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Cheap flights from Chicago to Port of Spain from $345

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 6/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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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
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$538Air Canada
Sat, Jun 13 - Fri, Jun 19
Air Canada Logo
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$540Air Canada
Sat, Jun 13 - Fri, Jun 19
Air Canada Logo
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
Air Canada Logo
1:25 am - 6:52 pm
POS
-
ORD
18h 27m
2 stops
$543Air Canada
Sat, Jun 13 - Fri, Jun 19
Air Canada Logo
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
Air Canada Logo
1:25 am - 6:52 pm
POS
-
ORD
18h 27m
2 stops
$545Air Canada
Sat, Jun 13 - Fri, Jun 19
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
1 stop
$548Air Canada
Thu, Sep 10 - Sun, Sep 20
Air Canada Logo
6:21 pm - 12:15 am
ORD
-
POS
28h 54m
2 stops
Air Canada Logo
1:25 am - 4:57 pm
POS
-
ORD
16h 32m
1 stop
$550Air Canada
Thu, Sep 3 - Sun, Sep 6
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
Air Canada Logo
1:20 am - 6:43 pm
POS
-
ORD
18h 23m
2 stops
$551Air Canada
Sun, Sep 6 - Mon, Sep 21
Multiple Airlines Logo
7:45 am - 8:00 pm
ORD
-
POS
11h 15m
1 stop
Multiple Airlines Logo
9:10 am - 9:34 pm
POS
-
ORD
37h 24m
2 stops
$553Multiple Airlines
Thu, Sep 10 - Wed, Sep 23
Multiple Airlines Logo
7:45 am - 8:00 pm
ORD
-
POS
11h 15m
1 stop
Multiple Airlines Logo
9:10 am - 9:34 pm
POS
-
ORD
37h 24m
2 stops
$566Multiple Airlines
Thu, Sep 10 - Sun, Sep 20
Multiple Airlines Logo
7:45 am - 8:00 pm
ORD
-
POS
11h 15m
1 stop
Multiple Airlines Logo
10:10 am - 3:26 pm
POS
-
ORD
30h 16m
1 stop
$568Multiple Airlines
Thu, Sep 10 - Thu, Sep 24

Air Canada flights from Chicago to Port of Spain

Our best Air Canada deals on Chicago to Port of Spain flight tickets
Air Canada
Jun 13
ORD8:20 pmChicago O'Hare Intl
26h 55m
1 stop
POS12:15 amPort of Spain Piarco Intl
Jun 19
POS1:25 amPort of Spain Piarco Intl
12h 57m
1 stop
ORD1:22 pmChicago O'Hare Intl
$538
Air Canada
Jun 13
ORD8:20 pmChicago O'Hare Intl
26h 55m
1 stop
POS12:15 amPort of Spain Piarco Intl
Jun 19
POS1:25 amPort of Spain Piarco Intl
12h 57m
1 stop
ORD1:22 pmChicago O'Hare Intl
$540
Air Canada
Jun 13
ORD8:20 pmChicago O'Hare Intl
26h 55m
1 stop
POS12:15 amPort of Spain Piarco Intl
Jun 19
POS1:25 amPort of Spain Piarco Intl
18h 27m
2 stops
ORD6:52 pmChicago O'Hare Intl
$543

JetBlue flights from Chicago to Port of Spain

Our best JetBlue deals on Chicago to Port of Spain flight tickets
JetBlue
Jun 18
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Jun 21
POS7:45 pmPort of Spain Piarco Intl
14h 00m
1 stop
ORD8:45 amChicago O'Hare Intl
$614
JetBlue
Jun 13
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Jun 14
POS7:45 pmPort of Spain Piarco Intl
14h 00m
1 stop
ORD8:45 amChicago O'Hare Intl
$624
JetBlue
Jun 18
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Jun 21
POS7:45 pmPort of Spain Piarco Intl
14h 00m
1 stop
ORD8:45 amChicago O'Hare Intl
$651

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 May 24, 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

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-1:22 pm

1 stop12h 57m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-1:22 pm

1 stop12h 57m

$540

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-6:52 pm

2 stops18h 27m

$543

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 6/13

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 6/19

1:25 am-6:52 pm

2 stops18h 27m

$545

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/10

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 9/20

1:20 am-2:55 pm

1 stop14h 35m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/3

6:21 pm-12:15 am

2 stops28h 54m

Port of Spain Piarco Intl

Sun 9/6

1:25 am-4:57 pm

1 stop16h 32m

$550
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 9/6

9:50 am-12:15 am

1 stop13h 25m

Port of Spain Piarco Intl

Mon 9/21

1:20 am-6:43 pm

2 stops18h 23m

$551

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/10

7:45 am-8:00 pm

1 stop11h 15m

Port of Spain Piarco Intl

Wed 9/23

9:10 am-9:34 pm

2 stops37h 24m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/10

7:45 am-8:00 pm

1 stop11h 15m

Port of Spain Piarco Intl

Sun 9/20

9:10 am-9:34 pm

2 stops37h 24m

$566

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/10

7:45 am-8:00 pm

1 stop11h 15m

Port of Spain Piarco Intl

Thu 9/24

10:10 am-3:26 pm

1 stop30h 16m

$568

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 June is, on average, the cheapest month to fly to Port of Spain from Chicago, with most prices found around $317. If you’re not able to fly to Port of Spain in June, then July is your next best option. Flight prices from Chicago to Port of Spain during July average around $372.

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

11h 35m

Direct flights

None
The fastest flight from Chicago to Port of Spain takes 11h 35m
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. 11h 35m 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
Air CanadaPriceFrom $392Free CancellationRating
7.1
11,083 reviews
Search Air Canada flights
Copa AirlinesPriceFrom $472Free CancellationRating
7.5
1,576 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $548Free CancellationRating
7.1
11,630 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,747 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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