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Cheap flights from Illinois to Port of Spain from $198

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 1/5. 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

Enter your travel dates to find the best prices.
Air Canada Logo
7:05 am - 1:10 amORD-POS
16h 05m2 stops
Air Canada Logo
2:15 am - 2:55 pmPOS-ORD
14h 40m2 stops
$433Air Canada
Find Deal
Tue, Dec 2 - Fri, Dec 5
Air Canada Logo
4:05 pm - 1:20 amSTL-POS
31h 15m1 stop
Air Canada Logo
2:20 am - 3:29 pmPOS-STL
15h 09m1 stop
$438Air Canada
Find Deal
Sat, Jan 10 - Fri, Jan 16
Multiple Airlines Logo
8:45 pm - 1:20 amORD-POS
26h 35m1 stop
Multiple Airlines Logo
9:10 am - 6:39 pmPOS-ORD
11h 29m1 stop
$455Multiple Airlines
Find Deal
Mon, Jan 5 - Mon, Jan 12
JetBlue Logo
8:38 pm - 4:04 pmORD-POS
17h 26m2 stops
JetBlue Logo
5:56 pm - 9:52 pmPOS-ORD
29h 56m1 stop
$494JetBlue
Find Deal
Mon, Dec 8 - Thu, Dec 11
Multiple Airlines Logo
5:00 am - 8:00 pmORD-POS
13h 00m1 stop
Multiple Airlines Logo
10:10 am - 8:01 pmPOS-ORD
11h 51m1 stop
$504Multiple Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 11
JetBlue Logo
8:45 am - 7:15 pmORD-POS
8h 30m1 stop
JetBlue Logo
8:30 am - 7:45 pmPOS-ORD
13h 15m1 stop
$514JetBlue
Find Deal
Wed, Jan 14 - Tue, Jan 20
American Airlines Logo
6:24 pm - 1:51 pmSTL-POS
18h 27m2 stops
American Airlines Logo
3:34 pm - 2:48 pmPOS-STL
24h 14m2 stops
$583American Airlines
Find Deal
Mon, Mar 16 - Mon, Mar 23
American Airlines Logo
6:24 pm - 1:51 pmSTL-POS
18h 27m2 stops
American Airlines Logo
3:34 pm - 10:04 pmPOS-STL
31h 30m1 stop
$596American Airlines
Find Deal
Mon, Mar 16 - Mon, Mar 23
United Airlines Logo
6:30 am - 12:23 amSTL-POS
15h 53m2 stops
United Airlines Logo
1:30 am - 3:39 pmPOS-STL
16h 09m1 stop
$599United Airlines
Find Deal
Sat, Jan 10 - Fri, Jan 16
United Airlines Logo
9:57 am - 12:23 amSTL-POS
12h 26m2 stops
United Airlines Logo
1:30 am - 4:03 pmPOS-STL
16h 33m2 stops
$603United Airlines
Find Deal
Sat, Jan 10 - Fri, Jan 16

Air Canada flights from Illinois to Port of Spain

Our best Air Canada deals on Illinois to Port of Spain flight tickets
Air Canada
Dec 2
ORD7:05 amChicago O'Hare Intl
16h 05m
2 stops
POS1:10 amPort of Spain Piarco Intl
Dec 5
POS2:15 amPort of Spain Piarco Intl
14h 40m
2 stops
ORD2:55 pmChicago O'Hare Intl
$433
Find similar
Air Canada
Mar 8
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 13
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$438
Find similar
Air Canada
May 11
STL1:30 pmLambert-St Louis
35h 05m
2 stops
POS1:35 amPort of Spain Piarco Intl
May 14
POS2:35 amPort of Spain Piarco Intl
40h 50m
2 stops
STL6:25 pmLambert-St Louis
$443
Find similar

JetBlue flights from Illinois to Port of Spain

Our best JetBlue deals on Illinois to Port of Spain flight tickets
JetBlue
Dec 8
ORD8:38 pmChicago O'Hare Intl
17h 26m
2 stops
POS4:04 pmPort of Spain Piarco Intl
Dec 11
POS5:56 pmPort of Spain Piarco Intl
29h 56m
1 stop
ORD9:52 pmChicago O'Hare Intl
$494
Find similar
JetBlue
Jan 14
ORD8:45 amChicago O'Hare Intl
8h 30m
1 stop
POS7:15 pmPort of Spain Piarco Intl
Jan 20
POS8:30 amPort of Spain Piarco Intl
13h 15m
1 stop
ORD7:45 pmChicago O'Hare Intl
$514
Find similar
JetBlue
Dec 8
ORD8:38 pmChicago O'Hare Intl
17h 26m
2 stops
POS4:04 pmPort of Spain Piarco Intl
Dec 12
POS5:42 pmPort of Spain Piarco Intl
30h 10m
1 stop
ORD9:52 pmChicago O'Hare Intl
$518
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 November 22, 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

Tue 12/2

7:05 am-1:10 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 12/5

2:15 am-2:55 pm

2 stops14h 40m

$433

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/10

4:05 pm-1:20 am

1 stop31h 15m

Port of Spain Piarco Intl

Fri 1/16

2:20 am-3:29 pm

1 stop15h 09m

$438

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/5

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Mon 1/12

9:10 am-6:39 pm

1 stop11h 29m

$455

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 12/8

8:38 pm-4:04 pm

2 stops17h 26m

Port of Spain Piarco Intl

Thu 12/11

5:56 pm-9:52 pm

1 stop29h 56m

$494

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 12/8

5:00 am-8:00 pm

1 stop13h 00m

Port of Spain Piarco Intl

Thu 12/11

10:10 am-8:01 pm

1 stop11h 51m

$504

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

8:45 am-7:15 pm

1 stop8h 30m

Port of Spain Piarco Intl

Tue 1/20

8:30 am-7:45 pm

1 stop13h 15m

$514

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Mon 3/16

6:24 pm-1:51 pm

2 stops18h 27m

Port of Spain Piarco Intl

Mon 3/23

3:34 pm-2:48 pm

2 stops24h 14m

$583

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Mon 3/16

6:24 pm-1:51 pm

2 stops18h 27m

Port of Spain Piarco Intl

Mon 3/23

3:34 pm-10:04 pm

1 stop31h 30m

$596

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/10

6:30 am-12:23 am

2 stops15h 53m

Port of Spain Piarco Intl

Fri 1/16

1:30 am-3:39 pm

1 stop16h 09m

$599

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 1/10

9:57 am-12:23 am

2 stops12h 26m

Port of Spain Piarco Intl

Fri 1/16

1:30 am-4:03 pm

2 stops16h 33m

$603

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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

Direct flights

None
There are no direct flights from Illinois to Port of Spain. There are no popular flight routes from Illinois to Port of Spain.
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
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,464 reviews
Search Air Canada flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
United AirlinesPriceFrom $560Free CancellationRating
7.4
9,033 reviews
Search United 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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