 6/19
1:25 am-12:21 pm
1 stop11h 56m
Lambert-St Louis
Sun 6/28
1:20 pm-12:30 am
2 stops34h 10m
$658
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Wed 7/22
1:25 am-1:22 pm
1 stop12h 57m
Chicago O'Hare Intl
Sun 7/26
8:45 am-12:15 am
2 stops14h 30m
$668
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Fri 6/19
7:45 pm-8:45 am
1 stop14h 00m
Chicago O'Hare Intl
Wed 6/24
6:27 pm-1:35 pm
1 stop18h 08m
$688
Port of SpainSt. Louis
POS - STL
POSSTL
Port of Spain Piarco Intl
Wed 5/27
12:30 am-5:42 pm
1 stop18h 12m
Lambert-St Louis
Thu 6/11
11:10 am-11:23 pm
1 stop11h 13m
$692
Port of SpainSt. Louis
POS - STL
POSSTL
Port of Spain Piarco Intl
Wed 5/27
7:00 am-10:58 pm
1 stop16h 58m
Lambert-St Louis
Wed 6/10
5:16 am-2:11 pm
1 stop7h 55m
$692
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Sun 5/31
12:30 am-10:20 am
1 stop10h 50m
Chicago O'Hare Intl
Sun 6/7
9:36 pm-11:23 pm
1 stop24h 47m
$693
Port of SpainSt. Louis
POS - STL
POSSTL
Port of Spain Piarco Intl
Sun 5/31
12:30 am-10:45 pm
1 stop23h 15m
Lambert-St Louis
Wed 6/10
6:00 am-11:23 pm
2 stops40h 23m
$693
Showing 1-10 of 25 resultsSorted by cheapest first
Best time to book a flight from Trinidad and Tobago to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Trinidad and Tobago 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 Trinidad and Tobago to Illinois
TT0-USIL
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What is the cheapest month to book a flight from Trinidad and Tobago to Illinois?
Currently, June is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $299). Flying from Trinidad and Tobago to Illinois in April is currently the most expensive (average of $913). 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.
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated May 4, 2026.
Read through reviews of airlines operating flights from Trinidad and Tobago to Illinois, such as Copa Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.8
Food
6.8
Crew
8.1
Comfort
7.4
Entertainment
6.8
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Food
6.8
Crew
8.1
Comfort
7.4
Entertainment
6.8
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Food
6.8
Crew
8.1
Comfort
7.4
Entertainment
6.8
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Food
6.8
Crew
8.1
Comfort
7.4
Entertainment
6.8
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Boarding
7.8
Food
6.8
Crew
8.1
Comfort
7.4
Entertainment
6.8
Overall
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Related info for your journey
Find useful and relevant information for your journey from Trinidad and Tobago to Illinois. 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 Trinidad and Tobago to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Trinidad and Tobago to Illinois by cabin class
Find flights from Trinidad and Tobago to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Trinidad and Tobago and Illinois flights
Browse other Trinidad and Tobago and Illinois flight options. Last updated on May 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Trinidad and Tobago after your stay in Illinois
Top 4 airlines flying from Trinidad and Tobago to Illinois
Discover the top 4 airlines that operate flights from Trinidad and Tobago to Illinois. 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$299 | Average$563 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$322 | Average$506 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$572 | Average$720 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$573 | Average$790 | FlexibilityNo cancel fee | On-time71% |