$310+ Cheap flights from Illinois to Trinidad and Tobago
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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Trinidad and Tobago 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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Last-minute
One-way
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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:30 am -
1 stop14h 48m
Sun 12/61:25 am -
1 stop10h 45m
Deal found 11/5![United Airlines logo]()
$680
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:22 am -
2 stops13h 18m
Mon 12/75:56 am -
2 stops15h 34m
Deal found 11/5![American Airlines logo]()
$721
This Air Canada deal was found by Cheapflights users on 11/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:45 am -
1 stop14h 15m
Thu 12/312:15 am -
1 stop19h 43m
Deal found 11/5![Air Canada logo]()
$767
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:22 pm -
1 stop31h 56m
Sat 12/121:25 am -
1 stop10h 46m
Deal found 11/5![United Airlines logo]()
$805
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.
Fri 12/259:47 pm -
1 stop25h 18m
Wed 12/302:20 am -
1 stop19h 41m
Deal found 11/10![United Airlines logo]()
$821
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:59 pm -
1 stop19h 36m
Sun 12/135:56 am -
2 stops18h 36m
Deal found 11/5![American Airlines logo]()
$827
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.
Fri 12/259:47 pm -
1 stop25h 18m
Tue 12/292:20 am -
1 stop21h 55m
Deal found 11/10![United Airlines logo]()
$870
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.
Thu 12/2410:05 am -
1 stop12h 55m
Thu 12/312:15 am -
1 stop15h 23m
Deal found 11/10![Air Canada logo]()
$884
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.
Thu 12/247:55 pm -
1 stop27h 10m
Wed 12/302:20 am -
1 stop19h 41m
Deal found 11/10![United Airlines logo]()
$912
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.
Fri 12/251:08 pm -
1 stop9h 57m
Thu 12/312:20 am -
1 stop10h 29m
Deal found 11/9![United Airlines logo]()
$940
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 12/136:07 am -
1 stop11h 53m
Thu 1/79:10 am -
2 stops17h 07m
Deal found 11/5![Multiple Airlines logo]()
$949
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 November 10, 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 November 10, 2026.
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/153:13 pm -
1 stop21h 44m
Sat 4/173:39 am -
1 stop22h 05m
Deal found 11/10![Copa Airlines logo]()
$668
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/57:29 pm -
1 stop17h 44m
Sat 3/134:13 pm -
2 stops15h 34m
Deal found 11/7![American Airlines logo]()
$685
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.
Sat 3/208:50 pm -
1 stop26h 11m
Fri 3/261:15 am -
2 stops14h 37m
Deal found 11/6![Air Canada logo]()
$791
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:22 pm -
1 stop31h 56m
Sat 12/121:25 am -
1 stop10h 46m
Deal found 11/5![United Airlines logo]()
$805
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/222:13 pm -
1 stop9h 42m
Fri 1/293:26 am -
1 stop22h 41m
Deal found 11/6![Copa Airlines logo]()
$668
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/172:13 pm -
1 stop21h 06m
Sat 1/233:26 am -
1 stop22h 41m
Deal found 11/9![Copa Airlines logo]()
$668
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Mon 1/115:30 am -
1 stop16h 50m
Mon 3/1512:25 am -
1 stop13h 01m
Deal found 11/8![United Airlines logo]()
$810
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.
Fri 12/259:47 pm -
1 stop25h 18m
Wed 12/302:20 am -
1 stop19h 41m
Deal found 11/10![United Airlines logo]()
$821
This United Airlines deal was found by Cheapflights users on 11/8. 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.
Sun 1/107:25 am -
1 stop14h 55m
Sat 3/1312:50 am -
1 stop22h 53m
Deal found 11/8![United Airlines logo]()
$822
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.
Fri 12/259:47 pm -
1 stop25h 18m
Tue 12/292:20 am -
1 stop21h 55m
Deal found 11/10![United Airlines logo]()
$870
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Sun 2/287:00 am -
1 stop15h 20m
Tue 3/21:25 am -
1 stop10h 44m
Deal found 11/7![United Airlines logo]()
$922
Last-minute flights from Illinois to Trinidad and TobagoDiscover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Trinidad and Tobago. Data last updated November 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:30 am -
1 stop14h 48m
Sun 12/61:25 am -
1 stop10h 45m
Deal found 11/5![United Airlines logo]()
$680
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/58:22 am -
2 stops13h 18m
Mon 12/75:56 am -
2 stops15h 34m
Deal found 11/5![American Airlines logo]()
$721
This United Airlines deal was found by Cheapflights users on 11/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:22 pm -
1 stop31h 56m
Sat 12/121:25 am -
1 stop10h 46m
Deal found 11/5![United Airlines logo]()
$805
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:59 pm -
1 stop19h 36m
Sun 12/135:56 am -
2 stops18h 36m
Deal found 11/5![American Airlines logo]()
$827
This Air Canada deal was found by Cheapflights users on 11/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:45 am -
1 stop14h 15m
Thu 12/312:15 am -
1 stop19h 43m
Deal found 11/5![Air Canada logo]()
$767
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Sun 12/136:07 am -
1 stop11h 53m
Thu 1/79:10 am -
2 stops17h 07m
Deal found 11/5![Multiple Airlines logo]()
$949
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.
Thu 12/2410:05 am -
1 stop12h 55m
Thu 12/312:15 am -
1 stop15h 23m
Deal found 11/10![Air Canada logo]()
$884
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.
Thu 12/247:55 pm -
1 stop27h 10m
Wed 12/302:20 am -
1 stop19h 41m
Deal found 11/10![United Airlines logo]()
$912
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.
Fri 12/259:47 pm -
1 stop25h 18m
Wed 12/302:20 am -
1 stop19h 41m
Deal found 11/10![United Airlines logo]()
$821
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.
Fri 12/259:47 pm -
1 stop25h 18m
Tue 12/292:20 am -
1 stop21h 55m
Deal found 11/10![United Airlines logo]()
$870
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.
Fri 12/251:08 pm -
1 stop9h 57m
Thu 12/312:20 am -
1 stop10h 29m
Deal found 11/9![United Airlines logo]()
$940
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 November 10, 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 November 10, 2026.
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.
Sat 12/54:30 pm -
1 stop30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Air Canada logo]()
$310
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/288:50 pm -
1 stop26h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Air Canada logo]()
$311
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.
Thu 4/1510:05 am -
1 stop13h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![Air Canada logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 11/8. 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.
Sun 11/156:00 am -
3 stops29h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$338
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/304:30 pm -
1 stop30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Air Canada logo]()
$346
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.
Sat 12/58:40 pm -
2 stops21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 11/7. 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.
Mon 1/47:55 am -
1 stop15h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![United Airlines logo]()
$387
This Orbitz deal was found by Cheapflights users on 11/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2310:15 am -
2 stops31h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Multiple Airlines logo]()
$388
This Expedia deal was found by Cheapflights users on 11/8. 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.
Sun 11/1512:50 pm -
1 stop10h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Air Canada logo]()
$397
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 2/19:18 am -
1 stop13h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$409
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $663 (Kiwi.com) |
One-way from | $310 (Flightnetwork) |
Popular in | September |
Cheapest in | May |
Average price | $710 |
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 7,457,451 searches. Data last updated November 10, 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 Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 12/5
4:30 pm-1:00 am
1 stop30h 30m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$310
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Thu 4/15
10:05 am-12:05 am
1 stop13h 00m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$324
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sun 11/15
6:00 am-1:17 pm
3 stops29h 17m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$338
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 1/29
8:45 am-1:00 am
1 stop14h 15m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$341
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 2/1
9:18 am-12:20 am
1 stop13h 02m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$409
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 1/4
8:50 pm-7:40 pm
2 stops20h 50m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$435
Quickest round-trip
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 11/23
10:34 am-12:18 am
1 stop11h 44m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$448
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 1/30
6:20 pm-7:40 pm
3 stops23h 20m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$517
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Thu 1/28
8:25 am-8:35 pm
3 stops34h 10m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$533
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 11/23
9:20 pm-1:17 pm
3 stops37h 57m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$550
Showing 1-10 of 21 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.
ORD-POS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Illinois to Trinidad and Tobago
USIL-TT0
ORD-POS
What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?
Currently, March is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $584). Flying from Illinois to Trinidad and Tobago in February is currently the most expensive (average of $948). 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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Trinidad and Tobago by adding a car rental and/or hotel reservation to your travel itinerary.
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 November 10, 2026.
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Illinois to Trinidad and Tobago flights
Consider these flights traveling from Illinois to Trinidad and Tobago.
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Top 2 airlines flying from Illinois to Trinidad and Tobago
Discover the top 2 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 7,457,451 searches. Data last updated November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$578 | Average$781 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$629 | Average$777 | FlexibilityNo cancel fee | On-time71% |