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Cheap flights from Port of Spain to Chicago from $316

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Port of Spain to Chicago departing on 7/20. 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 Port of Spain to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
1:20 am - 4:58 pm
POS
-
ORD
16h 38m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$534Air Canada
Wed, Oct 14 - Wed, Oct 21
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
$538Air Canada
Wed, Oct 14 - Wed, Oct 21
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$541Air Canada
Wed, Oct 14 - Wed, Oct 21
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$584Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$587Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$606Air Canada
Wed, Aug 26 - Fri, Aug 28
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
$607Air Canada
Wed, Jul 22 - Mon, Jul 27
Air Canada Logo
1:25 am - 7:51 am
POS
-
ORD
31h 26m
2 stops
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$610Air Canada
Wed, Aug 26 - Fri, Aug 28
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$611Air Canada
Wed, Jul 22 - Mon, Jul 27
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$625Air Canada
Wed, Aug 26 - Fri, Aug 28

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Air Canada flights from Port of Spain to Chicago O'Hare Intl Airport

Our best Air Canada deals on Port of Spain to Chicago O'Hare Intl Airport flight tickets
Air Canada
Oct 14
POS1:20 amPort of Spain Piarco Intl
16h 38m
1 stop
ORD4:58 pmChicago O'Hare Intl
Oct 21
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
$534
Air Canada
Oct 14
POS1:20 amPort of Spain Piarco Intl
14h 32m
2 stops
ORD2:52 pmChicago O'Hare Intl
Oct 21
ORD9:50 amChicago O'Hare Intl
13h 25m
1 stop
POS12:15 amPort of Spain Piarco Intl
$538
Air Canada
Oct 14
POS1:20 amPort of Spain Piarco Intl
14h 32m
2 stops
ORD2:52 pmChicago O'Hare Intl
Oct 21
ORD8:45 amChicago O'Hare Intl
14h 30m
2 stops
POS12:15 amPort of Spain Piarco Intl
$541

Copa Airlines flights from Port of Spain to Chicago O'Hare Intl Airport

Our best Copa Airlines deals on Port of Spain to Chicago O'Hare Intl Airport flight tickets
Copa Airlines
Dec 2
POS3:23 amPort of Spain Piarco Intl
22h 48m
1 stop
ORD12:11 amChicago O'Hare Intl
Dec 8
ORD2:13 pmChicago O'Hare Intl
9h 48m
1 stop
POS2:01 amPort of Spain Piarco Intl
$678
Copa Airlines
Jul 3
POS3:50 amPort of Spain Piarco Intl
21h 11m
1 stop
ORD12:01 amChicago O'Hare Intl
Jul 9
ORD8:02 amChicago O'Hare Intl
28h 14m
1 stop
POS1:16 pmPort of Spain Piarco Intl
$680

momondo Fare Finder

 
Customize your flight search to find flights from Port of Spain to Chicago O'Hare Intl Airport 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 June 10, 2026.
Use the filters below to find and compare flights from Port of Spain to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/14

1:20 am-4:58 pm

1 stop16h 38m

Chicago O'Hare Intl

Wed 10/21

2:15 pm-12:15 am

1 stop9h 00m

$534

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/14

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Wed 10/21

9:50 am-12:15 am

1 stop13h 25m

$538

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/14

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Wed 10/21

8:45 am-12:15 am

2 stops14h 30m

$541
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

2:15 pm-12:15 am

1 stop9h 00m

$584

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

8:45 am-12:15 am

2 stops14h 30m

$587

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/26

1:25 am-2:55 pm

1 stop14h 30m

Chicago O'Hare Intl

Fri 8/28

2:15 pm-12:15 am

1 stop9h 00m

$606

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Mon 7/27

9:50 am-12:15 am

1 stop13h 25m

$607

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/26

1:25 am-7:51 am

2 stops31h 26m

Chicago O'Hare Intl

Fri 8/28

2:15 pm-12:15 am

1 stop9h 00m

$610

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Mon 7/27

8:45 am-12:15 am

2 stops14h 30m

$611

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/26

1:25 am-2:55 pm

2 stops14h 30m

Chicago O'Hare Intl

Fri 8/28

8:45 am-12:15 am

2 stops14h 30m

$625

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Port of Spain to Chicago O'Hare Intl Airport

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 month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Port of Spain averaging around $0.

When to book flights from Port of Spain to Chicago O'Hare Intl Airport

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

Cheap Port of Spain to Chicago O'Hare Intl Airport (POS to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Port of Spain to Chicago O'Hare Intl Airport

Fastest flight time

14h 00m

Direct flights

None
The fastest flight from Port of Spain to Chicago O'Hare Intl Airport takes 14h 00m
There are no direct flights from Port of Spain to Chicago O'Hare Intl Airport. There are no popular flight routes from Port of Spain to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Port of Spain to Chicago O'Hare Intl Airport

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

    The straight-line distance from Port of Spain Piarco Intl to Chicago O'Hare Intl is 2686.5 mi. A reasonable flight in good conditions will take 14h 00m.

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

    Prices for flights from Port of Spain Piarco Intl Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

  • How old do you have to be to fly from Port of Spain Piarco Intl Airport to Chicago O'Hare 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 Port of Spain Piarco Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Port of Spain to Chicago O'Hare Intl Airport?

Best airlines flying from Port of Spain to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Port of Spain to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $572Free CancellationRating
7.4
9,804 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,635 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Tinley Park

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Port of Spain to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Port of Spain with this policy.

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

momondo helps you find the best flight between Port of Spain and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

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

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