Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Trinidad and Tobago from $185

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.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Trinidad and Tobago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
2:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
$417Air Canada
Sat, Feb 28 - Fri, Mar 6
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m
2 stops
Air Canada Logo
2:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
$421Air Canada
Tue, Mar 3 - Fri, Mar 6
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$422Air Canada
Sat, Mar 21 - Fri, Mar 27
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
2:20 am - 8:10 pm
POS
-
ORD
19h 50m
2 stops
$431Air Canada
Sat, Feb 28 - Fri, Mar 6
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
1:20 am - 3:13 pm
POS
-
ORD
14h 53m
1 stop
$447Air Canada
Thu, Mar 12 - Tue, Mar 17
JetBlue Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m
2 stops
JetBlue Logo
9:05 am - 8:09 am
POS
-
ORD
25h 04m
2 stops
$449JetBlue
Tue, Mar 3 - Sat, Mar 7
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$451Air Canada
Thu, Mar 12 - Tue, Mar 17
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$452Air Canada
Sat, Mar 21 - Fri, Mar 27
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m
2 stops
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$454Air Canada
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
5:58 pm - 1:00 pm
ORD
-
TAB
17h 02m
1 stop
Multiple Airlines Logo
12:30 am - 9:39 am
TAB
-
ORD
35h 09m
2 stops
$520Multiple Airlines
Wed, Feb 25 - Mon, Mar 2

American Airlines flights from Chicago to Trinidad and Tobago

Our best American Airlines deals on Chicago to Trinidad and Tobago flight tickets
American Airlines
Feb 26
ORD8:54 pmChicago O'Hare Intl
16h 12m
2 stops
POS3:06 pmPort of Spain Piarco Intl
Mar 3
POS4:06 pmPort of Spain Piarco Intl
17h 18m
2 stops
ORD7:24 amChicago O'Hare Intl
$629
American Airlines
Apr 17
ORD8:44 pmChicago O'Hare Intl
16h 48m
2 stops
POS2:32 pmPort of Spain Piarco Intl
Apr 26
POS3:47 pmPort of Spain Piarco Intl
16h 33m
2 stops
ORD7:20 amChicago O'Hare Intl
$674
American Airlines
Jan 25
ORD6:42 amChicago O'Hare Intl
14h 06m
2 stops
POS10:48 pmPort of Spain Piarco Intl
Feb 1
POS6:30 amPort of Spain Piarco Intl
14h 59m
2 stops
ORD7:29 pmChicago O'Hare Intl
$854

Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets
Air Canada
Feb 28
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS1:20 amPort of Spain Piarco Intl
Mar 6
POS2:20 amPort of Spain Piarco Intl
12h 41m
1 stop
ORD1:01 pmChicago O'Hare Intl
$417
Air Canada
Mar 3
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS1:20 amPort of Spain Piarco Intl
Mar 6
POS2:20 amPort of Spain Piarco Intl
12h 41m
1 stop
ORD1:01 pmChicago O'Hare Intl
$421
Air Canada
Mar 21
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS12:20 amPort of Spain Piarco Intl
Mar 27
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$422

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 16, 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

Sat 2/28

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 3/6

2:20 am-1:01 pm

1 stop12h 41m

$417

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 3/3

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 3/6

2:20 am-1:01 pm

1 stop12h 41m

$421

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/21

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 3/27

1:20 am-6:52 pm

2 stops18h 32m

$422

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 2/28

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 3/6

2:20 am-8:10 pm

2 stops19h 50m

$431

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-3:13 pm

1 stop14h 53m

$447

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 3/3

10:00 am-7:17 am

2 stops19h 17m

Port of Spain Piarco Intl

Sat 3/7

9:05 am-8:09 am

2 stops25h 04m

$449

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$451

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/21

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 3/27

1:20 am-6:52 pm

2 stops18h 32m

$452

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

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

$454

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Wed 2/25

5:58 pm-1:00 pm

1 stop17h 02m

Scarborough ANR Robinson Intl

Mon 3/2

12:30 am-9:39 am

2 stops35h 09m

$520

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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 50% 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 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
10,625 reviews
Search Air Canada flights
United AirlinesPriceFrom $501Free CancellationRating
7.4
9,163 reviews
Search United Airlines flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,138 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.

An easier way to manage your Trinidad and Tobago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 2/15
Sun 2/22
By creating a price alert you accept our terms of use and privacy policy.

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 $361