Cheap flights from Chicago (CHI) to Port of Spain (POS) from $427

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 9/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — POS
Apr 30 — May 71

The best prices from Chicago to Port of Spain Piarco Intl are usually found in January or October, booked 62 days in advance, depart on a Sunday or Tuesday and return on a Tuesday

Cheap flight deals from Chicago to Port of Spain

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) 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 April 25, 2024.

Popular in

July

Cheapest in

January

Average price

$664

Round-trip from

$464
High demand for flights, 23% potential price rise
Best time to find cheap flights, 37% potential price drop
Average for round-trip flights in April 2024
From Chicago (CHI) to Port of Spain Piarco Intl

What is the cheapest day to fly round-trip from Chicago to Port of Spain?

It’s generally more expensive to depart on a Saturday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

How far in advance should I book a flight from Chicago to Port of Spain?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 11 days in advance, which can save you up to 50% on flights from Chicago to Port of Spain compared to booking the week you need them. Waiting 11 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $379. For sooner than that we have options available in the next 3 days from $2,513.

What is the cheapest month to fly from Chicago to Port of Spain?

Flights from Chicago to Port of Spain lean towards being more expensive in July. Prices are generally better when you fly from Chicago to Port of Spain in January, with the cheapest ticket starting at $471.

When is the cheapest time to fly from Chicago to Port of Spain (CHI - POS)?

A simple way to save on the total cost of your ticket is to fly from Chicago to Port of Spain at noon. If you’re flexible enough to do this you can expect to save up to 29% on your trip compared to booking a flight in the morning.

Cheap American Airlines flights from Chicago to Port of Spain

Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Port of Spain. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,073,952 searches. Data last updated April 25, 2024.
Check out some of the cheapest American Airlines flights we've come across from Chicago to Port of Spain. Deals update often to give you more flight options matching your criteria
Thu 9/196:40 amORD - POS
1 stop13h 39mAmerican Airlines
Tue 9/247:58 amPOS - ORD
1 stop9h 08mAmerican Airlines
Deal found 4/24$427
Thu 9/198:20 amORD - POS
2 stops11h 59mAmerican Airlines
Tue 9/247:58 amPOS - ORD
1 stop10h 47mAmerican Airlines
Deal found 4/24$431
Thu 9/196:40 amORD - POS
1 stop13h 39mAmerican Airlines
Mon 9/233:18 pmPOS - ORD
1 stop20h 36mAmerican Airlines
Deal found 4/24$437
Thu 9/198:20 amORD - POS
2 stops11h 59mAmerican Airlines
Mon 9/233:18 pmPOS - ORD
1 stop20h 36mAmerican Airlines
Deal found 4/24$441
Thu 9/196:40 amORD - POS
1 stop13h 39mAmerican Airlines
Tue 9/247:58 amPOS - ORD
2 stops14h 36mAmerican Airlines
Deal found 4/24$453
Sat 9/146:40 amORD - POS
1 stop13h 39mAmerican Airlines
Sat 9/213:18 pmPOS - ORD
1 stop18h 44mAmerican Airlines
Deal found 4/24$460
Sat 9/148:20 amORD - POS
2 stops11h 59mAmerican Airlines
Sat 9/213:18 pmPOS - ORD
1 stop18h 44mAmerican Airlines
Deal found 4/24$465
Thu 5/167:00 amORD - POS
1 stop13h 34mAmerican Airlines
Mon 5/207:00 amPOS - ORD
1 stop13h 39mAmerican Airlines
Deal found 4/24$473
Thu 5/167:30 amORD - POS
2 stops13h 04mAmerican Airlines
Mon 5/207:00 amPOS - ORD
1 stop13h 39mAmerican Airlines
Deal found 4/24$476

Cheap United Airlines flights from Chicago to Port of Spain

Explore cheap flight options specifically provided by United Airlines for the route between Chicago and Port of Spain. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,073,952 searches. Data last updated April 25, 2024.
Some of the lowest-priced United Airlines flights we've found at this time heading from Chicago to Port of Spain. Deals frequently update to provide users with more options.
Thu 5/239:31 pmORD - POS
1 stop24h 52mUnited Airlines
Mon 5/2712:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Deal found 4/24$435
Thu 5/168:45 amORD - POS
1 stop13h 38mUnited Airlines
Sun 5/1912:30 amPOS - ORD
1 stop20h 55mUnited Airlines
Deal found 4/24$481
Tue 6/47:10 amORD - POS
1 stop15h 13mUnited Airlines
Sun 6/912:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 4/24$526
Thu 6/279:15 pmORD - POS
1 stop25h 08mUnited Airlines
Thu 7/412:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 4/25$535
Sat 9/143:45 pmORD - POS
1 stop30h 38mUnited Airlines
Fri 9/2012:30 amPOS - ORD
1 stop32h 17mUnited Airlines
Deal found 4/24$542
Tue 7/29:15 pmORD - POS
1 stop25h 08mUnited Airlines
Mon 7/812:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 4/24$639
Sat 5/118:45 amORD - POS
1 stop13h 38mUnited Airlines
Tue 5/1412:30 amPOS - ORD
1 stop11h 18mUnited Airlines
Deal found 4/23$650
Thu 8/152:01 pmORD - POS
1 stop32h 22mUnited Airlines
Sun 8/1812:30 amPOS - ORD
1 stop10h 37mUnited Airlines
Deal found 4/23$754
Sun 6/306:00 amORD - POS
1 stop16h 23mUnited Airlines
Mon 7/1512:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 4/24$865

Cheap Chicago to Port of Spain flights in April & May 2024

Find cheap flight options from Chicago to Port of Spain specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,073,952 searches. Prices were last updated on April 25, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Port of Spain in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/239:31 pmORD - POS
1 stop24h 52mUnited Airlines
Mon 5/2712:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Deal found 4/24$435
Thu 5/167:00 amORD - POS
1 stop13h 34mAmerican Airlines
Mon 5/207:00 amPOS - ORD
1 stop13h 39mAmerican Airlines
Deal found 4/24$473
Thu 5/167:30 amORD - POS
2 stops13h 04mAmerican Airlines
Mon 5/207:00 amPOS - ORD
1 stop13h 39mAmerican Airlines
Deal found 4/24$476
Thu 5/168:45 amORD - POS
1 stop13h 38mUnited Airlines
Sun 5/1912:30 amPOS - ORD
1 stop20h 55mUnited Airlines
Deal found 4/24$481
Thu 5/236:45 pmORD - POS
1 stop18h 25mAmerican Airlines
Tue 5/283:14 pmPOS - ORD
1 stop18h 53mAmerican Airlines
Deal found 4/24$517
Thu 5/237:35 amORD - POS
3 stops17h 07mMultiple Airlines
Tue 5/284:05 amPOS - ORD
2 stops18h 51mMultiple Airlines
Deal found 4/24$522
Thu 5/239:03 amORD - POS
2 stops15h 39mMultiple Airlines
Tue 5/284:05 amPOS - ORD
2 stops18h 51mMultiple Airlines
Deal found 4/24$548
Thu 5/236:30 amORD - POS
2 stops14h 04mAmerican Airlines
Tue 5/283:14 pmPOS - ORD
1 stop18h 53mAmerican Airlines
Deal found 4/24$565
Thu 5/237:35 amORD - POS
3 stops17h 07mMultiple Airlines
Tue 5/284:05 amPOS - ORD
3 stops20h 24mMultiple Airlines
Deal found 4/24$578

Chicago to Port of Spain 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Port of Spain in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,073,952 searches. Data last updated April 25, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Port of Spain in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 9/196:40 amORD - POS
1 stop13h 39mAmerican Airlines
Tue 9/247:58 amPOS - ORD
1 stop9h 08mAmerican Airlines
Deal found 4/24$427
Thu 9/198:20 amORD - POS
2 stops11h 59mAmerican Airlines
Tue 9/247:58 amPOS - ORD
2 stops12h 42mAmerican Airlines
Deal found 4/24$431
Thu 5/239:31 pmORD - POS
1 stop24h 52mUnited Airlines
Mon 5/2712:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Deal found 4/24$435
Thu 9/196:40 amORD - POS
1 stop13h 39mAmerican Airlines
Mon 9/233:18 pmPOS - ORD
1 stop20h 36mAmerican Airlines
Deal found 4/24$437
Thu 9/198:20 amORD - POS
2 stops11h 59mAmerican Airlines
Mon 9/233:18 pmPOS - ORD
1 stop20h 36mAmerican Airlines
Deal found 4/24$441
Thu 9/196:40 amORD - POS
1 stop13h 39mAmerican Airlines
Tue 9/247:58 amPOS - ORD
2 stops14h 36mAmerican Airlines
Deal found 4/24$453
Sat 9/146:40 amORD - POS
1 stop13h 39mAmerican Airlines
Sat 9/213:18 pmPOS - ORD
1 stop18h 44mAmerican Airlines
Deal found 4/24$460
Sat 9/148:20 amORD - POS
2 stops11h 59mAmerican Airlines
Sat 9/213:18 pmPOS - ORD
1 stop18h 44mAmerican Airlines
Deal found 4/24$465
Thu 5/167:00 amORD - POS
1 stop13h 34mAmerican Airlines
Mon 5/207:00 amPOS - ORD
1 stop13h 39mAmerican Airlines
Deal found 4/24$473

Chicago to Port of Spain flights leaving soon

Find last-minute flight options from Chicago to Port of Spain for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,073,952 searches. Data last updated April 25, 2024.
Users seeking a last-minute flight from Chicago to Port of Spain should consider booking one of these fares. To prevent any unwanted surprises, users should verify their flight info before booking.
Sat 5/47:56 amORD - POS
1 stop16h 46mCopa Airlines
Mon 7/14:09 amPOS - ORD
1 stop10h 09mCopa Airlines
Deal found 4/23$815
Sat 5/44:00 pmORD - POS
1 stop11h 40mMultiple Airlines
Mon 7/16:00 amPOS - ORD
2 stops13h 27mMultiple Airlines
Deal found 4/23$2,430

Find flights from Chicago to Port of Spain within your budget

Customize your flight search to find flights from Chicago 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 3,073,952 searches. Data last updated April 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$427 - $529

Route

Depart

Return

Price

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/19

1 stop13h 39m

Port of Spain Piarco Intl

Tue 9/24

1 stop9h 08m

$427

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/19

2 stops11h 59m

Port of Spain Piarco Intl

Tue 9/24

1 stop10h 47m

$431

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/23

1 stop24h 52m

Port of Spain Piarco Intl

Mon 5/27

1 stop11h 23m

$435

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/19

1 stop13h 39m

Port of Spain Piarco Intl

Mon 9/23

1 stop20h 36m

$437

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/19

2 stops11h 59m

Port of Spain Piarco Intl

Mon 9/23

1 stop20h 36m

$441

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/16

1 stop13h 38m

Port of Spain Piarco Intl

Sun 5/19

1 stop20h 55m

$481

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 6/4

1 stop20h 40m

Port of Spain Piarco Intl

Mon 6/10

1 stop24h 19m

$498

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/23

3 stops17h 07m

Port of Spain Piarco Intl

Tue 5/28

2 stops18h 51m

$522

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 7/2

1 stop16h 46m

Port of Spain Piarco Intl

Tue 7/9

1 stop10h 09m

$529

Flights are sorted by cheapest first

Deals found on 4/24

When is the best time to book a flight from Chicago to Port of Spain?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Port of Spain. Price data was last updated on January 28, 2024.
The price you pay for your flight from Chicago to Port of Spain may vary depending on when you book. For the best chance of a lower fare, look to book 62 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

When is the cheapest time to fly from Chicago to Port of Spain?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Port of Spain. Price data was last updated on April 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Port of Spain flight should consider departing on Sunday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Port of Spain by month

Plan your trip from Chicago to Port of Spain by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Port of Spain is currently $0 while a round-trip flight costs $467. Price data was last updated on April 21, 2024.

Currently, March is the cheapest month in which you can book a flight from Chicago to Port of Spain (average of $464). Flying from Chicago to Port of Spain in July is currently the most expensive (average of $694). 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.

January

$482

February

$571

March

$464

April

$479

May

$528

June

$589

July

$694

August

$648

September

$519

October

$516

November

$503

December

$530

Temperature and rainfall in Port of Spain by month

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

POS

Temperature

77 - 80.6 °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 April 25, 2024.
Peruse reviews from past customers who have flown with American Airlines, United Airlines and Copa Airlines from Chicago to Port of Spain to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good
2,875 reviews

Crew

8.3

Entertainment

7.2

Overall

8.0

Boarding

8.1

Food

7.4

Comfort

7.7

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

8.0
Very good
2,875 reviews
8.0
Very good
2,875 reviews

Crew

8.3

Entertainment

7.2

Overall

8.0

Boarding

8.1

Food

7.4

Comfort

7.7

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

7.4
Good
11,255 reviews
8.0
Very good
2,875 reviews

Crew

8.3

Entertainment

7.2

Overall

8.0

Boarding

8.1

Food

7.4

Comfort

7.7

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

7.3
Good
14,898 reviews
8.0
Very good
2,875 reviews

Crew

8.3

Entertainment

7.2

Overall

8.0

Boarding

8.1

Food

7.4

Comfort

7.7

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Port of Spain Piarco Intl (POS) is the airport you will fly into if you book a flight from Chicago to Port of Spain. You should not have trouble finding flights to Piarco Intl from Chicago; the airport handles an average of 0 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 3 airlines have flights to the Port of Spain airport from Chicago. It is only a 12.6 mi journey from Piarco Intl (POS) to Port of Spain’s city center.

  • Can I find flights from Chicago to Port of Spain for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago to Port of Spain for under $500. The cheapest flight booked recently is on American Airlines for just $427, but on average you can expect to pay $485.

  • Are there last-minute flights available from Chicago to Port of Spain for under $900?

    There are currently 2+ open flights from Chicago to Port of Spain within the next 7 days for less than $900.

  • What are the cheapest airlines flying from Chicago to Port of Spain round-trip?

    According to our current data, American Airlines ($427), United Airlines ($435), and Copa Airlines ($529) offers the cheapest pricing from Chicago to Port of Spain. Users have found that American Airlines is 43% cheaper than the other options available to this destination.

  • What are the most popular airlines that fly from Chicago to Port of Spain?

  • What does ORD to POS mean?

    ORD and POS are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to POS refers to a flight route from Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Port of Spain that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Port of Spain flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Port of Spain with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Port of Spain flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

  • How can I find direct flights from Chicago 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 Chicago to Port of Spain.

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

    Yes. Cheapflights offers flight deals from Chicago 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.

  • Can I find deals for flights from Chicago to Port of Spain that allow pets onboard?

    Many airlines flying from Chicago to Port of Spain offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Port of Spain?

    Yes, you can often find last-minute deals on Chicago to Port of Spain flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Port of Spain flight deals updated?

    The Chicago to Port of Spain flight deals you see on this page were last updated on 4/24.

See more FAQs

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Alternative routes for Chicago to Port of Spain
See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Chicago to Port of Spain

Discover the top 3 airlines that operate flights from Chicago 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 3,073,952 searches. Data last updated April 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$430Average$535FlexibilityNo cancel feeOn-time70%
Search Copa Airlines flights
American AirlinesCheapest$439Average$761FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$524Average$689FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Search flights from Chicago to Port of Spain by cabin class

Find flights from Chicago to Port of Spain, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Port of Spain?

When you search for this flight from Chicago to Port of Spain, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Port of Spain?

Cheapflights simply makes it quick and affordable to book flights from Chicago to Port of Spain by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chicago to Port of Spain with no change fees?

Yes, we can. To see specific flights from Chicago to Port of Spain with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Chicago to Port of Spain become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Port of Spain from Chicago today and book when prices fit your budget.

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