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Cheap flights from Chicago to Port of Spain from $174

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 2/28. 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
8:40 pm - 1:20 am
ORD
-
POS
26h 40m1 stop
Air Canada Logo
2:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
$423Air Canada
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:25 am - 6:33 pm
POS
-
ORD
18h 08m2 stops
$427Air Canada
Tue, Jan 13 - Wed, Jun 3
Multiple Airlines Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$447Multiple Airlines
Thu, Jan 29 - Tue, Apr 7
Air Canada Logo
6:04 pm - 12:20 am
ORD
-
POS
29h 16m2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$453Air Canada
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
9:10 am - 6:15 pm
POS
-
ORD
10h 05m1 stop
$454Multiple Airlines
Tue, Jan 13 - Wed, Jun 3
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$457Air Canada
Fri, Mar 13 - Tue, Mar 17
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$459JetBlue
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m2 stops
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$464Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Multiple Airlines Logo
6:22 pm - 1:36 pm
ORD
-
POS
18h 14m2 stops
Multiple Airlines Logo
1:20 am - 6:53 pm
POS
-
ORD
42h 33m2 stops
$466Multiple Airlines
Fri, Mar 27 - Fri, Apr 3
Air Canada Logo
6:00 pm - 1:20 am
ORD
-
POS
29h 20m2 stops
Air Canada Logo
1:25 am - 6:33 pm
POS
-
ORD
18h 08m2 stops
$473Air Canada
Thu, Jan 15 - Wed, Jun 3

Air Canada flights from Chicago to Port of Spain

Our best Air Canada deals on Chicago to Port of Spain flight tickets
Air Canada
Jan 12
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS1:20 amPort of Spain Piarco Intl
Jun 3
POS1:25 amPort of Spain Piarco Intl
18h 08m
2 stops
ORD6:33 pmChicago O'Hare Intl
$423
Find similar
Air Canada
Jan 13
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS1:20 amPort of Spain Piarco Intl
Jun 3
POS1:25 amPort of Spain Piarco Intl
18h 08m
2 stops
ORD6:33 pmChicago O'Hare Intl
$427
Find similar
Air Canada
Mar 12
ORD6:04 pmChicago O'Hare Intl
29h 16m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 17
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$453
Find similar

American Airlines flights from Chicago to Port of Spain

Our best American Airlines deals on Chicago to Port of Spain flight tickets
American Airlines
Mar 7
ORD7:57 pmChicago O'Hare Intl
16h 21m
2 stops
POS2:18 pmPort of Spain Piarco Intl
Mar 12
POS3:18 pmPort of Spain Piarco Intl
18h 03m
2 stops
ORD8:21 amChicago O'Hare Intl
$583
Find similar
American Airlines
Jan 30
ORD6:42 amChicago O'Hare Intl
14h 06m
2 stops
POS10:48 pmPort of Spain Piarco Intl
Apr 8
POS3:10 pmPort of Spain Piarco Intl
18h 39m
2 stops
ORD8:49 amChicago O'Hare Intl
$638
Find similar

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 December 28, 2025.
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

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/12

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Thu 1/15

2:20 am-3:10 pm

1 stop14h 50m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/13

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-6:33 pm

2 stops18h 08m

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/29

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Tue 4/7

3:40 pm-9:10 am

2 stops18h 30m

$447

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

6:04 pm-12:20 am

2 stops29h 16m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$453

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/13

9:23 am-6:55 pm

1 stop31h 32m

Port of Spain Piarco Intl

Wed 6/3

9:10 am-6:15 pm

1 stop10h 05m

$454

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$457

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/26

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Mon 2/2

8:20 am-5:43 pm

2 stops35h 23m

$459

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:21 pm-12:20 am

2 stops28h 59m

Port of Spain Piarco Intl

Mon 4/6

3:40 pm-9:10 am

2 stops18h 30m

$464

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

6:22 pm-1:36 pm

2 stops18h 14m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-6:53 pm

2 stops42h 33m

$466

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/15

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-6:33 pm

2 stops18h 08m

$473

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Port of Spain from

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 cheapest airline that flies from Chicago to Port of Spain Piarco Intl?

JetBlue, Copa Airlines, and American Airlines are the most popular carriers operating from Chicago to Port of Spain Piarco Intl

What airlines fly to Port of Spain?

American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Port of Spain from Chicago according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Port of Spain. Keep in mind that there are 3 different airlines that fly to Port of Spain on a routine basis, so you have a few additional options to choose from.

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 20m

Direct flights

None
The fastest flight from Chicago to Port of Spain takes 9h 20m
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

  • 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 20m 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 $432Free CancellationRating
7.1
10,562 reviews
Search Air Canada flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,070 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,113 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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