$155+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Mar 6 — Mar 131
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Trinidad 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
Cheapest
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 February 4, 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 February 4, 2026.
This Air Canada deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
ORD
- POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/3![Air Canada logo]()
$358
This Air Canada deal was found by Cheapflights users on 2/4. 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 2/218:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Fri 2/272:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Deal found 2/4![Air Canada logo]()
$363
This Air Canada deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:00 am
ORD
- POS
1 stop15h 20m
Air Canada
Thu 3/52:20 am
POS
- ORD
2 stops31h 40m
Air Canada
Deal found 2/3![Air Canada logo]()
$368
This Travelocity deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/297:13 am
ORD
- POS
2 stops16h 07m
Air Canada
Fri 4/31:20 am
POS
- ORD
2 stops31h 40m
Air Canada
Deal found 2/1![Air Canada logo]()
$375
This Air Canada deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:50 am
ORD
- POS
1 stop13h 30m
Air Canada
Fri 4/101:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/3![Air Canada logo]()
$383
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:00 am
ORD
- POS
1 stop15h 20m
Air Canada
Tue 3/171:20 am
POS
- ORD
1 stop19h 25m
Air Canada
Deal found 2/2![Air Canada logo]()
$398
This Air Canada deal was found by Cheapflights users on 2/4. 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 3/271:55 pm
ORD
- POS
1 stop9h 25m
Air Canada
Thu 4/21:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/4![Air Canada logo]()
$408
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 February 4, 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 February 4, 2026.
This Air Canada deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/288:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Fri 4/31:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/1![Air Canada logo]()
$358
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
ORD
- POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/2![Air Canada logo]()
$358
This Air Canada deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/298:40 am
ORD
- POS
2 stops14h 40m
Air Canada
Fri 4/31:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/1![Air Canada logo]()
$361
This Air Canada deal was found by Cheapflights users on 2/4. 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 2/218:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Fri 2/272:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Deal found 2/4![Air Canada logo]()
$363
This Travelocity deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:21 pm
ORD
- POS
2 stops28h 59m
Air Canada
Fri 4/101:20 am
POS
- ORD
2 stops31h 38m
Air Canada
Deal found 2/3![Air Canada logo]()
$393
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1510:00 am
ORD
- POS
1 stop13h 20m
Air Canada
Tue 3/171:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Deal found 2/2![Air Canada logo]()
$398
Last-minute flights from Chicago to TrinidadDiscover last-minute flight deals from Chicago to Trinidad. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Trinidad. Data last updated February 4, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 2/4. 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 2/218:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Fri 2/272:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Deal found 2/4![Air Canada logo]()
$363
This Expedia deal was found by Cheapflights users on 2/4. 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 2/2610:00 am
ORD
- POS
2 stops19h 17m
JetBlue
Sun 3/19:05 am
POS
- ORD
2 stops26h 05m
JetBlue
Deal found 2/4![JetBlue logo]()
$414
This Air Canada deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:00 am
ORD
- POS
1 stop15h 20m
Air Canada
Thu 3/52:20 am
POS
- ORD
2 stops31h 40m
Air Canada
Deal found 2/3![Air Canada logo]()
$368
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1510:00 am
ORD
- POS
1 stop13h 20m
Air Canada
Tue 3/171:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Deal found 2/2![Air Canada logo]()
$398
This Air Canada deal was found by Cheapflights users on 2/4. 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 3/271:55 pm
ORD
- POS
1 stop9h 25m
Air Canada
Thu 4/21:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/4![Air Canada logo]()
$408
This Air Canada deal was found by Cheapflights users on 2/4. 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 3/288:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Fri 4/31:20 am
POS
- ORD
2 stops18h 27m
Air Canada
Deal found 2/4![Air Canada logo]()
$416
This Travelocity deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/297:13 am
ORD
- POS
2 stops16h 07m
Air Canada
Fri 4/31:20 am
POS
- ORD
2 stops31h 40m
Air Canada
Deal found 2/1![Air Canada logo]()
$375
This Air Canada deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
ORD
- POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
- ORD
1 stop12h 45m
Air Canada
Deal found 2/3![Air Canada logo]()
$358
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 February 4, 2026.
Search for one-way flight options from Chicago to Trinidad. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Air Canada deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/78:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Deal found 2/3![Air Canada logo]()
$155
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:15 am
ORD
- POS
2 stops16h 05m
Air Canada
Deal found 2/2![Air Canada logo]()
$189
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/74:38 pm
ORD
- POS
3 stops30h 42m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/154:51 pm
ORD
- POS
3 stops55h 55m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$272
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/126:04 pm
ORD
- POS
2 stops29h 16m
Air Canada
Deal found 2/2![Air Canada logo]()
$480
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:45 pm
ORD
- POS
1 stop10h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$925
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 February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $358 (Air Canada) |
One-way from | $155 (Air Canada) |
Popular in | December |
Cheapest in | October |
Average price | $902 |
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 February 4, 2026.
Use the filters below to find and compare flights from Chicago to Trinidad that are best for you.
Fly from
Chicago
Fly to
Trinidad
Route
Depart
Return
Price
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 3/28
8:40 pm-12:20 am
1 stop26h 40m
Port of Spain Piarco Intl
Fri 4/3
1:20 am-1:05 pm
1 stop12h 45m
$358
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Mon 3/30
8:20 pm-12:20 am
1 stop27h 00m
Port of Spain Piarco Intl
Sun 4/5
1:20 am-1:05 pm
1 stop12h 45m
$358
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 3/29
8:40 am-12:20 am
2 stops14h 40m
Port of Spain Piarco Intl
Fri 4/3
1:20 am-1:05 pm
1 stop12h 45m
$361
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 2/21
8:40 pm-1:20 am
1 stop26h 40m
Port of Spain Piarco Intl
Fri 2/27
2:20 am-6:52 pm
2 stops18h 32m
$363
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 4/2
6:21 pm-12:20 am
2 stops28h 59m
Port of Spain Piarco Intl
Fri 4/10
1:20 am-7:58 am
2 stops31h 38m
$393
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 3/15
10:00 am-12:20 am
1 stop13h 20m
Port of Spain Piarco Intl
Tue 3/17
1:20 am-6:52 pm
2 stops18h 32m
$398
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 2/7
8:40 pm-1:20 am
1 stop26h 40m
$155
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 3/15
7:15 am-12:20 am
2 stops16h 05m
$189
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 2/7
4:38 pm-1:20 am
3 stops30h 42m
$266
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 3/15
4:51 pm-1:46 am
3 stops55h 55m
$272
Showing 1-10 of 12 results
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, November is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad in April is currently the most expensive (average of $628). 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 February 4, 2026.
Peruse reviews from past customers who have flown with United Airlines and American Airlines 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
7.1
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Boarding
7.7
Overall
7.4
Comfort
7.3
Crew
8.1
Food
6.6
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. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 3 airlines flying from Chicago to Trinidad
Discover the top 3 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$432 | Average$556 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$501 | Average$628 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$528 | Average$669 | FlexibilityNo cancel fee | On-time71% |