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$248+ Cheap flights from Port of Spain (POS) to Illinois

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
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Cheap flight deals from Port of Spain to Illinois

Keep the following information in mind while searching for Port of Spain to Illinois flight deals. Data was last updated November 4, 2025.

Round-trip from

$463
(Priceline)

One-way from

$248
(Trip.com)
From Port of Spain Piarco Intl to Illinois
Search Deals
One-way flight from Port of Spain Piarco Intl to Illinois
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Find flight deals from Port of Spain to Illinois

Cheapest flights from Port of Spain to Illinois
Explore the most affordable flight options available from Port of Spain to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2025.

This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/252:15 amPOS - ORD
2 stops14h 40mAir Canada
Mon 12/18:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 11/2$471
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:19 amPOS - ORD
1 stop12h 58mAmerican Airlines
Mon 12/17:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$574
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:19 amPOS - ORD
1 stop19h 18mAmerican Airlines
Sun 11/307:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$580
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/21:30 amPOS - STL
2 stops36h 45mUnited Airlines
Wed 12/106:15 amSTL - POS
1 stop16h 08mUnited Airlines
Deal found 11/3$612
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/27:19 amPOS - STL
1 stop17h 08mAmerican Airlines
Tue 12/95:10 amSTL - POS
1 stop16h 49mAmerican Airlines
Deal found 11/4$613
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/34:33 pmPOS - STL
1 stop9h 26mAmerican Airlines
Wed 12/105:10 amSTL - POS
1 stop16h 49mAmerican Airlines
Deal found 11/3$641
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 12/257:57 pmORD - POS
2 stops22h 03mMultiple Airlines
Deal found 11/3$669
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/221:30 amPOS - ORD
1 stop10h 32mUnited Airlines
Sun 11/306:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 11/2$672
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/11:30 amPOS - STL
2 stops47h 15mUnited Airlines
Tue 12/95:27 pmSTL - POS
3 stops28h 56mUnited Airlines
Deal found 11/2$1,122

Cheapflights Fare Finder

 
Customize your flight search to find flights from Port of Spain to Illinois 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 November 4, 2025.
Use the filters below to find and compare flights from Port of Spain to Illinois that are best for you.

Fly from

Port of Spain

Fly to

Illinois

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/13

2:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Tue 2/17

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/13

2:20 am-6:51 pm

2 stops18h 31m

Chicago O'Hare Intl

Tue 1/20

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 11/25

2:15 am-3:10 pm

1 stop14h 55m

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:20 am-6:52 pm

2 stops42h 32m

Chicago O'Hare Intl

Tue 3/3

2:00 pm-1:20 am

1 stop9h 20m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/14

2:16 pm-12:24 am

1 stop12h 08m

Chicago O'Hare Intl

Tue 1/20

7:35 am-1:44 am

1 stop16h 09m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-6:17 pm

1 stop12h 58m

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:30 pm

1 stop18h 13m

$574

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Mon 12/1

1:30 am-10:04 am

1 stop10h 34m

Lambert-St Louis

Tue 12/9

10:00 am-12:23 am

2 stops36h 23m

$612

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Tue 12/2

1:30 am-10:45 pm

2 stops23h 15m

Lambert-St Louis

Wed 12/10

5:27 pm-12:23 am

2 stops28h 56m

$612

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 1/14

4:30 pm-11:59 pm

1 stop9h 29m

Lambert-St Louis

Wed 5/27

5:25 am-9:25 pm

1 stop15h 00m

$613

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Tue 12/2

7:19 am-10:27 pm

1 stop17h 08m

Lambert-St Louis

Tue 12/9

5:10 am-11:59 pm

1 stop16h 49m

$613

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 18 results
1
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Best time to book a flight from Port of Spain to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Port of Spain 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 Port of Spain to Illinois

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

Currently, December is the cheapest month in which you can book a flight from Port of Spain to Illinois (average of $304). Flying from Port of Spain to Illinois in April is currently the most expensive (average of $632). 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 POS to IL?

Find hourly flight availability from Port of Spain to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 2025.

It’s optimal to fly from Port of Spain to Illinois at noon. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight in the afternoon.

How much does it cost to fly round-trip from Port of Spain to Illinois?

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated November 4, 2025.
Peruse reviews from past customers who have flown with Copa Airlines, United Airlines, and American Airlines from Port of Spain to Illinois to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,561 reviews

Overall

7.6

Boarding

7.8

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
Copa Airlines
7.6
Good
1,561 reviews
Copa Airlines
7.6
Good
1,561 reviews

Overall

7.6

Boarding

7.8

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
United Airlines
7.4
Good
8,998 reviews
Copa Airlines
7.6
Good
1,561 reviews

Overall

7.6

Boarding

7.8

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring
American Airlines
7.2
Good
11,038 reviews
Copa Airlines
7.6
Good
1,561 reviews

Overall

7.6

Boarding

7.8

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Juan Pablo,Sep 2025

MEX - PTY

never better, had a very plesent trip to panama, cant say the same thing of my trip, from panama to santa cruz... it was very poor, unconftrable and boring

Related info for your journey

Find useful and relevant information for your journey from Port of Spain to Illinois. 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 from for flights from Port of Spain to Illinois?

    Port of Spain Piarco Intl (POS), located 12.6 mi from the city center, is the airport you fly out of when you book flights from Port of Spain to Illinois.

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

    Departing from Port of Spain to Illinois will take you 10h 34m. Airlines will cover a distance of 2641 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Port of Spain to Illinois 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 Port of Spain to Illinois?

    Currently, December is the cheapest month in which you can book a flight from Port of Spain to Illinois (average of $304). Flying from Port of Spain to Illinois in April is currently the most expensive (average of $632). 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 Port of Spain to Illinois

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

Discover the top 3 airlines that operate flights from Port of Spain to Illinois. 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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$676FlexibilityNo cancel feeOn-time71%

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