$254+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Sep 7 — Sep 141
Round-trip
1 adult, Economy
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Find cheap flights from Trinidad and Tobago to Illinois with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 August 8, 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 August 8, 2026.
This Expedia deal was found by Cheapflights users on 8/8. 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.
Sat 8/298:00 pm -
1 stop13h 52m
Wed 9/26:00 am -
1 stop11h 35m
Deal found 8/8![JetBlue logo]()
$493
This Air Canada deal was found by Cheapflights users on 8/7. 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 9/251:20 am -
1 stop13h 03m
Thu 10/18:40 pm -
1 stop26h 35m
Deal found 8/7![Air Canada logo]()
$502
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:10 am -
1 stop29h 35m
Thu 9/247:25 am -
2 stops35h 35m
Deal found 8/7![Multiple Airlines logo]()
$504
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/3110:10 am -
1 stop27h 40m
Mon 9/78:05 am -
1 stop10h 55m
Deal found 8/3![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/510:10 am -
1 stop30h 10m
Fri 10/99:33 pm -
2 stops45h 27m
Deal found 8/6![Multiple Airlines logo]()
$518
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/3110:10 am -
1 stop27h 40m
Sun 9/68:05 am -
1 stop10h 55m
Deal found 8/3![Multiple Airlines logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/3110:10 am -
1 stop27h 40m
Wed 9/97:28 pm -
2 stops46h 27m
Deal found 8/3![Multiple Airlines logo]()
$530
This Air Canada deal was found by Cheapflights users on 8/6. 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 10/181:20 am -
2 stops14h 32m
Fri 10/239:50 am -
1 stop13h 25m
Deal found 8/6![Air Canada logo]()
$531
This Priceline deal was found by Cheapflights users on 8/5. 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.
Sat 9/58:00 pm -
1 stop13h 42m
Sun 9/132:15 pm -
1 stop9h 00m
Deal found 8/5![Multiple Airlines logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 10/19:10 am -
2 stops29h 00m
Sun 10/45:19 pm -
1 stop25h 11m
Deal found 8/8![Multiple Airlines logo]()
$608
This Booking.com deal was found by Cheapflights users on 8/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:20 am -
1 stop13h 40m
Sat 9/2612:10 pm -
2 stops35h 05m
Deal found 8/3![Air Canada logo]()
$637
This United Airlines deal was found by Cheapflights users on 8/8. 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 9/3012:30 am -
1 stop10h 40m
Sun 10/43:12 pm -
1 stop31h 11m
Deal found 8/8![United Airlines logo]()
$691
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 August 8, 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 August 8, 2026.
This Air Canada deal was found by Cheapflights users on 8/6. 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 10/181:20 am -
2 stops14h 32m
Fri 10/239:50 am -
1 stop13h 25m
Deal found 8/6![Air Canada logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/210:10 am -
1 stop30h 10m
Mon 10/57:28 pm -
2 stops22h 27m
Deal found 8/8![Multiple Airlines logo]()
$587
This Copa Airlines deal was found by Cheapflights users on 8/6. 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.
Mon 9/72:23 pm -
1 stop11h 39m
Tue 9/158:01 am -
1 stop16h 46m
Deal found 8/6![Copa Airlines logo]()
$624
This United Airlines deal was found by Cheapflights users on 8/7. 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 9/2912:30 am -
2 stops16h 13m
Sun 10/45:36 pm -
2 stops28h 47m
Deal found 8/7![United Airlines logo]()
$691
This Travelocity deal was found by Cheapflights users on 8/6. 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.
Sun 10/41:20 am -
1 stop14h 35m
Fri 10/99:50 am -
1 stop13h 25m
Deal found 8/6![Air Canada logo]()
$554
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/119:10 am -
2 stops37h 24m
Fri 10/167:45 am -
1 stop11h 15m
Deal found 8/4![Multiple Airlines logo]()
$601
This Copa Airlines deal was found by Cheapflights users on 8/4. 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 9/23:50 am -
1 stop22h 12m
Sun 9/68:01 am -
1 stop28h 16m
Deal found 8/4![Copa Airlines logo]()
$624
This Copa Airlines deal was found by Cheapflights users on 8/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/23:50 am -
1 stop22h 12m
Tue 9/88:01 am -
1 stop16h 46m
Deal found 8/3![Copa Airlines logo]()
$624
This United Airlines deal was found by Cheapflights users on 8/8. 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 9/3012:30 am -
1 stop10h 40m
Sun 10/43:12 pm -
1 stop31h 11m
Deal found 8/8![United Airlines logo]()
$691
This Booking.com deal was found by Cheapflights users on 8/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:20 am -
1 stop13h 40m
Sat 9/2612:10 pm -
2 stops35h 05m
Deal found 8/3![Air Canada logo]()
$637
This Copa Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:50 am -
1 stop22h 07m
Mon 10/53:20 pm -
1 stop9h 27m
Deal found 8/5![Copa Airlines logo]()
$624
This United Airlines deal was found by Cheapflights users on 8/8. 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 9/3012:30 am -
2 stops16h 13m
Tue 10/66:15 am -
1 stop16h 08m
Deal found 8/8![United Airlines logo]()
$691
This Copa Airlines deal was found by Cheapflights users on 8/4. 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 10/103:50 am -
1 stop11h 09m
Fri 10/168:01 am -
1 stop16h 46m
Deal found 8/4![Copa Airlines logo]()
$624
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 9/218:30 am -
1 stop9h 04m
Fri 9/252:29 pm -
2 stops27h 26m
Deal found 8/3![Multiple Airlines logo]()
$800
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:30 am -
1 stop19h 01m
Sat 9/268:35 am -
1 stop13h 48m
Deal found 8/3![United Airlines logo]()
$821
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2012:30 am -
2 stops22h 06m
Fri 9/256:00 am -
2 stops16h 23m
Deal found 8/3![United Airlines logo]()
$833
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:30 am -
1 stop10h 40m
Sat 9/266:15 am -
1 stop16h 08m
Deal found 8/3![United Airlines logo]()
$850
This United Airlines deal was found by Cheapflights users on 8/6. 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 8/202:00 am -
1 stop10h 17m
Tue 8/2512:27 pm -
1 stop11h 23m
Deal found 8/6![United Airlines logo]()
$1,024
Last-minute flights from Trinidad and Tobago to IllinoisDiscover last-minute flight deals from Trinidad and Tobago to Illinois. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad and Tobago to Illinois. Data last updated August 8, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 8/8. 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.
Sat 8/298:00 pm -
1 stop13h 52m
Wed 9/26:00 am -
1 stop11h 35m
Deal found 8/8![JetBlue logo]()
$493
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/3110:10 am -
1 stop27h 40m
Mon 9/78:05 am -
1 stop10h 55m
Deal found 8/3![Multiple Airlines logo]()
$513
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/3110:10 am -
1 stop27h 40m
Sun 9/68:05 am -
1 stop10h 55m
Deal found 8/3![Multiple Airlines logo]()
$527
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/3110:10 am -
1 stop27h 40m
Wed 9/97:28 pm -
2 stops46h 27m
Deal found 8/3![Multiple Airlines logo]()
$530
This Priceline deal was found by Cheapflights users on 8/5. 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.
Sat 9/58:00 pm -
1 stop13h 42m
Sun 9/132:15 pm -
1 stop9h 00m
Deal found 8/5![Multiple Airlines logo]()
$543
This Kiwi.com deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1710:10 am -
1 stop29h 35m
Thu 9/247:25 am -
2 stops35h 35m
Deal found 8/7![Multiple Airlines logo]()
$504
This Booking.com deal was found by Cheapflights users on 8/3. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/201:20 am -
1 stop13h 40m
Sat 9/2612:10 pm -
2 stops35h 05m
Deal found 8/3![Air Canada logo]()
$637
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sun 9/208:30 am -
1 stop9h 04m
Sat 9/268:10 pm -
2 stops45h 45m
Deal found 8/3![Multiple Airlines logo]()
$810
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 9/218:30 am -
1 stop9h 04m
Fri 9/252:29 pm -
2 stops27h 26m
Deal found 8/3![Multiple Airlines logo]()
$800
This United Airlines deal was found by Cheapflights users on 8/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2112:30 am -
1 stop19h 01m
Sat 9/268:35 am -
1 stop13h 48m
Deal found 8/3![United Airlines logo]()
$821
This Air Canada deal was found by Cheapflights users on 8/7. 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 9/251:20 am -
1 stop13h 03m
Thu 10/18:40 pm -
1 stop26h 35m
Deal found 8/7![Air Canada logo]()
$502
This United Airlines deal was found by Cheapflights users on 8/7. 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 9/2912:30 am -
2 stops16h 13m
Sun 10/45:36 pm -
2 stops28h 47m
Deal found 8/7![United Airlines logo]()
$691
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 August 8, 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 August 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:10 am -
1 stop30h 10m
Deal found 8/5![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 10/19:10 am -
2 stops29h 00m
Deal found 8/6![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/299:10 am -
2 stops29h 00m
Deal found 8/6![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:10 am -
2 stops16h 35m
Deal found 8/4![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:10 am -
2 stops40h 35m
Deal found 8/4![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:10 am -
3 stops25h 25m
Deal found 8/6![Multiple Airlines logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/29:10 am -
3 stops49h 25m
Deal found 8/6![Multiple Airlines logo]()
$323
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:10 am -
3 stops50h 22m
Deal found 8/6![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/279:10 am -
2 stops29h 00m
Deal found 8/6![Multiple Airlines logo]()
$354
This Air Canada deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:20 am -
1 stop13h 40m
Deal found 8/6![Air Canada logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/39:10 am -
3 stops25h 25m
Deal found 8/6![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:10 am -
1 stop27h 40m
Deal found 8/5![Multiple Airlines logo]()
$489
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 August 8, 2026.
Round-trip from | $502 (Air Canada) |
|---|---|
One-way from | $254 (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 August 8, 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 Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Sun 10/18
1:20 am-2:52 pm
2 stops14h 32m
Chicago O'Hare Intl
Fri 10/23
9:50 am-12:15 am
1 stop13h 25m
$531
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Sun 10/4
1:20 am-2:55 pm
1 stop14h 35m
Chicago O'Hare Intl
Fri 10/9
9:50 am-12:15 am
1 stop13h 25m
$554
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Fri 10/2
10:10 am-3:20 pm
1 stop30h 10m
Chicago O'Hare Intl
Mon 10/5
7:28 pm-6:55 pm
2 stops22h 27m
$587
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Sun 10/11
9:10 am-9:34 pm
2 stops37h 24m
Chicago O'Hare Intl
Fri 10/16
7:45 am-8:00 pm
1 stop11h 15m
$601
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Mon 9/7
2:23 pm-1:02 am
1 stop11h 39m
Chicago O'Hare Intl
Tue 9/15
8:01 am-1:47 am
1 stop16h 46m
$624
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 9/2
3:50 am-1:02 am
1 stop22h 12m
Chicago O'Hare Intl
Sun 9/6
8:01 am-1:17 pm
1 stop28h 16m
$624
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 9/2
3:50 am-1:02 am
1 stop22h 12m
Chicago O'Hare Intl
Tue 9/8
8:01 am-1:47 am
1 stop16h 46m
$624
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 10/1
3:50 am-12:57 am
1 stop22h 07m
Chicago O'Hare Intl
Mon 10/5
3:20 pm-1:47 am
1 stop9h 27m
$624
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Sat 10/10
3:50 am-1:59 pm
1 stop11h 09m
Chicago O'Hare Intl
Fri 10/16
8:01 am-1:47 am
1 stop16h 46m
$624
Port of SpainSt. Louis
POS Port of Spain Piarco Intl - STL Lambert-St Louis
POSSTL
Port of Spain Piarco Intl
Sun 9/20
1:20 am-2:00 pm
1 stop13h 40m
Lambert-St Louis
Sat 9/26
12:10 pm-12:15 am
2 stops35h 05m
$637
Showing 1-10 of 27 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.
POS-ORD
POS-STL
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
POS-ORD
POS-STL
No data available for this route at this time. Please check back soon.
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 August 8, 2026.
Read through reviews of airlines operating flights from Trinidad and Tobago to Illinois, such as Copa Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Crew
8.1
Boarding
7.8
Food
6.9
Overall
7.6
Comfort
7.4
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Entertainment
6.8
Crew
8.1
Boarding
7.8
Food
6.9
Overall
7.6
Comfort
7.4
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
Entertainment
6.8
Crew
8.1
Boarding
7.8
Food
6.9
Overall
7.6
Comfort
7.4
Reviews
1 / 20
4.0
OkayPaul,Jun 2025
PTY - MIA
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 August 8, 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 2 airlines flying from Trinidad and Tobago to Illinois
Discover the top 2 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 August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$304 | Average$563 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$573 | Average$825 | FlexibilityNo cancel fee | On-time71% |