$323+ Cheap flights from Chicago (CHI) 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Nov 22 — Nov 291
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Port of Spain
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Port of SpainExplore the most affordable flight options available from Chicago to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
Explore the most affordable flight options available from Chicago to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/18. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:13 pm -
1 stop21h 14m
Mon 12/213:23 am -
1 stop11h 23m
Deal found 10/18![Copa Airlines logo]()
$648
This American Airlines deal was found by Cheapflights users on 10/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:50 pm -
1 stop17h 45m
Sat 12/124:42 pm -
1 stop18h 48m
Deal found 10/21![American Airlines logo]()
$660
This Air Canada deal was found by Cheapflights users on 10/19. 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.
Thu 12/37:05 am -
2 stops15h 55m
Thu 12/102:15 am -
2 stops14h 47m
Deal found 10/19![Air Canada logo]()
$692
This deal was found by Cheapflights users on 10/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:05 am -
1 stop12h 55m
Fri 12/112:15 am -
1 stop12h 58m
Deal found 10/20![Air Canada logo]()
$694
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Sun 11/87:29 am -
1 stop14h 49m
Sat 11/141:25 am -
1 stop10h 46m
Deal found 10/18![United Airlines logo]()
$705
This Justfly.com deal was found by Cheapflights users on 10/19. 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.
Tue 11/105:58 pm -
2 stops53h 02m
Sun 11/222:15 am -
2 stops42h 15m
Deal found 10/19![Air Canada logo]()
$725
This Mytrip deal was found by Cheapflights users on 10/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:00 pm -
3 stops25h 30m
Sat 12/129:10 am -
2 stops24h 10m
Deal found 10/22![Multiple Airlines logo]()
$731
This Travelocity deal was found by Cheapflights users on 10/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:58 pm -
2 stops53h 02m
Tue 12/229:00 am -
2 stops28h 07m
Deal found 10/18![Multiple Airlines logo]()
$738
This Travelocity deal was found by Cheapflights users on 10/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:45 am -
2 stops32h 55m
Thu 11/262:15 am -
2 stops42h 15m
Deal found 10/18![Multiple Airlines logo]()
$743
Best flights from Chicago to Port of SpainDiscover carefully curated flight deals from Chicago to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
Discover carefully curated flight deals from Chicago to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
This Copa Airlines deal was found by Cheapflights users on 10/22. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/197:35 am -
1 stop16h 20m
Mon 1/252:14 pm -
1 stop24h 32m
Deal found 10/22![Copa Airlines logo]()
$648
This American Airlines deal was found by Cheapflights users on 10/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:15 pm -
1 stop19h 20m
Tue 12/226:05 am -
2 stops12h 14m
Deal found 10/18![American Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Sun 11/87:29 am -
1 stop14h 49m
Sat 11/141:25 am -
1 stop10h 46m
Deal found 10/18![United Airlines logo]()
$705
This Travelocity deal was found by Cheapflights users on 10/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:58 pm -
2 stops53h 02m
Tue 12/229:00 am -
2 stops28h 07m
Deal found 10/18![Multiple Airlines logo]()
$738
This Copa Airlines deal was found by Cheapflights users on 10/18. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:13 pm -
1 stop21h 14m
Mon 12/213:23 am -
1 stop11h 23m
Deal found 10/18![Copa Airlines logo]()
$648
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:40 pm -
1 stop9h 38m
Sun 11/221:25 am -
1 stop11h 52m
Deal found 10/19![United Airlines logo]()
$705
This Copa Airlines deal was found by Cheapflights users on 10/22. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/172:13 pm -
1 stop21h 06m
Sun 1/243:26 am -
1 stop22h 41m
Deal found 10/22![Copa Airlines logo]()
$648
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Sun 11/89:06 pm -
2 stops16h 31m
Sun 11/154:42 pm -
1 stop18h 50m
Deal found 10/19![American Airlines logo]()
$779
This Copa Airlines deal was found by Cheapflights users on 10/22. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/152:13 pm -
1 stop9h 42m
Sat 1/233:26 am -
1 stop22h 41m
Deal found 10/22![Copa Airlines logo]()
$648
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:40 pm -
1 stop9h 38m
Sat 12/121:25 am -
1 stop15h 18m
Deal found 10/22![United Airlines logo]()
$790
This United Airlines deal was found by Cheapflights users on 10/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/157:45 am -
1 stop14h 35m
Mon 3/2212:25 am -
1 stop10h 44m
Deal found 10/21![United Airlines logo]()
$790
This Copa Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 11/142:13 pm -
1 stop9h 41m
Sat 11/213:40 am -
1 stop22h 31m
Deal found 10/19![Copa Airlines logo]()
$788
Last-minute flights from Chicago to Port of SpainDiscover last-minute flight deals from Chicago to Port of Spain. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Port of Spain. Data last updated October 23, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:15 am -
1 stop13h 03m
Mon 11/21:25 am -
1 stop11h 52m
Deal found 10/19![United Airlines logo]()
$837
This Mytrip deal was found by Cheapflights users on 10/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:55 pm -
3 stops29h 05m
Tue 11/38:30 am -
2 stops34h 37m
Deal found 10/19![Multiple Airlines logo]()
$845
This United Airlines deal was found by Cheapflights users on 10/18. 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.
Sun 11/87:29 am -
1 stop14h 49m
Sat 11/141:25 am -
1 stop10h 46m
Deal found 10/18![United Airlines logo]()
$705
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Sun 11/89:06 pm -
2 stops16h 31m
Sun 11/154:42 pm -
1 stop18h 50m
Deal found 10/19![American Airlines logo]()
$779
This Justfly.com deal was found by Cheapflights users on 10/19. 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.
Tue 11/105:58 pm -
2 stops53h 02m
Sun 11/222:15 am -
2 stops42h 15m
Deal found 10/19![Air Canada logo]()
$725
This Copa Airlines deal was found by Cheapflights users on 10/19. 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.
Sat 11/142:13 pm -
1 stop9h 41m
Sat 11/213:40 am -
1 stop22h 31m
Deal found 10/19![Copa Airlines logo]()
$788
This American Airlines deal was found by Cheapflights users on 10/19. 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 11/1411:47 am -
2 stops25h 50m
Sun 11/224:42 pm -
1 stop17h 18m
Deal found 10/19![American Airlines logo]()
$835
This Travelocity deal was found by Cheapflights users on 10/18. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:45 am -
2 stops32h 55m
Thu 11/262:15 am -
2 stops42h 15m
Deal found 10/18![Multiple Airlines logo]()
$743
One-way flights from Chicago to Port of SpainSearch for one-way flight options from Chicago to Port of Spain. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
Search for one-way flight options from Chicago to Port of Spain. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:51 am -
3 stops38h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Multiple Airlines logo]()
$323
This Expedia deal was found by Cheapflights users on 10/22. 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.
Tue 12/15:58 pm -
2 stops53h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Air Canada logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/97:55 am -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$344
This Expedia deal was found by Cheapflights users on 10/18. 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.
Thu 1/214:30 pm -
1 stop30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Air Canada logo]()
$349
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/147:35 pm -
2 stops21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$350
This Expedia deal was found by Cheapflights users on 10/18. 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.
Tue 11/103:40 pm -
2 stops55h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Air Canada logo]()
$352
This Justfly.com deal was found by Cheapflights users on 10/18. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/114:30 pm -
1 stop30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Air Canada logo]()
$354
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/127:55 am -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/137:55 am -
1 stop10h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$374
Find flight deals from Chicago to Port of Spain
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $648 (Copa Airlines) |
One-way from | $323 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 October 23, 2026.
Use the filters below to find and compare flights from Chicago 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
Tue 11/10
9:51 am-1:54 am
3 stops38h 03m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$323
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 12/1
5:58 pm-1:00 am
2 stops53h 02m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$324
Quickest round-trip
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Thu 1/21
10:05 am-1:00 am
1 stop12h 55m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$354
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 12/1
5:45 am-12:18 am
1 stop16h 33m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$378
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 12/1
3:55 pm-7:30 pm
3 stops25h 35m
Port of Spain Piarco Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$402
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 1/19
7:35 am-1:55 am
1 stop16h 20m
Port of Spain Piarco Intl
Mon 1/25
2:14 pm-12:46 pm
1 stop24h 32m
$648
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 12/1
2:13 pm-1:27 pm
1 stop21h 14m
Port of Spain Piarco Intl
Mon 12/21
3:23 am-12:46 pm
1 stop11h 23m
$648
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sun 1/17
2:13 pm-1:19 pm
1 stop21h 06m
Port of Spain Piarco Intl
Sun 1/24
3:26 am-12:07 am
1 stop22h 41m
$648
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 1/15
2:13 pm-1:55 am
1 stop9h 42m
Port of Spain Piarco Intl
Sat 1/23
3:26 am-12:07 am
1 stop22h 41m
$648
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Tue 12/1
6:15 pm-3:35 pm
1 stop19h 20m
Port of Spain Piarco Intl
Tue 12/22
6:05 am-4:19 pm
2 stops12h 14m
$665
Showing 1-10 of 22 resultsSorted by cheapest first
Compare providers for flights from Chicago 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 Chicago to Port of Spain in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-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-Port of Spain flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Port of Spain flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-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-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 Chicago to Port of Spain
Have a flexible travel schedule? Discover the best time to fly to Port of Spain from Chicago with our price prediction graph.
CHI-POS
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 Port of Spain
CHI-POS
ORD-POS
What is the cheapest month to book a flight from Chicago to Port of Spain?
Currently, November is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $443). Flying from Chicago to Port of Spain in December is currently the most expensive (average of $1,248). 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.
What’s the top layover airport for flights from Chicago to Port of Spain?
Share of 1-stop round-trip flights from Chicago 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 57% of 1-stop itineraries from Chicago to Port of Spain on Cheapflights.
What’s the cheapest layover airport for flights from Chicago to Port of Spain?
Average round-trip fare for 1-stop flights from Chicago to Port of Spain, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Miami (MIA) is the most affordable 1-stop option, with an average round-trip price of $594.
What’s the fastest layover option from Chicago to Port of Spain?
Shortest average travel time for 1-stop one-way flights from Chicago 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 to Port of Spain?
Average layover duration for 1-stop one-way flights from Chicago 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 October 23, 2026.
Read reviews from past customers who have flown Air Canada and American Airlines from Chicago to Port of Spain. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.1
Entertainment
6.8
Food
6.3
Overall
7.1
Crew
7.8
Boarding
7.3
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
Comfort
7.1
Entertainment
6.8
Food
6.3
Overall
7.1
Crew
7.8
Boarding
7.3
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
Comfort
7.1
Entertainment
6.8
Food
6.3
Overall
7.1
Crew
7.8
Boarding
7.3
Reviews
1 / 20
6.0
GoodAnonymous,Aug 2026
PDX - YVR
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Top 3 airlines flying from Chicago to Port of Spain
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$317 | Average$443 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$578 | Average$759 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$623 | Average$739 | FlexibilityNo cancel fee | On-time71% |