$232+ Cheap flights from Chicago (CHI) to Trinidad
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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Aug 14 — Aug 211
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Trinidad with Cheapflights
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Best
Last-minute
One-way
Cheapest flights from Chicago to TrinidadExplore the most affordable flight options available from Chicago to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 15, 2026.
Explore the most affordable flight options available from Chicago to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 15, 2026.
This SmartFares deal was found by Cheapflights users on 7/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Fri 8/218:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/10![JetBlue logo]()
$498
This Air Canada deal was found by Cheapflights users on 7/12. 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.
Mon 8/312:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Fri 10/21:20 am
POS
- ORD
1 stop14h 35m
Air Canada
Deal found 7/12![Air Canada logo]()
$531
This Air Canada deal was found by Cheapflights users on 7/11. 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.
Wed 12/98:50 pm
ORD
- POS
1 stop26h 10m
Air Canada
Tue 12/152:05 am
POS
- ORD
1 stop15h 33m
Air Canada
Deal found 7/11![Air Canada logo]()
$539
This Gotogate deal was found by Cheapflights users on 7/10. 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.
Mon 8/242:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Sun 8/301:25 am
POS
- ORD
1 stop16h 32m
Air Canada
Deal found 7/10![Air Canada logo]()
$544
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Wed 9/21:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 7/13![Air Canada logo]()
$545
This Travelocity deal was found by Cheapflights users on 7/10. 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 8/146:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Sun 8/168:00 pm
POS
- ORD
1 stop13h 52m
JetBlue
Deal found 7/10![JetBlue logo]()
$553
This FlightHub deal was found by Cheapflights users on 7/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Mon 9/281:20 am
POS
- ORD
1 stop14h 35m
Air Canada
Deal found 7/12![Air Canada logo]()
$555
This Air Canada deal was found by Cheapflights users on 7/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Fri 9/181:20 am
POS
- ORD
2 stops14h 32m
Air Canada
Deal found 7/14![Air Canada logo]()
$558
Best flights from Chicago to TrinidadDiscover carefully curated flight deals from Chicago to Trinidad that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 15, 2026.
Discover carefully curated flight deals from Chicago to Trinidad that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 15, 2026.
This Air Canada deal was found by Cheapflights users on 7/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Fri 9/181:20 am
POS
- ORD
2 stops14h 32m
Air Canada
Deal found 7/14![Air Canada logo]()
$558
This JetBlue deal was found by Cheapflights users on 7/10. 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.
Wed 9/26:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Sat 9/58:00 pm
POS
- ORD
1 stop13h 48m
JetBlue
Deal found 7/10![JetBlue logo]()
$570
This Kiwi.com deal was found by Cheapflights users on 7/11. 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 8/2012:44 am
ORD
- POS
2 stops17h 11m
Multiple Airlines
Fri 8/2810:10 am
POS
- ORD
1 stop27h 40m
Multiple Airlines
Deal found 7/11![Multiple Airlines logo]()
$601
This Copa Airlines deal was found by Cheapflights users on 7/10. 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 8/213:21 pm
ORD
- POS
1 stop20h 56m
Copa Airlines
Fri 8/282:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 7/10![Copa Airlines logo]()
$618
This FlightHub deal was found by Cheapflights users on 7/11. 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 12/93:45 pm
ORD
- POS
2 stops31h 15m
Air Canada
Tue 12/152:05 am
POS
- ORD
2 stops18h 50m
Air Canada
Deal found 7/11![Air Canada logo]()
$590
This JetBlue deal was found by Cheapflights users on 7/10. 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 8/246:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Mon 8/318:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/10![JetBlue logo]()
$598
This Copa Airlines deal was found by Cheapflights users on 7/14. 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.
Thu 11/52:13 pm
ORD
- POS
1 stop21h 04m
Copa Airlines
Mon 11/163:40 am
POS
- ORD
1 stop11h 06m
Copa Airlines
Deal found 7/14![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 7/14. 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.
Wed 11/47:35 am
ORD
- POS
1 stop16h 19m
Copa Airlines
Mon 11/163:40 am
POS
- ORD
1 stop22h 31m
Copa Airlines
Deal found 7/14![Copa Airlines logo]()
$618
Last-minute flights from Chicago to TrinidadDiscover last-minute flight deals from Chicago to Trinidad. Data last updated July 15, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad. Data last updated July 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:44 am
ORD
- POS
2 stops24h 03m
Multiple Airlines
Fri 9/410:10 am
POS
- ORD
1 stop27h 40m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$561
This SmartFares deal was found by Cheapflights users on 7/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/136:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Fri 8/218:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/10![JetBlue logo]()
$498
This Travelocity deal was found by Cheapflights users on 7/10. 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 8/146:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Sun 8/168:00 pm
POS
- ORD
1 stop13h 52m
JetBlue
Deal found 7/10![JetBlue logo]()
$553
This Gotogate deal was found by Cheapflights users on 7/10. 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.
Mon 8/242:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Sun 8/301:25 am
POS
- ORD
1 stop16h 32m
Air Canada
Deal found 7/10![Air Canada logo]()
$544
This Gotogate deal was found by Cheapflights users on 7/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Wed 9/21:25 am
POS
- ORD
1 stop14h 30m
Air Canada
Deal found 7/13![Air Canada logo]()
$545
This Air Canada deal was found by Cheapflights users on 7/12. 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.
Mon 8/312:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Fri 10/21:20 am
POS
- ORD
1 stop14h 35m
Air Canada
Deal found 7/12![Air Canada logo]()
$531
One-way flights from Chicago to TrinidadSearch for one-way flight options from Chicago to Trinidad. Find affordable one-way fares based on user searches. Data last updated July 15, 2026.
Search for one-way flight options from Chicago to Trinidad. Find affordable one-way fares based on user searches. Data last updated July 15, 2026.
This Gotogate deal was found by Cheapflights users on 7/10. 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.
Mon 8/242:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Deal found 7/10![Air Canada logo]()
$232
This Travelocity deal was found by Cheapflights users on 7/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/29:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 7/12![Air Canada logo]()
$237
This Air Canada deal was found by Cheapflights users on 7/11. 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 7/269:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 7/11![Air Canada logo]()
$265
This Air Canada deal was found by Cheapflights users on 7/12. 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.
Fri 8/218:40 am
ORD
- POS
2 stops14h 35m
Air Canada
Deal found 7/12![Air Canada logo]()
$269
This Air Canada deal was found by Cheapflights users on 7/12. 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.
Sat 8/228:50 pm
ORD
- POS
1 stop26h 25m
Air Canada
Deal found 7/12![Air Canada logo]()
$270
This Orbitz deal was found by Cheapflights users on 7/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:30 pm
ORD
- POS
1 stop31h 30m
Air Canada
Deal found 7/14![Air Canada logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:59 pm
ORD
- POS
2 stops27h 56m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$292
Find flight deals from Chicago to Trinidad
Keep the following information in mind while searching for Chicago to Trinidad flight deals. Data was last updated July 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $492 (Air Canada) |
One-way from | $232 (Gotogate) |
Popular in | December |
Cheapest in | May |
Average price | $624 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Trinidad 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 July 15, 2026.
Use the filters below to find and compare flights from Chicago to Trinidad 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
Sat 9/5
8:40 pm-12:15 am
1 stop26h 35m
Port of Spain Piarco Intl
Fri 9/18
1:20 am-2:52 pm
2 stops14h 32m
$558
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 9/2
6:00 am-6:35 pm
1 stop11h 35m
Port of Spain Piarco Intl
Sat 9/5
8:00 pm-8:48 am
1 stop13h 48m
$570
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 12/9
3:45 pm-1:00 am
2 stops31h 15m
Port of Spain Piarco Intl
Tue 12/15
2:05 am-6:55 pm
2 stops18h 50m
$590
Quickest round-trip
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 8/24
6:00 am-6:35 pm
1 stop11h 35m
Port of Spain Piarco Intl
Mon 8/31
8:00 pm-8:43 am
1 stop13h 43m
$598
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 8/20
12:44 am-6:55 pm
2 stops17h 11m
Port of Spain Piarco Intl
Fri 8/28
10:10 am-12:50 pm
1 stop27h 40m
$601
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 8/21
3:21 pm-1:17 pm
1 stop20h 56m
Port of Spain Piarco Intl
Fri 8/28
2:19 pm-1:02 am
1 stop11h 43m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 11/5
2:13 pm-1:17 pm
1 stop21h 04m
Port of Spain Piarco Intl
Mon 11/16
3:40 am-12:46 pm
1 stop11h 06m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 11/4
7:35 am-1:54 am
1 stop16h 19m
Port of Spain Piarco Intl
Mon 11/16
3:40 am-12:11 am
1 stop22h 31m
$618
Cheapest one-way
Quickest one-way
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 8/24
2:15 pm-12:15 am
1 stop9h 00m
$232
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 7/26
9:50 am-12:15 am
1 stop13h 25m
$265
Showing 1-10 of 14 resultsSorted by cheapest first
Best time to book a flight from Chicago to Trinidad
Have a flexible travel schedule? Discover the best time to fly to Trinidad 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
CHI-zzLAZ
ORD-POS
What is the cheapest month to book a flight from Chicago to Trinidad?
Currently, January is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $285). Flying from Chicago to Trinidad 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
Get insights into the airlines that provide service to Trinidad. 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. Reviews last updated July 15, 2026.
Peruse reviews from past customers who have flown with American Airlines and Air Canada from Chicago to Trinidad to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
6.8
Food
6.4
Overall
7.1
Crew
7.9
Comfort
7.2
Boarding
7.5
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Entertainment
6.8
Food
6.4
Overall
7.1
Crew
7.9
Comfort
7.2
Boarding
7.5
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Entertainment
6.8
Food
6.4
Overall
7.1
Crew
7.9
Comfort
7.2
Boarding
7.5
Reviews
1 / 20
4.0
OkayElizabeth,Mar 2026
ORD - MIA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Trinidad. 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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Trinidad by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Trinidad by cabin class
Find flights from Chicago to Trinidad, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Trinidad flights
Browse other Chicago and Trinidad flight options. Last updated on July 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Chicago to Trinidad
Discover the top 4 airlines that operate flights from Chicago to Trinidad. 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 July 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$285 | Average$654 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$317 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$548 | Average$739 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$658 | FlexibilityNo cancel fee | On-time69% |