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Cheap flights from Port of Spain to Chicago from $183

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 5/8. 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 Port of Spain to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
2:19 pm - 12:15 am
ORD
-
POS
56h 56m
2 stops
$333Air Canada
Sun, Jul 19 - Fri, Aug 14
Air Canada Logo
1:20 am - 10:53 am
POS
-
ORD
34h 33m
2 stops
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
$405Air Canada
Sun, Apr 5 - Fri, Apr 10
Air Canada Logo
1:25 am - 7:45 am
POS
-
ORD
31h 20m
2 stops
Air Canada Logo
7:25 am - 12:15 am
ORD
-
POS
15h 50m
1 stop
$426Air Canada
Sun, Jul 19 - Fri, Aug 14
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
9:50 am - 12:20 am
ORD
-
POS
13h 30m
1 stop
$454Air Canada
Sun, Apr 5 - Fri, Apr 10
Multiple Airlines Logo
1:20 am - 7:45 pm
POS
-
ORD
19h 25m
1 stop
Multiple Airlines Logo
5:05 am - 8:00 pm
ORD
-
POS
13h 55m
1 stop
$455Multiple Airlines
Sun, Mar 15 - Thu, Mar 19
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$457Air Canada
Sun, Apr 5 - Fri, Apr 10
Multiple Airlines Logo
1:20 am - 7:45 pm
POS
-
ORD
19h 25m
1 stop
Multiple Airlines Logo
4:36 pm - 12:20 am
ORD
-
POS
30h 44m
3 stops
$458Multiple Airlines
Sun, Mar 15 - Thu, Mar 19
Air Canada Logo
1:20 am - 10:53 am
POS
-
ORD
34h 33m
2 stops
Air Canada Logo
6:21 pm - 12:20 am
ORD
-
POS
52h 59m
2 stops
$461Air Canada
Sun, Apr 5 - Fri, Apr 10
Air Canada Logo
1:20 am - 8:00 am
POS
-
ORD
31h 40m
2 stops
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$472Air Canada
Sun, Apr 5 - Fri, Apr 10
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
9:50 am - 12:20 am
ORD
-
POS
13h 30m
1 stop
$476Air Canada
Sun, Apr 5 - Fri, Apr 10

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
Jul 19
POS1:25 amPort of Spain Piarco Intl
18h 22m
2 stops
ORD6:47 pmChicago O'Hare Intl
Aug 14
ORD2:19 pmChicago O'Hare Intl
56h 56m
2 stops
POS12:15 amPort of Spain Piarco Intl
$333
Air Canada
Mar 10
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
Apr 14
ORD9:50 amChicago O'Hare Intl
13h 30m
1 stop
POS12:20 amPort of Spain Piarco Intl
$375
Air Canada
Apr 5
POS1:20 amPort of Spain Piarco Intl
34h 33m
2 stops
ORD10:53 amChicago O'Hare Intl
Apr 10
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS12:20 amPort of Spain Piarco Intl
$405

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

Our best United Airlines deals on Port of Spain to Chicago O'Hare Intl Airport flight tickets
United Airlines
Apr 15
POS12:30 amPort of Spain Piarco Intl
13h 27m
1 stop
ORD12:57 pmChicago O'Hare Intl
Apr 23
ORD6:15 pmChicago O'Hare Intl
28h 08m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$646
United Airlines
May 5
POS12:30 amPort of Spain Piarco Intl
15h 15m
1 stop
ORD2:45 pmChicago O'Hare Intl
May 10
ORD10:30 amChicago O'Hare Intl
11h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$647
United Airlines
Apr 1
POS12:30 amPort of Spain Piarco Intl
13h 27m
1 stop
ORD12:57 pmChicago O'Hare Intl
Apr 5
ORD8:15 pmChicago O'Hare Intl
26h 08m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$668

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 March 4, 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

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 7/19

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Fri 8/14

2:19 pm-12:15 am

2 stops56h 56m

$333

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-10:53 am

2 stops34h 33m

Chicago O'Hare Intl

Fri 4/10

2:00 pm-12:20 am

1 stop9h 20m

$405

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 7/19

1:25 am-7:45 am

2 stops31h 20m

Chicago O'Hare Intl

Fri 8/14

7:25 am-12:15 am

1 stop15h 50m

$426

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 4/10

9:50 am-12:20 am

1 stop13h 30m

$454

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/15

1:20 am-7:45 pm

1 stop19h 25m

Chicago O'Hare Intl

Thu 3/19

5:05 am-8:00 pm

1 stop13h 55m

$455

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 4/10

8:40 am-12:20 am

2 stops14h 40m

$457

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/15

1:20 am-7:45 pm

1 stop19h 25m

Chicago O'Hare Intl

Thu 3/19

4:36 pm-12:20 am

3 stops30h 44m

$458

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-10:53 am

2 stops34h 33m

Chicago O'Hare Intl

Fri 4/10

6:21 pm-12:20 am

2 stops52h 59m

$461

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-8:00 am

2 stops31h 40m

Chicago O'Hare Intl

Fri 4/10

8:40 am-12:20 am

2 stops14h 40m

$472

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 4/10

9:50 am-12:20 am

1 stop13h 30m

$476

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Port of Spain averaging around $375.

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

11h 53m

Direct flights

None
The fastest flight from Port of Spain to Chicago O'Hare Intl Airport takes 11h 53m
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

  • 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 11h 53m.

  • 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 $290Free CancellationRating
7.4
9,383 reviews
Search United Airlines flights
Copa AirlinesPriceFrom $299Free CancellationRating
7.5
1,557 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.1
11,380 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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Elgin
South Holland

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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