$251+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jan 17 — Jan 241
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 18, 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 18, 2025.
This Copa Airlines deal was found by Cheapflights users on 12/17. 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 12/187:33 amORD - POS
1 stop16h 15mCopa Airlines
Wed 12/243:13 amPOS - ORD
1 stop11h 39mCopa Airlines
Deal found 12/17![Copa Airlines logo]()
$567
This Expedia deal was found by Cheapflights users on 12/16. 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
Wed 1/78:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 12/16![JetBlue logo]()
$759
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Thu 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$765
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Fri 1/99:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$777
This Mytrip deal was found by Cheapflights users on 12/16. 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.
Wed 12/174:38 pmORD - POS
2 stops19h 17mMultiple Airlines
Tue 12/232:15 amPOS - ORD
1 stop14h 55mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$804
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
Wed 1/79:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$846
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/175:40 amORD - POS
2 stops12h 40mMultiple Airlines
Thu 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$867
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/246:35 pmSTL - POS
2 stops27h 48mUnited Airlines
Tue 12/301:30 amPOS - STL
2 stops23h 13mUnited Airlines
Deal found 12/16![United Airlines logo]()
$898
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/244:27 pmSTL - POS
2 stops31h 21mMultiple Airlines
Wed 12/318:30 amPOS - STL
1 stop16h 03mMultiple Airlines
Deal found 12/16![Multiple Airlines logo]()
$1,054
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/245:05 amSTL - POS
1 stop8h 39mAmerican Airlines
Wed 12/316:02 amPOS - STL
1 stop18h 33mAmerican Airlines
Deal found 12/16![American Airlines logo]()
$1,142
This Gotogate deal was found by Cheapflights users on 12/17. 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.
Tue 12/238:30 pmORD - TAB
2 stops20h 00mMultiple Airlines
Fri 12/2610:20 pmTAB - ORD
2 stops23h 25mMultiple Airlines
Deal found 12/17![Multiple Airlines logo]()
$1,314
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 18, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $391 (Trip.com) |
One-way from | $251 (Expedia) |
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 18, 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 1/15
5:15 am-8:00 pm
1 stop12h 45m
Port of Spain Piarco Intl
Thu 1/22
10:10 am-9:03 pm
1 stop12h 53m
$391
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 1/30
7:20 am-8:00 pm
1 stop10h 40m
Port of Spain Piarco Intl
Fri 2/6
10:10 am-7:38 pm
1 stop11h 28m
$435
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 1/30
2:00 pm-1:20 am
1 stop9h 20m
Port of Spain Piarco Intl
Thu 2/5
2:20 am-6:55 pm
2 stops18h 35m
$443
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 1/31
8:45 pm-1:20 am
1 stop26h 35m
Port of Spain Piarco Intl
Fri 2/6
2:20 am-1:01 pm
1 stop12h 41m
$453
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-6:52 pm
2 stops18h 32m
$473
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 3/30
6:20 pm-12:20 am
2 stops29h 00m
Port of Spain Piarco Intl
Mon 4/6
3:40 pm-9:10 am
2 stops18h 30m
$480
ChicagoScarborough
ORD - TAB
ORDTAB
Chicago O'Hare Intl
Sat 1/31
8:45 pm-7:05 pm
2 stops20h 20m
Scarborough ANR Robinson Intl
Sat 2/7
10:20 pm-6:16 pm
2 stops21h 56m
$855
ChicagoScarborough
ORD - TAB
ORDTAB
Chicago O'Hare Intl
Thu 2/12
8:40 pm-6:50 am
3 stops32h 10m
Scarborough ANR Robinson Intl
Thu 2/19
10:20 pm-11:47 pm
3 stops27h 27m
$1,293
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-3:38 pm
1 stop16h 08m
$1,669
Showing 1-10 of 14 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 18, 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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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 18, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$432 | Average$556 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$528 | Average$634 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$628 | FlexibilityNo cancel fee | On-time69% |