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Cheap flights from Chicago to Trinidad from $393

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 12/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
Logo
10:10 am - 10:48 pmPOS-ORD
13h 38m1 stop
$441
Find Deal
vie., sep. 12 - lun., sep. 15
Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
Logo
10:10 am - 10:48 pmPOS-ORD
13h 38m1 stop
$445
Find Deal
vie., sep. 12 - lun., sep. 22
Air Canada Logo
8:40 am - 1:20 amORD-POS
15h 40m2 stops
Air Canada Logo
2:25 am - 2:55 pmPOS-ORD
13h 30m2 stops
$523Air Canada
Find Deal
lun., sep. 22 - vie., sep. 26
Copa Airlines Logo
2:07 pm - 1:48 amORD-POS
9h 41m1 stop
Copa Airlines Logo
2:23 pm - 12:05 amPOS-ORD
11h 42m1 stop
$526Copa Airlines
Find Deal
vie., dic. 5 - lun., dic. 15
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
$528Air Canada
Find Deal
vie., sep. 12 - dom., sep. 14
American Airlines Logo
7:25 pm - 2:16 pmORD-POS
17h 51m1 stop
American Airlines Logo
3:25 pm - 8:40 amPOS-ORD
18h 15m1 stop
$548American Airlines
Find Deal
lun., sep. 22 - sáb., sep. 27
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$549Copa Airlines
Find Deal
mié., oct. 22 - sáb., oct. 25
American Airlines Logo
5:00 am - 2:25 pmORD-POS
8h 25m1 stop
American Airlines Logo
3:25 pm - 11:58 pmPOS-ORD
9h 33m1 stop
$553American Airlines
Find Deal
mié., oct. 22 - dom., oct. 26
United Airlines Logo
10:35 am - 11:23 pmORD-POS
11h 48m1 stop
United Airlines Logo
12:30 am - 12:17 pmPOS-ORD
12h 47m1 stop
$658United Airlines
Find Deal
mié., oct. 22 - sáb., oct. 25
United Airlines Logo
9:05 pm - 11:23 pmORD-POS
25h 18m1 stop
United Airlines Logo
12:30 am - 10:13 amPOS-ORD
10h 43m1 stop
$679United Airlines
Find Deal
vie., ago. 29 - jue., sep. 4

Copa Airlines flights from Chicago to Trinidad

Our best Copa Airlines deals on Chicago to Trinidad flight tickets
Copa Airlines
Dec 5
ORD2:07 pmChicago O'Hare Intl
9h 41m
1 stop
POS1:48 amPort of Spain Piarco Intl
Dec 15
POS2:23 pmPort of Spain Piarco Intl
11h 42m
1 stop
ORD12:05 amChicago O'Hare Intl
$526
Find similar
Copa Airlines
Oct 22
ORD3:07 pmChicago O'Hare Intl
9h 39m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 25
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$549
Find similar
Copa Airlines
Oct 22
ORD7:53 amChicago O'Hare Intl
16h 53m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 25
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$594
Find similar

Air Canada flights from Chicago to Trinidad

Our best Air Canada deals on Chicago to Trinidad flight tickets
Air Canada
Sep 22
ORD8:40 amChicago O'Hare Intl
15h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
Sep 26
POS2:25 amPort of Spain Piarco Intl
13h 30m
2 stops
ORD2:55 pmChicago O'Hare Intl
$523
Find similar
Air Canada
Sep 12
ORD10:40 amChicago O'Hare Intl
13h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
Sep 14
POS2:25 amPort of Spain Piarco Intl
17h 29m
2 stops
ORD6:54 pmChicago O'Hare Intl
$528
Find similar
Air Canada
Oct 4
ORD8:25 pmChicago O'Hare Intl
27h 55m
1 stop
POS1:20 amPort of Spain Piarco Intl
Oct 10
POS2:25 amPort of Spain Piarco Intl
11h 49m
1 stop
ORD1:14 pmChicago O'Hare Intl
$533
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 agosto 14, 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

vie. 9/12

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

lun. 9/15

10:10 am-10:48 pm

1 stop13h 38m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 9/12

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

lun. 9/22

10:10 am-10:48 pm

1 stop13h 38m

$445

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 9/22

8:40 am-1:20 am

2 stops15h 40m

Port of Spain Piarco Intl

vie. 9/26

2:25 am-2:55 pm

2 stops13h 30m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 12/5

2:07 pm-1:48 am

1 stop9h 41m

Port of Spain Piarco Intl

lun. 12/15

2:23 pm-12:05 am

1 stop11h 42m

$526

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 9/12

10:40 am-1:20 am

2 stops13h 40m

Port of Spain Piarco Intl

dom. 9/14

2:25 am-6:54 pm

2 stops17h 29m

$528

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 9/22

7:25 pm-2:16 pm

1 stop17h 51m

Port of Spain Piarco Intl

sáb. 9/27

3:25 pm-8:40 am

1 stop18h 15m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 10/22

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

sáb. 10/25

3:51 am-1:41 pm

1 stop10h 50m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 10/22

5:00 am-2:25 pm

1 stop8h 25m

Port of Spain Piarco Intl

dom. 10/26

3:25 pm-11:58 pm

1 stop9h 33m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 10/22

10:35 am-11:23 pm

1 stop11h 48m

Port of Spain Piarco Intl

sáb. 10/25

12:30 am-12:17 pm

1 stop12h 47m

$658

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 8/29

9:05 pm-11:23 pm

1 stop25h 18m

Port of Spain Piarco Intl

jue. 9/4

12:30 am-10:13 am

1 stop10h 43m

$679

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 day to depart on your flight to Trinidad?

The cheapest day to depart on your flight to Trinidad is on a Sunday when prices can be found for as low as $569. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Trinidad on Monday is $706.

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

Best Price Found

$393

Fastest flight time

8h 25m

Direct flights

None

Airports in Trinidad

1 airport
The best one-way flight to Trinidad from Chicago in the past 72 hours is $393. The best round-trip flight deal from Chicago to Trinidad found on momondo in the last 72 hours is $441.
The fastest flight from Chicago to Trinidad takes 8h 25m
There are no direct flights from Chicago to Trinidad. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Port of Spain Piarco Intl Airport.
There is 1 airport near Trinidad: Port of Spain Piarco Intl (POS)
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
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,916 reviews
Search United Airlines flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
10,000 reviews
Search American 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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