$253+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Jul 17 — Jul 241
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 June 17, 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 June 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Thu 8/207:55 am
ORD
- POS
1 stop11h 05m
Multiple Airlines
Sun 8/2310:10 am
POS
- ORD
1 stop27h 15m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$538
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/138:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/98:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$563
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Tue 8/117:41 pm
POS
- ORD
1 stop14h 07m
JetBlue
Deal found 6/17![JetBlue logo]()
$585
This Orbitz deal was found by Cheapflights users on 6/15. 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.
Sun 8/29:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Fri 8/71:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 6/15![Air Canada logo]()
$593
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/128:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$598
This Air Canada deal was found by Cheapflights users on 6/13. 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.
Mon 7/138:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Sun 7/191:25 am
POS
- ORD
2 stops18h 22m
Air Canada
Deal found 6/13![Air Canada logo]()
$602
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Thu 7/23:45 pm
ORD
- POS
1 stop31h 30m
Air Canada
Sun 7/51:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 6/15![Air Canada logo]()
$603
This Air Canada deal was found by Cheapflights users on 6/13. 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.
Fri 7/38:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Sun 7/191:25 am
POS
- ORD
2 stops18h 19m
Air Canada
Deal found 6/13![Air Canada logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Tue 7/79:57 pm
ORD
- POS
2 stops43h 58m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$611
This Mytrip deal was found by Cheapflights users on 6/15. 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 7/319:50 am
ORD
- TAB
2 stops29h 45m
Multiple Airlines
Fri 8/73:30 pm
TAB
- ORD
2 stops26h 27m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$950
This Travelocity deal was found by Cheapflights users on 6/14. 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.
Tue 12/154:40 pm
ORD
- TAB
2 stops19h 35m
Multiple Airlines
Sun 1/310:20 pm
TAB
- ORD
3 stops36h 40m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$4,053
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 June 17, 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 June 17, 2026.
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/46:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Tue 8/117:41 pm
POS
- ORD
1 stop14h 07m
JetBlue
Deal found 6/17![JetBlue logo]()
$585
This Copa Airlines deal was found by Cheapflights users on 6/12. 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 7/173:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Sun 7/192:19 pm
POS
- ORD
1 stop24h 38m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/1810:51 am
ORD
- POS
1 stop12h 59m
United Airlines
Thu 7/2312:30 am
POS
- ORD
1 stop10h 50m
United Airlines
Deal found 6/14![United Airlines logo]()
$630
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 7/145:00 am
ORD
- POS
1 stop16h 33m
American Airlines
Tue 7/217:00 am
POS
- ORD
2 stops16h 00m
American Airlines
Deal found 6/15![American Airlines logo]()
$634
This Mytrip deal was found by Cheapflights users on 6/15. 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 7/319:50 am
ORD
- TAB
2 stops29h 45m
Multiple Airlines
Fri 8/73:30 pm
TAB
- ORD
2 stops26h 27m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$950
This Copa Airlines deal was found by Cheapflights users on 6/13. 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 7/118:02 am
ORD
- POS
1 stop16h 44m
Copa Airlines
Sat 7/182:19 pm
POS
- ORD
1 stop10h 42m
Copa Airlines
Deal found 6/13![Copa Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 6/13. 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 7/117:02 am
ORD
- POS
2 stops14h 31m
American Airlines
Sat 7/187:00 am
POS
- ORD
1 stop16h 59m
American Airlines
Deal found 6/13![American Airlines logo]()
$634
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Tue 8/48:00 pm
POS
- ORD
1 stop13h 47m
JetBlue
Deal found 6/17![JetBlue logo]()
$635
This Copa Airlines deal was found by Cheapflights users on 6/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/211:20 am
ORD
- POS
1 stop10h 56m
Copa Airlines
Sun 7/262:19 pm
POS
- ORD
1 stop24h 38m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 6/14. 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 7/173:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Fri 7/242:19 pm
POS
- ORD
1 stop14h 41m
Copa Airlines
Deal found 6/14![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 6/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:02 am
ORD
- POS
1 stop16h 44m
Copa Airlines
Sun 8/92:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 6/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:02 am
ORD
- POS
1 stop28h 15m
Copa Airlines
Sun 8/162:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 6/16![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 7/148:02 am
ORD
- POS
1 stop16h 44m
Copa Airlines
Mon 7/203:50 am
POS
- ORD
1 stop21h 11m
Copa Airlines
Deal found 6/15![Copa Airlines logo]()
$618
Last-minute flights from Chicago to Trinidad and TobagoDiscover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated June 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated June 17, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Thu 7/23:45 pm
ORD
- POS
1 stop31h 30m
Air Canada
Sun 7/51:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 6/15![Air Canada logo]()
$603
This Air Canada deal was found by Cheapflights users on 6/13. 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.
Fri 7/38:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Sun 7/191:25 am
POS
- ORD
2 stops18h 19m
Air Canada
Deal found 6/13![Air Canada logo]()
$610
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Tue 7/79:57 pm
ORD
- POS
2 stops43h 58m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$611
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/98:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$563
This Air Canada deal was found by Cheapflights users on 6/13. 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 7/118:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Fri 7/171:25 am
POS
- ORD
2 stops18h 22m
Air Canada
Deal found 6/13![Air Canada logo]()
$623
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/128:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/138:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$549
This Air Canada deal was found by Cheapflights users on 6/13. 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.
Mon 7/138:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Sun 7/191:25 am
POS
- ORD
2 stops18h 22m
Air Canada
Deal found 6/13![Air Canada logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 7/168:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Fri 7/1710:10 am
POS
- ORD
1 stop27h 05m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$617
This Copa Airlines deal was found by Cheapflights users on 6/12. 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 7/173:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Sun 7/192:19 pm
POS
- ORD
1 stop24h 38m
Copa Airlines
Deal found 6/12![Copa Airlines logo]()
$618
This Mytrip deal was found by Cheapflights users on 6/15. 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 7/319:50 am
ORD
- TAB
2 stops29h 45m
Multiple Airlines
Fri 8/73:30 pm
TAB
- ORD
2 stops26h 27m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$950
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 June 17, 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 June 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Tue 8/1812:29 am
ORD
- POS
2 stops35h 48m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/157:05 am
ORD
- POS
2 stops34h 50m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Tue 7/149:57 pm
ORD
- POS
2 stops43h 58m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$268
This Air Canada deal was found by Cheapflights users on 6/13. 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.
Mon 7/279:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 6/13![Air Canada logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/168:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$274
This Travelocity deal was found by Cheapflights users on 6/14. 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 7/159:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 6/14![Air Canada logo]()
$298
This FlightHub deal was found by Cheapflights users on 6/14. 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.
Tue 7/148:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Deal found 6/14![Air Canada logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/13. 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 6/267:52 am
ORD
- POS
1 stop11h 08m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$382
This FlightHub deal was found by Cheapflights users on 6/13. 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 6/268:20 pm
ORD
- POS
2 stops21h 15m
JetBlue
Deal found 6/13![JetBlue logo]()
$390
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 June 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $538 (Kiwi.com) |
One-way from | $253 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $669 |
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 June 17, 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
Tue 8/4
6:00 am-6:35 pm
1 stop11h 35m
Port of Spain Piarco Intl
Tue 8/11
7:41 pm-8:48 am
1 stop14h 07m
$585
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 7/17
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Sun 7/19
2:19 pm-1:57 pm
1 stop24h 38m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 7/11
8:02 am-1:46 am
1 stop16h 44m
Port of Spain Piarco Intl
Sat 7/18
2:19 pm-12:01 am
1 stop10h 42m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 7/21
1:20 am-1:16 pm
1 stop10h 56m
Port of Spain Piarco Intl
Sun 7/26
2:19 pm-1:57 pm
1 stop24h 38m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 7/17
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Fri 7/24
2:19 pm-4:00 am
1 stop14h 41m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 7/18
8:02 am-1:46 am
1 stop16h 44m
Port of Spain Piarco Intl
Sun 8/9
2:19 pm-1:02 am
1 stop11h 43m
$618
ChicagoPort of Spain
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Chicago O'Hare Intl
Wed 8/12
8:02 am-1:17 pm
1 stop28h 15m
Port of Spain Piarco Intl
Sun 8/16
2:19 pm-1:02 am
1 stop11h 43m
$618
ChicagoPort of Spain
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Chicago O'Hare Intl
Tue 7/14
8:02 am-1:46 am
1 stop16h 44m
Port of Spain Piarco Intl
Mon 7/20
3:50 am-12:01 am
1 stop21h 11m
$618
Quickest round-trip
ChicagoPort of Spain
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Chicago O'Hare Intl
Sat 7/18
10:51 am-12:50 am
1 stop12h 59m
Port of Spain Piarco Intl
Thu 7/23
12:30 am-10:20 am
1 stop10h 50m
$630
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 7/14
5:00 am-10:33 pm
1 stop16h 33m
Port of Spain Piarco Intl
Tue 7/21
7:00 am-10:00 pm
2 stops16h 00m
$634
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.
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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
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What is the cheapest month to book a flight from Chicago to Trinidad and Tobago?
Currently, January is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $285). Flying from Chicago to Trinidad and Tobago in September is currently the most expensive (average of $562). 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 June 17, 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.
Entertainment
6.8
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Entertainment
6.8
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
Comfort
7.2
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Entertainment
6.8
Crew
7.9
Overall
7.1
Boarding
7.5
Food
6.4
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 June 17, 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 June 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$285 | Average$627 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$317 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$548 | Average$669 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$649 | FlexibilityNo cancel fee | On-time69% |