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Cheap flights from Chicago to Trinidad and Tobago from $264

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 12/30. 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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Find the cheapest flights from Chicago to Trinidad and Tobago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
7:15 am - 12:20 amORD-POS
16h 05m2 stops
Air Canada Logo
1:20 am - 3:10 pmPOS-ORD
14h 50m1 stop
$433Air Canada
Find Deal
Sun, Mar 8 - Fri, Mar 13
Air Canada Logo
7:15 am - 12:20 amORD-POS
16h 05m2 stops
Air Canada Logo
1:20 am - 6:52 pmPOS-ORD
18h 32m2 stops
$438Air Canada
Find Deal
Sun, Mar 8 - Fri, Mar 13
Air Canada Logo
8:45 pm - 1:20 amORD-POS
26h 35m1 stop
Air Canada Logo
2:20 am - 6:55 pmPOS-ORD
18h 35m2 stops
$443Air Canada
Find Deal
Wed, Jan 21 - Fri, Jan 23
Air Canada Logo
2:00 pm - 12:20 amORD-POS
9h 20m1 stop
Air Canada Logo
1:20 am - 1:01 pmPOS-ORD
12h 41m1 stop
$463Air Canada
Find Deal
Thu, Mar 12 - Tue, Mar 17
JetBlue Logo
8:45 am - 7:15 pmORD-POS
8h 30m1 stop
JetBlue Logo
8:30 am - 7:45 pmPOS-ORD
13h 15m1 stop
$515JetBlue
Find Deal
Wed, Jan 21 - Sat, Jan 24
Copa Airlines Logo
3:22 pm - 1:46 amORD-POS
9h 24m1 stop
Copa Airlines Logo
2:16 pm - 1:04 amPOS-ORD
11h 48m1 stop
$527Copa Airlines
Find Deal
Thu, Mar 12 - Wed, Mar 18
JetBlue Logo
12:41 pm - 6:17 amORD-POS
16h 36m1 stop
JetBlue Logo
3:26 pm - 10:05 amPOS-ORD
19h 39m2 stops
$532JetBlue
Find Deal
Sun, Mar 8 - Sat, Mar 14
Air Canada Logo
7:15 am - 12:20 amORD-POS
16h 05m2 stops
Air Canada Logo
1:20 am - 3:10 pmPOS-ORD
14h 50m1 stop
$543Air Canada
Find Deal
Sun, Mar 15 - Fri, Mar 20
American Airlines Logo
8:52 pm - 2:18 pmORD-POS
16h 26m2 stops
American Airlines Logo
3:18 pm - 12:35 amPOS-ORD
10h 17m1 stop
$563American Airlines
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Thu, Mar 12 - Wed, Mar 18
Copa Airlines Logo
2:22 pm - 1:44 amORD-POS
9h 22m1 stop
Copa Airlines Logo
3:40 am - 12:31 pmPOS-ORD
10h 51m1 stop
$573Copa Airlines
Find Deal
Thu, Feb 19 - Tue, Feb 24

United Airlines flights from Chicago to Trinidad and Tobago

Our best United Airlines deals on Chicago to Trinidad and Tobago flight tickets
United Airlines
Mar 30
ORD12:45 pmChicago O'Hare Intl
9h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Apr 5
POS12:30 amPort of Spain Piarco Intl
25h 00m
1 stop
ORD12:30 amChicago O'Hare Intl
$679
Find similar
United Airlines
Dec 23
ORD12:50 pmChicago O'Hare Intl
9h 33m
1 stop
POS12:23 amPort of Spain Piarco Intl
Dec 27
POS1:30 amPort of Spain Piarco Intl
12h 47m
1 stop
ORD12:17 pmChicago O'Hare Intl
$793
Find similar
United Airlines
Nov 30
ORD6:00 amChicago O'Hare Intl
16h 23m
1 stop
POS12:23 amPort of Spain Piarco Intl
Dec 6
POS1:30 amPort of Spain Piarco Intl
20h 16m
1 stop
ORD7:46 pmChicago O'Hare Intl
$804
Find similar

Air Canada flights from Chicago to Trinidad and Tobago

Our best Air Canada deals on Chicago to Trinidad and Tobago flight tickets
Air Canada
Mar 8
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 13
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$433
Find similar
Air Canada
Mar 8
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 13
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$438
Find similar
Air Canada
Jan 21
ORD6:00 pmChicago O'Hare Intl
29h 20m
2 stops
POS1:20 amPort of Spain Piarco Intl
Jan 23
POS2:20 amPort of Spain Piarco Intl
18h 35m
2 stops
ORD6:55 pmChicago O'Hare Intl
$443
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 24, 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

Sun 3/8

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 3/13

1:20 am-3:10 pm

1 stop14h 50m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/8

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 3/13

1:20 am-6:52 pm

2 stops18h 32m

$438

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/21

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 1/23

2:20 am-6:55 pm

2 stops18h 35m

$443

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-1:01 pm

1 stop12h 41m

$463

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/21

8:45 am-7:15 pm

1 stop8h 30m

Port of Spain Piarco Intl

Sat 1/24

8:30 am-7:45 pm

1 stop13h 15m

$515

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Wed 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/8

12:41 pm-6:17 am

1 stop16h 36m

Port of Spain Piarco Intl

Sat 3/14

3:26 pm-10:05 am

2 stops19h 39m

$532

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 3/20

1:20 am-3:10 pm

1 stop14h 50m

$543

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

8:52 pm-2:18 pm

2 stops16h 26m

Port of Spain Piarco Intl

Wed 3/18

3:18 pm-12:35 am

1 stop10h 17m

$563

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 2/19

2:22 pm-1:44 am

1 stop9h 22m

Port of Spain Piarco Intl

Tue 2/24

3:40 am-12:31 pm

1 stop10h 51m

$573

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
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,466 reviews
Search Air Canada flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
United AirlinesPriceFrom $560Free CancellationRating
7.4
9,039 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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