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Cheap flights from Chicago to Trinidad from $222

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 8/24. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Trinidad

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$504Air Canada
Tue, Jul 7 - Sun, Jul 12
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
$535Air Canada
Mon, Jul 6 - Sun, Jul 12
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
$539Air Canada
Mon, Jul 6 - Sun, Jul 12
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:25 am - 7:52 pm
POS
-
ORD
19h 27m
1 stop
$578Air Canada
Thu, Jul 30 - Sun, Aug 2
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
$590Air Canada
Tue, Jul 7 - Sun, Jul 12
Air Canada Logo
3:45 pm - 12:15 am
ORD
-
POS
31h 30m
1 stop
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
$593Air Canada
Thu, Jul 2 - Wed, Jul 8
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
$594Air Canada
Mon, Jul 6 - Sun, Jul 12
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 6:44 pm
POS
-
ORD
18h 19m
2 stops
$597Air Canada
Mon, Jul 6 - Sun, Jul 12
Air Canada Logo
6:22 pm - 12:15 am
ORD
-
POS
28h 53m
2 stops
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
$603Air Canada
Thu, Jul 2 - Wed, Jul 8
Copa Airlines Logo
8:02 am - 1:16 pm
ORD
-
POS
28h 14m
1 stop
Copa Airlines Logo
2:19 pm - 1:57 pm
POS
-
ORD
24h 38m
1 stop
$618Copa Airlines
Thu, Jul 16 - Sun, Jul 19

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United Airlines flights from Chicago to Trinidad

Our best United Airlines deals on Chicago to Trinidad flight tickets
United Airlines
Jul 5
ORD7:35 amChicago O'Hare Intl
14h 48m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Jul 11
POS12:30 amPort of Spain Piarco Intl
13h 03m
1 stop
ORD12:33 pmChicago O'Hare Intl
$750
United Airlines
Jun 17
ORD10:30 amChicago O'Hare Intl
11h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Jun 23
POS12:30 amPort of Spain Piarco Intl
11h 32m
1 stop
ORD11:02 amChicago O'Hare Intl
$752
United Airlines
Jun 24
ORD10:30 amChicago O'Hare Intl
11h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Jul 6
POS2:00 amPort of Spain Piarco Intl
12h 08m
1 stop
ORD1:08 pmChicago O'Hare Intl
$811

Air Canada flights from Chicago to Trinidad

Our best Air Canada deals on Chicago to Trinidad flight tickets
Air Canada
Jul 7
ORD8:40 pmChicago O'Hare Intl
26h 35m
1 stop
POS12:15 amPort of Spain Piarco Intl
Jul 12
POS1:25 amPort of Spain Piarco Intl
12h 57m
1 stop
ORD1:22 pmChicago O'Hare Intl
$504
Air Canada
Jul 6
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
Jul 12
POS1:25 amPort of Spain Piarco Intl
12h 57m
1 stop
ORD1:22 pmChicago O'Hare Intl
$535
Air Canada
Jul 6
ORD8:45 amChicago O'Hare Intl
14h 30m
2 stops
POS12:15 amPort of Spain Piarco Intl
Jul 12
POS1:25 amPort of Spain Piarco Intl
12h 57m
1 stop
ORD1:22 pmChicago O'Hare Intl
$539

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 June 10, 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

Tue 7/7

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 7/12

1:25 am-1:22 pm

1 stop12h 57m

$504
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/6

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Sun 7/12

1:25 am-1:22 pm

1 stop12h 57m

$535

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/6

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Sun 7/12

1:25 am-1:22 pm

1 stop12h 57m

$539

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/30

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 8/2

1:25 am-7:52 pm

1 stop19h 27m

$578

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 7/7

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 7/12

1:25 am-6:47 pm

2 stops18h 22m

$590

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/2

3:45 pm-12:15 am

1 stop31h 30m

Port of Spain Piarco Intl

Wed 7/8

1:25 am-2:55 pm

1 stop14h 30m

$593

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/6

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Sun 7/12

1:25 am-6:47 pm

2 stops18h 22m

$594

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/6

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Sun 7/12

1:25 am-6:44 pm

2 stops18h 19m

$597

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/2

6:22 pm-12:15 am

2 stops28h 53m

Port of Spain Piarco Intl

Wed 7/8

1:25 am-2:55 pm

1 stop14h 30m

$603

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/16

8:02 am-1:16 pm

1 stop28h 14m

Port of Spain Piarco Intl

Sun 7/19

2:19 pm-1:57 pm

1 stop24h 38m

$618

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

What is the cheapest month to fly to Trinidad?

The cheapest month to fly to Trinidad from Chicago is in January. Flight prices, which tend to average around $285, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Trinidad from Chicago during June instead. Flights to Trinidad in June, while not as cheap as those in January, still average around $317.

Can stopping save me money on Chicago to Trinidad flights?

You could potentially save up to 8% on your flight if you consider stops on a Chicago to Trinidad flight.

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 43m

Direct flights

None
The fastest flight from Chicago to Trinidad takes 9h 43m
There are no direct flights from Chicago to Trinidad. There are no popular flight routes from Chicago to Trinidad.
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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
Copa AirlinesPriceFrom $285Free CancellationRating
7.5
1,569 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $317Free CancellationRating
7.1
11,160 reviews
Search Air Canada flights
American AirlinesPriceFrom $548Free CancellationRating
7.1
11,640 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,805 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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