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Cheap flights from Illinois to Port of Spain from $395

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Port of Spain departing on 12/17. 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 Illinois to Port of Spain

Cheap round-trip flights

Logo
7:11 pm - 8:00 pmORD-POS
23h 49m1 stop
Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
$533
Find Deal
Wed, Oct 22 - Sun, Oct 26
Air Canada Logo
8:40 am - 1:20 amORD-POS
15h 40m2 stops
Air Canada Logo
2:25 am - 2:55 pmPOS-ORD
13h 30m2 stops
$537Air Canada
Find Deal
Mon, Oct 13 - Fri, Oct 17
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$542Air Canada
Find Deal
Mon, Dec 1 - Sun, Dec 7
Logo
8:41 am - 8:00 pmORD-POS
9h 19m1 stop
Logo
10:10 am - 9:23 amPOS-ORD
25h 13m1 stop
$546
Find Deal
Mon, Jan 12 - Mon, Feb 16
American Airlines Logo
8:06 am - 9:20 pmORD-POS
12h 14m1 stop
American Airlines Logo
7:00 am - 11:58 pmPOS-ORD
17h 58m1 stop
$548American Airlines
Find Deal
Mon, Oct 13 - Sat, Oct 18
American Airlines Logo
7:00 am - 9:20 pmORD-POS
13h 20m1 stop
American Airlines Logo
3:25 pm - 8:53 amPOS-ORD
18h 28m1 stop
$553American Airlines
Find Deal
Wed, Oct 22 - Sun, Oct 26
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
Copa Airlines Logo
3:51 am - 12:21 amPOS-ORD
21h 30m1 stop
$589Copa Airlines
Find Deal
Wed, Oct 8 - Sat, Oct 11
Copa Airlines Logo
7:53 am - 1:46 amORD-POS
16h 53m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$594Copa Airlines
Find Deal
Wed, Oct 22 - Wed, Oct 29
United Airlines Logo
10:35 am - 11:23 pmORD-POS
11h 48m1 stop
United Airlines Logo
12:30 am - 10:02 amPOS-ORD
10h 32m1 stop
$668United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
United Airlines Logo
6:00 am - 12:23 amSTL-POS
16h 23m1 stop
United Airlines Logo
1:30 am - 11:31 pmPOS-STL
24h 01m1 stop
$2,079United Airlines
Find Deal
Sat, Dec 20 - Sat, Jan 3

Air Canada flights from Illinois to Port of Spain

Our best Air Canada deals on Illinois to Port of Spain flight tickets
Air Canada
Oct 13
ORD8:40 amChicago O'Hare Intl
15h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
Oct 17
POS2:25 amPort of Spain Piarco Intl
13h 30m
2 stops
ORD2:55 pmChicago O'Hare Intl
$537
Find similar
Air Canada
Dec 1
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
Dec 7
POS2:15 amPort of Spain Piarco Intl
18h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
$542
Find similar
Air Canada
Jan 12
ORD6:20 pmChicago O'Hare Intl
28h 50m
2 stops
POS1:10 amPort of Spain Piarco Intl
Feb 15
POS2:15 amPort of Spain Piarco Intl
18h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
$547
Find similar

Copa Airlines flights from Illinois to Port of Spain

Our best Copa Airlines deals on Illinois to Port of Spain flight tickets
Copa Airlines
Oct 8
ORD3:07 pmChicago O'Hare Intl
9h 39m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 11
POS3:51 amPort of Spain Piarco Intl
21h 30m
1 stop
ORD12:21 amChicago O'Hare Intl
$589
Find similar
Copa Airlines
Oct 22
ORD7:53 amChicago O'Hare Intl
16h 53m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 29
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$594
Find similar
Copa Airlines
Oct 22
ORD7:53 amChicago O'Hare Intl
16h 53m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 25
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$609
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Port of Spain 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 11, 2025.
Use the filters below to find and compare flights from Illinois to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:11 pm-8:00 pm

1 stop23h 49m

Port of Spain Piarco Intl

Sun 10/26

6:25 pm-9:18 am

1 stop15h 53m

$533

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/13

8:40 am-1:20 am

2 stops15h 40m

Port of Spain Piarco Intl

Fri 10/17

2:25 am-2:55 pm

2 stops13h 30m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Sun 12/7

2:15 am-6:55 pm

2 stops18h 40m

$542

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/12

8:41 am-8:00 pm

1 stop9h 19m

Port of Spain Piarco Intl

Mon 2/16

10:10 am-9:23 am

1 stop25h 13m

$546

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/13

8:06 am-9:20 pm

1 stop12h 14m

Port of Spain Piarco Intl

Sat 10/18

7:00 am-11:58 pm

1 stop17h 58m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:00 am-9:20 pm

1 stop13h 20m

Port of Spain Piarco Intl

Sun 10/26

3:25 pm-8:53 am

1 stop18h 28m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/8

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Sat 10/11

3:51 am-12:21 am

1 stop21h 30m

$589

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:53 am-1:46 am

1 stop16h 53m

Port of Spain Piarco Intl

Wed 10/29

3:51 am-1:41 pm

1 stop10h 50m

$594

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

10:35 am-11:23 pm

1 stop11h 48m

Port of Spain Piarco Intl

Sat 10/25

12:30 am-10:02 am

1 stop10h 32m

$668

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 12/20

6:00 am-12:23 am

1 stop16h 23m

Port of Spain Piarco Intl

Sat 1/3

1:30 am-11:31 pm

1 stop24h 01m

$2,079

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to Port of Spain from

How to get the cheapest flight ticket from Illinois to Port of Spain

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 Port of Spain?

The cheapest day to depart from Illinois to Port of Spain is on a Sunday when prices can be found for as low as $569. Flights from Illinois to Port of Spain on a Monday will generally be more expensive and average around $706. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

In the afternoon is the cheapest time of day to fly from Illinois to Port of Spain when you can find flight prices for as low as $535. Flying to Port of Spain in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Port of Spain, so prices are often more expensive at around $847 per ticket.

Cheap Illinois to Port of Spain flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Port of Spain

Best Price Found

$395

Fastest flight time

7h 49m

Direct flights

None

Airports in Port of Spain

1 airport
The best one-way flight to Port of Spain from Illinois in the past 72 hours is $395. The best round-trip flight deal from Illinois to Port of Spain found on momondo in the last 72 hours is $533.
The fastest flight from Illinois to Port of Spain takes 7h 49m
There are no direct flights from Illinois to Port of Spain. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Port of Spain Piarco Intl Airport.
There is 1 airport near Port of Spain: Port of Spain Piarco Intl (POS)
Search flight deals

  • When did momondo last update prices for flights from Illinois to Port of Spain Piarco Intl Airport?

    Prices for flights from Illinois to Port of Spain Piarco Intl Airport are updated daily.

  • How many operators does momondo search for flights from Illinois to Port of Spain Piarco Intl Airport?

  • How old do you have to be to fly from Illinois to Port of Spain Piarco 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 Illinois to Port of Spain Piarco Intl Airport.

  • What documentation or ID do you need to fly to Port of Spain Piarco Intl Airport?

    The required travel and health documents for your Port of Spain Piarco 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 Port of Spain Piarco Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Port of Spain

Compare and see reviews for airlines that fly from Illinois to Port of Spain with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,920 reviews
Search United Airlines flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Port of Spain?

Book flights to Port of Spain if you plan to visit one of these locations
Piarco

Why use momondo?

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

It is quick and easy to find Illinois to Port of Spain flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Port of Spain that suits you.

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

Yes. All flights to Port of Spain from Illinois on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Illinois to Port of Spain?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Illinois to Port of Spain.

I’m not ready to book a flight from Illinois to Port of Spain right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Illinois to Port of Spain 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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