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Cheap flights from Illinois to Trinidad and Tobago from $260

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 Trinidad and Tobago departing on 6/4. 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

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Find the cheapest flights from Illinois to Trinidad and Tobago

Cheap round-trip flights

Enter your travel dates to find the best prices.
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:45 am - 5:43 pm
POS
-
ORD
34h 58m2 stops
$430JetBlue
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m1 stop
Multiple Airlines Logo
8:45 am - 5:43 pm
POS
-
ORD
34h 58m2 stops
$432Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Multiple Airlines Logo
6:57 pm - 6:55 pm
ORD
-
POS
21h 58m1 stop
Multiple Airlines Logo
9:10 am - 8:18 am
POS
-
ORD
25h 08m1 stop
$442Multiple Airlines
Sat, Jan 17 - Sat, Jan 24
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m1 stop
Air Canada Logo
1:20 am - 1:00 pm
POS
-
ORD
12h 40m1 stop
$453Air Canada
Sun, Mar 29 - Fri, Apr 3
Air Canada Logo
4:05 pm - 1:20 am
STL
-
POS
31h 15m1 stop
Air Canada Logo
2:20 am - 3:29 pm
POS
-
STL
15h 09m1 stop
$503Air Canada
Sat, Feb 21 - Fri, Feb 27
American Airlines Logo
1:36 pm - 3:39 pm
STL
-
POS
24h 03m2 stops
American Airlines Logo
4:40 pm - 10:26 am
POS
-
STL
19h 46m1 stop
$616American Airlines
Sat, Feb 21 - Sat, Feb 28
American Airlines Logo
1:36 pm - 3:39 pm
STL
-
POS
24h 03m2 stops
American Airlines Logo
4:40 pm - 3:01 pm
POS
-
STL
24h 21m2 stops
$653American Airlines
Sat, Feb 21 - Sat, Feb 28
United Airlines Logo
6:00 am - 12:23 am
STL
-
POS
16h 23m1 stop
United Airlines Logo
1:30 am - 9:23 am
POS
-
STL
9h 53m1 stop
$1,435United Airlines
Wed, Feb 11 - Tue, Feb 17
United Airlines Logo
6:00 am - 12:23 am
STL
-
POS
16h 23m1 stop
United Airlines Logo
1:30 am - 9:23 am
POS
-
STL
9h 53m1 stop
$1,669United Airlines
Wed, Feb 11 - Tue, Feb 17
Copa Airlines Logo
8:30 am - 2:13 am
STL
-
POS
15h 43m2 stops
Copa Airlines Logo
3:13 am - 8:23 pm
POS
-
STL
19h 10m2 stops
$1,807Copa Airlines
Wed, Feb 11 - Tue, Feb 17

JetBlue flights from Illinois to Trinidad and Tobago

Our best JetBlue deals on Illinois to Trinidad and Tobago flight tickets
JetBlue
Jan 17
ORD7:45 amChicago O'Hare Intl
33h 26m
2 stops
POS7:11 pmPort of Spain Piarco Intl
Jan 24
POS8:45 amPort of Spain Piarco Intl
34h 58m
2 stops
ORD5:43 pmChicago O'Hare Intl
$430
Find similar
JetBlue
Jan 16
ORD7:45 amChicago O'Hare Intl
33h 26m
2 stops
POS7:11 pmPort of Spain Piarco Intl
Jan 20
POS8:00 amPort of Spain Piarco Intl
35h 43m
2 stops
ORD5:43 pmChicago O'Hare Intl
$571
Find similar
JetBlue
Feb 13
ORD10:00 amChicago O'Hare Intl
22h 57m
2 stops
POS10:57 amPort of Spain Piarco Intl
Feb 16
POS8:50 amPort of Spain Piarco Intl
26h 20m
2 stops
ORD9:10 amChicago O'Hare Intl
$917
Find similar

Air Canada flights from Illinois to Trinidad and Tobago

Our best Air Canada deals on Illinois to Trinidad and Tobago flight tickets
Air Canada
Mar 29
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 3
POS1:20 amPort of Spain Piarco Intl
12h 40m
1 stop
ORD1:00 pmChicago O'Hare Intl
$453
Find similar
Air Canada
Mar 12
ORD6:04 pmChicago O'Hare Intl
29h 16m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 17
POS1:20 amPort of Spain Piarco Intl
42h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$483
Find similar
Air Canada
Feb 21
STL4:05 pmLambert-St Louis
31h 15m
1 stop
POS1:20 amPort of Spain Piarco Intl
Feb 27
POS2:20 amPort of Spain Piarco Intl
15h 09m
1 stop
STL3:29 pmLambert-St Louis
$503
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Trinidad and Tobago 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 December 23, 2025.
Use the filters below to find and compare flights from Illinois to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/17

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Sat 1/24

8:45 am-5:43 pm

2 stops34h 58m

$430

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/17

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Sat 1/24

8:45 am-5:43 pm

2 stops34h 58m

$432

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/17

6:57 pm-6:55 pm

1 stop21h 58m

Port of Spain Piarco Intl

Sat 1/24

9:10 am-8:18 am

1 stop25h 08m

$442

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/29

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-1:00 pm

1 stop12h 40m

$453

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/21

4:05 pm-1:20 am

1 stop31h 15m

Port of Spain Piarco Intl

Fri 2/27

2:20 am-3:29 pm

1 stop15h 09m

$503

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/21

1:36 pm-3:39 pm

2 stops24h 03m

Port of Spain Piarco Intl

Sat 2/28

4:40 pm-10:26 am

1 stop19h 46m

$616

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Sat 2/21

1:36 pm-3:39 pm

2 stops24h 03m

Port of Spain Piarco Intl

Sat 2/28

4:40 pm-3:01 pm

2 stops24h 21m

$653

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Wed 2/11

6:00 am-12:23 am

1 stop16h 23m

Port of Spain Piarco Intl

Tue 2/17

1:30 am-9:23 am

1 stop9h 53m

$1,435

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Wed 2/11

6:00 am-12:23 am

1 stop16h 23m

Port of Spain Piarco Intl

Tue 2/17

1:30 am-9:23 am

1 stop9h 53m

$1,669

St. LouisPort of Spain

STL - POS

STLPOS

Lambert-St Louis

Wed 2/11

8:30 am-2:13 am

2 stops15h 43m

Port of Spain Piarco Intl

Tue 2/17

3:13 am-8:23 pm

2 stops19h 10m

$1,807

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 Trinidad and Tobago from

How to get the cheapest flight ticket from Illinois to Trinidad and Tobago

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 Trinidad and Tobago?

On average, the least expensive day to fly to Trinidad and Tobago from Illinois is on a Sunday. momondo users have found tickets for Sunday departures for as low as $569. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Trinidad and Tobago is Monday, with ticket prices averaging around $706.

What is the cheapest time of day to depart on your flight to Trinidad and Tobago?

According to our data, the cheapest time of day to fly to Trinidad and Tobago is in the afternoon. momondo users have found flights departing from Illinois to Trinidad and Tobago in the afternoon for as low as $533. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the evening is when there is more demand to fly to Trinidad and Tobago, so prices are often more expensive at around $905 per ticket.

Cheap Illinois to Trinidad and Tobago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to Trinidad and Tobago

Fastest flight time

9h 20m

Direct flights

None
The fastest flight from Illinois to Trinidad and Tobago takes 9h 20m
There are no direct flights from Illinois to Trinidad and Tobago. There are no popular flight routes from Illinois to Trinidad and Tobago.
Search flight deals

  • When did momondo last update prices for flights from Illinois to Trinidad and Tobago?

    Prices for flights from Illinois to Trinidad and Tobago are updated daily.

  • How many operators does momondo search for flights from Illinois to Trinidad and Tobago?

  • How old do you have to be to fly from Illinois to Trinidad and Tobago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Illinois to Trinidad and Tobago.

  • What documentation or ID do you need to fly to Trinidad and Tobago?

    The required travel and health documents for your Trinidad and Tobago 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 Trinidad and Tobago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Trinidad and Tobago

Compare and see reviews for airlines that fly from Illinois to Trinidad and Tobago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,551 reviews
Search Air Canada flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Trinidad and Tobago?

It is quick and easy to find Illinois to Trinidad and Tobago 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 Trinidad and Tobago that suits you.

Can I find flights from Illinois to Trinidad and Tobago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Trinidad and Tobago flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to Trinidad and Tobago?

Once you have performed a search for Illinois to Trinidad and Tobago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Illinois to Trinidad and Tobago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Illinois to Trinidad and Tobago 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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