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Port of Spain

$174+ Cheap flights from Illinois 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Illinois to Port of Spain

Best flights from Illinois to Port of Spain
Discover carefully curated flight deals from Illinois to Port of Spain that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 28, 2025.

This Trip.com deal was found by Cheapflights users on 12/25. 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.
Mon 1/127:20 amORD - POS
1 stop10h 40mMultiple Airlines
Fri 1/1610:10 amPOS - ORD
1 stop11h 28mMultiple Airlines
Deal found 12/25$414
This Air Canada deal was found by Cheapflights users on 12/25. 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.
Wed 1/146:00 pmORD - POS
2 stops29h 20mAir Canada
Wed 6/31:25 amPOS - ORD
1 stop14h 30mAir Canada
Deal found 12/25$423
This United Airlines deal was found by Cheapflights users on 12/26. 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 6/195:00 amSTL - POS
2 stops17h 23mUnited Airlines
Fri 6/2612:30 amPOS - STL
2 stops14h 48mUnited Airlines
Deal found 12/26$653
This American Airlines deal was found by Cheapflights users on 12/27. 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 2/216:56 pmSTL - POS
2 stops18h 43mAmerican Airlines
Sat 2/284:40 pmPOS - STL
1 stop19h 46mAmerican Airlines
Deal found 12/27$667
This Air Canada deal was found by Cheapflights users on 12/25. 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 1/1310:00 amORD - POS
1 stop13h 20mAir Canada
Wed 6/31:25 amPOS - ORD
2 stops18h 08mAir Canada
Deal found 12/25$423
This Air Canada deal was found by Cheapflights users on 12/27. 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 1/268:45 pmORD - POS
1 stop26h 35mAir Canada
Sun 2/12:20 amPOS - ORD
2 stops18h 35mAir Canada
Deal found 12/27$423
This Air Canada deal was found by Cheapflights users on 12/25. 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 1/316:00 pmORD - POS
2 stops29h 20mAir Canada
Wed 6/31:25 amPOS - ORD
2 stops18h 08mAir Canada
Deal found 12/25$423
This Booking.com deal was found by Cheapflights users on 12/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:04 pmORD - POS
2 stops53h 16mAir Canada
Fri 4/31:20 amPOS - ORD
2 stops18h 33mAir Canada
Deal found 12/27$423
This FlightHub deal was found by Cheapflights users on 12/25. 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 1/126:00 pmORD - POS
2 stops29h 20mAir Canada
Thu 1/152:20 amPOS - ORD
2 stops18h 35mAir Canada
Deal found 12/25$423
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Fri 6/195:25 amSTL - POS
1 stop7h 40mAmerican Airlines
Sat 6/277:55 amPOS - STL
2 stops14h 05mAmerican Airlines
Deal found 12/27$673
This Air Canada deal was found by Cheapflights users on 12/25. 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.
Wed 1/288:45 pmORD - POS
1 stop26h 35mAir Canada
Wed 6/31:25 amPOS - ORD
1 stop19h 00mAir Canada
Deal found 12/25$423
This United Airlines deal was found by Cheapflights users on 12/27. 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 6/206:15 amSTL - POS
1 stop16h 08mUnited Airlines
Fri 6/2612:30 amPOS - STL
1 stop17h 05mUnited Airlines
Deal found 12/27$683
This Air Canada deal was found by Cheapflights users on 12/25. 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 1/292:00 pmORD - POS
1 stop9h 20mAir Canada
Wed 6/31:25 amPOS - ORD
2 stops18h 08mAir Canada
Deal found 12/25$423
This Air Canada deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/214:05 pmSTL - POS
1 stop31h 15mAir Canada
Fri 2/272:20 amPOS - STL
1 stop15h 09mAir Canada
Deal found 12/27$473

Find flight deals from Illinois to Port of Spain

Keep the following information in mind while searching for Illinois to Port of Spain flight deals. Data was last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Air Canada)

One-way from

$174
(JetBlue)

Popular in

December

Cheapest in

October

Average price

$1,705
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
Search Deals
From Illinois to Port of Spain Piarco Intl
Search Deals
One-way flight from Illinois to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($425 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($107 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 December 28, 2025.
Use the filters below to find and compare flights from Illinois to Port of Spain that are best for you.

Fly from

Illinois

Fly to

Port of Spain

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/12

7:20 am-8:00 pm

1 stop10h 40m

Port of Spain Piarco Intl

Fri 1/16

10:10 am-7:38 pm

1 stop11h 28m

$414

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-2:55 pm

1 stop14h 30m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/13

10:00 am-1:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-6:33 pm

2 stops18h 08m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/26

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 2/1

2:20 am-6:55 pm

2 stops18h 35m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/31

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-6:33 pm

2 stops18h 08m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

6:04 pm-12:20 am

2 stops53h 16m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-6:53 pm

2 stops18h 33m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/12

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Thu 1/15

2:20 am-6:55 pm

2 stops18h 35m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/28

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-7:25 pm

1 stop19h 00m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/29

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-6:33 pm

2 stops18h 08m

$423

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/21

4:05 pm-1:20 am

1 stop31h 15m

Port of Spain Piarco Intl

Fri 2/27

2:20 am-3:29 pm

1 stop15h 09m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 19 results
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Best time to book a flight from Illinois to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain from Illinois with our price prediction graph.
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 Illinois to Port of Spain

What is the cheapest month to book a flight from Illinois to Port of Spain?

Currently, November is the cheapest month in which you can book a flight from Illinois to Port of Spain (average of $435). Flying from Illinois to Port of Spain in April is currently the most expensive (average of $628). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to POS?

Find hourly flight availability from Illinois to Port of Spain. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 28, 2025.

A simple way to save on the total cost of your ticket is to fly from Illinois to Port of Spain in the morning. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the evening.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Port of Spain. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Port of Spain from Illinois?

    Most people fly into Port of Spain Piarco Intl (POS) if they book a flight to Port of Spain from Illinois. Piarco Intl is conveniently located just 12.6 mi from Port of Spain’s city center.

  • How long is the flight from Illinois to Port of Spain?

    Airlines like Air Canada, United Airlines, and American Airlines fly from Illinois to Port of Spain in about 17h 23m. The time it takes to get you to your destination can typically vary by up to 11h 57m. There are 2641 mi between Illinois and Port of Spain. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Illinois to Port of Spain that include hotel bookings?

    Yes. In addition to deals on Illinois to Port of Spain flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Port of Spain?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Port of Spain.

  • Can I find deals for business class flights from Illinois to Port of Spain?

    Yes. Cheapflights offers flight deals from Illinois to Port of Spain by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Port of Spain?

    Currently, November is the cheapest month in which you can book a flight from Illinois to Port of Spain (average of $435). Flying from Illinois to Port of Spain in April is currently the most expensive (average of $628). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Illinois to Port of Spain

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Illinois to Port of Spain

Discover the top 3 airlines that operate flights from Illinois 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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