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Cheap flights from Port of Spain to Chicago from $348

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 7/10. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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 - 12:15 pm
POS
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
$597Multiple Airlines
Mon, Jul 27 - Mon, Aug 3
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$606Air Canada
Wed, Aug 26 - Fri, Aug 28
Air Canada Logo
1:25 am - 7:51 am
POS
-
ORD
31h 26m
2 stops
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$610Air Canada
Wed, Aug 26 - Fri, Aug 28
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$625Air Canada
Wed, Aug 26 - Fri, Aug 28
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$632Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 8:05 pm
POS
-
ORD
19h 40m
2 stops
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$635Air Canada
Wed, Jul 8 - Wed, Jul 22
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
28h 05m
2 stops
$638Multiple Airlines
Mon, Jul 27 - Mon, Aug 3
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$649Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$652Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
2:08 pm - 12:15 am
ORD
-
POS
33h 07m
2 stops
$663Air Canada
Fri, Jul 3 - Thu, Jul 9

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Air Canada flights from Port of Spain to Chicago

Our best Air Canada deals on Port of Spain to Chicago flight tickets
Air Canada
Jun 21
POS1:25 amPort of Spain Piarco Intl
18h 27m
2 stops
ORD6:52 pmChicago O'Hare Intl
Jul 6
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
$601
Air Canada
Jun 21
POS1:25 amPort of Spain Piarco Intl
18h 27m
2 stops
ORD6:52 pmChicago O'Hare Intl
Jul 6
ORD8:45 amChicago O'Hare Intl
14h 30m
2 stops
POS12:15 amPort of Spain Piarco Intl
$605
Air Canada
Aug 26
POS1:25 amPort of Spain Piarco Intl
14h 30m
1 stop
ORD2:55 pmChicago O'Hare Intl
Aug 28
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
$606

Copa Airlines flights from Port of Spain to Chicago

Our best Copa Airlines deals on Port of Spain to Chicago flight tickets
Copa Airlines
Nov 30
POS3:23 amPort of Spain Piarco Intl
22h 48m
1 stop
ORD12:11 amChicago O'Hare Intl
Dec 8
ORD7:35 amChicago O'Hare Intl
16h 26m
1 stop
POS2:01 amPort of Spain Piarco Intl
$678
Copa Airlines
Jul 4
POS2:19 pmPort of Spain Piarco Intl
14h 41m
1 stop
ORD4:00 amChicago O'Hare Intl
Jul 9
ORD3:21 pmChicago O'Hare Intl
9h 25m
1 stop
POS1:46 amPort of Spain Piarco Intl
$680

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 June 13, 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

Mon 7/27

10:10 am-12:15 pm

1 stop27h 05m

Chicago O'Hare Intl

Mon 8/3

8:05 am-8:00 pm

1 stop10h 55m

$597

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/26

1:25 am-2:55 pm

1 stop14h 30m

Chicago O'Hare Intl

Fri 8/28

2:15 pm-12:15 am

1 stop9h 00m

$606

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/26

1:25 am-7:51 am

2 stops31h 26m

Chicago O'Hare Intl

Fri 8/28

2:15 pm-12:15 am

1 stop9h 00m

$610

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/26

1:25 am-2:55 pm

2 stops14h 30m

Chicago O'Hare Intl

Fri 8/28

8:45 am-12:15 am

2 stops14h 30m

$625
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

2:15 pm-12:15 am

1 stop9h 00m

$632

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-8:05 pm

2 stops19h 40m

Chicago O'Hare Intl

Wed 7/22

2:15 pm-12:15 am

1 stop9h 00m

$635

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 7/27

10:10 am-12:15 pm

1 stop27h 05m

Chicago O'Hare Intl

Mon 8/3

1:50 pm-6:55 pm

2 stops28h 05m

$638

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

2:15 pm-12:15 am

1 stop9h 00m

$649

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

8:45 am-12:15 am

2 stops14h 30m

$652

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 7/3

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Thu 7/9

2:08 pm-12:15 am

2 stops33h 07m

$663

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 month to fly to Chicago?

The month of June is, on average, the cheapest month to fly to Chicago from Port of Spain, with most prices found around $0. If you’re not able to fly to Chicago in June, then April is your next best option. Flight prices from Port of Spain to Chicago during April average around $0.

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

14h 07m

Direct flights

None
The fastest flight from Port of Spain to Chicago takes 14h 07m
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 14h 07m.

  • 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 $572Free CancellationRating
7.4
9,815 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,648 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
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Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
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Porter
Griffith
Saint John

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