$241+ Cheap flights from O'Hare Intl (ORD) to Port of Spain (POS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Oct 9 — Oct 161
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
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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 September 9, 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 September 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:04 am -
1 stop10h 56m
Thu 10/2210:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:04 am -
1 stop10h 56m
Fri 10/2310:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$536
This Air Canada deal was found by Cheapflights users on 9/8. 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 10/158:40 pm -
1 stop26h 35m
Sun 10/181:20 am -
1 stop13h 03m
Deal found 9/8![Air Canada logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 am -
1 stop10h 56m
Mon 10/1910:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$551
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:04 am -
1 stop10h 56m
Thu 10/2210:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:04 am -
1 stop10h 56m
Wed 10/219:10 am -
2 stops25h 11m
Deal found 9/4![Multiple Airlines logo]()
$562
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/168:04 am -
1 stop10h 56m
Thu 10/2210:10 am -
1 stop30h 20m
Deal found 9/6![Multiple Airlines logo]()
$565
This Expedia deal was found by Cheapflights users on 9/4. 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.
Fri 10/169:55 am -
1 stop13h 20m
Mon 10/191:20 am -
1 stop14h 35m
Deal found 9/4![Air Canada logo]()
$575
This Air Canada deal was found by Cheapflights users on 9/5. 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 10/92:15 pm -
1 stop9h 00m
Sun 10/111:20 am -
1 stop13h 03m
Deal found 9/5![Air Canada logo]()
$576
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 am -
1 stop10h 56m
Fri 10/2310:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$577
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 September 9, 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 September 9, 2026.
This Air Canada deal was found by Cheapflights users on 9/8. 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 1/188:50 pm -
1 stop26h 10m
Sun 1/312:15 am -
2 stops14h 37m
Deal found 9/8![Air Canada logo]()
$591
This Copa Airlines deal was found by Cheapflights users on 9/5. 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 -
1 stop28h 16m
Mon 10/263:44 am -
1 stop22h 21m
Deal found 9/5![Copa Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 9/8. 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 2/207:10 pm -
1 stop16h 20m
Thu 2/252:30 pm -
1 stop12h 08m
Deal found 9/8![American Airlines logo]()
$630
This United Airlines deal was found by Cheapflights users on 9/6. 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 1/2911:29 am -
1 stop11h 36m
Sat 2/62:20 am -
1 stop10h 40m
Deal found 9/6![United Airlines logo]()
$640
This Copa Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/227:35 am -
1 stop16h 20m
Mon 2/12:12 pm -
1 stop11h 59m
Deal found 9/6![Copa Airlines logo]()
$618
This Air Canada deal was found by Cheapflights users on 9/6. 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 1/227:05 am -
2 stops15h 55m
Sun 1/312:15 am -
1 stop12h 58m
Deal found 9/6![Air Canada logo]()
$633
This Copa Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:35 am -
1 stop16h 19m
Sat 11/143:40 am -
1 stop11h 06m
Deal found 9/8![Copa Airlines logo]()
$618
This American Airlines deal was found by Cheapflights users on 9/8. 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 11/48:57 pm -
2 stops16h 40m
Sun 11/154:42 pm -
1 stop18h 50m
Deal found 9/8![American Airlines logo]()
$689
This United Airlines deal was found by Cheapflights users on 9/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:45 pm -
1 stop9h 38m
Thu 10/2212:30 am -
1 stop12h 55m
Deal found 9/4![United Airlines logo]()
$755
This United Airlines deal was found by Cheapflights users on 9/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:45 pm -
1 stop9h 38m
Fri 10/3012:25 am -
1 stop11h 52m
Deal found 9/4![United Airlines logo]()
$760
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 September 9, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Port of Spain. Data last updated September 9, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 9/5. 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 10/92:15 pm -
1 stop9h 00m
Sun 10/111:20 am -
1 stop13h 03m
Deal found 9/5![Air Canada logo]()
$576
This Air Canada deal was found by Cheapflights users on 9/8. 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 10/158:40 pm -
1 stop26h 35m
Sun 10/181:20 am -
1 stop13h 03m
Deal found 9/8![Air Canada logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 am -
1 stop10h 56m
Mon 10/1910:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$551
This Kiwi.com deal was found by Cheapflights users on 9/6. 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 10/168:04 am -
1 stop10h 56m
Thu 10/2210:10 am -
1 stop30h 20m
Deal found 9/6![Multiple Airlines logo]()
$565
This Expedia deal was found by Cheapflights users on 9/4. 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.
Fri 10/169:55 am -
1 stop13h 20m
Mon 10/191:20 am -
1 stop14h 35m
Deal found 9/4![Air Canada logo]()
$575
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:04 am -
1 stop10h 56m
Fri 10/2310:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$577
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:04 am -
1 stop10h 56m
Thu 10/2210:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$557
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:04 am -
1 stop10h 56m
Thu 10/2210:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:04 am -
1 stop10h 56m
Fri 10/2310:10 am -
1 stop30h 20m
Deal found 9/4![Multiple Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:04 am -
1 stop10h 56m
Wed 10/219:10 am -
2 stops25h 11m
Deal found 9/4![Multiple Airlines logo]()
$562
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 September 9, 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 September 9, 2026.
This Trip.com deal was found by Cheapflights users on 9/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:35 pm -
1 stop29h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Air Canada logo]()
$241
This Expedia deal was found by Cheapflights users on 9/8. 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.
Sat 9/265:35 pm -
1 stop29h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Air Canada logo]()
$245
This Travelocity deal was found by Cheapflights users on 9/8. 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 10/76:21 pm -
2 stops52h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Air Canada logo]()
$269
This Travelocity deal was found by Cheapflights users on 9/7. 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.
Sat 1/234:30 pm -
1 stop30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Air Canada logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 10/77:11 am -
3 stops17h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:44 pm -
2 stops22h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Multiple Airlines logo]()
$337
This United Airlines deal was found by Cheapflights users on 9/8. 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 10/710:32 am -
1 stop11h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![United Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 9/223:50 pm -
3 stops20h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$366
This Mytrip deal was found by Cheapflights users on 9/8. 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 9/265:35 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Multiple Airlines logo]()
$379
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 September 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $510 (Kiwi.com) |
One-way from | $241 (Trip.com) |
Popular in | February |
Cheapest in | November |
Average price | $820 |
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 7,457,451 searches. Data last updated September 9, 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 Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 9/26
2:01 pm-12:15 am
2 stops33h 14m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$283
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 1/23
4:30 pm-1:00 am
1 stop30h 30m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$319
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Wed 10/7
7:11 am-1:47 am
3 stops17h 36m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$331
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Wed 10/7
10:32 am-11:23 pm
1 stop11h 51m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$348
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 9/22
9:55 am-5:30 am
1 stop18h 35m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$370
Quickest round-trip
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 9/26
5:35 pm-5:30 am
1 stop10h 55m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$379
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 2/26
6:00 am-12:23 am
1 stop16h 23m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$416
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Thu 9/17
3:45 pm-12:15 am
1 stop31h 30m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$445
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 1/23
6:20 pm-7:40 pm
3 stops23h 20m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$535
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 1/18
8:50 pm-1:00 am
1 stop26h 10m
Port of Spain Piarco Intl
Sun 1/31
2:15 am-2:52 pm
2 stops14h 37m
$591
Showing 1-10 of 19 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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’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 September 9, 2026.
Get a feel of what it's like to fly with United Airlines,American Airlines, andAir Canada 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
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.6
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Entertainment
7.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
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O'Hare Intl and Port of Spain flights
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Top 3 airlines flying from O'Hare Intl to Port of Spain
Discover the top 3 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 7,457,451 searches. Data last updated September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$317 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$578 | Average$759 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$589 | Average$739 | FlexibilityNo cancel fee | On-time71% |