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Cheap flights from Chicago to Trinidad and Tobago from $193

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 12/5. 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.
Multiple Airlines Logo
11:40 am - 6:55 pmORD-POS
29h 15m1 stop
Multiple Airlines Logo
8:55 am - 2:57 pmPOS-ORD
32h 02m1 stop
$427Multiple Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Multiple Airlines Logo
11:40 am - 6:55 pmORD-POS
29h 15m1 stop
Multiple Airlines Logo
3:35 pm - 2:57 pmPOS-ORD
25h 22m2 stops
$428Multiple Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Air Canada Logo
8:15 pm - 12:20 amORD-POS
27h 05m1 stop
Air Canada Logo
1:20 am - 3:10 pmPOS-ORD
14h 50m1 stop
$443Air Canada
Find Deal
Sat, Mar 28 - Fri, Apr 3
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$483Air Canada
Find Deal
Sat, Nov 22 - Fri, Nov 28
JetBlue Logo
8:45 am - 7:15 pmORD-POS
8h 30m1 stop
JetBlue Logo
8:30 am - 7:45 pmPOS-ORD
13h 15m1 stop
$509JetBlue
Find Deal
Wed, Jan 14 - Tue, Jan 20
JetBlue Logo
6:45 am - 3:07 pmORD-POS
30h 22m1 stop
JetBlue Logo
5:42 pm - 9:52 pmPOS-ORD
30h 10m1 stop
$511JetBlue
Find Deal
Mon, Nov 17 - Wed, Dec 3
United Airlines Logo
6:00 am - 12:23 amORD-POS
16h 23m1 stop
United Airlines Logo
1:30 am - 12:34 pmPOS-ORD
13h 04m1 stop
$549United Airlines
Find Deal
Tue, Dec 2 - Mon, Dec 8
American Airlines Logo
7:20 pm - 1:51 pmORD-POS
17h 31m2 stops
American Airlines Logo
3:34 pm - 12:14 amPOS-ORD
9h 40m1 stop
$553American Airlines
Find Deal
Thu, Mar 12 - Wed, Mar 18
United Airlines Logo
7:50 pm - 12:23 amORD-POS
26h 33m1 stop
United Airlines Logo
1:30 am - 2:40 pmPOS-ORD
15h 10m1 stop
$558United Airlines
Find Deal
Wed, Jan 14 - Mon, Jan 19
American Airlines Logo
7:20 pm - 1:51 pmORD-POS
17h 31m2 stops
American Airlines Logo
3:34 pm - 8:48 amPOS-ORD
18h 14m2 stops
$601American Airlines
Find Deal
Thu, Mar 12 - Wed, Mar 18

American Airlines flights from Chicago to Trinidad and Tobago

Our best American Airlines deals on Chicago to Trinidad and Tobago flight tickets
American Airlines
Mar 12
ORD7:20 pmChicago O'Hare Intl
17h 31m
2 stops
POS1:51 pmPort of Spain Piarco Intl
Mar 18
POS3:34 pmPort of Spain Piarco Intl
9h 40m
1 stop
ORD12:14 amChicago O'Hare Intl
$553
Find similar
American Airlines
Nov 6
ORD12:02 pmChicago O'Hare Intl
9h 37m
1 stop
POS11:39 pmPort of Spain Piarco Intl
Nov 9
POS4:30 pmPort of Spain Piarco Intl
18h 35m
1 stop
ORD9:05 amChicago O'Hare Intl
$554
Find similar
American Airlines
Nov 6
ORD7:10 amChicago O'Hare Intl
14h 29m
2 stops
POS11:39 pmPort of Spain Piarco Intl
Nov 9
POS7:19 amPort of Spain Piarco Intl
12h 50m
1 stop
ORD6:09 pmChicago O'Hare Intl
$558
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 28
ORD8:15 pmChicago O'Hare Intl
27h 05m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 3
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$443
Find similar
Air Canada
Nov 22
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
Nov 28
POS2:15 amPort of Spain Piarco Intl
14h 55m
1 stop
ORD3:10 pmChicago O'Hare Intl
$483
Find similar
Air Canada
Nov 21
ORD6:05 pmChicago O'Hare Intl
53h 05m
2 stops
POS1:10 amPort of Spain Piarco Intl
Nov 28
POS2:15 amPort of Spain Piarco Intl
14h 55m
1 stop
ORD3:10 pmChicago O'Hare Intl
$493
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 3, 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

11:40 am-6:55 pm

1 stop29h 15m

Port of Spain Piarco Intl

Tue 12/9

8:55 am-2:57 pm

1 stop32h 02m

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/2

11:40 am-6:55 pm

1 stop29h 15m

Port of Spain Piarco Intl

Tue 12/9

3:35 pm-2:57 pm

2 stops25h 22m

$428

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

8:15 pm-12:20 am

1 stop27h 05m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-3:10 pm

1 stop14h 50m

$443

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-3:10 pm

1 stop14h 55m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

8:45 am-7:15 pm

1 stop8h 30m

Port of Spain Piarco Intl

Tue 1/20

8:30 am-7:45 pm

1 stop13h 15m

$509

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 11/17

6:45 am-3:07 pm

1 stop30h 22m

Port of Spain Piarco Intl

Wed 12/3

5:42 pm-9:52 pm

1 stop30h 10m

$511

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/2

6:00 am-12:23 am

1 stop16h 23m

Port of Spain Piarco Intl

Mon 12/8

1:30 am-12:34 pm

1 stop13h 04m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

7:20 pm-1:51 pm

2 stops17h 31m

Port of Spain Piarco Intl

Wed 3/18

3:34 pm-12:14 am

1 stop9h 40m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

7:50 pm-12:23 am

1 stop26h 33m

Port of Spain Piarco Intl

Mon 1/19

1:30 am-2:40 pm

1 stop15h 10m

$558

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

7:20 pm-1:51 pm

2 stops17h 31m

Port of Spain Piarco Intl

Wed 3/18

3:34 pm-8:48 am

2 stops18h 14m

$601

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
10,394 reviews
Search Air Canada flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
11,036 reviews
Search American Airlines flights
United AirlinesPriceFrom $560Free CancellationRating
7.4
8,997 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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