$219+ Cheap flights from O'Hare Intl (ORD) to Port of Spain (POS)
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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Aug 22 — Aug 291
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Port of Spain 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 O'Hare Intl to Port of Spain
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Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to Port of SpainExplore the most affordable flight options available from O'Hare Intl to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
Explore the most affordable flight options available from O'Hare Intl to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.
This Justfly.com deal was found by Cheapflights users on 7/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- POS
1 stop11h 20m
JetBlue
Mon 8/318:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$456
This Expedia deal was found by Cheapflights users on 7/18. 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 9/289:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Fri 10/21:20 am
POS
- ORD
1 stop16h 38m
Air Canada
Deal found 7/18![Air Canada logo]()
$485
This Air Canada deal was found by Cheapflights users on 7/19. 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 12/58:50 pm
ORD
- POS
1 stop26h 10m
Air Canada
Fri 12/112:15 am
POS
- ORD
1 stop12h 58m
Air Canada
Deal found 7/19![Air Canada logo]()
$533
This Expedia deal was found by Cheapflights users on 7/22. 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.
Wed 8/196:30 pm
ORD
- POS
1 stop18h 14m
JetBlue
Wed 8/268:00 pm
POS
- ORD
1 stop13h 46m
JetBlue
Deal found 7/22![JetBlue logo]()
$540
This Travelocity deal was found by Cheapflights users on 7/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:21 pm
ORD
- POS
2 stops52h 54m
Air Canada
Sun 9/201:20 am
POS
- ORD
1 stop14h 35m
Air Canada
Deal found 7/21![Air Canada logo]()
$575
This FlightHub deal was found by Cheapflights users on 7/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:01 am
ORD
- POS
2 stops30h 34m
JetBlue
Fri 8/288:00 pm
POS
- ORD
1 stop13h 46m
JetBlue
Deal found 7/21![JetBlue logo]()
$578
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 9/68:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Sun 9/1310:10 am
POS
- ORD
2 stops26h 52m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$605
Best flights from O'Hare Intl to Port of SpainDiscover carefully curated flight deals from O'Hare Intl to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
Discover carefully curated flight deals from O'Hare Intl to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 23, 2026.
This FlightHub deal was found by Cheapflights users on 7/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:01 am
ORD
- POS
2 stops30h 34m
JetBlue
Fri 8/288:00 pm
POS
- ORD
1 stop13h 46m
JetBlue
Deal found 7/21![JetBlue logo]()
$578
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 9/68:05 am
ORD
- POS
1 stop10h 55m
Multiple Airlines
Sun 9/1310:10 am
POS
- ORD
2 stops26h 52m
Multiple Airlines
Deal found 7/23![Multiple Airlines logo]()
$605
This Copa Airlines deal was found by Cheapflights users on 7/20. 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.
Sat 8/228:02 am
ORD
- POS
1 stop28h 15m
Copa Airlines
Mon 8/312:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 7/20![Copa Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Wed 9/212:47 pm
ORD
- POS
1 stop9h 36m
United Airlines
Tue 9/812:30 am
POS
- ORD
1 stop10h 45m
United Airlines
Deal found 7/18![United Airlines logo]()
$630
This Copa Airlines deal was found by Cheapflights users on 7/19. 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 8/168:02 am
ORD
- POS
1 stop28h 15m
Copa Airlines
Sun 8/232:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 7/19![Copa Airlines logo]()
$618
This Air Canada deal was found by Cheapflights users on 7/21. 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.
Thu 10/228:40 pm
ORD
- POS
2 stops22h 00m
Multiple Airlines
Fri 10/231:20 am
POS
- ORD
2 stops14h 32m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$621
This United Airlines deal was found by Cheapflights users on 7/23. 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 9/612:16 pm
ORD
- POS
1 stop11h 34m
United Airlines
Sat 9/1212:30 am
POS
- ORD
1 stop11h 50m
United Airlines
Deal found 7/23![United Airlines logo]()
$630
This Justfly.com deal was found by Cheapflights users on 7/19. 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.
Wed 8/126:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Mon 8/178:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/19![JetBlue logo]()
$633
This Copa Airlines deal was found by Cheapflights users on 7/20. 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 10/208:01 am
ORD
- POS
1 stop28h 16m
Copa Airlines
Wed 10/283:44 am
POS
- ORD
1 stop22h 21m
Copa Airlines
Deal found 7/20![Copa Airlines logo]()
$618
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Fri 9/412:47 pm
ORD
- POS
1 stop9h 36m
United Airlines
Thu 9/1012:30 am
POS
- ORD
1 stop11h 50m
United Airlines
Deal found 7/23![United Airlines logo]()
$630
Last-minute flights from O'Hare Intl to Port of SpainDiscover last-minute flight deals from O'Hare Intl to Port of Spain. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Port of Spain. Data last updated July 23, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 7/21. 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 8/118:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Mon 8/171:25 am
POS
- ORD
1 stop12h 57m
Air Canada
Deal found 7/21![Air Canada logo]()
$615
This Orbitz deal was found by Cheapflights users on 7/19. 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.
Tue 8/113:45 pm
ORD
- POS
1 stop31h 30m
Multiple Airlines
Mon 8/178:00 pm
POS
- ORD
1 stop13h 43m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$629
This Justfly.com deal was found by Cheapflights users on 7/19. 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.
Wed 8/126:00 am
ORD
- POS
1 stop11h 35m
JetBlue
Mon 8/178:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/19![JetBlue logo]()
$633
This Expedia deal was found by Cheapflights users on 7/22. 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.
Wed 8/196:30 pm
ORD
- POS
1 stop18h 14m
JetBlue
Wed 8/268:00 pm
POS
- ORD
1 stop13h 46m
JetBlue
Deal found 7/22![JetBlue logo]()
$540
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:00 am
ORD
- POS
2 stops14h 18m
American Airlines
Wed 8/267:00 am
POS
- ORD
1 stop11h 54m
American Airlines
Deal found 7/22![American Airlines logo]()
$639
This Justfly.com deal was found by Cheapflights users on 7/22. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 am
ORD
- POS
1 stop11h 20m
JetBlue
Mon 8/318:00 pm
POS
- ORD
1 stop13h 43m
JetBlue
Deal found 7/22![JetBlue logo]()
$456
This Copa Airlines deal was found by Cheapflights users on 7/20. 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.
Sat 8/228:02 am
ORD
- POS
1 stop28h 15m
Copa Airlines
Mon 8/312:19 pm
POS
- ORD
1 stop11h 43m
Copa Airlines
Deal found 7/20![Copa Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 8/228:19 am
ORD
- POS
2 stops13h 59m
American Airlines
Mon 8/317:00 am
POS
- ORD
2 stops14h 30m
American Airlines
Deal found 7/19![American Airlines logo]()
$634
This FlightHub deal was found by Cheapflights users on 7/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2411:01 am
ORD
- POS
2 stops30h 34m
JetBlue
Fri 8/288:00 pm
POS
- ORD
1 stop13h 46m
JetBlue
Deal found 7/21![JetBlue logo]()
$578
One-way flights from O'Hare Intl to Port of SpainSearch for one-way flight options from O'Hare Intl to Port of Spain. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
Search for one-way flight options from O'Hare Intl to Port of Spain. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Expedia deal was found by Cheapflights users on 7/19. 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 9/178:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Deal found 7/19![Air Canada logo]()
$219
This Air Canada deal was found by Cheapflights users on 7/19. 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 8/169:50 am
ORD
- POS
1 stop13h 25m
Air Canada
Deal found 7/19![Air Canada logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Fri 9/187:45 am
ORD
- POS
1 stop11h 15m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$247
This Air Canada deal was found by Cheapflights users on 7/19. 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 9/186:21 pm
ORD
- POS
2 stops52h 54m
Air Canada
Deal found 7/19![Air Canada logo]()
$259
This Air Canada deal was found by Cheapflights users on 7/23. 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 8/278:40 pm
ORD
- POS
1 stop26h 35m
Air Canada
Deal found 7/23![Air Canada logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/177:45 am
ORD
- POS
1 stop11h 15m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$261
This Air Canada deal was found by Cheapflights users on 7/19. 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 9/148:45 am
ORD
- POS
2 stops14h 30m
Air Canada
Deal found 7/19![Air Canada logo]()
$262
This Air Canada deal was found by Cheapflights users on 7/23. 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 8/288:40 am
ORD
- POS
2 stops14h 35m
Air Canada
Deal found 7/23![Air Canada logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 8/1912:44 am
ORD
- POS
2 stops35h 33m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/19. 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.
Sat 9/192:46 pm
ORD
- POS
3 stops27h 09m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/142:46 pm
ORD
- POS
2 stops27h 09m
Multiple Airlines
Deal found 7/19![Multiple Airlines logo]()
$300
Find flight deals from O'Hare Intl to Port of Spain
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Port of Spain (POS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $456 (Justfly.com) |
One-way from | $219 (Expedia) |
Popular in | February |
Cheapest in | November |
Average price | $649 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Port of Spain 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 23, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Port of Spain 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
Mon 8/24
11:01 am-6:35 pm
2 stops30h 34m
Port of Spain Piarco Intl
Fri 8/28
8:00 pm-8:46 am
1 stop13h 46m
$578
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 9/6
8:05 am-8:00 pm
1 stop10h 55m
Port of Spain Piarco Intl
Sun 9/13
10:10 am-12:02 pm
2 stops26h 52m
$605
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sat 8/22
8:02 am-1:17 pm
1 stop28h 15m
Port of Spain Piarco Intl
Mon 8/31
2:19 pm-1:02 am
1 stop11h 43m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 8/16
8:02 am-1:17 pm
1 stop28h 15m
Port of Spain Piarco Intl
Sun 8/23
2:19 pm-1:02 am
1 stop11h 43m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Tue 10/20
8:01 am-1:17 pm
1 stop28h 16m
Port of Spain Piarco Intl
Wed 10/28
3:44 am-1:05 am
1 stop22h 21m
$618
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Thu 10/22
8:40 pm-7:40 pm
2 stops22h 00m
Port of Spain Piarco Intl
Fri 10/23
1:20 am-2:52 pm
2 stops14h 32m
$621
Quickest round-trip
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 9/2
12:47 pm-11:23 pm
1 stop9h 36m
Port of Spain Piarco Intl
Tue 9/8
12:30 am-10:15 am
1 stop10h 45m
$630
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Sun 9/6
12:16 pm-12:50 am
1 stop11h 34m
Port of Spain Piarco Intl
Sat 9/12
12:30 am-11:20 am
1 stop11h 50m
$630
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Fri 9/4
12:47 pm-11:23 pm
1 stop9h 36m
Port of Spain Piarco Intl
Thu 9/10
12:30 am-11:20 am
1 stop11h 50m
$630
ChicagoPort of Spain
ORD - POS
ORDPOS
Chicago O'Hare Intl
Wed 8/12
6:00 am-6:35 pm
1 stop11h 35m
Port of Spain Piarco Intl
Mon 8/17
8:00 pm-8:43 am
1 stop13h 43m
$633
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from O'Hare Intl to Port of Spain
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Port of Spain in July.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Port of Spain flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Port of Spain flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Port of Spain flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Port of Spain flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Port of Spain flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from O'Hare Intl to Port of Spain
Have a flexible travel schedule? Discover the best time to fly to Port of Spain from O'Hare Intl 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 O'Hare Intl Airport to Port of Spain
Prices
More
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Port of Spain?
Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Port of Spain (average of $443). Flying from Chicago O'Hare Intl Airport to Port of Spain in February is currently the most expensive (average of $948). 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.
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Port of Spain?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Port of Spain flights typically cost between $576 and $706 in August.The cheapest round-trip price found within the last 5 days was $456 on JetBlue (Aug 22-Aug 31).
What’s the top layover airport for flights from Chicago O'Hare Intl Airport to Port of Spain?
Share of 1-stop round-trip flights from Chicago O'Hare Intl Airport to Port of Spain chosen by Cheapflights users in the past 12 months, using the same layover each way.
Miami (MIA) – chosen by Cheapflights users on 50% of 1-stop itineraries from Chicago O'Hare Intl Airport to Port of Spain on Cheapflights.
What’s the cheapest layover airport for flights from Chicago O'Hare Intl Airport to Port of Spain?
Average round-trip fare for 1-stop flights from Chicago O'Hare Intl Airport to Port of Spain, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $432.
What’s the fastest layover option from Chicago O'Hare Intl Airport to Port of Spain?
Shortest average travel time for 1-stop one-way flights from Chicago O'Hare Intl Airport to Port of Spain, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Miami (MIA) have the shortest average one-way travel time for 1-stop routes: 8h 03m.
Which airport typically offers the quickest layover for flights from Chicago O'Hare Intl Airport to Port of Spain?
Average layover duration for 1-stop one-way flights from Chicago O'Hare Intl Airport to Port of Spain, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 27m.
Reviews of airlines servicing Port of Spain
Get insights into the airlines that provide service to Port of Spain. 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 Port of Spain. Reviews last updated July 23, 2026.
Get a feel of what it's like to fly with Copa Airlines,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Port of Spain by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.9
Boarding
7.8
Overall
7.6
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Food
6.9
Boarding
7.8
Overall
7.6
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Food
6.9
Boarding
7.8
Overall
7.6
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Food
6.9
Boarding
7.8
Overall
7.6
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Food
6.9
Boarding
7.8
Overall
7.6
Crew
8.1
Entertainment
6.8
Comfort
7.4
Reviews
1 / 20
2.0
MediocreAnonymous,Jul 2026
BOS - PTY
Related info for your journey
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O'Hare Intl and Port of Spain flights
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Top 4 airlines flying from O'Hare Intl to Port of Spain
Discover the top 4 airlines that operate flights from O'Hare Intl to Port of Spain. 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$285 | Average$627 | 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$706 | FlexibilityNo cancel fee | On-time69% |