$249+ Cheap flights from Chicago (CHI) 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Jun 3 — Jun 101
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
Cheapest
Best
Last-minute
One-way
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 May 4, 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 May 4, 2026.
This Orbitz deal was found by Cheapflights users on 5/1. 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 6/188:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Sun 6/211:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/1![Air Canada logo]()
$546
This Travelocity deal was found by Cheapflights users on 5/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:35 pm
ORD
- POS
1 stop26h 40m
Air Canada
Sun 5/241:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 5/2![Air Canada logo]()
$576
This Air Canada deal was found by Cheapflights users on 4/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Fri 7/31:25 am
POS
- ORD
2 stops14h 30m
Air Canada
Deal found 4/29![Air Canada logo]()
$579
This FlightHub deal was found by Cheapflights users on 5/3. 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.
Fri 9/47:25 am
ORD
- POS
1 stop15h 50m
Air Canada
Mon 9/71:20 am
POS
- ORD
1 stop16h 38m
Air Canada
Deal found 5/3![Air Canada logo]()
$580
This Justfly.com deal was found by Cheapflights users on 4/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:22 pm
ORD
- POS
2 stops28h 53m
Air Canada
Fri 7/31:25 am
POS
- ORD
2 stops18h 22m
Air Canada
Deal found 4/30![Air Canada logo]()
$586
This Expedia deal was found by Cheapflights users on 4/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Sun 7/261:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 4/30![Air Canada logo]()
$606
This Air Canada deal was found by Cheapflights users on 5/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/99:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Fri 8/211:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/2![Air Canada logo]()
$608
This Priceline deal was found by Cheapflights users on 5/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:27 pm
ORD
- POS
1 stop18h 08m
Multiple Airlines
Mon 6/221:25 am
POS
- ORD
2 stops18h 27m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$609
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 May 4, 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 May 4, 2026.
This Air Canada deal was found by Cheapflights users on 5/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Sun 6/211:25 am
POS
- ORD
2 stops18h 27m
Air Canada
Deal found 5/1![Air Canada logo]()
$551
This Copa Airlines deal was found by Cheapflights users on 4/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/103:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Wed 6/172:22 pm
POS
- ORD
1 stop14h 38m
Copa Airlines
Deal found 4/29![Copa Airlines logo]()
$633
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:30 am
ORD
- POS
1 stop11h 53m
United Airlines
Sat 6/612:30 am
POS
- ORD
1 stop11h 29m
United Airlines
Deal found 5/2![United Airlines logo]()
$650
This Mytrip deal was found by Cheapflights users on 4/29. 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 6/61:18 pm
ORD
- POS
3 stops33h 57m
Multiple Airlines
Fri 7/31:25 am
POS
- ORD
2 stops14h 30m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:23 am
ORD
- POS
1 stop13h 10m
American Airlines
Fri 8/143:13 pm
POS
- ORD
1 stop18h 47m
American Airlines
Deal found 4/30![American Airlines logo]()
$729
This Justfly.com deal was found by Cheapflights users on 4/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/186:22 pm
ORD
- POS
2 stops28h 53m
Air Canada
Fri 7/31:25 am
POS
- ORD
2 stops18h 22m
Air Canada
Deal found 4/30![Air Canada logo]()
$586
This Copa Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 6/183:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Sat 6/203:49 am
POS
- ORD
1 stop11h 17m
Copa Airlines
Deal found 4/30![Copa Airlines logo]()
$633
This Justfly.com deal was found by Cheapflights users on 5/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/163:40 pm
ORD
- POS
2 stops31h 35m
Air Canada
Sun 5/241:25 am
POS
- ORD
2 stops18h 27m
Air Canada
Deal found 5/3![Air Canada logo]()
$589
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 5/258:51 am
ORD
- POS
1 stop13h 32m
United Airlines
Sat 5/3012:30 am
POS
- ORD
1 stop11h 31m
United Airlines
Deal found 5/1![United Airlines logo]()
$695
This Copa Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 6/143:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Sat 6/203:49 am
POS
- ORD
1 stop11h 17m
Copa Airlines
Deal found 4/30![Copa Airlines logo]()
$683
Last-minute flights from Chicago to Trinidad and TobagoDiscover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated May 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/18:46 pm
ORD
- POS
2 stops16h 46m
American Airlines
Sun 5/33:47 pm
POS
- ORD
2 stops16h 52m
American Airlines
Deal found 4/29![American Airlines logo]()
$805
This Travelocity deal was found by Cheapflights users on 5/2. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:35 pm
ORD
- POS
1 stop26h 40m
Air Canada
Sun 5/241:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 5/2![Air Canada logo]()
$576
This Air Canada deal was found by Cheapflights users on 5/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:35 pm
ORD
- POS
2 stops22h 05m
Multiple Airlines
Sun 5/241:25 am
POS
- ORD
2 stops18h 27m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$709
This Justfly.com deal was found by Cheapflights users on 5/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:15 am
ORD
- POS
1 stop31h 06m
JetBlue
Fri 7/37:45 pm
POS
- ORD
1 stop14h 00m
JetBlue
Deal found 5/2![JetBlue logo]()
$640
This Priceline deal was found by Cheapflights users on 5/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/247:10 am
ORD
- POS
2 stops16h 05m
Multiple Airlines
Fri 7/37:45 pm
POS
- ORD
1 stop14h 00m
Multiple Airlines
Deal found 5/2![Multiple Airlines logo]()
$740
This American Airlines deal was found by Cheapflights users on 5/2. 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.
Sun 5/248:19 am
ORD
- POS
2 stops13h 40m
American Airlines
Fri 7/37:00 am
POS
- ORD
2 stops13h 43m
American Airlines
Deal found 5/2![American Airlines logo]()
$753
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Mon 5/258:51 am
ORD
- POS
1 stop13h 32m
United Airlines
Sat 5/3012:30 am
POS
- ORD
1 stop11h 31m
United Airlines
Deal found 5/1![United Airlines logo]()
$695
This Mytrip deal was found by Cheapflights users on 5/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/252:15 pm
ORD
- POS
1 stop9h 00m
Multiple Airlines
Sun 5/3110:10 am
POS
- ORD
2 stops23h 50m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$800
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sat 5/3012:40 pm
ORD
- POS
1 stop9h 43m
United Airlines
Tue 6/212:30 am
POS
- ORD
1 stop15h 21m
United Airlines
Deal found 4/29![United Airlines logo]()
$770
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 May 4, 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 May 4, 2026.
This Expedia deal was found by Cheapflights users on 5/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/252:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Deal found 5/1![Air Canada logo]()
$249
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:22 pm
ORD
- POS
2 stops28h 53m
Air Canada
Deal found 4/30![Air Canada logo]()
$254
This Expedia deal was found by Cheapflights users on 5/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:40 pm
ORD
- POS
1 stop26h 45m
Air Canada
Deal found 5/2![Air Canada logo]()
$279
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:18 pm
ORD
- POS
3 stops33h 57m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Wed 7/812:11 pm
ORD
- POS
1 stop11h 39m
United Airlines
Deal found 5/1![United Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 5/1. 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 7/88:00 am
ORD
- POS
2 stops13h 33m
American Airlines
Deal found 5/1![American Airlines logo]()
$454
This Booking.com deal was found by Cheapflights users on 5/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:35 pm
ORD
- POS
3 stops22h 40m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$465
This FlightHub deal was found by Cheapflights users on 5/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:30 pm
ORD
- POS
2 stops17h 44m
JetBlue
Deal found 5/1![JetBlue logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 7/86:19 am
ORD
- POS
3 stops46h 56m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$1,726
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 May 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $546 (Orbitz) |
One-way from | $249 (Expedia) |
Popular in | December |
Cheapest in | February |
Average price | $558 |
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 2,558,603 searches. Data last updated May 4, 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 - POS
ORDPOS
Chicago O'Hare Intl
Thu 6/18
8:40 pm-12:15 am
1 stop26h 35m
Port of Spain Piarco Intl
Sun 6/21
1:25 am-6:52 pm
2 stops18h 27m
$551
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 6/18
6:22 pm-12:15 am
2 stops28h 53m
Port of Spain Piarco Intl
Fri 7/3
1:25 am-6:47 pm
2 stops18h 22m
$586
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 5/16
3:40 pm-12:15 am
2 stops31h 35m
Port of Spain Piarco Intl
Sun 5/24
1:25 am-6:52 pm
2 stops18h 27m
$589
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 6/10
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Wed 6/17
2:22 pm-4:00 am
1 stop14h 38m
$633
Quickest round-trip
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 6/18
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Sat 6/20
3:49 am-2:06 pm
1 stop11h 17m
$633
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 6/2
10:30 am-11:23 pm
1 stop11h 53m
Port of Spain Piarco Intl
Sat 6/6
12:30 am-10:59 am
1 stop11h 29m
$650
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 6/6
1:18 pm-12:15 am
3 stops33h 57m
Port of Spain Piarco Intl
Fri 7/3
1:25 am-2:55 pm
2 stops14h 30m
$670
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 6/14
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Sat 6/20
3:49 am-2:06 pm
1 stop11h 17m
$683
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 5/25
8:51 am-11:23 pm
1 stop13h 32m
Port of Spain Piarco Intl
Sat 5/30
12:30 am-11:01 am
1 stop11h 31m
$695
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 7/25
8:23 am-10:33 pm
1 stop13h 10m
Port of Spain Piarco Intl
Fri 8/14
3:13 pm-9:00 am
1 stop18h 47m
$729
Showing 1-10 of 17 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, June is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $317). Flying from Chicago to Trinidad and Tobago in January is currently the most expensive (average of $638). 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 May 4, 2026.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as American Airlines and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
Entertainment
6.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
Entertainment
6.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
Entertainment
6.9
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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 May 4, 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 4 airlines flying from Chicago to Trinidad and Tobago
Discover the top 4 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 2,558,603 searches. Data last updated May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$392 | Average$516 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$472 | Average$597 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$548 | Average$688 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$629 | FlexibilityNo cancel fee | On-time69% |