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Cheap flights from Chicago to Trinidad and Tobago from $155

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 2/19. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:20 pm - 12:20 am
ORD
-
POS
27h 00m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$358Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
8:20 pm - 12:20 am
ORD
-
POS
27h 00m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$361Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
2:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$363Air Canada
Sat, Feb 21 - Fri, Feb 27
Air Canada Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m
1 stop
Air Canada Logo
2:20 am - 8:00 am
POS
-
ORD
31h 40m
2 stops
$368Air Canada
Fri, Feb 27 - Thu, Mar 5
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
33h 25m
2 stops
Air Canada Logo
1:20 am - 8:05 pm
POS
-
ORD
19h 45m
2 stops
$371Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
9h 25m
1 stop
Air Canada Logo
1:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
$398Air Canada
Sun, Mar 15 - Tue, Mar 17
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
9h 25m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$408Air Canada
Fri, Mar 27 - Thu, Apr 2
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
9h 25m
1 stop
Air Canada Logo
1:20 am - 6:53 pm
POS
-
ORD
18h 33m
2 stops
$413Air Canada
Fri, Mar 27 - Thu, Apr 2
JetBlue Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m
2 stops
JetBlue Logo
9:05 am - 9:10 am
POS
-
ORD
26h 05m
2 stops
$414JetBlue
Thu, Feb 26 - Sun, Mar 1
Multiple Airlines Logo
6:51 pm - 6:10 am
ORD
-
TAB
33h 19m
3 stops
Multiple Airlines Logo
12:30 am - 7:54 am
TAB
-
ORD
33h 24m
3 stops
$866Multiple Airlines
Thu, Feb 19 - Fri, Feb 27

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 30
ORD8:20 pmChicago O'Hare Intl
27h 00m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 5
POS1:20 amPort of Spain Piarco Intl
12h 45m
1 stop
ORD1:05 pmChicago O'Hare Intl
$358
Air Canada
Mar 30
ORD8:20 pmChicago O'Hare Intl
27h 00m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 5
POS1:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
$361
Air Canada
Feb 21
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS1:20 amPort of Spain Piarco Intl
Feb 27
POS2:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$363

United Airlines flights from Chicago to Trinidad and Tobago

Our best United Airlines deals on Chicago to Trinidad and Tobago flight tickets
United Airlines
Feb 13
ORD5:20 pmChicago O'Hare Intl
29h 03m
1 stop
POS12:23 amPort of Spain Piarco Intl
Feb 21
POS1:30 amPort of Spain Piarco Intl
10h 37m
1 stop
ORD10:07 amChicago O'Hare Intl
$1,081
United Airlines
Feb 13
ORD9:15 pmChicago O'Hare Intl
25h 08m
1 stop
POS12:23 amPort of Spain Piarco Intl
Feb 20
POS1:30 amPort of Spain Piarco Intl
10h 37m
1 stop
ORD10:07 amChicago O'Hare Intl
$1,180
United Airlines
Feb 13
ORD2:00 pmChicago O'Hare Intl
32h 23m
1 stop
POS12:23 amPort of Spain Piarco Intl
Feb 20
POS1:30 amPort of Spain Piarco Intl
32h 17m
1 stop
ORD7:47 amChicago O'Hare Intl
$1,253

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 February 7, 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

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-2:55 pm

2 stops14h 35m

$361

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 2/21

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 2/27

2:20 am-6:52 pm

2 stops18h 32m

$363

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/27

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Thu 3/5

2:20 am-8:00 am

2 stops31h 40m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

1:55 pm-12:20 am

2 stops33h 25m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-8:05 pm

2 stops19h 45m

$371

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

1:55 pm-12:20 am

1 stop9h 25m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-1:01 pm

1 stop12h 41m

$398

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

1:55 pm-12:20 am

1 stop9h 25m

Port of Spain Piarco Intl

Thu 4/2

1:20 am-1:05 pm

1 stop12h 45m

$408

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

1:55 pm-12:20 am

1 stop9h 25m

Port of Spain Piarco Intl

Thu 4/2

1:20 am-6:53 pm

2 stops18h 33m

$413

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 2/26

10:00 am-7:17 am

2 stops19h 17m

Port of Spain Piarco Intl

Sun 3/1

9:05 am-9:10 am

2 stops26h 05m

$414

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Thu 2/19

6:51 pm-6:10 am

3 stops33h 19m

Scarborough ANR Robinson Intl

Fri 2/27

12:30 am-7:54 am

3 stops33h 24m

$866

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 00m

Direct flights

None
The fastest flight from Chicago to Trinidad and Tobago takes 9h 00m
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
10,697 reviews
Search Air Canada flights
United AirlinesPriceFrom $501Free CancellationRating
7.4
9,245 reviews
Search United Airlines flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,248 reviews
Search American 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

Popular cities in Trinidad and Tobago

Popular flights according to clicks in the last 7 days on momondo
Flights to Port of Spainfrom $242
Flights to Scarborough, Eastern Tobagofrom $350