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$237+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap 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 December 26, 2025.

This FlightHub deal was found by Cheapflights users on 12/24. 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.
Thu 12/252:15 amPOS - ORD
1 stop12h 46mAir Canada
Fri 1/26:00 pmORD - POS
2 stops53h 20mAir Canada
Deal found 12/24$590

Find 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 December 26, 2025.

Round-trip from

$418
(Priceline)
From Port of Spain Piarco Intl to Illinois
Search Deals

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 December 26, 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

Sat 2/7

8:20 am-5:44 pm

2 stops35h 24m

Chicago O'Hare Intl

Sat 2/14

8:40 pm-1:20 am

1 stop26h 40m

$418

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/14

9:10 am-8:18 am

1 stop25h 08m

Chicago O'Hare Intl

Sun 1/25

3:05 pm-8:00 pm

1 stop26h 55m

$431

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/1

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Mon 3/16

8:40 pm-12:20 am

1 stop26h 40m

$455

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/6

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Sat 2/14

6:04 pm-1:20 am

2 stops29h 16m

$460

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/5

2:20 am-1:01 pm

1 stop12h 41m

Chicago O'Hare Intl

Fri 2/13

6:04 pm-1:20 am

2 stops53h 16m

$494

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

2:22 pm-1:15 am

1 stop11h 53m

Chicago O'Hare Intl

Sun 5/10

3:21 pm-1:46 am

1 stop9h 25m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 2/3

2:20 am-6:55 pm

2 stops18h 35m

$237

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 2/4

2:28 pm-11:16 pm

3 stops34h 48m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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 December 26, 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.

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 December 26, 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
1,559 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.4

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.6
Good
1,559 reviews
Copa Airlines
7.6
Good
1,559 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.4

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
United Airlines
7.4
Good
9,115 reviews
Copa Airlines
7.6
Good
1,559 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.4

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
American Airlines
7.2
Good
11,061 reviews
Copa Airlines
7.6
Good
1,559 reviews

Entertainment

6.8

Food

6.8

Overall

7.6

Comfort

7.4

Boarding

7.8

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

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 14h 50m. Airlines will cover a distance of 2697 mi.

  • 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 December 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$474Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$698FlexibilityNo cancel feeOn-time71%

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