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Cheap flights from Chicago to Trinidad and Tobago from $246

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 7/16. 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
1 adult, Economy, 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.
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
Air Canada Logo
1:20 am - 1:23 pm
POS
-
ORD
13h 03m
1 stop
$492Air Canada
Mon, Oct 5 - Fri, Oct 9
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$495Air Canada
Mon, Oct 5 - Fri, Oct 9
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$498Air Canada
Mon, Oct 5 - Fri, Oct 9
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$519Air Canada
Mon, Aug 24 - Mon, Aug 31
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
2 stops
$523Air Canada
Mon, Aug 24 - Mon, Aug 31
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
2 stops
$526Air Canada
Mon, Aug 24 - Mon, Aug 31
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$538Air Canada
Wed, Jul 8 - Fri, Jul 17
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$541Air Canada
Wed, Jul 8 - Fri, Jul 17
Multiple Airlines Logo
3:40 pm - 9:10 am
ORD
-
TAB
16h 30m
3 stops
Multiple Airlines Logo
11:45 am - 9:20 pm
TAB
-
ORD
34h 35m
3 stops
$1,467Multiple Airlines
Sat, Aug 1 - Sat, Aug 8
Multiple Airlines Logo
3:45 pm - 8:30 am
ORD
-
TAB
15h 45m
2 stops
Multiple Airlines Logo
11:45 am - 9:20 pm
TAB
-
ORD
34h 35m
3 stops
$1,502Multiple Airlines
Sat, Aug 1 - Sat, Aug 8

American Airlines flights from Chicago to Trinidad and Tobago

Our best American Airlines deals on Chicago to Trinidad and Tobago flight tickets
American Airlines
Jul 29
ORD5:00 amChicago O'Hare Intl
16h 33m
1 stop
POS10:33 pmPort of Spain Piarco Intl
Aug 12
POS7:00 amPort of Spain Piarco Intl
11h 54m
1 stop
ORD5:54 pmChicago O'Hare Intl
$630
American Airlines
Jul 29
ORD8:00 amChicago O'Hare Intl
13h 33m
2 stops
POS10:33 pmPort of Spain Piarco Intl
Aug 12
POS7:00 amPort of Spain Piarco Intl
15h 30m
2 stops
ORD9:30 pmChicago O'Hare Intl
$634
American Airlines
Sep 24
ORD8:55 pmChicago O'Hare Intl
16h 06m
2 stops
POS2:01 pmPort of Spain Piarco Intl
Sep 27
POS3:06 pmPort of Spain Piarco Intl
17h 23m
1 stop
ORD7:29 amChicago O'Hare Intl
$639

JetBlue flights from Chicago to Trinidad and Tobago

Our best JetBlue deals on Chicago to Trinidad and Tobago flight tickets
JetBlue
Jul 31
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Sep 2
POS7:41 pmPort of Spain Piarco Intl
14h 07m
1 stop
ORD8:48 amChicago O'Hare Intl
$635
JetBlue
Jul 30
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Sep 2
POS7:41 pmPort of Spain Piarco Intl
14h 07m
1 stop
ORD8:48 amChicago O'Hare Intl
$665
JetBlue
Jun 18
ORD6:00 amChicago O'Hare Intl
11h 35m
1 stop
POS6:35 pmPort of Spain Piarco Intl
Jun 21
POS7:45 pmPort of Spain Piarco Intl
14h 00m
1 stop
ORD8:45 amChicago O'Hare Intl
$685

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 June 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

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/5

9:50 am-12:15 am

1 stop13h 25m

Port of Spain Piarco Intl

Fri 10/9

1:20 am-1:23 pm

1 stop13h 03m

$492

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/5

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Fri 10/9

1:20 am-2:52 pm

2 stops14h 32m

$495

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/5

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Fri 10/9

1:20 am-2:52 pm

2 stops14h 32m

$498

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 8/24

9:50 am-12:15 am

1 stop13h 25m

Port of Spain Piarco Intl

Mon 8/31

1:25 am-1:22 pm

1 stop12h 57m

$519

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 8/24

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Mon 8/31

1:25 am-2:55 pm

2 stops14h 30m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 8/24

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Mon 8/31

1:25 am-2:55 pm

2 stops14h 30m

$526
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 7/8

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Fri 7/17

1:25 am-1:22 pm

1 stop12h 57m

$538

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 7/8

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Fri 7/17

1:25 am-1:22 pm

1 stop12h 57m

$541

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sat 8/1

3:40 pm-9:10 am

3 stops16h 30m

Scarborough ANR Robinson Intl

Sat 8/8

11:45 am-9:20 pm

3 stops34h 35m

$1,467

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sat 8/1

3:45 pm-8:30 am

2 stops15h 45m

Scarborough ANR Robinson Intl

Sat 8/8

11:45 am-9:20 pm

3 stops34h 35m

$1,502

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 month to fly to Trinidad and Tobago?

In general, June is the cheapest month to fly from Chicago to Trinidad and Tobago. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $317. If you aren’t able to travel to Trinidad and Tobago during the month of June, then flying in July is also cheap. Prices for this month can be found on momondo for an average of $372.

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

11h 15m

Direct flights

None
The fastest flight from Chicago to Trinidad and Tobago takes 11h 15m
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

Frequently asked questions about flying from Chicago to Trinidad and Tobago

  • 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 $317Free CancellationRating
7.1
11,127 reviews
Search Air Canada flights
Copa AirlinesPriceFrom $472Free CancellationRating
7.5
1,568 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $548Free CancellationRating
7.1
11,646 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,777 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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Sat 7/4
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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 $280
Flights to Scarborough, Eastern Tobagofrom $348