$348+ Cheap flights from Illinois to Trinidad and Tobago
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jan 11 — Jan 181
1 adult, Economy
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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 Illinois to Trinidad and Tobago
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 December 12, 2025.
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 December 12, 2025.
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:09 pmORD - POS
2 stops30h 06mMultiple Airlines
Fri 1/910:10 amPOS - ORD
1 stop11h 28mMultiple Airlines
Deal found 12/10![Multiple Airlines logo]()
$617
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/155:40 amORD - POS
2 stops12h 40mMultiple Airlines
Wed 12/179:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 12/11![Multiple Airlines logo]()
$681
This Expedia deal was found by Cheapflights users on 12/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:41 pmORD - POS
2 stops32h 37mJetBlue
Tue 12/308:02 amPOS - ORD
2 stops36h 44mJetBlue
Deal found 12/9![JetBlue logo]()
$739
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:38 pmORD - POS
2 stops17h 26mJetBlue
Tue 12/165:42 pmPOS - ORD
2 stops18h 53mJetBlue
Deal found 12/10![JetBlue logo]()
$745
This Copa Airlines deal was found by Cheapflights users on 12/10. 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.
Sun 12/147:33 amORD - POS
1 stop16h 15mCopa Airlines
Mon 12/153:47 amPOS - ORD
1 stop11h 05mCopa Airlines
Deal found 12/10![Copa Airlines logo]()
$750
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/149:14 pmORD - POS
2 stops19h 41mMultiple Airlines
Tue 12/169:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 12/10![Multiple Airlines logo]()
$868
This Mytrip deal was found by Cheapflights users on 12/9. 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.
Fri 12/199:09 pmORD - POS
2 stops20h 51mMultiple Airlines
Tue 12/309:10 amPOS - ORD
3 stops35h 52mMultiple Airlines
Deal found 12/9![Multiple Airlines logo]()
$1,210
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 December 12, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $473 (Air Canada) |
One-way from | $348 (FlightHub) |
Popular in | December |
Cheapest in | October |
Average price | $1,705 |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Trinidad and Tobago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Illinois to Trinidad and Tobago that are best for you.
Fly from
Illinois
Fly to
Trinidad and Tobago
Route
Depart
Return
Price
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 3/12
6:04 pm-12:20 am
2 stops29h 16m
Port of Spain Piarco Intl
Tue 3/17
1:20 am-6:52 pm
2 stops18h 32m
$473
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 3/13
2:00 pm-12:20 am
1 stop9h 20m
Port of Spain Piarco Intl
Tue 3/17
1:20 am-1:01 pm
1 stop12h 41m
$473
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 3/30
4:15 pm-12:20 am
1 stop31h 05m
Port of Spain Piarco Intl
Mon 4/6
3:40 pm-9:10 am
2 stops18h 30m
$480
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 3/15
10:00 am-12:20 am
1 stop13h 20m
Port of Spain Piarco Intl
Fri 3/20
1:20 am-1:01 pm
1 stop12h 41m
$503
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Wed 2/11
6:00 am-12:23 am
1 stop16h 23m
Port of Spain Piarco Intl
Tue 2/17
1:30 am-9:23 am
1 stop9h 53m
$1,669
St. LouisPort of Spain
STL - POS
STLPOS
Lambert-St Louis
Wed 2/11
6:02 pm-4:58 pm
1 stop20h 56m
Port of Spain Piarco Intl
Wed 2/18
4:40 pm-10:59 am
2 stops20h 19m
$1,780
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 12/30
2:00 pm-1:10 am
1 stop9h 10m
$348
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 12/29
6:00 pm-1:10 am
2 stops29h 10m
$398
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 12/28
10:35 am-12:23 am
1 stop11h 48m
$418
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 12/28
4:05 pm-3:46 pm
2 stops21h 41m
$424
Showing 1-10 of 16 results
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.
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
What is the cheapest month to book a flight from Illinois to Trinidad and Tobago?
Currently, November is the cheapest month in which you can book a flight from Illinois to Trinidad and Tobago (average of $435). Flying from Illinois to Trinidad and Tobago in April is currently the most expensive (average of $628). 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.
What is the cheapest time of day to fly from IL to TT?
Find hourly flight availability from Illinois to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.
Unlike in the evening, when flights are generally more expensive, you can save up to 33% on flights from Illinois to Trinidad and Tobago by exploring options for tickets in the afternoon.
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.
Top 3 airlines flying from Illinois to Trinidad and Tobago
Discover the top 3 airlines that operate flights from Illinois to Trinidad and Tobago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$432 | Average$556 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$528 | Average$644 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$628 | FlexibilityNo cancel fee | On-time69% |