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Cheap flights from Trinidad and Tobago to Chicago from $266

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Trinidad and Tobago to Chicago departing on 4/9. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Trinidad and Tobago to Chicago

Recent round-trip flight deals from Trinidad and Tobago to Chicago

Enter your travel dates to find the best prices.
Air Canada Logo
1:20 am - 9:50 am
POS
-
ORD
9h 30m
1 stop
Air Canada Logo
6:40 pm - 12:20 am
ORD
-
POS
28h 40m
1 stop
$414Air Canada
Thu, Apr 23 - Mon, Apr 27
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
3:05 pm - 1:40 am
ORD
-
POS
9h 35m
1 stop
$417Copa Airlines
Fri, Apr 17 - Sun, Apr 26
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
Air Canada Logo
6:40 pm - 12:20 am
ORD
-
POS
28h 40m
1 stop
$418Air Canada
Thu, Apr 23 - Mon, Apr 27
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$423Air Canada
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$429Air Canada
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 7:58 am
POS
-
ORD
31h 38m
2 stops
Air Canada Logo
7:55 am - 12:20 am
ORD
-
POS
15h 25m
1 stop
$431Air Canada
Sun, Apr 5 - Fri, Apr 10
Air Canada Logo
1:20 am - 11:18 am
POS
-
ORD
34h 58m
2 stops
Air Canada Logo
6:21 pm - 12:20 am
ORD
-
POS
52h 59m
2 stops
$434Air Canada
Tue, Mar 24 - Wed, Apr 1
Air Canada Logo
1:20 am - 7:58 am
POS
-
ORD
31h 38m
2 stops
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$435Air Canada
Sun, Apr 5 - Fri, Apr 10
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
3:21 pm - 1:46 am
ORD
-
POS
9h 25m
1 stop
$455Copa Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
9:10 am - 9:12 pm
POS
-
ORD
13h 02m
2 stops
Multiple Airlines Logo
1:27 pm - 8:00 pm
ORD
-
POS
29h 33m
1 stop
$488Multiple Airlines
Sat, Apr 25 - Sat, May 2

JetBlue flights from Trinidad and Tobago to Chicago

Our best JetBlue deals on Trinidad and Tobago to Chicago flight tickets
JetBlue
May 6
POS2:45 pmPort of Spain Piarco Intl
31h 51m
2 stops
ORD9:36 pmChicago O'Hare Intl
May 10
ORD6:00 amChicago O'Hare Intl
30h 35m
2 stops
POS1:35 pmPort of Spain Piarco Intl
$560
JetBlue
May 23
POS3:46 pmPort of Spain Piarco Intl
19h 07m
1 stop
ORD9:53 amChicago O'Hare Intl
Jun 26
ORD8:20 pmChicago O'Hare Intl
21h 09m
2 stops
POS6:29 pmPort of Spain Piarco Intl
$582
JetBlue
May 23
POS3:46 pmPort of Spain Piarco Intl
19h 07m
1 stop
ORD9:53 amChicago O'Hare Intl
Jun 24
ORD8:20 pmChicago O'Hare Intl
21h 09m
2 stops
POS6:29 pmPort of Spain Piarco Intl
$588

Air Canada flights from Trinidad and Tobago to Chicago

Our best Air Canada deals on Trinidad and Tobago to Chicago flight tickets
Air Canada
Apr 23
POS1:20 amPort of Spain Piarco Intl
9h 30m
1 stop
ORD9:50 amChicago O'Hare Intl
Apr 27
ORD6:40 pmChicago O'Hare Intl
28h 40m
1 stop
POS12:20 amPort of Spain Piarco Intl
$414
Air Canada
Apr 23
POS1:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
Apr 27
ORD6:40 pmChicago O'Hare Intl
28h 40m
1 stop
POS12:20 amPort of Spain Piarco Intl
$418
Air Canada
Apr 16
POS1:20 amPort of Spain Piarco Intl
12h 45m
1 stop
ORD1:05 pmChicago O'Hare Intl
Apr 26
ORD8:40 amChicago O'Hare Intl
14h 40m
2 stops
POS12:20 amPort of Spain Piarco Intl
$423

momondo Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Chicago 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 March 11, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/23

1:20 am-9:50 am

1 stop9h 30m

Chicago O'Hare Intl

Mon 4/27

6:40 pm-12:20 am

1 stop28h 40m

$414

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 4/17

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

Sun 4/26

3:05 pm-1:40 am

1 stop9h 35m

$417

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/23

1:20 am-2:55 pm

2 stops14h 35m

Chicago O'Hare Intl

Mon 4/27

6:40 pm-12:20 am

1 stop28h 40m

$418

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Sun 4/26

8:40 am-12:20 am

2 stops14h 40m

$423

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

Sun 4/26

8:40 am-12:20 am

2 stops14h 40m

$429

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-7:58 am

2 stops31h 38m

Chicago O'Hare Intl

Fri 4/10

7:55 am-12:20 am

1 stop15h 25m

$431

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/24

1:20 am-11:18 am

2 stops34h 58m

Chicago O'Hare Intl

Wed 4/1

6:21 pm-12:20 am

2 stops52h 59m

$434

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/5

1:20 am-7:58 am

2 stops31h 38m

Chicago O'Hare Intl

Fri 4/10

8:40 am-12:20 am

2 stops14h 40m

$435
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 4/25

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

Sat 5/2

3:21 pm-1:46 am

1 stop9h 25m

$455

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 4/25

9:10 am-9:12 pm

2 stops13h 02m

Chicago O'Hare Intl

Sat 5/2

1:27 pm-8:00 pm

1 stop29h 33m

$488

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 airline that flies from Trinidad and Tobago to Chicago?

Air Canada is the most popular carrier operating from Trinidad and Tobago to Chicago

What airlines fly to Chicago?

American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Chicago from Trinidad and Tobago according to our data. American Airlines is the first choice among our users, with 32% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Cheap Trinidad and Tobago to Chicago flight deals and tips

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

Fastest flight time

11h 43m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago takes 11h 43m
There are no direct flights from Trinidad and Tobago to Chicago. There are no popular flight routes from Trinidad and Tobago to Chicago.
Search flight deals

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

    Prices for flights from Trinidad and Tobago to Chicago refresh daily.

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

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

    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 Trinidad and Tobago to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago 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.

Best airlines flying from Trinidad and Tobago to Chicago

Compare and see reviews for airlines that fly from Trinidad and Tobago to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $299Free CancellationRating
7.5
1,569 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $322Free CancellationRating
7.1
10,800 reviews
Search Air Canada flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
9,415 reviews
Search United Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.1
11,423 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Trinidad and Tobago to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Trinidad and Tobago to Chicago for you.

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

All flight searches from Trinidad and Tobago to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Trinidad and Tobago.

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

Yes. momondo can track prices for Trinidad and Tobago to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport