$217+ Cheap flights from Trinidad to Chicago (CHI)
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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Mar 6 — Mar 131
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Trinidad to Chicago 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 Trinidad to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from Trinidad to ChicagoExplore the most affordable flight options available from Trinidad to Chicago. 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 Trinidad to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/101:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Wed 3/188:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Deal found 2/3![Air Canada logo]()
$348
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
- ORD
2 stops38h 35m
Air Canada
Sat 4/116:40 pm
ORD
- POS
1 stop28h 40m
Air Canada
Deal found 2/2![Air Canada logo]()
$386
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:20 am
POS
- ORD
1 stop9h 30m
Air Canada
Fri 3/271:55 pm
ORD
- POS
1 stop9h 25m
Air Canada
Deal found 2/1![Air Canada logo]()
$466
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.
Thu 5/149:10 am
POS
- ORD
1 stop15h 49m
Multiple Airlines
Tue 5/196:31 am
ORD
- POS
2 stops30h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$481
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.
Tue 3/101:20 am
POS
- ORD
2 stops34h 00m
Multiple Airlines
Wed 3/187:31 pm
ORD
- POS
3 stops27h 49m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$497
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
- ORD
2 stops34h 58m
Multiple Airlines
Sat 4/117:31 pm
ORD
- POS
3 stops27h 49m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$504
Best flights from Trinidad to ChicagoDiscover carefully curated flight deals from Trinidad to Chicago 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 Trinidad to Chicago 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 2/3. 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.
Tue 3/101:20 am
POS
- ORD
1 stop14h 50m
Air Canada
Wed 3/188:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Deal found 2/3![Air Canada logo]()
$363
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.
Thu 5/149:10 am
POS
- ORD
1 stop15h 49m
Multiple Airlines
Tue 5/196:31 am
ORD
- POS
2 stops30h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$481
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
- ORD
2 stops38h 35m
Air Canada
Sat 4/116:40 pm
ORD
- POS
1 stop28h 40m
Air Canada
Deal found 2/2![Air Canada logo]()
$386
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.
Tue 3/101:20 am
POS
- ORD
2 stops34h 00m
Multiple Airlines
Wed 3/187:31 pm
ORD
- POS
3 stops27h 49m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$497
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Fri 3/271:55 pm
ORD
- POS
1 stop9h 25m
Air Canada
Deal found 2/1![Air Canada logo]()
$466
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
- ORD
2 stops34h 58m
Multiple Airlines
Sat 4/117:31 pm
ORD
- POS
3 stops27h 49m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$504
Last-minute flights from Trinidad to ChicagoDiscover last-minute flight deals from Trinidad to Chicago. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Trinidad to Chicago. Data last updated February 4, 2026 and is based on user searches.
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/101:20 am
POS
- ORD
2 stops18h 32m
Air Canada
Wed 3/188:40 pm
ORD
- POS
1 stop26h 40m
Air Canada
Deal found 2/3![Air Canada logo]()
$348
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.
Tue 3/101:20 am
POS
- ORD
2 stops34h 00m
Multiple Airlines
Wed 3/187:31 pm
ORD
- POS
3 stops27h 49m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$497
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:20 am
POS
- ORD
1 stop9h 30m
Air Canada
Fri 3/271:55 pm
ORD
- POS
1 stop9h 25m
Air Canada
Deal found 2/1![Air Canada logo]()
$466
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:20 am
POS
- ORD
2 stops14h 35m
Multiple Airlines
Fri 3/278:40 pm
ORD
- POS
3 stops21h 55m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$790
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
- ORD
2 stops38h 35m
Air Canada
Sat 4/116:40 pm
ORD
- POS
1 stop28h 40m
Air Canada
Deal found 2/2![Air Canada logo]()
$386
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
- ORD
2 stops34h 58m
Multiple Airlines
Sat 4/117:31 pm
ORD
- POS
3 stops27h 49m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$504
One-way flights from Trinidad to ChicagoSearch for one-way flight options from Trinidad to Chicago. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Trinidad to Chicago. 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.
Tue 3/171:20 am
POS
- ORD
1 stop12h 41m
Air Canada
Deal found 2/3![Air Canada logo]()
$217
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/239:10 am
POS
- ORD
1 stop24h 15m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$244
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/233:26 pm
POS
- ORD
2 stops19h 44m
JetBlue
Deal found 2/1![JetBlue logo]()
$250
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.
Tue 3/171:20 am
POS
- ORD
3 stops24h 02m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$297
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:10 am
POS
- ORD
1 stop24h 33m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$345
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/712:30 am
POS
- ORD
1 stop20h 31m
United Airlines
Deal found 2/1![United Airlines logo]()
$564
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:22 pm
POS
- ORD
1 stop12h 59m
JetBlue
Deal found 2/2![JetBlue logo]()
$854
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/87:00 am
POS
- ORD
2 stops15h 43m
American Airlines
Deal found 2/1![American Airlines logo]()
$1,007
Find flight deals from Trinidad to Chicago
Keep the following information in mind while searching for Trinidad to Chicago flight deals. Data was last updated February 4, 2026.
Round-trip from | $348 (Flysmarter) |
|---|---|
One-way from | $217 (Air Canada) |
Cheapflights Fare Finder
Customize your flight search to find flights from Trinidad to Chicago 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 Trinidad to Chicago that are best for you.
Fly from
Trinidad
Fly to
Chicago
Route
Depart
Return
Price
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Tue 3/10
1:20 am-3:10 pm
1 stop14h 50m
Chicago O'Hare Intl
Wed 3/18
8:40 pm-12:20 am
1 stop26h 40m
$363
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Tue 3/24
1:20 am-2:55 pm
2 stops38h 35m
Chicago O'Hare Intl
Sat 4/11
6:40 pm-12:20 am
1 stop28h 40m
$386
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Thu 3/19
1:20 am-6:52 pm
2 stops18h 32m
Chicago O'Hare Intl
Fri 3/27
1:55 pm-12:20 am
1 stop9h 25m
$466
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Thu 5/14
9:10 am-11:59 pm
1 stop15h 49m
Chicago O'Hare Intl
Tue 5/19
6:31 am-2:30 pm
2 stops30h 59m
$481
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Tue 3/10
1:20 am-10:20 am
2 stops34h 00m
Chicago O'Hare Intl
Wed 3/18
7:31 pm-12:20 am
3 stops27h 49m
$497
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Tue 3/24
1:20 am-11:18 am
2 stops34h 58m
Chicago O'Hare Intl
Sat 4/11
7:31 pm-12:20 am
3 stops27h 49m
$504
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Tue 3/17
1:20 am-1:01 pm
1 stop12h 41m
$217
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Mon 3/23
9:10 am-8:25 am
1 stop24h 15m
$244
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Mon 3/23
3:26 pm-10:10 am
2 stops19h 44m
$250
Port of SpainChicago
POS - ORD
POSORD
Port of Spain Piarco Intl
Tue 3/17
1:20 am-12:22 am
3 stops24h 02m
$297
Showing 1-10 of 14 results
Best time to book a flight from Trinidad to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Trinidad with our price prediction graph.
POS-ORD
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 Trinidad to Chicago
zzLAZ-CHI
POS-ORD
What is the cheapest month to book a flight from Trinidad to Chicago?
Currently, December is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $304). Flying from Trinidad to Chicago in April is currently the most expensive (average of $632). 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.
Related info for your journey
Find useful and relevant information for your journey from Trinidad to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Alternative routes for Trinidad to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 4, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Trinidad to Chicago by cabin class
Find flights from Trinidad to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Trinidad and Chicago flights
Browse other Trinidad and Chicago 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 Trinidad to Chicago
Discover the top 3 airlines that operate flights from Trinidad to Chicago. 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$290 | Average$706 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$299 | Average$374 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$562 | Average$698 | FlexibilityNo cancel fee | On-time71% |