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Cheap flights from Chicago to Trinidad and Tobago from $173

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 1/25. 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 Chicago to Trinidad and Tobago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
10:10 am - 11:22 am
POS
-
ORD
27h 12m1 stop
$440Multiple Airlines
Tue, Jan 27 - Sun, Feb 1
Multiple Airlines Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$441Multiple Airlines
Tue, Jan 27 - Sun, Feb 1
Multiple Airlines Logo
10:35 am - 1:20 am
ORD
-
POS
12h 45m2 stops
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$444Multiple Airlines
Tue, Jan 27 - Sun, Feb 1
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:00 am - 5:43 pm
POS
-
ORD
35h 43m2 stops
$460JetBlue
Wed, Jan 14 - Tue, Jan 20
Multiple Airlines Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
Multiple Airlines Logo
8:00 am - 5:43 pm
POS
-
ORD
35h 43m2 stops
$474Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m1 stop
Air Canada Logo
1:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
$477Air Canada
Thu, Mar 12 - Tue, Mar 17
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m2 stops
$481Air Canada
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m2 stops
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$482Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
9:10 am - 8:18 am
POS
-
ORD
25h 08m1 stop
$483Multiple Airlines
Wed, Jan 14 - Tue, Jan 20
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m2 stops
$484Air Canada
Fri, Mar 13 - Tue, Mar 17

JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago to Trinidad and Tobago flight tickets
JetBlue
Jan 14
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
$460
Find similar
JetBlue
Jan 10
ORD7:45 amChicago O'Hare Intl
33h 26m
2 stops
POS7:11 pmPort of Spain Piarco Intl
Jan 14
POS8:00 amPort of Spain Piarco Intl
35h 43m
2 stops
ORD5:43 pmChicago O'Hare Intl
$650
Find similar

Copa Airlines flights from Chicago to Trinidad and Tobago

Our best Copa Airlines deals on Chicago to Trinidad and Tobago flight tickets
Copa Airlines
Mar 12
ORD8:34 amChicago O'Hare Intl
16h 12m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 18
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$528
Find similar
Copa Airlines
Feb 9
ORD2:22 pmChicago O'Hare Intl
9h 51m
1 stop
POS2:13 amPort of Spain Piarco Intl
Feb 11
POS3:13 amPort of Spain Piarco Intl
11h 18m
1 stop
ORD12:31 pmChicago O'Hare Intl
$554
Find similar
Copa Airlines
Feb 14
ORD2:22 pmChicago O'Hare Intl
9h 51m
1 stop
POS2:13 amPort of Spain Piarco Intl
Feb 17
POS3:13 amPort of Spain Piarco Intl
11h 18m
1 stop
ORD12:31 pmChicago O'Hare Intl
$905
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 January 4, 2026.
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

Tue 1/27

9:23 am-6:55 pm

1 stop31h 32m

Port of Spain Piarco Intl

Sun 2/1

10:10 am-11:22 am

1 stop27h 12m

$440

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/27

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/27

10:35 am-1:20 am

2 stops12h 45m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$444

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Tue 1/20

8:00 am-5:43 pm

2 stops35h 43m

$460

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Tue 1/20

8:00 am-5:43 pm

2 stops35h 43m

$474

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-3:10 pm

1 stop14h 50m

$477

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$481

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:21 pm-12:20 am

2 stops28h 59m

Port of Spain Piarco Intl

Mon 4/6

3:40 pm-9:10 am

2 stops18h 30m

$482

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

9:23 am-6:55 pm

1 stop31h 32m

Port of Spain Piarco Intl

Tue 1/20

9:10 am-8:18 am

1 stop25h 08m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$484

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 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 airline that flies from Chicago to Trinidad and Tobago?

Air Canada is the most popular carrier operating from Chicago to Trinidad and Tobago

What airlines fly to Trinidad and Tobago?

American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Trinidad and Tobago from Chicago according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to Trinidad and Tobago. Keep in mind that there are 3 different airlines that fly to Trinidad and Tobago on a routine basis, so you have a few additional options to choose from.

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 19m

Direct flights

None
The fastest flight from Chicago to Trinidad and Tobago takes 9h 19m
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
10,589 reviews
Search Air Canada flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,078 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,137 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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Find better results for your trip to Trinidad and Tobago

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