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Cheap flights from Chicago to Trinidad from $174

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 2/28. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:20 am - 8:00 pm
ORD
-
POS
10h 40m1 stop
Multiple Airlines Logo
10:10 am - 7:38 pm
POS
-
ORD
11h 28m1 stop
$414Multiple Airlines
Mon, Jan 12 - Fri, Jan 16
Air Canada Logo
6:00 pm - 1:20 am
ORD
-
POS
29h 20m2 stops
Air Canada Logo
2:20 am - 5:48 pm
POS
-
ORD
17h 28m1 stop
$423Air Canada
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:25 am - 6:33 pm
POS
-
ORD
18h 08m2 stops
$427Air Canada
Tue, Jan 13 - Wed, Jun 3
Multiple Airlines Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$447Multiple Airlines
Thu, Jan 29 - Tue, Apr 7
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m1 stop
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$453Air Canada
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
9:10 am - 6:15 pm
POS
-
ORD
10h 05m1 stop
$454Multiple Airlines
Tue, Jan 13 - Wed, Jun 3
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$457Air Canada
Fri, Mar 13 - Tue, Mar 17
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$459JetBlue
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m2 stops
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$464Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Multiple Airlines Logo
6:22 pm - 1:36 pm
ORD
-
POS
18h 14m2 stops
Multiple Airlines Logo
1:20 am - 6:53 pm
POS
-
ORD
42h 33m2 stops
$466Multiple Airlines
Fri, Mar 27 - Fri, Apr 3

Air Canada flights from Chicago to Trinidad

Our best Air Canada deals on Chicago to Trinidad flight tickets
Air Canada
Jan 12
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS1:20 amPort of Spain Piarco Intl
Jun 3
POS1:25 amPort of Spain Piarco Intl
18h 08m
2 stops
ORD6:33 pmChicago O'Hare Intl
$423
Find similar
Air Canada
Jan 13
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS1:20 amPort of Spain Piarco Intl
Jun 3
POS1:25 amPort of Spain Piarco Intl
18h 08m
2 stops
ORD6:33 pmChicago O'Hare Intl
$427
Find similar
Air Canada
Mar 12
ORD6:04 pmChicago O'Hare Intl
29h 16m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 17
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$453
Find similar

American Airlines flights from Chicago to Trinidad

Our best American Airlines deals on Chicago to Trinidad flight tickets
American Airlines
Mar 7
ORD7:57 pmChicago O'Hare Intl
16h 21m
2 stops
POS2:18 pmPort of Spain Piarco Intl
Mar 12
POS3:18 pmPort of Spain Piarco Intl
18h 03m
2 stops
ORD8:21 amChicago O'Hare Intl
$583
Find similar
American Airlines
Jan 30
ORD6:42 amChicago O'Hare Intl
14h 06m
2 stops
POS10:48 pmPort of Spain Piarco Intl
Apr 8
POS3:10 pmPort of Spain Piarco Intl
18h 39m
2 stops
ORD8:49 amChicago O'Hare Intl
$638
Find similar

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 December 27, 2025.
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 1/12

7:20 am-8:00 pm

1 stop10h 40m

Port of Spain Piarco Intl

Fri 1/16

10:10 am-7:38 pm

1 stop11h 28m

$414

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/12

6:00 pm-1:20 am

2 stops29h 20m

Port of Spain Piarco Intl

Thu 1/15

2:20 am-5:48 pm

1 stop17h 28m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/13

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Wed 6/3

1:25 am-6:33 pm

2 stops18h 08m

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/29

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Tue 4/7

3:40 pm-9:10 am

2 stops18h 30m

$447

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-6:52 pm

2 stops18h 32m

$453

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/13

9:23 am-6:55 pm

1 stop31h 32m

Port of Spain Piarco Intl

Wed 6/3

9:10 am-6:15 pm

1 stop10h 05m

$454

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$457

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/26

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Mon 2/2

8:20 am-5:43 pm

2 stops35h 23m

$459

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:21 pm-12:20 am

2 stops28h 59m

Port of Spain Piarco Intl

Mon 4/6

3:40 pm-9:10 am

2 stops18h 30m

$464

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

6:22 pm-1:36 pm

2 stops18h 14m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-6:53 pm

2 stops42h 33m

$466

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 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 time of day to depart on your flight to Trinidad?

Flying to Trinidad from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $533 when looking at flights departing in the afternoon. Flights in the evening are often more expensive with an average ticket price of $905.

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 19m

Direct flights

None
The fastest flight from Chicago to Trinidad takes 9h 19m
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
10,562 reviews
Search Air Canada flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,066 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,114 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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