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Cheap flights from Port of Spain to Chicago from $346

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 7/22. 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
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.
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
1:57 pm - 12:15 am
ORD
-
POS
33h 18m
2 stops
$546Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
Multiple Airlines Logo
9:20 am - 6:55 pm
ORD
-
POS
8h 35m
1 stop
$547Multiple Airlines
Sun, Jun 7 - Sun, Jun 14
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
9:55 am - 12:15 am
ORD
-
POS
13h 20m
1 stop
$554Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
12:59 pm - 6:55 pm
ORD
-
POS
28h 56m
2 stops
$563Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
9:55 am - 12:15 am
ORD
-
POS
13h 20m
1 stop
$569Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
1:49 pm - 6:55 pm
ORD
-
POS
28h 06m
2 stops
$574Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
5:35 pm - 12:15 am
ORD
-
POS
29h 40m
1 stop
$585Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
10:10 am - 7:55 am
POS
-
ORD
22h 45m
2 stops
Multiple Airlines Logo
9:20 am - 6:55 pm
ORD
-
POS
8h 35m
1 stop
$587Multiple Airlines
Sun, Jun 7 - Sun, Jun 14
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
Multiple Airlines Logo
7:33 pm - 8:00 pm
ORD
-
POS
23h 27m
1 stop
$590Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
5:35 pm - 12:15 am
ORD
-
POS
29h 40m
1 stop
$591Multiple Airlines
Fri, May 22 - Tue, Jun 30

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 22
POS1:25 amPort of Spain Piarco Intl
13h 00m
1 stop
ORD1:25 pmChicago O'Hare Intl
Jun 8
ORD9:55 amChicago O'Hare Intl
13h 20m
1 stop
POS12:15 amPort of Spain Piarco Intl
$616
Air Canada
May 22
POS1:25 amPort of Spain Piarco Intl
13h 00m
1 stop
ORD1:25 pmChicago O'Hare Intl
Jun 30
ORD8:40 pmChicago O'Hare Intl
26h 35m
1 stop
POS12:15 amPort of Spain Piarco Intl
$646
Air Canada
May 22
POS1:25 amPort of Spain Piarco Intl
18h 27m
2 stops
ORD6:52 pmChicago O'Hare Intl
Jun 30
ORD6:22 pmChicago O'Hare Intl
28h 53m
2 stops
POS12:15 amPort of Spain Piarco Intl
$676

American Airlines flights from Port of Spain to Chicago

Our best American Airlines deals on Port of Spain to Chicago flight tickets
American Airlines
Jun 19
POS7:00 amPort of Spain Piarco Intl
15h 29m
2 stops
ORD9:29 pmChicago O'Hare Intl
Jun 24
ORD7:58 amChicago O'Hare Intl
14h 03m
2 stops
POS11:01 pmPort of Spain Piarco Intl
$697
American Airlines
Jun 19
POS7:00 amPort of Spain Piarco Intl
15h 29m
2 stops
ORD9:29 pmChicago O'Hare Intl
Jun 24
ORD8:48 amChicago O'Hare Intl
13h 13m
2 stops
POS11:01 pmPort of Spain Piarco Intl
$742
American Airlines
May 22
POS7:00 amPort of Spain Piarco Intl
15h 39m
2 stops
ORD9:39 pmChicago O'Hare Intl
Jun 23
ORD10:41 amChicago O'Hare Intl
11h 20m
2 stops
POS11:01 pmPort of Spain Piarco Intl
$747

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 April 24, 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

Cheapest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/22

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Tue 6/30

1:57 pm-12:15 am

2 stops33h 18m

$546
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/7

9:10 am-11:56 pm

1 stop15h 46m

Chicago O'Hare Intl

Sun 6/14

9:20 am-6:55 pm

1 stop8h 35m

$547

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

9:55 am-12:15 am

1 stop13h 20m

$554

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

12:59 pm-6:55 pm

2 stops28h 56m

$563

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

9:55 am-12:15 am

1 stop13h 20m

$569

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

1:49 pm-6:55 pm

2 stops28h 06m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/22

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Tue 6/30

5:35 pm-12:15 am

1 stop29h 40m

$585

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/7

10:10 am-7:55 am

2 stops22h 45m

Chicago O'Hare Intl

Sun 6/14

9:20 am-6:55 pm

1 stop8h 35m

$587

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 6/4

9:10 am-11:56 pm

1 stop15h 46m

Chicago O'Hare Intl

Thu 6/11

7:33 pm-8:00 pm

1 stop23h 27m

$590

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/22

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Tue 6/30

5:35 pm-12:15 am

1 stop29h 40m

$591

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 airlines fly to Chicago?

United Airlines, American Airlines and Air Canada are the top three most popular airlines that fly to Chicago from Port of Spain according to our data. United Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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

10h 42m

Direct flights

None
The fastest flight from Port of Spain to Chicago takes 10h 42m
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

Frequently asked questions about flying from Port of Spain to Chicago

  • 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 10h 42m.

  • 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
Copa AirlinesPriceFrom $299Free CancellationRating
7.5
1,577 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $322Free CancellationRating
7.1
10,964 reviews
Search Air Canada flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
9,648 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,669 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