$277+ Cheap flights from Trinidad and Tobago to Illinois
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Dec 10 — Dec 171
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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/221:25 am -
1 stop13h 38m
Thu 12/311:08 pm -
1 stop9h 57m
Deal found 11/10![United Airlines logo]()
$748
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/241:25 am -
1 stop19h 05m
Sat 12/269:47 pm -
1 stop25h 18m
Deal found 11/6![United Airlines logo]()
$752
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/21:25 am -
1 stop10h 45m
Fri 12/42:22 pm -
1 stop31h 56m
Deal found 11/6![United Airlines logo]()
$753
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:50 am -
2 stops13h 39m
Sat 12/59:53 am -
2 stops11h 47m
Deal found 11/6![American Airlines logo]()
$763
This FlightHub deal was found by Cheapflights users on 11/10. 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.
Wed 12/239:00 am -
2 stops26h 08m
Thu 12/3110:05 am -
1 stop12h 55m
Deal found 11/10![Multiple Airlines logo]()
$826
This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:05 am -
2 stops15h 54m
Thu 12/316:50 am -
2 stops14h 55m
Deal found 11/10![American Airlines logo]()
$832
This Gotogate deal was found by Cheapflights users on 11/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:15 am -
2 stops14h 47m
Sat 12/268:50 pm -
1 stop26h 10m
Deal found 11/6![Air Canada logo]()
$836
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/161:25 am -
1 stop13h 38m
Sat 12/196:00 am -
1 stop17h 05m
Deal found 11/6![United Airlines logo]()
$1,118
This Air Canada deal was found by Cheapflights users on 11/6. 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.
Thu 12/242:15 am -
2 stops14h 47m
Sat 12/269:22 pm -
2 stops25h 38m
Deal found 11/6![Multiple Airlines logo]()
$1,359
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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/221:25 am -
1 stop13h 38m
Thu 12/311:08 pm -
1 stop9h 57m
Deal found 11/10![United Airlines logo]()
$748
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/35:50 am -
2 stops13h 39m
Sat 12/59:53 am -
2 stops11h 47m
Deal found 11/6![American Airlines logo]()
$763
This Air Canada deal was found by Cheapflights users on 11/10. 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 1/82:15 am -
2 stops14h 37m
Sun 1/107:05 am -
2 stops15h 55m
Deal found 11/10![Air Canada logo]()
$776
This FlightHub deal was found by Cheapflights users on 11/10. 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.
Wed 12/239:00 am -
2 stops26h 08m
Thu 12/3110:05 am -
1 stop12h 55m
Deal found 11/10![Multiple Airlines logo]()
$826
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/21:25 am -
1 stop11h 50m
Sat 12/57:50 pm -
1 stop26h 28m
Deal found 11/6![United Airlines logo]()
$753
This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:05 am -
2 stops15h 54m
Thu 12/316:50 am -
2 stops14h 55m
Deal found 11/10![American Airlines logo]()
$832
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/21:25 am -
2 stops19h 23m
Fri 12/42:22 pm -
1 stop31h 56m
Deal found 11/6![United Airlines logo]()
$1,051
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/161:25 am -
1 stop13h 38m
Sat 12/196:00 am -
1 stop17h 05m
Deal found 11/6![United Airlines logo]()
$1,118
Last-minute flights from Trinidad and Tobago to IllinoisDiscover last-minute flight deals from Trinidad and Tobago to Illinois. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad and Tobago to Illinois. Data last updated November 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/21:25 am -
1 stop10h 45m
Fri 12/42:22 pm -
1 stop31h 56m
Deal found 11/6![United Airlines logo]()
$753
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/34:42 pm -
1 stop10h 11m
Sat 12/510:53 am -
2 stops10h 47m
Deal found 11/6![American Airlines logo]()
$763
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/161:25 am -
1 stop13h 38m
Sat 12/196:00 am -
1 stop17h 05m
Deal found 11/6![United Airlines logo]()
$1,118
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/221:25 am -
1 stop13h 38m
Thu 12/311:08 pm -
1 stop9h 57m
Deal found 11/10![United Airlines logo]()
$748
This FlightHub deal was found by Cheapflights users on 11/10. 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.
Wed 12/239:00 am -
2 stops26h 08m
Thu 12/3110:05 am -
1 stop12h 55m
Deal found 11/10![Multiple Airlines logo]()
$826
This American Airlines deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/236:05 am -
2 stops15h 54m
Thu 12/316:50 am -
2 stops14h 55m
Deal found 11/10![American Airlines logo]()
$832
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/241:25 am -
1 stop19h 05m
Sat 12/269:47 pm -
1 stop25h 18m
Deal found 11/6![United Airlines logo]()
$752
This Gotogate deal was found by Cheapflights users on 11/6. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/242:15 am -
2 stops14h 47m
Sat 12/268:50 pm -
1 stop26h 10m
Deal found 11/6![Air Canada logo]()
$836
This Air Canada deal was found by Cheapflights users on 11/6. 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.
Thu 12/242:15 am -
2 stops14h 47m
Sat 12/269:22 pm -
2 stops25h 38m
Deal found 11/6![Multiple Airlines logo]()
$1,359
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 November 10, 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 November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 2/110:10 am -
2 stops27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Multiple Airlines logo]()
$277
This Travelocity deal was found by Cheapflights users on 11/9. 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 1/312:15 am -
1 stop15h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Air Canada logo]()
$423
This United Airlines deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/282:20 am -
1 stop10h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$445
This deal was found by Cheapflights users on 11/6. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/111:25 am -
1 stop13h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![United Airlines logo]()
$449
This deal was found by Cheapflights users on 11/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1412:30 am -
1 stop10h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![United Airlines logo]()
$451
This deal was found by Cheapflights users on 11/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1712:30 am -
1 stop11h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![United Airlines logo]()
$490
This Flightnetwork deal was found by Cheapflights users on 11/6. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/39:00 am -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 11/9. 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 12/296:05 am -
2 stops13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$519
This United Airlines deal was found by Cheapflights users on 11/6. 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.
Wed 12/21:25 am -
1 stop18h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![United Airlines logo]()
$530
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 November 10, 2026.
Round-trip from | $748 (United Airlines) |
|---|---|
One-way from | $277 (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 7,457,451 searches. Data last updated November 10, 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
Mon 2/1
10:10 am-11:50 am
2 stops27h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$277
Quickest round-trip
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Mon 12/28
2:20 am-10:49 am
1 stop10h 29m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$445
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Mon 1/11
1:25 am-12:58 pm
1 stop13h 33m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$449
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 4/14
12:30 am-10:07 am
1 stop10h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$451
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Sat 4/17
12:30 am-11:27 am
1 stop11h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$490
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Tue 12/29
6:05 am-5:45 pm
2 stops13h 40m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$519
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 12/2
1:25 am-6:20 pm
1 stop18h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$530
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Tue 12/22
1:25 am-1:03 pm
1 stop13h 38m
Chicago O'Hare Intl
Thu 12/31
1:08 pm-1:05 am
1 stop9h 57m
$748
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Wed 12/2
1:25 am-11:15 am
1 stop11h 50m
Chicago O'Hare Intl
Sat 12/5
7:50 pm-12:18 am
1 stop26h 28m
$753
Port of SpainChicago
POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl
POSORD
Port of Spain Piarco Intl
Thu 12/3
5:50 am-5:29 pm
2 stops13h 39m
Chicago O'Hare Intl
Sat 12/5
9:53 am-11:40 pm
2 stops11h 47m
$763
Showing 1-10 of 15 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
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
No data available for this route at this time. Please check back soon.
Related info for your journey
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