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Cheap flights from Chicago to Port of Spain from $198

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 1/17. 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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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
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$433Air Canada
Find Deal
Sat, Nov 22 - Thu, Nov 27
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$438Air Canada
Find Deal
Sat, Nov 22 - Thu, Nov 27
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$443Air Canada
Find Deal
Sat, Nov 22 - Sun, Nov 30
Multiple Airlines Logo
5:00 am - 8:00 pmORD-POS
13h 00m1 stop
Multiple Airlines Logo
10:10 am - 11:13 pmPOS-ORD
15h 03m1 stop
$503Multiple Airlines
Find Deal
Thu, Nov 20 - Thu, Nov 27
Multiple Airlines Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Multiple Airlines Logo
9:10 am - 1:23 pmPOS-ORD
30h 13m3 stops
$516Multiple Airlines
Find Deal
Sun, Nov 30 - Tue, Dec 2
United Airlines Logo
10:36 am - 12:23 amORD-POS
11h 47m1 stop
United Airlines Logo
1:30 am - 7:46 pmPOS-ORD
20h 16m1 stop
$549United Airlines
Find Deal
Sun, Nov 30 - Mon, Dec 1
American Airlines Logo
8:20 am - 11:38 pmORD-POS
13h 18m2 stops
American Airlines Logo
7:19 am - 4:03 pmPOS-ORD
10h 44m1 stop
$553American Airlines
Find Deal
Thu, Nov 20 - Thu, Nov 27
American Airlines Logo
5:00 am - 3:25 pmORD-POS
8h 25m1 stop
American Airlines Logo
4:30 pm - 12:30 amPOS-ORD
10h 00m1 stop
$554American Airlines
Find Deal
Sat, Jan 17 - Sun, Jan 18
United Airlines Logo
10:35 am - 12:23 amORD-POS
11h 48m1 stop
United Airlines Logo
1:30 am - 2:40 pmPOS-ORD
15h 10m1 stop
$586United Airlines
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Thu, Dec 25 - Sun, Dec 28
Copa Airlines Logo
7:33 am - 1:31 pmORD-POS
27h 58m1 stop
Copa Airlines Logo
3:47 am - 12:05 amPOS-ORD
22h 18m1 stop
$710Copa Airlines
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Tue, Dec 23 - Mon, Dec 29

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 22
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
Nov 27
POS2:15 amPort of Spain Piarco Intl
14h 55m
1 stop
ORD3:10 pmChicago O'Hare Intl
$433
Find similar
Air Canada
Nov 22
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
Nov 27
POS2:15 amPort of Spain Piarco Intl
18h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
$438
Find similar
Air Canada
Nov 22
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
Nov 30
POS2:15 amPort of Spain Piarco Intl
18h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
$443
Find similar

United Airlines flights from Chicago to Port of Spain

Our best United Airlines deals on Chicago to Port of Spain flight tickets
United Airlines
Nov 30
ORD10:36 amChicago O'Hare Intl
11h 47m
1 stop
POS12:23 amPort of Spain Piarco Intl
Dec 1
POS1:30 amPort of Spain Piarco Intl
20h 16m
1 stop
ORD7:46 pmChicago O'Hare Intl
$549
Find similar
United Airlines
Dec 25
ORD10:35 amChicago O'Hare Intl
11h 48m
1 stop
POS12:23 amPort of Spain Piarco Intl
Dec 28
POS1:30 amPort of Spain Piarco Intl
15h 10m
1 stop
ORD2:40 pmChicago O'Hare Intl
$586
Find similar
United Airlines
Dec 25
ORD12:09 pmChicago O'Hare Intl
10h 56m
1 stop
POS1:05 amPort of Spain Piarco Intl
Dec 31
POS2:20 amPort of Spain Piarco Intl
11h 45m
1 stop
ORD12:05 pmChicago O'Hare Intl
$662
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 November 9, 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

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-3:10 pm

1 stop14h 55m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-6:55 pm

2 stops18h 40m

$438

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Sun 11/30

2:15 am-6:55 pm

2 stops18h 40m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

5:00 am-8:00 pm

1 stop13h 00m

Port of Spain Piarco Intl

Thu 11/27

10:10 am-11:13 pm

1 stop15h 03m

$503

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 11/30

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Tue 12/2

9:10 am-1:23 pm

3 stops30h 13m

$516

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 11/30

10:36 am-12:23 am

1 stop11h 47m

Port of Spain Piarco Intl

Mon 12/1

1:30 am-7:46 pm

1 stop20h 16m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

8:20 am-11:38 pm

2 stops13h 18m

Port of Spain Piarco Intl

Thu 11/27

7:19 am-4:03 pm

1 stop10h 44m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/17

5:00 am-3:25 pm

1 stop8h 25m

Port of Spain Piarco Intl

Sun 1/18

4:30 pm-12:30 am

1 stop10h 00m

$554

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 12/25

10:35 am-12:23 am

1 stop11h 48m

Port of Spain Piarco Intl

Sun 12/28

1:30 am-2:40 pm

1 stop15h 10m

$586

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/23

7:33 am-1:31 pm

1 stop27h 58m

Port of Spain Piarco Intl

Mon 12/29

3:47 am-12:05 am

1 stop22h 18m

$710

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 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

Direct flights

None
There are no direct flights from Chicago to Port of Spain. There are no popular flight routes from Chicago to Port of Spain.
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  • 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 25m 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
10,429 reviews
Search Air Canada flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights
United AirlinesPriceFrom $560Free CancellationRating
7.4
9,014 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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