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Port of Spain

$181+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
dic 4 — dic 111
gio 12/4
gio 12/11
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 novembre 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$424
(Trip.com)

One-way from

$181
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$621
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
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From Illinois to Port of Spain Piarco Intl
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One-way flight from Illinois to Port of Spain Piarco Intl
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Highest demand for flights based on searches. 16% potential increase in price ($134 potential increase over avg. RT price).
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Cheapest flight prices on average. 11% potential price decrease ($71 potential savings vs. average RT price).
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Average for round-trip flights in November 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 novembre 4, 2025.

This Trip.com deal was found by Cheapflights users on 11/3. 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.
lun 12/87:10 amORD - POS
1 stop10h 50mMultiple Airlines
ven 12/1210:10 amPOS - ORD
1 stop15h 59mMultiple Airlines
Deal found 11/3$424
This Mytrip deal was found by Cheapflights users on 11/2. 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.
mer 12/38:15 pmORD - POS
1 stop26h 55mMultiple Airlines
gio 12/119:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 11/2$455
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
mer 11/123:26 pmORD - POS
1 stop26h 34mMultiple Airlines
mar 11/183:35 pmPOS - ORD
2 stops23h 10mMultiple Airlines
Deal found 11/2$477
This Kiwi.com deal was found by Cheapflights users on 11/2. 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.
lun 11/175:10 amORD - POS
1 stop12h 50mMultiple Airlines
mer 12/35:55 pmPOS - ORD
2 stops25h 32mMultiple Airlines
Deal found 11/2$481
This Air Canada deal was found by Cheapflights users on 11/3. 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.
sab 11/228:15 pmORD - POS
1 stop26h 55mAir Canada
ven 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/3$483
This Air Canada deal was found by Cheapflights users on 11/3. 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.
ven 11/216:05 pmORD - POS
2 stops53h 05mAir Canada
ven 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 11/3$493
This Mytrip deal was found by Cheapflights users on 11/2. 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.
sab 11/88:15 pmORD - POS
1 stop26h 55mMultiple Airlines
gio 11/1310:10 amPOS - ORD
1 stop16h 17mMultiple Airlines
Deal found 11/2$506
This Priceline deal was found by Cheapflights users on 11/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 11/176:45 amORD - POS
1 stop30h 22mJetBlue
mer 12/35:42 pmPOS - ORD
1 stop30h 10mJetBlue
Deal found 11/2$511

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 novembre 4, 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

mer 1/14

1:35 pm-6:55 pm

1 stop27h 20m

Port of Spain Piarco Intl

mar 1/20

9:10 am-10:23 pm

2 stops15h 13m

$470

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sab 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

ven 11/28

2:15 am-1:01 pm

1 stop12h 46m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

gio 3/19

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

gio 3/26

1:20 am-2:55 pm

2 stops14h 35m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun 11/17

5:10 am-8:00 pm

1 stop12h 50m

Port of Spain Piarco Intl

mar 12/2

2:15 am-2:55 pm

2 stops14h 40m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun 12/8

7:10 am-8:00 pm

1 stop10h 50m

Port of Spain Piarco Intl

gio 12/11

12:10 am-2:57 pm

1 stop16h 47m

$525

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven 3/13

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

mer 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

gio 3/19

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

ven 3/27

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

gio 3/12

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

mer 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

sab 2/7

4:35 pm-12:23 am

1 stop29h 48m

Port of Spain Piarco Intl

mar 2/10

2:20 am-10:41 am

1 stop10h 21m

$699

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

sab 1/3

6:35 pm-3:46 pm

2 stops19h 11m

Port of Spain Piarco Intl

sab 1/17

6:30 am-10:59 pm

2 stops18h 29m

$738

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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 $436). Flying from Illinois to Port of Spain in July is currently the most expensive (average of $613). 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 novembre 4, 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 and United Airlines fly from Illinois to Port of Spain in about 26h 55m. The time it takes to get you to your destination can typically vary by up to 2h 53m. There are 2697 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 $436). Flying from Illinois to Port of Spain in July is currently the most expensive (average of $613). 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 novembre 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$487Average$572FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$560Average$628FlexibilityNo cancel feeOn-time69%

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