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Cheap flights from Chicago to Trinidad from $238

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 5/30. 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.
Multiple Airlines Logo
3:52 pm - 6:55 pm
ORD
-
POS
26h 03m
1 stop
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$525Multiple Airlines
Sat, May 2 - Thu, May 7
Multiple Airlines Logo
10:00 am - 1:40 am
ORD
-
POS
14h 40m
2 stops
Multiple Airlines Logo
9:10 am - 2:05 pm
POS
-
ORD
29h 55m
1 stop
$541Multiple Airlines
Mon, Apr 27 - Fri, May 1
Multiple Airlines Logo
10:00 am - 1:40 am
ORD
-
POS
14h 40m
2 stops
Multiple Airlines Logo
9:10 am - 1:05 pm
POS
-
ORD
28h 55m
1 stop
$548Multiple Airlines
Mon, Apr 27 - Wed, Apr 29
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
Multiple Airlines Logo
10:10 am - 7:55 am
POS
-
ORD
22h 45m
2 stops
$551Multiple Airlines
Thu, May 21 - Mon, May 25
Air Canada Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m
2 stops
Air Canada Logo
1:25 am - 4:59 pm
POS
-
ORD
16h 34m
1 stop
$556Air Canada
Mon, Apr 27 - Sun, May 3
Multiple Airlines Logo
9:44 pm - 8:00 pm
ORD
-
POS
21h 16m
2 stops
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$562Multiple Airlines
Sat, May 2 - Thu, May 7
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
Multiple Airlines Logo
10:10 am - 12:37 pm
POS
-
ORD
27h 27m
1 stop
$568Multiple Airlines
Thu, May 21 - Mon, May 25
Multiple Airlines Logo
1:18 pm - 8:00 pm
ORD
-
POS
29h 42m
1 stop
Multiple Airlines Logo
10:10 am - 12:25 pm
POS
-
ORD
27h 15m
1 stop
$571Multiple Airlines
Wed, Jun 10 - Mon, Jul 20
Multiple Airlines Logo
10:00 am - 1:40 am
ORD
-
POS
14h 40m
2 stops
Multiple Airlines Logo
9:10 am - 11:59 pm
POS
-
ORD
15h 49m
1 stop
$577Multiple Airlines
Mon, Apr 27 - Sat, May 2
Multiple Airlines Logo
6:55 am - 6:55 pm
ORD
-
POS
35h 00m
2 stops
Multiple Airlines Logo
10:10 am - 12:25 pm
POS
-
ORD
27h 15m
1 stop
$578Multiple Airlines
Wed, Jun 10 - Mon, Jul 20

JetBlue flights from Chicago to Trinidad

Our best JetBlue deals on Chicago to Trinidad flight tickets
JetBlue
Jun 1
ORD8:30 pmChicago O'Hare Intl
17h 44m
2 stops
POS3:14 pmPort of Spain Piarco Intl
Jun 5
POS3:46 pmPort of Spain Piarco Intl
32h 10m
1 stop
ORD10:56 pmChicago O'Hare Intl
$612
JetBlue
May 2
ORD6:00 amChicago O'Hare Intl
33h 13m
2 stops
POS4:13 pmPort of Spain Piarco Intl
May 7
POS2:46 pmPort of Spain Piarco Intl
19h 13m
2 stops
ORD8:59 amChicago O'Hare Intl
$663
JetBlue
May 2
ORD8:31 amChicago O'Hare Intl
30h 42m
1 stop
POS4:13 pmPort of Spain Piarco Intl
May 7
POS2:46 pmPort of Spain Piarco Intl
19h 13m
2 stops
ORD8:59 amChicago O'Hare Intl
$725

Air Canada flights from Chicago to Trinidad

Our best Air Canada deals on Chicago to Trinidad flight tickets
Air Canada
Apr 19
ORD7:55 amChicago O'Hare Intl
15h 25m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 24
POS1:20 amPort of Spain Piarco Intl
19h 05m
1 stop
ORD7:25 pmChicago O'Hare Intl
$427
Air Canada
Apr 19
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 24
POS1:20 amPort of Spain Piarco Intl
12h 45m
1 stop
ORD1:05 pmChicago O'Hare Intl
$428
Air Canada
Apr 19
ORD2:00 pmChicago O'Hare Intl
9h 20m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 24
POS1:20 amPort of Spain Piarco Intl
18h 38m
2 stops
ORD6:58 pmChicago O'Hare Intl
$432

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 April 18, 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

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/2

3:52 pm-6:55 pm

1 stop26h 03m

Port of Spain Piarco Intl

Thu 5/7

9:10 am-11:56 pm

1 stop15h 46m

$525

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/27

10:00 am-1:40 am

2 stops14h 40m

Port of Spain Piarco Intl

Fri 5/1

9:10 am-2:05 pm

1 stop29h 55m

$541

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/27

10:00 am-1:40 am

2 stops14h 40m

Port of Spain Piarco Intl

Wed 4/29

9:10 am-1:05 pm

1 stop28h 55m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/21

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Mon 5/25

10:10 am-7:55 am

2 stops22h 45m

$551

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/27

6:21 pm-12:20 am

2 stops28h 59m

Port of Spain Piarco Intl

Sun 5/3

1:25 am-4:59 pm

1 stop16h 34m

$556

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/2

9:44 pm-8:00 pm

2 stops21h 16m

Port of Spain Piarco Intl

Thu 5/7

9:10 am-11:56 pm

1 stop15h 46m

$562

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/21

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Mon 5/25

10:10 am-12:37 pm

1 stop27h 27m

$568

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/10

1:18 pm-8:00 pm

1 stop29h 42m

Port of Spain Piarco Intl

Mon 7/20

10:10 am-12:25 pm

1 stop27h 15m

$571
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 4/27

10:00 am-1:40 am

2 stops14h 40m

Port of Spain Piarco Intl

Sat 5/2

9:10 am-11:59 pm

1 stop15h 49m

$577

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/10

6:55 am-6:55 pm

2 stops35h 00m

Port of Spain Piarco Intl

Mon 7/20

10:10 am-12:25 pm

1 stop27h 15m

$578

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 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

8h 35m

Direct flights

None
The fastest flight from Chicago to Trinidad takes 8h 35m
There are no direct flights from Chicago to Trinidad. There are no popular flight routes from Chicago to Trinidad.
Search flight deals

Frequently asked questions about flying from Chicago to Trinidad

  • 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 $392Free CancellationRating
7.1
10,935 reviews
Search Air Canada flights
Copa AirlinesPriceFrom $472Free CancellationRating
7.5
1,576 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $548Free CancellationRating
7.1
11,604 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,605 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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