$174+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Apr 17 — Apr 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
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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 March 18, 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 March 18, 2026.
This Copa Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 3/163:22 pm
ORD
- POS
1 stop9h 24m
Copa Airlines
Wed 3/182:16 pm
POS
- ORD
1 stop11h 48m
Copa Airlines
Deal found 3/15![Copa Airlines logo]()
$384
This Expedia deal was found by Cheapflights users on 3/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:50 am
ORD
- POS
1 stop13h 30m
Air Canada
Sun 4/121:20 am
POS
- ORD
1 stop17h 30m
Air Canada
Deal found 3/12![Air Canada logo]()
$388
This Expedia deal was found by Cheapflights users on 3/16. 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.
Wed 4/154:15 pm
ORD
- POS
1 stop31h 05m
Air Canada
Tue 4/211:20 am
POS
- ORD
2 stops19h 45m
Air Canada
Deal found 3/16![Air Canada logo]()
$391
This Air Canada deal was found by Cheapflights users on 3/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/72:00 pm
ORD
- POS
1 stop9h 20m
Air Canada
Sun 4/121:20 am
POS
- ORD
2 stops18h 38m
Air Canada
Deal found 3/15![Air Canada logo]()
$393
This FlightHub deal was found by Cheapflights users on 3/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:21 pm
ORD
- POS
2 stops28h 59m
Air Canada
Sun 4/121:20 am
POS
- ORD
2 stops31h 38m
Air Canada
Deal found 3/15![Air Canada logo]()
$398
This Expedia deal was found by Cheapflights users on 3/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:40 pm
ORD
- POS
1 stop28h 40m
Air Canada
Sun 4/121:20 am
POS
- ORD
1 stop17h 30m
Air Canada
Deal found 3/15![Air Canada logo]()
$413
This FlightHub deal was found by Cheapflights users on 3/14. 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.
Mon 4/66:01 pm
ORD
- POS
2 stops29h 19m
Air Canada
Thu 4/91:20 am
POS
- ORD
1 stop31h 43m
Air Canada
Deal found 3/14![Air Canada logo]()
$426
This Gotogate deal was found by Cheapflights users on 3/17. 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 3/176:04 pm
ORD
- POS
2 stops53h 16m
Air Canada
Sun 3/221:20 am
POS
- ORD
1 stop19h 25m
Air Canada
Deal found 3/17![Air Canada logo]()
$478
This Mytrip deal was found by Cheapflights users on 3/15. 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.
Tue 4/72:00 pm
ORD
- POS
1 stop9h 20m
Multiple Airlines
Sun 4/121:20 am
POS
- ORD
3 stops24h 02m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$486
This FlightHub deal was found by Cheapflights users on 3/14. 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.
Fri 5/16:00 am
ORD
- POS
2 stops33h 13m
JetBlue
Sun 5/35:38 pm
POS
- ORD
2 stops28h 58m
JetBlue
Deal found 3/14![JetBlue logo]()
$489
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:40 pm
ORD
- TAB
2 stops22h 50m
Multiple Airlines
Tue 5/511:45 am
TAB
- ORD
2 stops22h 20m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$1,134
This Flightnetwork deal was found by Cheapflights users on 3/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:37 pm
ORD
- TAB
2 stops15h 33m
Multiple Airlines
Tue 6/99:55 am
TAB
- ORD
2 stops24h 10m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$1,637
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 March 18, 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 March 18, 2026.
This Copa Airlines deal was found by Cheapflights users on 3/14. 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.
Tue 4/283:05 pm
ORD
- POS
1 stop9h 35m
Copa Airlines
Mon 5/43:49 am
POS
- ORD
1 stop11h 17m
Copa Airlines
Deal found 3/14![Copa Airlines logo]()
$508
This Air Canada deal was found by Cheapflights users on 3/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:40 am
ORD
- POS
2 stops14h 40m
Air Canada
Sun 4/121:20 am
POS
- ORD
2 stops18h 38m
Air Canada
Deal found 3/12![Air Canada logo]()
$546
This FlightHub deal was found by Cheapflights users on 3/14. 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.
Fri 5/16:00 am
ORD
- POS
2 stops33h 13m
JetBlue
Sun 5/35:38 pm
POS
- ORD
1 stop15h 03m
JetBlue
Deal found 3/14![JetBlue logo]()
$552
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:01 pm
ORD
- POS
3 stops29h 19m
Multiple Airlines
Sun 4/121:20 am
POS
- ORD
2 stops24h 02m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$576
This Copa Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 5/103:21 pm
ORD
- POS
1 stop9h 25m
Copa Airlines
Wed 5/202:22 pm
POS
- ORD
1 stop11h 53m
Copa Airlines
Deal found 3/15![Copa Airlines logo]()
$508
This Expedia deal was found by Cheapflights users on 3/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Sun 5/311:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 3/13![Air Canada logo]()
$574
This Mytrip deal was found by Cheapflights users on 3/16. 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.
Thu 6/118:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Wed 6/171:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 3/16![Air Canada logo]()
$584
This Air Canada deal was found by Cheapflights users on 3/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:21 pm
ORD
- POS
2 stops28h 59m
Air Canada
Sun 4/51:20 am
POS
- ORD
2 stops34h 33m
Air Canada
Deal found 3/17![Air Canada logo]()
$601
This Expedia deal was found by Cheapflights users on 3/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Wed 5/201:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 3/15![Air Canada logo]()
$604
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:40 pm
ORD
- TAB
2 stops22h 50m
Multiple Airlines
Tue 5/511:45 am
TAB
- ORD
2 stops22h 20m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$1,134
This Flightnetwork deal was found by Cheapflights users on 3/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:37 pm
ORD
- TAB
2 stops15h 33m
Multiple Airlines
Tue 6/99:55 am
TAB
- ORD
2 stops24h 10m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$1,637
This Travelocity deal was found by Cheapflights users on 3/17. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:09 am
ORD
- TAB
2 stops24h 21m
Multiple Airlines
Fri 6/1211:45 am
TAB
- ORD
2 stops28h 10m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$3,972
Last-minute flights from Chicago to Trinidad and TobagoDiscover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated March 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad and Tobago. Data last updated March 18, 2026 and is based on user searches.
This Gotogate deal was found by Cheapflights users on 3/17. 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 3/176:04 pm
ORD
- POS
2 stops53h 16m
Air Canada
Sun 3/221:20 am
POS
- ORD
1 stop19h 25m
Air Canada
Deal found 3/17![Air Canada logo]()
$478
This Air Canada deal was found by Cheapflights users on 3/17. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/24:15 pm
ORD
- POS
1 stop31h 05m
Air Canada
Thu 4/91:20 am
POS
- ORD
1 stop31h 43m
Air Canada
Deal found 3/17![Air Canada logo]()
$493
This Expedia deal was found by Cheapflights users on 3/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:40 pm
ORD
- POS
1 stop28h 40m
Air Canada
Sun 4/121:20 am
POS
- ORD
1 stop17h 30m
Air Canada
Deal found 3/15![Air Canada logo]()
$413
This FlightHub deal was found by Cheapflights users on 3/14. 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.
Mon 4/66:01 pm
ORD
- POS
2 stops29h 19m
Air Canada
Thu 4/91:20 am
POS
- ORD
1 stop31h 43m
Air Canada
Deal found 3/14![Air Canada logo]()
$426
This Air Canada deal was found by Cheapflights users on 3/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/72:00 pm
ORD
- POS
1 stop9h 20m
Air Canada
Sun 4/121:20 am
POS
- ORD
2 stops18h 38m
Air Canada
Deal found 3/15![Air Canada logo]()
$393
This Mytrip deal was found by Cheapflights users on 3/15. 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.
Tue 4/72:00 pm
ORD
- POS
1 stop9h 20m
Multiple Airlines
Sun 4/121:20 am
POS
- ORD
3 stops24h 02m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$486
This FlightHub deal was found by Cheapflights users on 3/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:21 pm
ORD
- POS
2 stops28h 59m
Air Canada
Sun 4/121:20 am
POS
- ORD
2 stops31h 38m
Air Canada
Deal found 3/15![Air Canada logo]()
$398
This Expedia deal was found by Cheapflights users on 3/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:50 am
ORD
- POS
1 stop13h 30m
Air Canada
Sun 4/121:20 am
POS
- ORD
1 stop17h 30m
Air Canada
Deal found 3/12![Air Canada logo]()
$388
This Copa Airlines deal was found by Cheapflights users on 3/16. 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 4/153:05 pm
ORD
- POS
1 stop9h 35m
Copa Airlines
Wed 4/222:17 pm
POS
- ORD
1 stop11h 56m
Copa Airlines
Deal found 3/16![Copa Airlines logo]()
$384
This Expedia deal was found by Cheapflights users on 3/16. 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.
Wed 4/154:15 pm
ORD
- POS
1 stop31h 05m
Air Canada
Tue 4/211:20 am
POS
- ORD
2 stops19h 45m
Air Canada
Deal found 3/16![Air Canada logo]()
$391
This Mytrip deal was found by Cheapflights users on 3/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:40 pm
ORD
- TAB
2 stops22h 50m
Multiple Airlines
Tue 5/511:45 am
TAB
- ORD
2 stops22h 20m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$1,134
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 March 18, 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 March 18, 2026.
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/89:20 pm
ORD
- POS
1 stop26h 00m
Air Canada
Deal found 3/16![Air Canada logo]()
$174
This Mytrip deal was found by Cheapflights users on 3/16. 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.
Sun 4/57:55 am
ORD
- POS
1 stop15h 25m
Air Canada
Deal found 3/16![Air Canada logo]()
$187
This Mytrip deal was found by Cheapflights users on 3/16. 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.
Fri 4/32:00 pm
ORD
- POS
1 stop9h 20m
Air Canada
Deal found 3/16![Air Canada logo]()
$188
This Mytrip deal was found by Cheapflights users on 3/16. 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.
Sat 4/49:20 pm
ORD
- POS
1 stop26h 00m
Air Canada
Deal found 3/16![Air Canada logo]()
$198
This Air Canada deal was found by Cheapflights users on 3/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/24:15 pm
ORD
- POS
1 stop31h 05m
Air Canada
Deal found 3/16![Air Canada logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Tue 4/710:55 am
ORD
- POS
3 stops37h 45m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 3/16. 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 6/118:10 am
ORD
- POS
1 stop9h 45m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$267
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:01 pm
ORD
- POS
3 stops29h 19m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$286
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 March 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $384 (Copa Airlines) |
One-way from | $174 (Booking.com) |
Popular in | December |
Cheapest in | February |
Average price | $596 |
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 March 18, 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
Quickest round-trip
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 4/28
3:05 pm-1:40 am
1 stop9h 35m
Port of Spain Piarco Intl
Mon 5/4
3:49 am-2:06 pm
1 stop11h 17m
$508
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 5/10
3:21 pm-1:46 am
1 stop9h 25m
Port of Spain Piarco Intl
Wed 5/20
2:22 pm-1:15 am
1 stop11h 53m
$508
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 4/9
8:40 am-12:20 am
2 stops14h 40m
Port of Spain Piarco Intl
Sun 4/12
1:20 am-6:58 pm
2 stops18h 38m
$546
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 5/1
6:00 am-4:13 pm
2 stops33h 13m
Port of Spain Piarco Intl
Sun 5/3
5:38 pm-7:41 am
1 stop15h 03m
$552
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 5/29
2:15 pm-12:15 am
1 stop9h 00m
Port of Spain Piarco Intl
Sun 5/31
1:25 am-1:25 pm
1 stop13h 00m
$574
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 4/9
6:01 pm-12:20 am
3 stops29h 19m
Port of Spain Piarco Intl
Sun 4/12
1:20 am-12:22 am
2 stops24h 02m
$576
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 6/11
8:20 pm-12:15 am
1 stop26h 55m
Port of Spain Piarco Intl
Wed 6/17
1:25 am-1:22 pm
1 stop12h 57m
$584
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 3/30
6:21 pm-12:20 am
2 stops28h 59m
Port of Spain Piarco Intl
Sun 4/5
1:20 am-10:53 am
2 stops34h 33m
$601
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 5/14
8:20 pm-12:15 am
1 stop26h 55m
Port of Spain Piarco Intl
Wed 5/20
1:25 am-1:25 pm
1 stop13h 00m
$604
ChicagoScarborough
ORD - TAB
ORDTAB
Chicago O'Hare Intl
Tue 4/28
6:40 pm-6:30 pm
2 stops22h 50m
Scarborough ANR Robinson Intl
Tue 5/5
11:45 am-9:05 am
2 stops22h 20m
$1,134
Showing 1-10 of 20 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
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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 $376). 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 March 18, 2026.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as United Airlines,American Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
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 March 18, 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 March 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$392 | Average$516 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$472 | Average$567 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$548 | Average$688 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$628 | FlexibilityNo cancel fee | On-time69% |