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Cheap flights from Chicago to Trinidad and Tobago from $408

This is the cheapest round-trip 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 12/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$408Air Canada
Find Deal
Tue, Dec 2 - Fri, Dec 5
Air Canada Logo
7:15 am - 1:20 amORD-POS
16h 05m2 stops
Air Canada Logo
2:20 am - 2:55 pmPOS-ORD
14h 35m2 stops
$433Air Canada
Find Deal
Fri, Jan 16 - Sun, Jan 18
Air Canada Logo
7:05 am - 1:10 amORD-POS
16h 05m2 stops
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$435Air Canada
Find Deal
Tue, Dec 2 - Fri, Dec 5
Air Canada Logo
3:35 pm - 1:20 amORD-POS
31h 45m2 stops
Air Canada Logo
2:20 am - 6:51 pmPOS-ORD
18h 31m2 stops
$443Air Canada
Find Deal
Mon, Jan 5 - Tue, Jan 13
Multiple Airlines Logo
6:57 pm - 6:55 pmORD-POS
21h 58m1 stop
Multiple Airlines Logo
9:10 am - 8:09 amPOS-ORD
24h 59m1 stop
$455Multiple Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
10:00 am - 1:10 amORD-POS
13h 10m1 stop
Multiple Airlines Logo
9:10 am - 6:36 pmPOS-ORD
11h 26m1 stop
$478Multiple Airlines
Find Deal
Tue, Dec 2 - Sat, Dec 6
Multiple Airlines Logo
6:05 pm - 6:55 pmORD-POS
22h 50m1 stop
Multiple Airlines Logo
9:10 am - 8:09 amPOS-ORD
24h 59m1 stop
$491Multiple Airlines
Find Deal
Tue, Jan 6 - Mon, Jan 12
Air Canada Logo
6:00 pm - 1:20 amORD-POS
53h 20m2 stops
Air Canada Logo
2:20 am - 6:55 pmPOS-ORD
18h 35m2 stops
$493Air Canada
Find Deal
Tue, Jan 6 - Fri, Jan 9
Multiple Airlines Logo
8:00 am - 1:10 amORD-POS
15h 10m1 stop
Multiple Airlines Logo
9:10 am - 10:11 pmPOS-ORD
15h 01m2 stops
$497Multiple Airlines
Find Deal
Tue, Dec 2 - Sat, Dec 6
Multiple Airlines Logo
7:29 am - 8:00 pmORD-POS
10h 31m1 stop
Multiple Airlines Logo
9:10 am - 8:09 amPOS-ORD
24h 59m1 stop
$505Multiple Airlines
Find Deal
Fri, Jan 16 - Mon, Jan 19

Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets
Air Canada
Dec 2
ORD2:00 pmChicago O'Hare Intl
9h 10m
1 stop
POS1:10 amPort of Spain Piarco Intl
Dec 5
POS2:15 amPort of Spain Piarco Intl
14h 55m
1 stop
ORD3:10 pmChicago O'Hare Intl
$408
Find similar
Air Canada
Jan 16
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS1:20 amPort of Spain Piarco Intl
Jan 18
POS2:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
$433
Find similar
Air Canada
Dec 2
ORD7:05 amChicago O'Hare Intl
16h 05m
2 stops
POS1:10 amPort of Spain Piarco Intl
Dec 5
POS2:15 amPort of Spain Piarco Intl
14h 55m
1 stop
ORD3:10 pmChicago O'Hare Intl
$435
Find similar

Copa Airlines flights from Chicago to Trinidad and Tobago

Our best Copa Airlines deals on Chicago to Trinidad and Tobago flight tickets
Copa Airlines
Mar 12
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 18
POS2:16 pmPort of Spain Piarco Intl
11h 48m
1 stop
ORD1:04 amChicago O'Hare Intl
$527
Find similar
Copa Airlines
Dec 11
ORD7:33 amChicago O'Hare Intl
16h 15m
1 stop
POS1:48 amPort of Spain Piarco Intl
Dec 13
POS3:47 amPort of Spain Piarco Intl
11h 05m
1 stop
ORD12:52 pmChicago O'Hare Intl
$533
Find similar
Copa Airlines
Mar 13
ORD8:34 amChicago O'Hare Intl
16h 12m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 18
POS2:16 pmPort of Spain Piarco Intl
11h 48m
1 stop
ORD1:04 amChicago O'Hare Intl
$550
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 November 17, 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

Tue 12/2

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 12/5

2:15 am-3:10 pm

1 stop14h 55m

$408

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/16

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Sun 1/18

2:20 am-2:55 pm

2 stops14h 35m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/2

7:05 am-1:10 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 12/5

2:15 am-3:10 pm

1 stop14h 55m

$435

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/5

3:35 pm-1:20 am

2 stops31h 45m

Port of Spain Piarco Intl

Tue 1/13

2:20 am-6:51 pm

2 stops18h 31m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/8

6:57 pm-6:55 pm

1 stop21h 58m

Port of Spain Piarco Intl

Mon 1/12

9:10 am-8:09 am

1 stop24h 59m

$455

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/2

10:00 am-1:10 am

1 stop13h 10m

Port of Spain Piarco Intl

Sat 12/6

9:10 am-6:36 pm

1 stop11h 26m

$478

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/6

6:05 pm-6:55 pm

1 stop22h 50m

Port of Spain Piarco Intl

Mon 1/12

9:10 am-8:09 am

1 stop24h 59m

$491

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 1/6

6:00 pm-1:20 am

2 stops53h 20m

Port of Spain Piarco Intl

Fri 1/9

2:20 am-6:55 pm

2 stops18h 35m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/2

8:00 am-1:10 am

1 stop15h 10m

Port of Spain Piarco Intl

Sat 12/6

9:10 am-10:11 pm

2 stops15h 01m

$497

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/16

7:29 am-8:00 pm

1 stop10h 31m

Port of Spain Piarco Intl

Mon 1/19

9:10 am-8:09 am

1 stop24h 59m

$505

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 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
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,457 reviews
Search Air Canada flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
11,048 reviews
Search American Airlines flights
United AirlinesPriceFrom $560Free CancellationRating
7.4
9,014 reviews
Search United 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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