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Cheap flights from Port of Spain to Chicago from $444

This is the cheapest round-trip 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 2/12. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
8:50 am - 11:10 pm
POS
-
ORD
16h 20m1 stop
JetBlue Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m2 stops
$444JetBlue
Thu, Feb 12 - Thu, Feb 19
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
$463Air Canada
Tue, Jan 27 - Fri, Feb 6
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
Multiple Airlines Logo
10:00 am - 1:20 am
ORD
-
POS
13h 20m1 stop
$478Multiple Airlines
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
12:22 pm - 11:10 pm
POS
-
ORD
12h 48m1 stop
Multiple Airlines Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
$480Multiple Airlines
Thu, Feb 12 - Thu, Feb 19
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
42h 35m2 stops
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m1 stop
$483Air Canada
Thu, Jan 29 - Sat, Feb 7
Air Canada Logo
2:20 am - 8:10 pm
POS
-
ORD
19h 50m2 stops
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m1 stop
$486Air Canada
Sun, Jan 25 - Sat, Feb 7
Air Canada Logo
2:20 am - 8:10 pm
POS
-
ORD
19h 50m2 stops
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
$490Air Canada
Sun, Jan 25 - Tue, Feb 3
Multiple Airlines Logo
9:10 am - 6:16 pm
POS
-
ORD
11h 06m1 stop
Multiple Airlines Logo
5:53 pm - 1:20 am
ORD
-
POS
29h 27m2 stops
$498Multiple Airlines
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
9:10 am - 6:16 pm
POS
-
ORD
11h 06m1 stop
Multiple Airlines Logo
5:53 pm - 1:20 am
ORD
-
POS
29h 27m3 stops
$501Multiple Airlines
Thu, Jan 29 - Thu, Feb 5
Multiple Airlines Logo
9:10 am - 6:16 pm
POS
-
ORD
11h 06m1 stop
Multiple Airlines Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m1 stop
$513Multiple Airlines
Thu, Jan 29 - Thu, Feb 5

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 27
POS12:30 amPort of Spain Piarco Intl
20h 27m
1 stop
ORD7:57 pmChicago O'Hare Intl
May 2
ORD12:45 pmChicago O'Hare Intl
9h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$680
Find similar
United Airlines
Jan 26
POS1:30 amPort of Spain Piarco Intl
23h 28m
1 stop
ORD10:58 pmChicago O'Hare Intl
Feb 5
ORD9:05 pmChicago O'Hare Intl
25h 18m
1 stop
POS12:23 amPort of Spain Piarco Intl
$689
Find similar
United Airlines
Jan 26
POS1:30 amPort of Spain Piarco Intl
20h 19m
1 stop
ORD7:49 pmChicago O'Hare Intl
Feb 7
ORD7:35 amChicago O'Hare Intl
14h 48m
1 stop
POS12:23 amPort of Spain Piarco Intl
$786
Find similar

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

Our best JetBlue deals on Port of Spain to Chicago O'Hare Intl Airport flight tickets
JetBlue
Feb 12
POS8:50 amPort of Spain Piarco Intl
16h 20m
1 stop
ORD11:10 pmChicago O'Hare Intl
Feb 19
ORD10:00 amChicago O'Hare Intl
19h 17m
2 stops
POS7:17 amPort of Spain Piarco Intl
$444
Find similar
JetBlue
Dec 18
POS3:56 pmPort of Spain Piarco Intl
28h 50m
2 stops
ORD6:46 pmChicago O'Hare Intl
Dec 23
ORD7:41 pmChicago O'Hare Intl
16h 49m
2 stops
POS2:30 pmPort of Spain Piarco Intl
$895
Find similar

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 December 17, 2025.
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

Thu 2/12

8:50 am-11:10 pm

1 stop16h 20m

Chicago O'Hare Intl

Thu 2/19

10:00 am-7:17 am

2 stops19h 17m

$444

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/27

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 2/6

2:00 pm-1:20 am

1 stop9h 20m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 1/30

8:20 am-5:43 pm

2 stops35h 23m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/12

12:22 pm-11:10 pm

1 stop12h 48m

Chicago O'Hare Intl

Thu 2/19

2:00 pm-1:20 am

1 stop9h 20m

$480

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

2:20 am-6:55 pm

2 stops42h 35m

Chicago O'Hare Intl

Sat 2/7

8:40 pm-1:20 am

1 stop26h 40m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 1/25

2:20 am-8:10 pm

2 stops19h 50m

Chicago O'Hare Intl

Sat 2/7

8:40 pm-1:20 am

1 stop26h 40m

$486

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 1/25

2:20 am-8:10 pm

2 stops19h 50m

Chicago O'Hare Intl

Tue 2/3

7:15 am-1:20 am

2 stops16h 05m

$490

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

9:10 am-6:16 pm

1 stop11h 06m

Chicago O'Hare Intl

Thu 2/5

5:53 pm-1:20 am

2 stops29h 27m

$498

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

9:10 am-6:16 pm

1 stop11h 06m

Chicago O'Hare Intl

Thu 2/5

5:53 pm-1:20 am

3 stops29h 27m

$501

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

9:10 am-6:16 pm

1 stop11h 06m

Chicago O'Hare Intl

Thu 2/5

8:40 pm-1:20 am

1 stop26h 40m

$513

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 June is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Port of Spain averaging around $453.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $603. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Port of Spain because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $717.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Port of Spain in the morning is the least expensive time of day to depart. momondo users have found prices as low as $637 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $672. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

9h 50m

Direct flights

None
The fastest flight from Port of Spain to Chicago O'Hare Intl Airport takes 9h 50m
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 9h 50m.

  • 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
Copa AirlinesPriceFrom $299Free CancellationRating
7.6
1,556 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $474Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
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Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Aurora
Elgin
Benton Harbor

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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