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Cheap flights from Chicago to Trinidad and Tobago from $209

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 and Tobago departing on 9/10. 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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Find the cheapest flights from Chicago to Trinidad and Tobago

Cheap round-trip flights

Logo
6:44 pm - 8:00 pmORD-POS
24h 16m1 stop
Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
$441
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Wed, Sep 17 - Sun, Sep 21
Logo
6:44 pm - 8:00 pmORD-POS
24h 16m1 stop
Logo
9:10 am - 9:22 amPOS-ORD
25h 12m1 stop
$450
Find Deal
Sat, Sep 20 - Sat, Oct 11
Air Canada Logo
2:00 pm - 1:20 amORD-POS
10h 20m1 stop
Air Canada Logo
2:25 am - 10:53 amPOS-ORD
9h 28m1 stop
$523Air Canada
Find Deal
Mon, Sep 15 - Fri, Sep 26
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$528Air Canada
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Sat, Nov 22 - Fri, Nov 28
Copa Airlines Logo
8:02 am - 1:46 amORD-POS
16h 44m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$532Copa Airlines
Find Deal
Sat, Sep 20 - Fri, Oct 10
United Airlines Logo
7:10 am - 11:23 pmORD-POS
15h 13m1 stop
United Airlines Logo
12:30 am - 10:53 amPOS-ORD
11h 23m1 stop
$548United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
American Airlines Logo
7:25 pm - 2:16 pmORD-POS
17h 51m1 stop
American Airlines Logo
3:25 pm - 9:25 amPOS-ORD
19h 00m2 stops
$553American Airlines
Find Deal
Mon, Sep 15 - Sat, Sep 27
Copa Airlines Logo
2:13 pm - 1:44 amORD-POS
9h 31m1 stop
Copa Airlines Logo
2:33 pm - 12:34 amPOS-ORD
11h 01m1 stop
$624Copa Airlines
Find Deal
Thu, Jan 1 - Wed, Apr 1
American Airlines Logo
7:05 am - 9:20 pmORD-POS
13h 15m1 stop
American Airlines Logo
7:00 am - 11:58 pmPOS-ORD
17h 58m1 stop
$648American Airlines
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Wed, Oct 22 - Sun, Oct 26
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
United Airlines Logo
12:30 am - 11:05 amPOS-ORD
11h 35m1 stop
$658United Airlines
Find Deal
Mon, Sep 22 - Wed, Sep 24

Copa Airlines flights from Chicago to Trinidad and Tobago

Our best Copa Airlines deals on Chicago to Trinidad and Tobago flight tickets
Copa Airlines
Sep 20
ORD8:02 amChicago O'Hare Intl
16h 44m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 10
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$532
Find similar
Copa Airlines
Jan 1
ORD2:13 pmChicago O'Hare Intl
9h 31m
1 stop
POS1:44 amPort of Spain Piarco Intl
Apr 1
POS2:33 pmPort of Spain Piarco Intl
11h 01m
1 stop
ORD12:34 amChicago O'Hare Intl
$624
Find similar
Copa Airlines
Feb 9
ORD6:56 amChicago O'Hare Intl
16h 48m
1 stop
POS1:44 amPort of Spain Piarco Intl
Feb 23
POS3:40 amPort of Spain Piarco Intl
10h 51m
1 stop
ORD12:31 pmChicago O'Hare Intl
$752
Find similar

United Airlines flights from Chicago to Trinidad and Tobago

Our best United Airlines deals on Chicago to Trinidad and Tobago flight tickets
United Airlines
Oct 22
ORD7:10 amChicago O'Hare Intl
15h 13m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Oct 25
POS12:30 amPort of Spain Piarco Intl
11h 23m
1 stop
ORD10:53 amChicago O'Hare Intl
$548
Find similar
United Airlines
Aug 30
ORD7:00 amChicago O'Hare Intl
15h 23m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Sep 5
POS12:30 amPort of Spain Piarco Intl
20h 28m
1 stop
ORD7:58 pmChicago O'Hare Intl
$621
Find similar
United Airlines
Sep 3
ORD12:45 pmChicago O'Hare Intl
9h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Sep 6
POS12:30 amPort of Spain Piarco Intl
23h 11m
1 stop
ORD10:41 pmChicago O'Hare Intl
$648
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Trinidad and Tobago 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 August 28, 2025.
Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 9/17

6:44 pm-8:00 pm

1 stop24h 16m

Port of Spain Piarco Intl

Sun 9/21

6:25 pm-9:18 am

1 stop15h 53m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 9/20

6:44 pm-8:00 pm

1 stop24h 16m

Port of Spain Piarco Intl

Sat 10/11

9:10 am-9:22 am

1 stop25h 12m

$450

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/15

2:00 pm-1:20 am

1 stop10h 20m

Port of Spain Piarco Intl

Fri 9/26

2:25 am-10:53 am

1 stop9h 28m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-6:55 pm

2 stops18h 40m

$528

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 9/20

8:02 am-1:46 am

1 stop16h 44m

Port of Spain Piarco Intl

Fri 10/10

3:51 am-1:41 pm

1 stop10h 50m

$532

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:10 am-11:23 pm

1 stop15h 13m

Port of Spain Piarco Intl

Sat 10/25

12:30 am-10:53 am

1 stop11h 23m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/15

7:25 pm-2:16 pm

1 stop17h 51m

Port of Spain Piarco Intl

Sat 9/27

3:25 pm-9:25 am

2 stops19h 00m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/1

2:13 pm-1:44 am

1 stop9h 31m

Port of Spain Piarco Intl

Wed 4/1

2:33 pm-12:34 am

1 stop11h 01m

$624

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:05 am-9:20 pm

1 stop13h 15m

Port of Spain Piarco Intl

Sun 10/26

7:00 am-11:58 pm

1 stop17h 58m

$648

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/22

6:00 am-11:23 pm

1 stop16h 23m

Port of Spain Piarco Intl

Wed 9/24

12:30 am-11:05 am

1 stop11h 35m

$658

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 and Tobago from

How to get the cheapest flight ticket from Chicago to Trinidad and Tobago

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 and Tobago?

On average, the least expensive day to fly to Trinidad and Tobago from Chicago is on a Sunday. momondo users have found tickets for Sunday departures for as low as $569. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Trinidad and Tobago is Monday, with ticket prices averaging around $706.

What is the cheapest time of day to depart on your flight to Trinidad and Tobago?

According to our data, the cheapest time of day to fly to Trinidad and Tobago is in the afternoon. momondo users have found flights departing from Chicago to Trinidad and Tobago in the afternoon for as low as $533. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the evening is when there is more demand to fly to Trinidad and Tobago, so prices are often more expensive at around $905 per ticket.

Cheap Chicago to Trinidad and Tobago flight deals and tips

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

Direct flights

None
There are no direct flights from Chicago to Trinidad and Tobago. There are no popular flight routes from Chicago to Trinidad and Tobago.
Search flight deals

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

    Prices for flights from Chicago to Trinidad and Tobago are refreshed on a daily basis.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Trinidad and Tobago.

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

    The required travel and health documents for your Trinidad and Tobago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Trinidad and Tobago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Chicago to Trinidad and Tobago

Compare and see reviews for airlines that fly from Chicago to Trinidad and Tobago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,944 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 and Tobago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Trinidad and Tobago from Chicago.

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

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

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

Once all potential Chicago to Trinidad and Tobago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are simply researching potential flights to Trinidad and Tobago, momondo offers a useful price alert feature which will track prices for flights to Trinidad and Tobago from Chicago and alert you when they change.

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Find better results for your trip to Trinidad and Tobago

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