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Cheap flights from Port of Spain to Chicago from $471

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 11/25. 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
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
$471Air Canada
Find Deal
Tue, Nov 25 - Mon, Dec 1
Air Canada Logo
2:15 am - 6:52 pmPOS-ORD
42h 37m2 stops
Air Canada Logo
10:00 am - 1:10 amORD-POS
13h 10m1 stop
$483Air Canada
Find Deal
Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
1:30 am - 10:37 pmPOS-ORD
23h 07m1 stop
United Airlines Logo
8:54 am - 12:23 amORD-POS
13h 29m1 stop
$571United Airlines
Find Deal
Sat, Dec 20 - Wed, Dec 31
American Airlines Logo
7:19 am - 10:59 pmPOS-ORD
17h 40m1 stop
American Airlines Logo
7:17 pm - 3:30 pmORD-POS
18h 13m1 stop
$574American Airlines
Find Deal
Wed, Nov 26 - Mon, Dec 1
American Airlines Logo
7:19 am - 7:42 pmPOS-ORD
14h 23m2 stops
American Airlines Logo
7:17 pm - 3:30 pmORD-POS
18h 13m1 stop
$579American Airlines
Find Deal
Wed, Nov 26 - Mon, Dec 1
American Airlines Logo
4:30 pm - 9:05 amPOS-ORD
18h 35m1 stop
American Airlines Logo
7:17 pm - 3:30 pmORD-POS
18h 13m1 stop
$580American Airlines
Find Deal
Sun, Nov 23 - Sun, Nov 30
Multiple Airlines Logo
7:35 pm - 5:00 pmPOS-ORD
23h 25m1 stop
Multiple Airlines Logo
7:30 am - 1:48 amORD-POS
16h 18m2 stops
$581Multiple Airlines
Find Deal
Sun, Dec 21 - Wed, Dec 31
United Airlines Logo
1:30 am - 7:41 amPOS-ORD
32h 11m1 stop
United Airlines Logo
11:55 pm - 12:23 amORD-POS
22h 28m1 stop
$593United Airlines
Find Deal
Sat, Nov 22 - Sun, Nov 30
Multiple Airlines Logo
7:35 pm - 5:00 pmPOS-ORD
23h 25m1 stop
Multiple Airlines Logo
5:45 am - 8:20 pmORD-POS
12h 35m2 stops
$598Multiple Airlines
Find Deal
Sun, Dec 21 - Sat, Jan 3
Copa Airlines Logo
2:16 pm - 12:31 pmPOS-ORD
24h 15m1 stop
Copa Airlines Logo
7:34 am - 1:46 amORD-POS
16h 12m1 stop
$653Copa Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3

United Airlines flights from Port of Spain to Chicago

Our best United Airlines deals on Port of Spain to Chicago flight tickets
United Airlines
Dec 20
POS1:30 amPort of Spain Piarco Intl
23h 07m
1 stop
ORD10:37 pmChicago O'Hare Intl
Jan 1
ORD2:37 pmChicago O'Hare Intl
8h 28m
1 stop
POS1:05 amPort of Spain Piarco Intl
$571
Find similar
United Airlines
Nov 22
POS1:30 amPort of Spain Piarco Intl
32h 11m
1 stop
ORD7:41 amChicago O'Hare Intl
Nov 30
ORD11:55 pmChicago O'Hare Intl
22h 28m
1 stop
POS12:23 amPort of Spain Piarco Intl
$593
Find similar
United Airlines
Dec 19
POS1:30 amPort of Spain Piarco Intl
32h 17m
1 stop
ORD7:47 amChicago O'Hare Intl
Jan 1
ORD2:37 pmChicago O'Hare Intl
8h 28m
1 stop
POS1:05 amPort of Spain Piarco Intl
$670
Find similar

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 25
POS2:15 amPort of Spain Piarco Intl
14h 40m
2 stops
ORD2:55 pmChicago O'Hare Intl
Dec 1
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
$471
Find similar
Air Canada
Feb 26
POS2:15 amPort of Spain Piarco Intl
42h 37m
2 stops
ORD6:52 pmChicago O'Hare Intl
Mar 3
ORD10:00 amChicago O'Hare Intl
13h 10m
1 stop
POS1:10 amPort of Spain Piarco Intl
$483
Find similar
Air Canada
Dec 19
POS2:15 amPort of Spain Piarco Intl
17h 33m
1 stop
ORD5:48 pmChicago O'Hare Intl
Jan 3
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
$820
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 October 30, 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

Tue 11/25

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-6:52 pm

2 stops42h 37m

Chicago O'Hare Intl

Tue 3/3

10:00 am-1:10 am

1 stop13h 10m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/20

1:30 am-10:37 pm

1 stop23h 07m

Chicago O'Hare Intl

Wed 12/31

8:54 am-12:23 am

1 stop13h 29m

$571

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-10:59 pm

1 stop17h 40m

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:30 pm

1 stop18h 13m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-7:42 pm

2 stops14h 23m

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:30 pm

1 stop18h 13m

$579

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/23

4:30 pm-9:05 am

1 stop18h 35m

Chicago O'Hare Intl

Sun 11/30

7:17 pm-3:30 pm

1 stop18h 13m

$580

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 12/21

7:35 pm-5:00 pm

1 stop23h 25m

Chicago O'Hare Intl

Wed 12/31

7:30 am-1:48 am

2 stops16h 18m

$581

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 11/22

1:30 am-7:41 am

1 stop32h 11m

Chicago O'Hare Intl

Sun 11/30

11:55 pm-12:23 am

1 stop22h 28m

$593

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 12/21

7:35 pm-5:00 pm

1 stop23h 25m

Chicago O'Hare Intl

Sat 1/3

5:45 am-8:20 pm

2 stops12h 35m

$598

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/27

2:16 pm-12:31 pm

1 stop24h 15m

Chicago O'Hare Intl

Tue 3/3

7:34 am-1:46 am

1 stop16h 12m

$653

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

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

Direct flights

None
There are no direct flights from Port of Spain to Chicago. There are no popular flight routes from Port of Spain to Chicago.
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  • 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 50m.

  • 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
Copa AirlinesPriceFrom $299Free CancellationRating
7.6
1,563 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
8,998 reviews
Search United Airlines flights
American AirlinesPriceFrom $561Free CancellationRating
7.2
11,030 reviews
Search American Airlines flights

Traveling to a place near Chicago?

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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