$246+ 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 6/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Jun 25 — Jul 21
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Trinidad with Cheapflights
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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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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
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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 May 26, 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 May 26, 2026.
This Orbitz deal was found by Cheapflights users on 5/21. 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 5/249:55 am
ORD
- POS
1 stop13h 20m
Air Canada
Fri 6/121:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 5/21![Air Canada logo]()
$538
This Air Canada deal was found by Cheapflights users on 5/25. 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 6/138:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Fri 6/191:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/25![Air Canada logo]()
$540
This Expedia deal was found by Cheapflights users on 5/22. 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 9/36:21 pm
ORD
- POS
2 stops28h 54m
Air Canada
Sun 9/61:25 am
POS
- ORD
1 stop16h 32m
Air Canada
Deal found 5/22![Air Canada logo]()
$550
This Orbitz deal was found by Cheapflights users on 5/22. 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.
Fri 9/42:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Sun 9/61:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/22![Air Canada logo]()
$615
This Copa Airlines deal was found by Cheapflights users on 5/21. 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 7/68:02 am
ORD
- POS
1 stop16h 44m
Copa Airlines
Mon 7/132:19 pm
POS
- ORD
1 stop24h 38m
Copa Airlines
Deal found 5/21![Copa Airlines logo]()
$618
This Travelocity deal was found by Cheapflights users on 5/24. 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.
Sun 6/218:40 pm
ORD
- POS
1 stop26h 35m
Multiple Airlines
Sun 6/287:45 pm
POS
- ORD
1 stop14h 00m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$621
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 May 26, 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 May 26, 2026.
This Air Canada deal was found by Cheapflights users on 5/24. 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 6/138:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Fri 6/191:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/24![Air Canada logo]()
$540
This Copa Airlines deal was found by Cheapflights users on 5/25. 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 7/138:02 am
ORD
- POS
1 stop16h 44m
Copa Airlines
Mon 7/202:19 pm
POS
- ORD
1 stop14h 41m
Copa Airlines
Deal found 5/25![Copa Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Thu 9/310:40 am
ORD
- POS
1 stop11h 43m
United Airlines
Sun 9/62:00 am
POS
- ORD
1 stop9h 58m
United Airlines
Deal found 5/22![United Airlines logo]()
$630
This Air Canada deal was found by Cheapflights users on 5/21. 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 9/18:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Sun 9/61:25 am
POS
- ORD
2 stops18h 21m
Air Canada
Deal found 5/21![Air Canada logo]()
$543
This Copa Airlines deal was found by Cheapflights users on 5/24. 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 8/53:21 pm
ORD
- POS
1 stop20h 56m
Copa Airlines
Tue 8/112:19 pm
POS
- ORD
1 stop24h 40m
Copa Airlines
Deal found 5/24![Copa Airlines logo]()
$618
This Orbitz deal was found by Cheapflights users on 5/22. 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.
Fri 9/42:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Sun 9/61:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/22![Air Canada logo]()
$615
This Copa Airlines deal was found by Cheapflights users on 5/25. 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 7/218:02 am
ORD
- POS
1 stop28h 14m
Copa Airlines
Sat 7/253:50 am
POS
- ORD
1 stop25h 10m
Copa Airlines
Deal found 5/25![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 5/21. 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 11/117:35 am
ORD
- POS
1 stop16h 09m
Copa Airlines
Mon 11/162:16 pm
POS
- ORD
1 stop11h 46m
Copa Airlines
Deal found 5/21![Copa Airlines logo]()
$618
This Copa Airlines deal was found by Cheapflights users on 5/24. 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 8/68:02 am
ORD
- POS
1 stop16h 45m
Copa Airlines
Tue 8/112:19 pm
POS
- ORD
1 stop24h 40m
Copa Airlines
Deal found 5/24![Copa Airlines logo]()
$618
Last-minute flights from Chicago to TrinidadDiscover last-minute flight deals from Chicago to Trinidad. Data last updated May 26, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad. Data last updated May 26, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 5/21. 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 5/249:55 am
ORD
- POS
1 stop13h 20m
Air Canada
Fri 6/121:25 am
POS
- ORD
1 stop13h 00m
Air Canada
Deal found 5/21![Air Canada logo]()
$538
This Air Canada deal was found by Cheapflights users on 5/25. 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 6/138:20 pm
ORD
- POS
1 stop26h 55m
Air Canada
Fri 6/191:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/25![Air Canada logo]()
$540
This Air Canada deal was found by Cheapflights users on 5/24. 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 6/138:20 pm
ORD
- POS
2 stops22h 20m
Multiple Airlines
Fri 6/191:25 am
POS
- ORD
2 stops18h 27m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$672
This Expedia deal was found by Cheapflights users on 5/21. 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 6/159:55 am
ORD
- POS
1 stop13h 20m
Multiple Airlines
Fri 7/178:00 pm
POS
- ORD
1 stop26h 58m
Multiple Airlines
Deal found 5/21![Multiple Airlines logo]()
$665
This Justfly.com deal was found by Cheapflights users on 5/26. 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.
Fri 6/195:22 pm
ORD
- POS
1 stop19h 13m
JetBlue
Sun 6/217:45 pm
POS
- ORD
1 stop14h 00m
JetBlue
Deal found 5/26![JetBlue logo]()
$655
This Travelocity deal was found by Cheapflights users on 5/24. 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.
Sun 6/218:40 pm
ORD
- POS
1 stop26h 35m
Multiple Airlines
Sun 6/287:45 pm
POS
- ORD
1 stop14h 00m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$621
This deal was found by Cheapflights users on 5/24. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/222:15 pm
ORD
- POS
1 stop9h 00m
Air Canada
Sun 6/281:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 5/24![Air Canada logo]()
$670
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 May 26, 2026.
Search for one-way flight options from Chicago to Trinidad. Find affordable one-way fares based on user searches. Data last updated May 26, 2026.
This Air Canada deal was found by Cheapflights users on 5/25. 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 6/79:55 am
ORD
- POS
1 stop13h 20m
Air Canada
Deal found 5/25![Air Canada logo]()
$246
This Orbitz deal was found by Cheapflights users on 5/25. 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 7/269:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 5/25![Air Canada logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 6/99:48 pm
ORD
- POS
2 stops44h 07m
Multiple Airlines
Deal found 5/24![Multiple Airlines logo]()
$345
This Justfly.com deal was found by Cheapflights users on 5/24. 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.
Tue 6/93:27 pm
ORD
- POS
1 stop21h 54m
JetBlue
Deal found 5/24![JetBlue logo]()
$381
This Mytrip deal was found by Cheapflights users on 5/25. 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 7/264:40 pm
ORD
- POS
3 stops30h 35m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$599
This Booking.com deal was found by Cheapflights users on 5/25. 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.
Sun 6/77:45 pm
ORD
- POS
3 stops28h 40m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$3,245
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 May 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $538 (Air Canada) |
One-way from | $246 (Air Canada) |
Popular in | December |
Cheapest in | February |
Average price | $498 |
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 May 26, 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 6/13
8:20 pm-12:15 am
1 stop26h 55m
Port of Spain Piarco Intl
Fri 6/19
1:25 am-1:22 pm
1 stop12h 57m
$540
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 9/1
8:40 pm-12:15 am
1 stop26h 35m
Port of Spain Piarco Intl
Sun 9/6
1:25 am-6:46 pm
2 stops18h 21m
$543
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 9/4
2:15 pm-12:15 am
1 stop9h 00m
Port of Spain Piarco Intl
Sun 9/6
1:25 am-1:22 pm
1 stop12h 57m
$615
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 7/13
8:02 am-1:46 am
1 stop16h 44m
Port of Spain Piarco Intl
Mon 7/20
2:19 pm-4:00 am
1 stop14h 41m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 8/5
3:21 pm-1:17 pm
1 stop20h 56m
Port of Spain Piarco Intl
Tue 8/11
2:19 pm-1:59 pm
1 stop24h 40m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 7/21
8:02 am-1:16 pm
1 stop28h 14m
Port of Spain Piarco Intl
Sat 7/25
3:50 am-4:00 am
1 stop25h 10m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 11/11
7:35 am-1:44 am
1 stop16h 09m
Port of Spain Piarco Intl
Mon 11/16
2:16 pm-12:02 am
1 stop11h 46m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 8/6
8:02 am-1:47 am
1 stop16h 45m
Port of Spain Piarco Intl
Tue 8/11
2:19 pm-1:59 pm
1 stop24h 40m
$618
Quickest round-trip
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 9/3
10:40 am-11:23 pm
1 stop11h 43m
Port of Spain Piarco Intl
Sun 9/6
2:00 am-10:58 am
1 stop9h 58m
$630
Cheapest one-way
Quickest one-way
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 7/26
9:50 am-12:15 am
1 stop13h 25m
$294
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, June is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $317). Flying from Chicago to Trinidad 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
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 May 26, 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.
Overall
7.1
Food
6.4
Entertainment
6.9
Boarding
7.5
Comfort
7.2
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Overall
7.1
Food
6.4
Entertainment
6.9
Boarding
7.5
Comfort
7.2
Crew
7.9
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Overall
7.1
Food
6.4
Entertainment
6.9
Boarding
7.5
Comfort
7.2
Crew
7.9
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. 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 May 26, 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 May 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$392 | Average$526 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$472 | Average$627 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$548 | Average$669 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$548 | Average$649 | FlexibilityNo cancel fee | On-time69% |