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Cheap flights from Port of Spain to Chicago from $447

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 9/9. 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

Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
Logo
10:27 am - 6:55 pmORD-POS
31h 28m1 stop
$447
Find Deal
mar., sep. 9 - mar., sep. 16
Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
Logo
10:27 am - 6:55 pmORD-POS
31h 28m1 stop
$451
Find Deal
mar., sep. 9 - mar., sep. 16
Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
Logo
6:44 pm - 8:00 pmORD-POS
24h 16m1 stop
$463
Find Deal
mié., sep. 10 - mié., sep. 17
Copa Airlines Logo
2:40 pm - 12:21 amPOS-ORD
10h 41m1 stop
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
$562Copa Airlines
Find Deal
vie., oct. 17 - vie., oct. 24
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
Air Canada Logo
8:20 pm - 1:15 amORD-POS
26h 55m1 stop
$565Air Canada
Find Deal
dom., nov. 2 - lun., nov. 10
United Airlines Logo
12:30 am - 7:58 pmPOS-ORD
20h 28m1 stop
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$573United Airlines
Find Deal
lun., sep. 8 - mar., sep. 16
United Airlines Logo
12:30 am - 12:15 amPOS-ORD
24h 45m1 stop
United Airlines Logo
5:50 pm - 11:23 pmORD-POS
28h 33m1 stop
$574United Airlines
Find Deal
lun., sep. 8 - mar., sep. 16
American Airlines Logo
3:25 pm - 11:49 pmPOS-ORD
9h 24m1 stop
American Airlines Logo
8:47 pm - 2:16 pmORD-POS
16h 29m2 stops
$578American Airlines
Find Deal
mar., sep. 9 - mar., sep. 16
American Airlines Logo
7:01 am - 4:49 pmPOS-ORD
11h 48m2 stops
American Airlines Logo
10:29 am - 11:36 pmORD-POS
11h 07m2 stops
$620American Airlines
Find Deal
lun., nov. 3 - lun., nov. 10
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
Air Canada Logo
7:15 am - 1:15 amORD-POS
16h 00m2 stops
$734Air Canada
Find Deal
mar., dic. 23 - vie., ene. 2

Air Canada flights from Port of Spain to Chicago

Our best Air Canada deals on Port of Spain to Chicago flight tickets
Air Canada
Nov 2
POS2:15 amPort of Spain Piarco Intl
12h 46m
1 stop
ORD1:01 pmChicago O'Hare Intl
Nov 10
ORD8:20 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:15 amPort of Spain Piarco Intl
$565
Find similar
Air Canada
Dec 23
POS2:15 amPort of Spain Piarco Intl
12h 46m
1 stop
ORD1:01 pmChicago O'Hare Intl
Jan 2
ORD7:15 amChicago O'Hare Intl
16h 00m
2 stops
POS1:15 amPort of Spain Piarco Intl
$734
Find similar
Air Canada
Dec 23
POS2:15 amPort of Spain Piarco Intl
14h 40m
2 stops
ORD2:55 pmChicago O'Hare Intl
Jan 2
ORD7:15 amChicago O'Hare Intl
16h 00m
2 stops
POS1:15 amPort of Spain Piarco Intl
$1,187
Find similar

American Airlines flights from Port of Spain to Chicago

Our best American Airlines deals on Port of Spain to Chicago flight tickets
American Airlines
Sep 9
POS3:25 pmPort of Spain Piarco Intl
9h 24m
1 stop
ORD11:49 pmChicago O'Hare Intl
Sep 16
ORD8:47 pmChicago O'Hare Intl
16h 29m
2 stops
POS2:16 pmPort of Spain Piarco Intl
$578
Find similar
American Airlines
Nov 3
POS7:01 amPort of Spain Piarco Intl
11h 48m
2 stops
ORD4:49 pmChicago O'Hare Intl
Nov 10
ORD10:29 amChicago O'Hare Intl
11h 07m
2 stops
POS11:36 pmPort of Spain Piarco Intl
$620
Find similar
American Airlines
Dec 23
POS4:40 pmPort of Spain Piarco Intl
18h 22m
1 stop
ORD9:02 amChicago O'Hare Intl
Jan 2
ORD6:37 amChicago O'Hare Intl
13h 38m
1 stop
POS10:15 pmPort of Spain Piarco Intl
$829
Find similar

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 julio 31, 2025.
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

mar. 9/9

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

mar. 9/16

10:27 am-6:55 pm

1 stop31h 28m

$447

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 9/9

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

mar. 9/16

10:27 am-6:55 pm

1 stop31h 28m

$451

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mié. 9/10

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

mié. 9/17

6:44 pm-8:00 pm

1 stop24h 16m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

vie. 10/17

2:40 pm-12:21 am

1 stop10h 41m

Chicago O'Hare Intl

vie. 10/24

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

dom. 11/2

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

lun. 11/10

8:20 pm-1:15 am

1 stop26h 55m

$565

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 9/8

12:30 am-7:58 pm

1 stop20h 28m

Chicago O'Hare Intl

mar. 9/16

6:00 am-11:23 pm

1 stop16h 23m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 9/8

12:30 am-12:15 am

1 stop24h 45m

Chicago O'Hare Intl

mar. 9/16

5:50 pm-11:23 pm

1 stop28h 33m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 9/9

3:25 pm-11:49 pm

1 stop9h 24m

Chicago O'Hare Intl

mar. 9/16

8:47 pm-2:16 pm

2 stops16h 29m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 11/3

7:01 am-4:49 pm

2 stops11h 48m

Chicago O'Hare Intl

lun. 11/10

10:29 am-11:36 pm

2 stops11h 07m

$620

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 12/23

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

vie. 1/2

7:15 am-1:15 am

2 stops16h 00m

$734

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $597. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Port of Spain to Chicago for around $1,058.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Port of Spain to Chicago during this time can be as low as $716. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $830.

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

Best Price Found

$447

Fastest flight time

9h 24m

Direct flights

None

Airports in Chicago

1 airport
The best flight deal from Port of Spain to Chicago found on momondo in the last 72 hours is $447
The fastest flight from Port of Spain to Chicago takes 9h 24m
There are no direct flights from Port of Spain to Chicago. Popular non-direct route for this connection is Port of Spain Piarco Intl Airport - Chicago O'Hare Intl Airport.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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 9h 24m.

  • 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.

  • What is the most popular airline from Port of Spain to Chicago?

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 $493Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $561Free CancellationRating
7.2
10,000 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