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Port of Spain

$374+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Illinois to Port of Spain

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Port of Spain (POS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$374
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$477
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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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Trip.com deal was found by Cheapflights users on 1/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/217:18 pmORD - POS
2 stops20h 19mFrontier
Sun 3/27:06 pmPOS - ORD
2 stops53h 32mFrontier
Deal found 1/30$374
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Tue 3/118:39 amORD - POS
1 stop8h 46mMultiple Airlines
Mon 3/173:39 amPOS - ORD
2 stops30h 27mMultiple Airlines
Deal found 1/29$405
This Copa Airlines deal was found by Cheapflights users on 1/29. 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.
Tue 3/117:55 amORD - POS
1 stop16h 46mCopa Airlines
Mon 3/173:39 amPOS - ORD
1 stop11h 03mCopa Airlines
Deal found 1/29$486
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Thu 2/68:15 amORD - POS
1 stop12h 59mAmerican Airlines
Tue 2/114:35 pmPOS - ORD
1 stop9h 52mAmerican Airlines
Deal found 1/30$528
This American Airlines deal was found by Cheapflights users on 1/30. 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.
Fri 5/27:03 pmSTL - POS
2 stops18h 06mAmerican Airlines
Fri 5/93:10 pmPOS - STL
2 stops18h 43mAmerican Airlines
Deal found 1/30$603
This United deal was found by Cheapflights users on 1/30. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/68:50 amORD - POS
1 stop13h 33mUnited Airlines
Mon 2/101:30 amPOS - ORD
1 stop10h 44mUnited Airlines
Deal found 1/30$618
This United Airlines deal was found by Cheapflights users on 1/30. 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.
Fri 5/28:30 amSTL - POS
1 stop13h 53mUnited Airlines
Thu 5/812:30 amPOS - STL
1 stop16h 19mUnited Airlines
Deal found 1/30$668
This Air Canada deal was found by Cheapflights users on 1/29. 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.
Sun 6/16:20 pmORD - POS
2 stops30h 15mAir Canada
Fri 6/62:35 amPOS - ORD
2 stops33h 49mAir Canada
Deal found 1/29$751

Find flights from Illinois to Port of Spain within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/21

7:18 pm-5:37 pm

2 stops20h 19m

Port of Spain Piarco Intl

Sun 3/2

7:06 pm-10:38 pm

2 stops53h 32m

$374

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 3/11

8:39 am-6:25 pm

1 stop8h 46m

Port of Spain Piarco Intl

Mon 3/17

3:39 am-9:06 am

2 stops30h 27m

$405

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 3/11

7:55 am-1:41 am

1 stop16h 46m

Port of Spain Piarco Intl

Mon 3/17

3:39 am-1:42 pm

1 stop11h 03m

$486

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/25

7:45 am-11:23 pm

1 stop14h 38m

Port of Spain Piarco Intl

Tue 4/29

12:30 am-7:55 pm

1 stop20h 25m

$528

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 6/1

7:16 pm-2:10 pm

1 stop17h 54m

Port of Spain Piarco Intl

Sat 6/7

3:20 pm-11:53 pm

1 stop9h 33m

$563

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Fri 5/2

7:03 pm-2:09 pm

2 stops18h 06m

Port of Spain Piarco Intl

Fri 5/9

3:10 pm-8:53 am

2 stops18h 43m

$603

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Fri 5/2

8:30 am-11:23 pm

1 stop13h 53m

Port of Spain Piarco Intl

Thu 5/8

12:30 am-3:49 pm

1 stop16h 19m

$668

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 6/1

10:55 am-1:35 am

2 stops37h 40m

Port of Spain Piarco Intl

Fri 6/6

2:35 am-9:59 pm

1 stop20h 24m

$751

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

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.

Travel insights for flights from Illinois to Port of Spain

Get recent, data-driven insights about flights from Illinois to Port of Spain including ideal travel times, pricing trends, and more.

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 January 30, 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.

Rainfall in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Port of Spain ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Port of Spain when rainfall is around 1.2 in.

Temperature in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Port of Spain, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 January 30, 2025.
Read through reviews of airlines operating flights from Illinois to Port of Spain, such as Copa Airlines, United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,617 reviews

Overall

7.6

Boarding

7.9

Food

6.9

Comfort

7.5

Entertainment

6.9

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Copa Airlines
7.6
Good
1,617 reviews
Copa Airlines
7.6
Good
1,617 reviews

Overall

7.6

Boarding

7.9

Food

6.9

Comfort

7.5

Entertainment

6.9

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

United Airlines
7.4
Good
8,906 reviews
Copa Airlines
7.6
Good
1,617 reviews

Overall

7.6

Boarding

7.9

Food

6.9

Comfort

7.5

Entertainment

6.9

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,617 reviews

Overall

7.6

Boarding

7.9

Food

6.9

Comfort

7.5

Entertainment

6.9

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Frontier
6.0
Okay
3,424 reviews
Copa Airlines
7.6
Good
1,617 reviews

Overall

7.6

Boarding

7.9

Food

6.9

Comfort

7.5

Entertainment

6.9

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

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.

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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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$426Average$633FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$452Average$555FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$478Average$618FlexibilityNo cancel feeOn-time69%
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