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Port of Spain

$455+ Cheap flights from Illinois 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
1 adult, Economy
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Cheap 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 julio 31, 2025.

Round-trip from

$455
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$735
From Illinois to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($163 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($62 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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Find flight deals from Illinois to Port of Spain

Cheapest flights from Illinois to Port of Spain
Explore the most affordable flight options available from Illinois to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on julio 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
mar. 9/1610:27 amORD - POS
1 stop31h 28mMultiple Airlines
vie. 9/269:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 7/30$455
This Copa Airlines deal was found by Cheapflights users on 7/30. 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.
vie. 9/193:07 pmORD - POS
1 stop9h 39mCopa Airlines
dom. 9/283:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Deal found 7/30$526
This Air Canada deal was found by Cheapflights users on 7/30. 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.
mar. 11/1110:00 amORD - POS
1 stop13h 15mAir Canada
vie. 11/212:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 7/30$537
This American Airlines deal was found by Cheapflights users on 7/31. 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.
vie. 8/85:00 amORD - POS
1 stop8h 25mAmerican Airlines
mar. 8/197:00 amPOS - ORD
1 stop16h 41mAmerican Airlines
Deal found 7/31$548
This American Airlines deal was found by Cheapflights users on 7/30. 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.
dom. 11/95:21 amSTL - POS
1 stop7h 55mAmerican Airlines
dom. 11/167:01 amPOS - STL
1 stop17h 31mAmerican Airlines
Deal found 7/30$603
This United Airlines deal was found by Cheapflights users on 7/31. 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.
mié. 10/2212:45 pmORD - POS
1 stop9h 38mUnited Airlines
sáb. 10/2512:30 amPOS - ORD
1 stop20h 26mUnited Airlines
Deal found 7/31$658
This United Airlines deal was found by Cheapflights users on 7/30. 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.
dom. 11/96:15 amSTL - POS
1 stop16h 08mUnited Airlines
sáb. 11/151:30 amPOS - STL
1 stop19h 17mUnited Airlines
Deal found 7/30$688
This Air Canada deal was found by Cheapflights users on 7/28. 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.
mié. 12/174:05 pmSTL - POS
1 stop31h 10mAir Canada
mar. 1/62:15 amPOS - STL
1 stop15h 14mAir Canada
Deal found 7/28$1,571
This Justfly.com deal was found by Cheapflights users on 7/28. 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.
vie. 12/194:05 pmSTL - POS
1 stop11h 35mMultiple Airlines
vie. 1/22:15 amPOS - STL
1 stop15h 14mMultiple Airlines
Deal found 7/28$3,767

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 julio 31, 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

mar. 9/16

10:27 am-6:55 pm

1 stop31h 28m

Port of Spain Piarco Intl

vie. 9/26

9:10 am-9:18 am

1 stop25h 08m

$455

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 9/19

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

dom. 9/28

3:51 am-1:41 pm

1 stop10h 50m

$526

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 11/11

10:00 am-1:15 am

1 stop13h 15m

Port of Spain Piarco Intl

vie. 11/21

2:15 am-1:01 pm

1 stop12h 46m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 9/19

7:15 pm-2:16 pm

1 stop18h 01m

Port of Spain Piarco Intl

lun. 9/29

3:25 pm-11:49 pm

1 stop9h 24m

$548

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

dom. 11/9

5:21 am-3:16 pm

1 stop7h 55m

Port of Spain Piarco Intl

dom. 11/16

7:01 am-10:32 pm

1 stop17h 31m

$603

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 10/22

12:45 pm-11:23 pm

1 stop9h 38m

Port of Spain Piarco Intl

sáb. 10/25

12:30 am-7:56 pm

1 stop20h 26m

$658

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

dom. 11/9

6:15 am-12:23 am

1 stop16h 08m

Port of Spain Piarco Intl

sáb. 11/15

1:30 am-6:47 pm

1 stop19h 17m

$688

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 11/25

8:35 pm-4:28 pm

2 stops17h 53m

Port of Spain Piarco Intl

dom. 11/30

5:53 pm-10:45 pm

1 stop30h 52m

$866

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

mié. 12/17

4:05 pm-1:15 am

1 stop31h 10m

Port of Spain Piarco Intl

mar. 1/6

2:15 am-3:29 pm

1 stop15h 14m

$1,571

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

vie. 12/19

4:05 pm-5:40 am

1 stop11h 35m

Port of Spain Piarco Intl

vie. 1/2

2:15 am-3:29 pm

1 stop15h 14m

$3,767

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 11 results
1
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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, October 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 December is currently the most expensive (average of $710). 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 julio 31, 2025.

When flying from Illinois to Port of Spain, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 julio 31, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines from Illinois to Port of Spain by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,493 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,900 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,851 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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.

  • 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, October 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 December is currently the most expensive (average of $710). 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 2 airlines flying from Illinois to Port of Spain

Discover the top 2 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$605FlexibilityNo cancel feeOn-time71%

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