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Cheap flights from Chicago to Port of Spain from $450

This is the cheapest round-trip 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 9/18. 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

Logo
10:27 am - 4:15 amORD-POS
16h 48m1 stop
Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
$450
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Thu, Sep 18 - Sun, Sep 28
Logo
10:27 am - 6:55 pmORD-POS
31h 28m1 stop
Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
$455
Find Deal
Tue, Sep 16 - Fri, Sep 26
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$526Copa Airlines
Find Deal
Fri, Sep 19 - Sun, Sep 28
Air Canada Logo
10:00 am - 1:15 amORD-POS
13h 15m1 stop
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
$537Air Canada
Find Deal
Tue, Nov 11 - Fri, Nov 21
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$541Copa Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
$542Air Canada
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Fri, Sep 19 - Sun, Sep 28
American Airlines Logo
8:15 am - 10:20 pmORD-POS
12h 05m1 stop
American Airlines Logo
7:10 am - 7:37 pmPOS-ORD
14h 27m1 stop
$548American Airlines
Find Deal
Thu, Jan 15 - Fri, Jan 23
American Airlines Logo
10:28 am - 10:20 pmORD-POS
9h 52m2 stops
American Airlines Logo
4:45 pm - 12:30 amPOS-ORD
9h 45m1 stop
$553American Airlines
Find Deal
Thu, Jan 15 - Fri, Jan 23
United Airlines Logo
7:10 am - 11:23 pmORD-POS
15h 13m1 stop
United Airlines Logo
12:30 am - 10:02 amPOS-ORD
10h 32m1 stop
$658United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
United Airlines Logo
12:30 am - 12:20 pmPOS-ORD
12h 50m1 stop
$668United Airlines
Find Deal
Thu, Sep 18 - Sat, Sep 27

American Airlines flights from Chicago to Port of Spain

Our best American Airlines deals on Chicago to Port of Spain flight tickets
American Airlines
Jan 15
ORD8:15 amChicago O'Hare Intl
12h 05m
1 stop
POS10:20 pmPort of Spain Piarco Intl
Jan 23
POS7:10 amPort of Spain Piarco Intl
14h 27m
1 stop
ORD7:37 pmChicago O'Hare Intl
$548
Find similar
American Airlines
Jan 15
ORD10:28 amChicago O'Hare Intl
9h 52m
2 stops
POS10:20 pmPort of Spain Piarco Intl
Jan 23
POS4:45 pmPort of Spain Piarco Intl
9h 45m
1 stop
ORD12:30 amChicago O'Hare Intl
$553
Find similar
American Airlines
Oct 22
ORD7:10 amChicago O'Hare Intl
13h 10m
2 stops
POS9:20 pmPort of Spain Piarco Intl
Oct 26
POS3:25 pmPort of Spain Piarco Intl
18h 28m
1 stop
ORD8:53 amChicago O'Hare Intl
$558
Find similar

Air Canada flights from Chicago to Port of Spain

Our best Air Canada deals on Chicago to Port of Spain flight tickets
Air Canada
Nov 11
ORD10:00 amChicago O'Hare Intl
13h 15m
1 stop
POS1:15 amPort of Spain Piarco Intl
Nov 21
POS2:15 amPort of Spain Piarco Intl
12h 46m
1 stop
ORD1:01 pmChicago O'Hare Intl
$537
Find similar
Air Canada
Sep 19
ORD10:40 amChicago O'Hare Intl
13h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
Sep 28
POS2:25 amPort of Spain Piarco Intl
17h 29m
2 stops
ORD6:54 pmChicago O'Hare Intl
$542
Find similar
Air Canada
Sep 6
ORD6:06 pmChicago O'Hare Intl
30h 14m
2 stops
POS1:20 amPort of Spain Piarco Intl
Sep 19
POS2:25 amPort of Spain Piarco Intl
18h 04m
1 stop
ORD7:29 pmChicago O'Hare Intl
$547
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 July 30, 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

Thu 9/18

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Sun 9/28

6:25 pm-9:18 am

1 stop15h 53m

$450

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

10:27 am-6:55 pm

1 stop31h 28m

Port of Spain Piarco Intl

Fri 9/26

9:10 am-9:18 am

1 stop25h 08m

$455

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/19

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Sun 9/28

3:51 am-1:41 pm

1 stop10h 50m

$526

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 11/11

10:00 am-1:15 am

1 stop13h 15m

Port of Spain Piarco Intl

Fri 11/21

2:15 am-1:01 pm

1 stop12h 46m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Sat 10/25

3:51 am-1:41 pm

1 stop10h 50m

$541

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/19

10:40 am-1:20 am

2 stops13h 40m

Port of Spain Piarco Intl

Sun 9/28

2:25 am-6:54 pm

2 stops17h 29m

$542

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/15

8:15 am-10:20 pm

1 stop12h 05m

Port of Spain Piarco Intl

Fri 1/23

7:10 am-7:37 pm

1 stop14h 27m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/15

10:28 am-10:20 pm

2 stops9h 52m

Port of Spain Piarco Intl

Fri 1/23

4:45 pm-12:30 am

1 stop9h 45m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:10 am-11:23 pm

1 stop15h 13m

Port of Spain Piarco Intl

Sat 10/25

12:30 am-10:02 am

1 stop10h 32m

$658

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/18

6:00 am-11:23 pm

1 stop16h 23m

Port of Spain Piarco Intl

Sat 9/27

12:30 am-12:20 pm

1 stop12h 50m

$668

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 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 day to depart on your flight to Port of Spain?

The cheapest day to depart from Chicago to Port of Spain is on a Sunday when prices can be found for as low as $569. Flights from Chicago to Port of Spain on a Monday will generally be more expensive and average around $706. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Port of Spain?

In the afternoon is the cheapest time of day to fly from Chicago to Port of Spain when you can find flight prices for as low as $535. Flying to Port of Spain in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Port of Spain, so prices are often more expensive at around $847 per ticket.

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

Best Price Found

$553

Fastest flight time

8h 18m

Direct flights

None

Airports in Port of Spain

1 airport
The best one-way flight to Port of Spain from Chicago in the past 72 hours is $553. The best round-trip flight deal from Chicago to Port of Spain found on momondo in the last 72 hours is $450.
The fastest flight from Chicago to Port of Spain takes 8h 18m
There are no direct flights from Chicago to Port of Spain. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Port of Spain Piarco Intl Airport.
There is 1 airport near Port of Spain: Port of Spain Piarco Intl (POS)
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. 8h 18m 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
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,896 reviews
Search United Airlines flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
10,000 reviews
Search American 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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