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Cheap flights from Chicago 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 Chicago 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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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
Multiple Airlines Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
Multiple Airlines Logo
8:00 am - 5:43 pm
POS
-
ORD
35h 43m2 stops
$447Multiple Airlines
Fri, Jan 16 - Tue, Jan 20
Multiple Airlines Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
Multiple Airlines Logo
8:30 am - 5:44 pm
POS
-
ORD
35h 14m2 stops
$448Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Multiple Airlines Logo
8:30 am - 5:44 pm
POS
-
ORD
35h 14m2 stops
$451Multiple Airlines
Tue, Feb 3 - Tue, Feb 10
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
Multiple Airlines Logo
9:10 am - 8:18 am
POS
-
ORD
25h 08m1 stop
$452Multiple Airlines
Fri, Jan 16 - Tue, Jan 20
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
Multiple Airlines Logo
8:40 pm - 12:20 am
ORD
-
POS
25h 40m1 stop
Multiple Airlines Logo
8:05 am - 9:09 am
POS
-
ORD
26h 04m2 stops
$457Multiple Airlines
Sat, Mar 7 - Tue, Mar 10
Multiple Airlines Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$460Multiple Airlines
Thu, Jan 29 - Sun, Feb 1

JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago 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 Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago 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
Mar 15
ORD10:00 amChicago O'Hare Intl
13h 20m
1 stop
POS12:20 amPort of Spain Piarco Intl
Mar 20
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$513
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 Chicago 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

Fri 1/16

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 1/20

8:00 am-5:43 pm

2 stops35h 43m

$447

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 2/3

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 2/10

8:30 am-5:44 pm

2 stops35h 14m

$448

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 2/3

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 2/10

8:30 am-5:44 pm

2 stops35h 14m

$451

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/16

5:15 am-8:00 pm

1 stop12h 45m

Port of Spain Piarco Intl

Tue 1/20

9:10 am-8:18 am

1 stop25h 08m

$452

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

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/7

8:40 pm-12:20 am

1 stop25h 40m

Port of Spain Piarco Intl

Tue 3/10

8:05 am-9:09 am

2 stops26h 04m

$457

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/29

2:00 pm-1:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$460

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 Chicago 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 Chicago 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 Chicago 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 Chicago to Trinidad and Tobago flight deals and tips

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

Fastest flight time

9h 20m

Direct flights

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

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

    Prices for flights from Chicago to Trinidad and Tobago are refreshed on a daily basis.

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

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

Compare and see reviews for airlines that fly from Chicago 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 Chicago to Trinidad and Tobago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Trinidad and Tobago from Chicago.

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

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

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

Once all potential Chicago to Trinidad and Tobago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

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

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