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Cheap flights from Trinidad and Tobago to Chicago from $413

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 8/16. 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 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
чт, квіт. 23 - пн, квіт. 27
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
8:06 am - 1:40 am
ORD
-
POS
16h 34m
1 stop
$417Copa Airlines
пт, квіт. 10 - пн, квіт. 13
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
чт, квіт. 23 - пн, квіт. 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
чт, квіт. 16 - нд, квіт. 26
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
9:05 am - 12:20 am
ORD
-
POS
14h 15m
1 stop
$425Air Canada
чт, квіт. 16 - нд, квіт. 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
чт, квіт. 16 - нд, квіт. 26
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m
2 stops
$431Air Canada
чт, квіт. 23 - пн, квіт. 27
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
вт, бер. 24 - ср, квіт. 1
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
$443Air Canada
чт, квіт. 9 - нд, квіт. 12
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
7:13 am - 12:20 am
ORD
-
POS
16h 07m
2 stops
$446Air Canada
чт, квіт. 9 - нд, квіт. 12

Air Canada flights from Trinidad and Tobago to Chicago O'Hare Intl Airport

Our best Air Canada deals on Trinidad and Tobago to Chicago O'Hare Intl Airport 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

Copa Airlines flights from Trinidad and Tobago to Chicago O'Hare Intl Airport

Our best Copa Airlines deals on Trinidad and Tobago to Chicago O'Hare Intl Airport flight tickets
Copa Airlines
Apr 10
POS2:17 pmPort of Spain Piarco Intl
11h 56m
1 stop
ORD1:13 amChicago O'Hare Intl
Apr 13
ORD8:06 amChicago O'Hare Intl
16h 34m
1 stop
POS1:40 amPort of Spain Piarco Intl
$417
Copa Airlines
Apr 25
POS2:17 pmPort of Spain Piarco Intl
11h 56m
1 stop
ORD1:13 amChicago O'Hare Intl
May 2
ORD3:21 pmChicago O'Hare Intl
9h 25m
1 stop
POS1:46 amPort of Spain Piarco Intl
$455
Copa Airlines
May 5
POS3:49 amPort of Spain Piarco Intl
11h 17m
1 stop
ORD2:06 pmChicago O'Hare Intl
May 10
ORD3:21 pmChicago O'Hare Intl
9h 25m
1 stop
POS1:46 amPort of Spain Piarco Intl
$492

momondo Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Chicago O'Hare Intl Airport 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 березень 15, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago O'Hare Intl Airport 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

чт 4/23

1:20 am-9:50 am

1 stop9h 30m

Chicago O'Hare Intl

пн 4/27

6:40 pm-12:20 am

1 stop28h 40m

$414

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

пт 4/10

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

пн 4/13

8:06 am-1:40 am

1 stop16h 34m

$417

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/23

1:20 am-2:55 pm

2 stops14h 35m

Chicago O'Hare Intl

пн 4/27

6:40 pm-12:20 am

1 stop28h 40m

$418

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/16

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

нд 4/26

8:40 am-12:20 am

2 stops14h 40m

$423
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/16

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

нд 4/26

9:05 am-12:20 am

1 stop14h 15m

$425

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/16

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

нд 4/26

8:40 am-12:20 am

2 stops14h 40m

$429

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/23

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

пн 4/27

6:21 pm-12:20 am

2 stops28h 59m

$431

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

вт 3/24

1:20 am-11:18 am

2 stops34h 58m

Chicago O'Hare Intl

ср 4/1

6:21 pm-12:20 am

2 stops52h 59m

$434

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/9

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

нд 4/12

2:00 pm-12:20 am

1 stop9h 20m

$443

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

чт 4/9

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

нд 4/12

7:13 am-12:20 am

2 stops16h 07m

$446

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Trinidad and Tobago to Chicago O'Hare Intl Airport

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 month to fly to Chicago O'Hare Intl Airport?

The month of June is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Trinidad and Tobago averaging around $453.

Cheap Trinidad and Tobago to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Trinidad and Tobago to Chicago O'Hare Intl Airport

Fastest flight time

11h 43m

Direct flights

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

  • When did momondo last update prices for flights from Trinidad and Tobago to Chicago O'Hare Intl Airport?

    Prices for flights from Trinidad and Tobago to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Trinidad and Tobago to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Trinidad and Tobago to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Trinidad and Tobago to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport

Compare and see reviews for airlines that fly from Trinidad and Tobago to Chicago O'Hare Intl Airport 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
10,801 reviews
Search Air Canada flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
9,427 reviews
Search United Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.1
11,472 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Kenosha
Oak Brook
Joliet
Racine
Janesville
Hammond
Aurora
Tinley Park
Elgin
South Holland

Why use momondo?

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

It is quick and easy to find Trinidad and Tobago to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits 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?

momondo helps you find the best flight between Trinidad and Tobago and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Trinidad and Tobago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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вт 4/14
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