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Cheap flights from Chicago to Trinidad from $130

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 departing on 3/18. 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

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
9:20 pm - 12:20 am
ORD
-
POS
26h 00m
1 stop
Air Canada Logo
1:20 am - 8:03 am
POS
-
ORD
31h 43m
1 stop
$270Air Canada
Mon, Apr 13 - Sun, Apr 19
Air Canada Logo
10:43 am - 12:20 am
ORD
-
POS
36h 37m
2 stops
Air Canada Logo
1:20 am - 7:58 am
POS
-
ORD
31h 38m
2 stops
$289Air Canada
Mon, Apr 13 - Sun, Apr 19
Air Canada Logo
9:20 pm - 12:20 am
ORD
-
POS
26h 00m
1 stop
Air Canada Logo
1:20 am - 7:58 am
POS
-
ORD
31h 38m
2 stops
$290Air Canada
Mon, Apr 13 - Sun, Apr 19
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$298Air Canada
Fri, Apr 17 - Sun, Apr 19
Air Canada Logo
9:55 am - 12:15 am
ORD
-
POS
13h 20m
1 stop
Air Canada Logo
1:25 am - 2:53 pm
POS
-
ORD
14h 28m
2 stops
$301Air Canada
Wed, May 13 - Sun, May 17
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
1:20 am - 6:53 pm
POS
-
ORD
18h 33m
2 stops
$303Air Canada
Fri, Apr 17 - Sun, Apr 19
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 2:53 pm
POS
-
ORD
14h 28m
2 stops
$305Air Canada
Wed, May 13 - Sun, May 17
Air Canada Logo
9:15 pm - 12:20 am
ORD
-
POS
26h 05m
1 stop
Air Canada Logo
1:20 am - 3:15 pm
POS
-
ORD
14h 55m
1 stop
$308Air Canada
Sat, Mar 28 - Fri, Apr 3
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
38h 35m
2 stops
$311Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
$323Air Canada
Sat, Mar 28 - Fri, Apr 3

Air Canada flights from Chicago to Trinidad

Our best Air Canada deals on Chicago to Trinidad flight tickets
Air Canada
Apr 13
ORD9:20 pmChicago O'Hare Intl
26h 00m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 19
POS1:20 amPort of Spain Piarco Intl
31h 43m
1 stop
ORD8:03 amChicago O'Hare Intl
$270
Air Canada
Apr 13
ORD10:43 amChicago O'Hare Intl
36h 37m
2 stops
POS12:20 amPort of Spain Piarco Intl
Apr 19
POS1:20 amPort of Spain Piarco Intl
31h 38m
2 stops
ORD7:58 amChicago O'Hare Intl
$289
Air Canada
Apr 13
ORD9:20 pmChicago O'Hare Intl
26h 00m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 19
POS1:20 amPort of Spain Piarco Intl
31h 38m
2 stops
ORD7:58 amChicago O'Hare Intl
$290

JetBlue flights from Chicago to Trinidad

Our best JetBlue deals on Chicago to Trinidad flight tickets
JetBlue
Mar 10
ORD10:00 amChicago O'Hare Intl
19h 17m
2 stops
POS6:17 amPort of Spain Piarco Intl
Mar 12
POS3:26 pmPort of Spain Piarco Intl
19h 44m
2 stops
ORD10:10 amChicago O'Hare Intl
$626
JetBlue
Mar 16
ORD6:20 pmChicago O'Hare Intl
18h 16m
2 stops
POS1:36 pmPort of Spain Piarco Intl
Mar 23
POS3:26 pmPort of Spain Piarco Intl
19h 44m
2 stops
ORD10:10 amChicago O'Hare Intl
$641
JetBlue
Mar 10
ORD10:00 amChicago O'Hare Intl
19h 17m
2 stops
POS6:17 amPort of Spain Piarco Intl
Mar 14
POS3:26 pmPort of Spain Piarco Intl
26h 58m
2 stops
ORD5:24 pmChicago O'Hare Intl
$712

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Trinidad 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 March 3, 2026.
Use the filters below to find and compare flights from Chicago to Trinidad that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/13

9:20 pm-12:20 am

1 stop26h 00m

Port of Spain Piarco Intl

Sun 4/19

1:20 am-8:03 am

1 stop31h 43m

$270

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/13

10:43 am-12:20 am

2 stops36h 37m

Port of Spain Piarco Intl

Sun 4/19

1:20 am-7:58 am

2 stops31h 38m

$289

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/13

9:20 pm-12:20 am

1 stop26h 00m

Port of Spain Piarco Intl

Sun 4/19

1:20 am-7:58 am

2 stops31h 38m

$290

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/17

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Sun 4/19

1:20 am-1:05 pm

1 stop12h 45m

$298

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 5/13

9:55 am-12:15 am

1 stop13h 20m

Port of Spain Piarco Intl

Sun 5/17

1:25 am-2:53 pm

2 stops14h 28m

$301

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/17

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Sun 4/19

1:20 am-6:53 pm

2 stops18h 33m

$303

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 5/13

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Sun 5/17

1:25 am-2:53 pm

2 stops14h 28m

$305

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

9:15 pm-12:20 am

1 stop26h 05m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-3:15 pm

1 stop14h 55m

$308

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 stops38h 35m

$311

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-6:58 pm

2 stops18h 38m

$323

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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See travel insights to Trinidad from

How to get the cheapest flight ticket from Chicago to Trinidad

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

Can stopping save me money on Chicago to Trinidad flights?

No. A direct flight is the cheapest option for a flight between Chicago to Trinidad.

Cheap Chicago to Trinidad flight deals and tips

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

Fastest flight time

9h 00m

Direct flights

None
The fastest flight from Chicago to Trinidad takes 9h 00m
There are no direct flights from Chicago to Trinidad. There are no popular flight routes from Chicago to Trinidad.
Search flight deals

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

    Prices for flights from Chicago to Trinidad are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Trinidad.

  • What documentation or ID do you need to fly to Trinidad?

    The necessary travel and health documents for your Trinidad trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Trinidad?

Best airlines flying from Chicago to Trinidad

Compare and see reviews for airlines that fly from Chicago to Trinidad with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,770 reviews
Search Air Canada flights
Copa AirlinesPriceFrom $472Free CancellationRating
7.5
1,559 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $548Free CancellationRating
7.1
11,373 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,375 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Trinidad?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Trinidad. momondo saves you time and could save you money on your trip.

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

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

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

momondo helps you find the best flight between Chicago and Trinidad by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Chicago to Trinidad flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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