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Cheap flights from Chicago to Port of Spain from $232

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 8/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Port of Spain

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$492Air Canada
Fri, Oct 2 - Fri, Oct 9
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$496Air Canada
Fri, Oct 2 - Fri, Oct 9
JetBlue Logo
6:00 am - 6:35 pm
ORD
-
POS
11h 35m
1 stop
JetBlue Logo
8:00 pm - 8:43 am
POS
-
ORD
13h 43m
1 stop
$498JetBlue
Thu, Aug 13 - Fri, Aug 21
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:20 am - 1:23 pm
POS
-
ORD
13h 03m
1 stop
$513Air Canada
Fri, Oct 9 - Mon, Oct 12
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$516Air Canada
Fri, Oct 9 - Mon, Oct 12
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$520Air Canada
Fri, Oct 9 - Mon, Oct 12
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
1 stop
$531Air Canada
Mon, Aug 31 - Sun, Sep 27
JetBlue Logo
6:00 am - 6:20 pm
ORD
-
POS
11h 20m
1 stop
JetBlue Logo
8:00 pm - 8:43 am
POS
-
ORD
13h 43m
1 stop
$537JetBlue
Sat, Aug 22 - Mon, Aug 31
Air Canada Logo
8:50 pm - 1:00 am
ORD
-
POS
26h 10m
1 stop
Air Canada Logo
2:05 am - 3:38 pm
POS
-
ORD
15h 33m
1 stop
$539Air Canada
Wed, Dec 9 - Tue, Dec 15
Air Canada Logo
8:50 pm - 1:00 am
ORD
-
POS
26h 10m
1 stop
Air Canada Logo
2:05 am - 2:52 pm
POS
-
ORD
14h 47m
2 stops
$542Air Canada
Wed, Dec 9 - Tue, Dec 15

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JetBlue flights from Chicago to Port of Spain

Our best JetBlue deals on Chicago to Port of Spain flight tickets
JetBlue
Aug 13
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Aug 21
POS8:00 pmPort of Spain Piarco Intl
13h 43m
1 stop
ORD8:43 amChicago O'Hare Intl
$498
JetBlue
Aug 22
ORD6:00 amChicago O'Hare Intl
11h 20m
1 stop
POS6:20 pmPort of Spain Piarco Intl
Aug 31
POS8:00 pmPort of Spain Piarco Intl
13h 43m
1 stop
ORD8:43 amChicago O'Hare Intl
$537
JetBlue
Aug 22
ORD6:00 amChicago O'Hare Intl
11h 20m
1 stop
POS6:20 pmPort of Spain Piarco Intl
Aug 31
POS8:00 pmPort of Spain Piarco Intl
22h 35m
1 stop
ORD5:35 pmChicago O'Hare Intl
$546

Air Canada flights from Chicago to Port of Spain

Our best Air Canada deals on Chicago to Port of Spain flight tickets
Air Canada
Oct 2
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
Oct 9
POS1:20 amPort of Spain Piarco Intl
14h 32m
2 stops
ORD2:52 pmChicago O'Hare Intl
$492
Air Canada
Oct 2
ORD8:45 amChicago O'Hare Intl
14h 30m
2 stops
POS12:15 amPort of Spain Piarco Intl
Oct 9
POS1:20 amPort of Spain Piarco Intl
14h 32m
2 stops
ORD2:52 pmChicago O'Hare Intl
$496
Air Canada
Oct 9
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
Oct 12
POS1:20 amPort of Spain Piarco Intl
13h 03m
1 stop
ORD1:23 pmChicago O'Hare Intl
$513

momondo Fare Finder

 
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, momondo users made 832,500 searches. Data last updated July 12, 2026.
Use the filters below to find and compare flights from Chicago to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/2

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Fri 10/9

1:20 am-2:52 pm

2 stops14h 32m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/2

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Fri 10/9

1:20 am-2:52 pm

2 stops14h 32m

$496

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 8/13

6:00 am-6:35 pm

1 stop11h 35m

Port of Spain Piarco Intl

Fri 8/21

8:00 pm-8:43 am

1 stop13h 43m

$498
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/9

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Mon 10/12

1:20 am-1:23 pm

1 stop13h 03m

$513

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/9

9:50 am-12:15 am

1 stop13h 25m

Port of Spain Piarco Intl

Mon 10/12

1:20 am-2:52 pm

2 stops14h 32m

$516

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/9

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Mon 10/12

1:20 am-2:52 pm

2 stops14h 32m

$520

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 8/31

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Sun 9/27

1:20 am-2:55 pm

1 stop14h 35m

$531

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 8/22

6:00 am-6:20 pm

1 stop11h 20m

Port of Spain Piarco Intl

Mon 8/31

8:00 pm-8:43 am

1 stop13h 43m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/9

8:50 pm-1:00 am

1 stop26h 10m

Port of Spain Piarco Intl

Tue 12/15

2:05 am-3:38 pm

1 stop15h 33m

$539

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/9

8:50 pm-1:00 am

1 stop26h 10m

Port of Spain Piarco Intl

Tue 12/15

2:05 am-2:52 pm

2 stops14h 47m

$542

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago to Port of Spain

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and Port of Spain?

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

The month of January is, on average, the cheapest month to fly to Port of Spain from Chicago, with most prices found around $285. If you’re not able to fly to Port of Spain in January, then June is your next best option. Flight prices from Chicago to Port of Spain during June average around $317.

When to book flights from Chicago to Port of Spain

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Port of Spain according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Port of Spain (CHI to POS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Port of Spain

Fastest flight time

9h 41m

Direct flights

None
The fastest flight from Chicago to Port of Spain takes 9h 41m
There are no direct flights from Chicago to Port of Spain. There are no popular flight routes from Chicago to Port of Spain.
Search flight deals

Frequently asked questions about flying from Chicago to Port of Spain

  • How far is Chicago to Port of Spain Piarco Intl by plane?

    Port of Spain Piarco Intl is 2671.5 mi away from Chicago. 9h 41m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to Port of Spain Piarco Intl Airport?

    Prices for flights from Chicago to Port of Spain Piarco Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Port of Spain Piarco Intl Airport?

  • How old do you have to be to fly from Chicago to Port of Spain Piarco Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Port of Spain Piarco Intl Airport.

  • What documentation or ID do you need to fly to Port of Spain Piarco Intl Airport?

    The travel and health documents required for your trip to Port of Spain Piarco Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Port of Spain Piarco Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago to Port of Spain?

Best airlines flying from Chicago to Port of Spain

Compare and see reviews for airlines that fly from Chicago to Port of Spain with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $285Free CancellationRating
7.6
1,561 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $317Free CancellationRating
7.1
11,331 reviews
Search Air Canada flights
American AirlinesPriceFrom $548Free CancellationRating
7.1
11,809 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,979 reviews
Search United Airlines flights

Traveling to a place near Port of Spain?

Book flights to Port of Spain if you plan to visit one of these locations
Piarco

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Port of Spain?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Port of Spain. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Port of Spain with flexible booking policies on momondo?

Flights from Chicago to Port of Spain with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Port of Spain?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Port of Spain from Chicago.

I’m not ready to book a flight from Chicago to Port of Spain right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Port of Spain, momondo offers a useful price alert feature which will track prices for flights to Port of Spain from Chicago and alert you when they change.

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