Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 - 2:55 pmPOS-ORD
14h 40m2 stops
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
2:37 pm - 1:05 amORD-POS
8h 28m1 stop
$571United Airlines
Find Deal
Sat, Dec 20 - Thu, Jan 1
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 O'Hare Intl Airport

Our best United Airlines deals on Port of Spain to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport

Our best Air Canada deals on Port of Spain to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport 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-2:55 pm

2 stops14h 40m

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

Thu 1/1

2:37 pm-1:05 am

1 stop8h 28m

$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 O'Hare Intl Airport

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 typical price of a round-trip flight between Port of Spain and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Port of Spain averaging around $542.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $603. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Port of Spain because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $717.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Port of Spain in the morning is the least expensive time of day to depart. momondo users have found prices as low as $637 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $672. Of course, these prices can vary depending on the time of year and what airport you fly to.

How have Port of Spain to Chicago O'Hare Intl Airport flight prices changed over time?

When to book flights from Port of Spain to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Port of Spain to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (POS to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Port of Spain to Chicago O'Hare Intl Airport

Direct flights

None
There are no direct flights from Port of Spain to Chicago O'Hare Intl Airport. There are no popular flight routes from Port of Spain to Chicago O'Hare Intl Airport.
Search flight deals

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

    The straight-line distance from Port of Spain Piarco Intl to Chicago O'Hare Intl is 2686.5 mi. 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 O'Hare Intl Airport?

    Prices for flights from Port of Spain Piarco Intl Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Port of Spain Piarco Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular airline from Port of Spain to Chicago O'Hare Intl Airport?

Best airlines flying from Port of Spain to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Port of Spain to Chicago O'Hare Intl Airport 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?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Port of Spain to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Chicago from Port of Spain with this policy.

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?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Port of Spain and alert you when they change.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 11/29
Sat 12/6
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago