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Cheap flights from Port of Spain to Chicago from $349

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 8/19. 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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Find the cheapest flights from Port of Spain to Chicago

Cheap round-trip flights

Logo
10:10 am - 10:48 pmPOS-ORD
13h 38m1 stop
Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
$429
Find Deal
Mon, Sep 15 - Mon, Sep 22
Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
Logo
6:44 pm - 8:00 pmORD-POS
24h 16m1 stop
$461
Find Deal
Tue, Sep 16 - Sat, Sep 20
Logo
3:51 am - 10:48 pmPOS-ORD
19h 57m2 stops
Logo
6:44 pm - 8:00 pmORD-POS
24h 16m1 stop
$470
Find Deal
Mon, Sep 15 - Sat, Sep 20
Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
Logo
10:27 am - 4:15 amORD-POS
16h 48m1 stop
$478
Find Deal
Sun, Sep 14 - Sun, Sep 21
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
$565Air Canada
Find Deal
Sun, Sep 14 - Mon, Sep 22
United Airlines Logo
12:30 am - 10:13 amPOS-ORD
10h 43m1 stop
United Airlines Logo
8:45 am - 11:23 pmORD-POS
13h 38m1 stop
$574United Airlines
Find Deal
Sat, Sep 13 - Sun, Sep 21
American Airlines Logo
3:25 pm - 8:40 amPOS-ORD
18h 15m1 stop
American Airlines Logo
8:34 pm - 2:16 pmORD-POS
16h 42m2 stops
$578American Airlines
Find Deal
Tue, Sep 16 - Sat, Sep 20
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
Air Canada Logo
6:00 pm - 1:20 amORD-POS
30h 20m2 stops
$584Air Canada
Find Deal
Mon, Sep 15 - Sat, Sep 20
United Airlines Logo
12:30 am - 9:53 amPOS-ORD
10h 23m1 stop
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$696United Airlines
Find Deal
Mon, Aug 18 - Sun, Aug 24
American Airlines Logo
7:00 am - 6:29 pmPOS-ORD
12h 29m2 stops
American Airlines Logo
5:00 am - 9:36 pmORD-POS
15h 36m1 stop
$716American Airlines
Find Deal
Tue, Aug 19 - Sun, Aug 24

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
Sep 14
POS2:25 amPort of Spain Piarco Intl
17h 29m
2 stops
ORD6:54 pmChicago O'Hare Intl
Sep 22
ORD10:40 amChicago O'Hare Intl
13h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
$565
Find similar
Air Canada
Sep 15
POS2:25 amPort of Spain Piarco Intl
17h 29m
2 stops
ORD6:54 pmChicago O'Hare Intl
Sep 20
ORD6:00 pmChicago O'Hare Intl
30h 20m
2 stops
POS1:20 amPort of Spain Piarco Intl
$584
Find similar

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
Sep 13
POS12:30 amPort of Spain Piarco Intl
10h 43m
1 stop
ORD10:13 amChicago O'Hare Intl
Sep 21
ORD8:45 amChicago O'Hare Intl
13h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$574
Find similar
United Airlines
Aug 18
POS12:30 amPort of Spain Piarco Intl
10h 23m
1 stop
ORD9:53 amChicago O'Hare Intl
Aug 24
ORD6:00 amChicago O'Hare Intl
16h 23m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$696
Find similar
United Airlines
Aug 16
POS12:30 amPort of Spain Piarco Intl
24h 45m
1 stop
ORD12:15 amChicago O'Hare Intl
Sep 1
ORD9:05 pmChicago O'Hare Intl
25h 18m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$768
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 August 3, 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

Mon 9/15

10:10 am-10:48 pm

1 stop13h 38m

Chicago O'Hare Intl

Mon 9/22

5:05 am-8:00 pm

1 stop13h 55m

$429

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/16

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

Sat 9/20

6:44 pm-8:00 pm

1 stop24h 16m

$461

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/15

3:51 am-10:48 pm

2 stops19h 57m

Chicago O'Hare Intl

Sat 9/20

6:44 pm-8:00 pm

1 stop24h 16m

$470

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/14

6:25 pm-9:18 am

1 stop15h 53m

Chicago O'Hare Intl

Sun 9/21

10:27 am-4:15 am

1 stop16h 48m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/14

2:25 am-6:54 pm

2 stops17h 29m

Chicago O'Hare Intl

Mon 9/22

10:40 am-1:20 am

2 stops13h 40m

$565

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 9/13

12:30 am-10:13 am

1 stop10h 43m

Chicago O'Hare Intl

Sun 9/21

8:45 am-11:23 pm

1 stop13h 38m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/16

3:25 pm-8:40 am

1 stop18h 15m

Chicago O'Hare Intl

Sat 9/20

8:34 pm-2:16 pm

2 stops16h 42m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/15

2:25 am-6:54 pm

2 stops17h 29m

Chicago O'Hare Intl

Sat 9/20

6:00 pm-1:20 am

2 stops30h 20m

$584

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 8/18

12:30 am-9:53 am

1 stop10h 23m

Chicago O'Hare Intl

Sun 8/24

6:00 am-11:23 pm

1 stop16h 23m

$696

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 8/19

7:00 am-6:29 pm

2 stops12h 29m

Chicago O'Hare Intl

Sun 8/24

5:00 am-9:36 pm

1 stop15h 36m

$716

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 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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Port of Spain averaging around $561.

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

Best Price Found

$349

Fastest flight time

10h 23m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Port of Spain in the past 72 hours is $349. The best round-trip flight deal from Port of Spain to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $429.
The fastest flight from Port of Spain to Chicago O'Hare Intl Airport takes 10h 23m
There are no direct flights from Port of Spain to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Port of Spain Piarco Intl Airport - 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 10h 23m.

  • 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
United AirlinesPriceFrom $493Free CancellationRating
7.4
8,909 reviews
Search United Airlines flights
American AirlinesPriceFrom $561Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

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Lake Geneva
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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.

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