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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 - 1:25 pm
POS
-
ORD
13h 00m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$318Air Canada
Wed, May 27 - Tue, Jun 23
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$319Air Canada
Wed, May 27 - Thu, Jun 18
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$322Air Canada
Fri, May 22 - Fri, Jun 19
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
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$372Air Canada
Wed, May 27 - Wed, Jun 24
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
6:22 pm - 12:15 am
ORD
-
POS
28h 53m
2 stops
$386Air Canada
Wed, May 27 - Thu, Jun 18
Air Canada Logo
1:25 am - 7:50 am
POS
-
ORD
31h 25m
2 stops
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$389Air Canada
Wed, May 27 - Wed, Jun 24
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 - 8:16 pm
POS
-
ORD
19h 51m
1 stop
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
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$442Air Canada
Wed, May 27 - Wed, Jun 17

Air Canada flights from Port of Spain to Chicago

Our best Air Canada deals on Port of Spain to Chicago flight tickets
Air Canada
May 27
POS1:25 amPort of Spain Piarco Intl
13h 00m
1 stop
ORD1:25 pmChicago O'Hare Intl
Jun 23
ORD8:40 pmChicago O'Hare Intl
26h 35m
1 stop
POS12:15 amPort of Spain Piarco Intl
$318
Air Canada
May 27
POS1:25 amPort of Spain Piarco Intl
18h 22m
2 stops
ORD6:47 pmChicago O'Hare Intl
Jun 18
ORD8:40 pmChicago O'Hare Intl
26h 35m
1 stop
POS12:15 amPort of Spain Piarco Intl
$319
Air Canada
May 22
POS1:25 amPort of Spain Piarco Intl
18h 22m
2 stops
ORD6:47 pmChicago O'Hare Intl
Jun 19
ORD8:45 amChicago O'Hare Intl
14h 30m
2 stops
POS12:15 amPort of Spain Piarco Intl
$322

American Airlines flights from Port of Spain to Chicago

Our best American Airlines deals on Port of Spain to Chicago flight tickets
American Airlines
May 28
POS7:00 amPort of Spain Piarco Intl
15h 37m
2 stops
ORD9:37 pmChicago O'Hare Intl
Jun 24
ORD7:59 amChicago O'Hare Intl
14h 00m
2 stops
POS10:59 pmPort of Spain Piarco Intl
$686
American Airlines
May 24
POS7:00 amPort of Spain Piarco Intl
15h 37m
2 stops
ORD9:37 pmChicago O'Hare Intl
Jun 20
ORD6:56 amChicago O'Hare Intl
15h 03m
2 stops
POS10:59 pmPort of Spain Piarco Intl
$702
American Airlines
Apr 14
POS3:47 pmPort of Spain Piarco Intl
17h 49m
2 stops
ORD8:36 amChicago O'Hare Intl
Apr 21
ORD8:46 pmChicago O'Hare Intl
16h 46m
2 stops
POS2:32 pmPort of Spain Piarco Intl
$708

momondo Fare Finder

 
Customize your flight search to find flights from Port of Spain to Chicago 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 2, 2026.
Use the filters below to find and compare flights from Port of Spain to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/27

1:25 am-1:25 pm

1 stop13h 00m

Chicago O'Hare Intl

Tue 6/23

8:40 pm-12:15 am

1 stop26h 35m

$318

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/27

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Thu 6/18

8:40 pm-12:15 am

1 stop26h 35m

$319

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/22

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Fri 6/19

8:45 am-12:15 am

2 stops14h 30m

$322

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

Wed 5/27

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Wed 6/24

8:45 am-12:15 am

2 stops14h 30m

$372

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/27

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Thu 6/18

6:22 pm-12:15 am

2 stops28h 53m

$386

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/27

1:25 am-7:50 am

2 stops31h 25m

Chicago O'Hare Intl

Wed 6/24

2:15 pm-12:15 am

1 stop9h 00m

$389

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-8:16 pm

1 stop19h 51m

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

Wed 5/27

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Wed 6/17

8:45 am-12:15 am

2 stops14h 30m

$442

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

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 airline that flies from Port of Spain Piarco Intl to Chicago?

Air Canada is the most popular carrier operating from Port of Spain Piarco Intl to Chicago

What airlines fly to Chicago?

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from Port of Spain according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Port of Spain to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Port of Spain to Chicago 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 (POS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Port of Spain to Chicago

Fastest flight time

11h 53m

Direct flights

None
The fastest flight from Port of Spain to Chicago takes 11h 53m
There are no direct flights from Port of Spain to Chicago. There are no popular flight routes from Port of Spain to Chicago.
Search flight deals

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

    Port of Spain Piarco Intl and Chicago are 2671.5 mi apart from one another. 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?

    Prices for flights from Port of Spain Piarco Intl Airport to Chicago were last updated today.

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

  • How old do you have to be to fly from Port of Spain Piarco Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Port of Spain Piarco Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago 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 Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Port of Spain to Chicago

Compare and see reviews for airlines that fly from Port of Spain to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $290Free CancellationRating
7.4
9,376 reviews
Search United Airlines flights
Copa AirlinesPriceFrom $299Free CancellationRating
7.5
1,559 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.1
11,369 reviews
Search American Airlines flights

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Why use momondo?

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

Finding the right flight to Chicago from Port of Spain is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Port of Spain to Chicago flights to just show those with flexible booking policies.

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?

Of course. momondo tracks the price of Port of Spain to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport