$306+ Cheap flights from Chicago (CHI) 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Nov 1 — Nov 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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 Chicago to Trinidad and Tobago
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Cheapest flights from Chicago to Trinidad and TobagoExplore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2026.
Explore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 10/198:04 am -
1 stop10h 56m
Fri 10/2310:10 am -
2 stops26h 22m
Deal found 9/29![Multiple Airlines logo]()
$632
This Copa Airlines deal was found by Cheapflights users on 10/2. 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 11/22:13 pm -
1 stop9h 41m
Mon 11/92:19 pm -
1 stop11h 52m
Deal found 10/2![Copa Airlines logo]()
$638
This Mytrip deal was found by Cheapflights users on 9/29. 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 10/178:40 pm -
1 stop26h 35m
Fri 10/239:10 am -
2 stops27h 22m
Deal found 9/29![Multiple Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/128:57 pm -
2 stops16h 40m
Thu 11/194:42 pm -
2 stops16h 53m
Deal found 9/28![American Airlines logo]()
$654
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Mon 11/29:06 pm -
2 stops16h 31m
Mon 11/94:42 pm -
2 stops18h 18m
Deal found 10/2![American Airlines logo]()
$655
This Copa Airlines deal was found by Cheapflights users on 9/28. 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 12/302:13 pm -
1 stop9h 48m
Wed 2/172:12 pm -
1 stop24h 34m
Deal found 9/28![Copa Airlines logo]()
$658
This Mytrip deal was found by Cheapflights users on 9/29. 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 10/175:35 pm -
1 stop29h 40m
Thu 10/229:10 am -
2 stops25h 11m
Deal found 9/29![Multiple Airlines logo]()
$659
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Sun 11/157:50 pm -
1 stop17h 47m
Sun 11/224:42 pm -
2 stops16h 43m
Deal found 10/1![American Airlines logo]()
$660
This FlightHub deal was found by Cheapflights users on 9/29. 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.
Sat 10/175:35 pm -
1 stop29h 40m
Wed 10/211:20 am -
1 stop14h 35m
Deal found 9/29![Air Canada logo]()
$687
Best flights from Chicago to Trinidad and TobagoDiscover carefully curated flight deals from Chicago to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2026.
Discover carefully curated flight deals from Chicago to Trinidad and Tobago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2026.
This Copa Airlines deal was found by Cheapflights users on 9/30. 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 3/122:13 pm -
1 stop10h 07m
Fri 3/192:57 pm -
1 stop10h 47m
Deal found 9/30![Copa Airlines logo]()
$638
This United Airlines deal was found by Cheapflights users on 10/1. 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 11/1512:40 pm -
1 stop9h 38m
Sat 11/211:25 am -
1 stop11h 52m
Deal found 10/1![United Airlines logo]()
$650
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Mon 11/28:57 pm -
2 stops16h 40m
Mon 11/94:42 pm -
1 stop10h 02m
Deal found 10/2![American Airlines logo]()
$655
This Mytrip deal was found by Cheapflights users on 9/29. 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 10/1712:37 pm -
3 stops30h 23m
Thu 10/229:10 am -
2 stops25h 11m
Deal found 9/29![Multiple Airlines logo]()
$784
This Copa Airlines deal was found by Cheapflights users on 9/28. 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 3/273:13 pm -
1 stop10h 07m
Fri 4/23:39 am -
1 stop22h 05m
Deal found 9/28![Copa Airlines logo]()
$638
This Copa Airlines deal was found by Cheapflights users on 9/27. 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 1/292:13 pm -
1 stop9h 42m
Mon 2/153:36 am -
1 stop11h 10m
Deal found 9/27![Copa Airlines logo]()
$638
This Copa Airlines deal was found by Cheapflights users on 10/2. 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 11/22:13 pm -
1 stop9h 41m
Mon 11/92:19 pm -
1 stop11h 52m
Deal found 10/2![Copa Airlines logo]()
$638
This United Airlines deal was found by Cheapflights users on 9/29. 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 11/135:30 am -
1 stop16h 48m
Thu 11/191:25 am -
1 stop17h 04m
Deal found 9/29![United Airlines logo]()
$780
This American Airlines deal was found by Cheapflights users on 10/1. 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 11/255:00 am -
1 stop8h 47m
Tue 12/14:47 pm -
2 stops18h 18m
Deal found 10/1![American Airlines logo]()
$782
This Copa Airlines deal was found by Cheapflights users on 9/28. 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 1/62:13 pm -
1 stop9h 42m
Wed 2/172:12 pm -
1 stop11h 59m
Deal found 9/28![Copa Airlines logo]()
$638
This United Airlines deal was found by Cheapflights users on 9/29. 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 3/164:05 pm -
1 stop30h 18m
Wed 3/3112:30 am -
1 stop10h 37m
Deal found 9/29![United Airlines logo]()
$792
This Copa Airlines deal was found by Cheapflights users on 9/28. 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 12/302:13 pm -
1 stop9h 48m
Wed 2/172:12 pm -
1 stop24h 34m
Deal found 9/28![Copa Airlines logo]()
$658
Last-minute flights from Chicago to Trinidad and TobagoDiscover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated October 2, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 9/29. 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 10/178:40 pm -
1 stop26h 35m
Fri 10/239:10 am -
2 stops27h 22m
Deal found 9/29![Multiple Airlines logo]()
$650
This Mytrip deal was found by Cheapflights users on 9/29. 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 10/175:35 pm -
1 stop29h 40m
Thu 10/229:10 am -
2 stops25h 11m
Deal found 9/29![Multiple Airlines logo]()
$659
This FlightHub deal was found by Cheapflights users on 9/29. 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.
Sat 10/175:35 pm -
1 stop29h 40m
Wed 10/211:20 am -
1 stop14h 35m
Deal found 9/29![Air Canada logo]()
$687
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 10/198:04 am -
1 stop10h 56m
Fri 10/2310:10 am -
2 stops26h 22m
Deal found 9/29![Multiple Airlines logo]()
$632
This Copa Airlines deal was found by Cheapflights users on 10/2. 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 11/22:13 pm -
1 stop9h 41m
Mon 11/92:19 pm -
1 stop11h 52m
Deal found 10/2![Copa Airlines logo]()
$638
This American Airlines deal was found by Cheapflights users on 10/2. 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.
Mon 11/28:57 pm -
2 stops16h 40m
Mon 11/94:42 pm -
1 stop10h 02m
Deal found 10/2![American Airlines logo]()
$655
This American Airlines deal was found by Cheapflights users on 9/28. 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 11/128:57 pm -
2 stops16h 40m
Thu 11/194:42 pm -
2 stops16h 53m
Deal found 9/28![American Airlines logo]()
$654
This American Airlines deal was found by Cheapflights users on 9/29. 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 11/148:57 pm -
2 stops16h 40m
Sat 11/214:42 pm -
2 stops16h 53m
Deal found 9/29![American Airlines logo]()
$699
This American Airlines deal was found by Cheapflights users on 10/1. 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.
Sun 11/157:50 pm -
1 stop17h 47m
Sun 11/224:42 pm -
2 stops16h 43m
Deal found 10/1![American Airlines logo]()
$660
One-way flights from Chicago to Trinidad and TobagoSearch for one-way flight options from Chicago to Trinidad and Tobago. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
Search for one-way flight options from Chicago to Trinidad and Tobago. Find affordable one-way fares based on user searches. Data last updated October 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 12/125:24 pm -
3 stops42h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 10/2. 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 10/156:58 pm -
3 stops29h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$335
This Orbitz deal was found by Cheapflights users on 10/1. 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.
Thu 10/153:45 pm -
1 stop31h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 10/76:20 am -
3 stops36h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$379
This Travelocity deal was found by Cheapflights users on 9/29. 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.
Wed 10/76:21 pm -
2 stops52h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Air Canada logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/168:11 pm -
2 stops38h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$394
This Travelocity deal was found by Cheapflights users on 9/30. 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.
Fri 3/198:45 am -
1 stop14h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Air Canada logo]()
$410
Find flight deals from Chicago to Trinidad and Tobago
Keep the following information in mind while searching for Chicago to Trinidad and Tobago flight deals. Data was last updated October 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $632 (Kiwi.com) |
One-way from | $306 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 October 2, 2026.
Use the filters below to find and compare flights from Chicago 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 12/12
5:24 pm-1:27 pm
3 stops42h 03m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$306
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Thu 10/15
3:45 pm-12:15 am
1 stop31h 30m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$349
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Wed 10/7
6:20 am-7:25 pm
3 stops36h 05m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$379
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Wed 10/7
6:21 pm-12:15 am
2 stops52h 54m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$386
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 10/16
8:11 pm-1:47 am
3 stops28h 36m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$397
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 3/19
7:05 am-12:01 am
2 stops15h 56m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$413
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 12/12
7:50 pm-3:35 pm
1 stop17h 45m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$441
Quickest round-trip
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Wed 10/7
10:32 am-11:23 pm
1 stop11h 51m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$468
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 3/12
2:13 pm-2:20 am
1 stop10h 07m
Port of Spain Piarco Intl
Fri 3/19
2:57 pm-12:44 am
1 stop10h 47m
$638
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 3/27
3:13 pm-2:20 am
1 stop10h 07m
Port of Spain Piarco Intl
Fri 4/2
3:39 am-12:44 am
1 stop22h 05m
$638
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from Chicago to Trinidad and Tobago
Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from Chicago 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 Chicago to Trinidad and Tobago
CHI-TT0
ORD-POS
What is the cheapest month to book a flight from Chicago to Trinidad and Tobago?
Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $432). Flying from Chicago to Trinidad and Tobago in December is currently the most expensive (average of $1,248). 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.
Reviews of airlines servicing Trinidad and Tobago
Get insights into the airlines that provide service to Trinidad and Tobago. 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 Trinidad and Tobago. Reviews last updated October 2, 2026.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as Air Canada and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.1
Crew
7.8
Comfort
7.1
Entertainment
6.8
Boarding
7.3
Food
6.3
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
Overall
7.1
Crew
7.8
Comfort
7.1
Entertainment
6.8
Boarding
7.3
Food
6.3
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
Overall
7.1
Crew
7.8
Comfort
7.1
Entertainment
6.8
Boarding
7.3
Food
6.3
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 Chicago 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 Chicago to Trinidad and Tobago by cabin class
Find flights from Chicago to Trinidad and Tobago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Trinidad and Tobago flights
Browse other Chicago and Trinidad and Tobago flight options. Last updated on October 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Trinidad and Tobago regions
Consider these flights traveling to Trinidad and Tobago regions.
Top 3 airlines flying from Chicago to Trinidad and Tobago
Discover the top 3 airlines that operate flights from Chicago 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 October 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$317 | Average$443 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$578 | Average$759 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$623 | Average$739 | FlexibilityNo cancel fee | On-time71% |