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Cheap flights from Trinidad and Tobago to Chicago from $322

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 12/25. 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 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
2:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
Air Canada Logo
10:00 am - 1:20 am
ORD
-
POS
13h 20m1 stop
$440Air Canada
Tue, Jan 20 - Fri, Jan 23
Multiple Airlines Logo
9:10 am - 6:16 pm
POS
-
ORD
11h 06m1 stop
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
$456Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
10:00 am - 1:20 am
ORD
-
POS
13h 20m1 stop
$461Air Canada
Tue, Jan 20 - Fri, Jan 23
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
$463Air Canada
Thu, Jan 22 - Fri, Jan 30
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
10:35 am - 1:20 am
ORD
-
POS
12h 45m2 stops
$464Air Canada
Tue, Jan 20 - Fri, Jan 23
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
$466Air Canada
Thu, Jan 22 - Fri, Jan 30
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
$483Air Canada
Thu, Jan 22 - Fri, Jan 30
Multiple Airlines Logo
10:10 am - 7:38 pm
POS
-
ORD
11h 28m1 stop
Multiple Airlines Logo
7:20 am - 8:00 pm
ORD
-
POS
10h 40m1 stop
$486Multiple Airlines
Thu, Jan 8 - Thu, Jan 15
Air Canada Logo
2:15 am - 1:01 pm
POS
-
ORD
12h 46m1 stop
Air Canada Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
$519Air Canada
Fri, Dec 26 - Wed, Jan 14
Multiple Airlines Logo
10:10 am - 10:39 pm
POS
-
ORD
14h 29m2 stops
Multiple Airlines Logo
7:20 am - 8:00 pm
ORD
-
POS
10h 40m1 stop
$527Multiple Airlines
Thu, Jan 8 - Thu, Jan 15

American Airlines flights from Trinidad and Tobago to Chicago

Our best American Airlines deals on Trinidad and Tobago to Chicago flight tickets
American Airlines
May 6
POS3:10 pmPort of Spain Piarco Intl
17h 00m
2 stops
ORD7:10 amChicago O'Hare Intl
May 10
ORD5:00 amChicago O'Hare Intl
8h 00m
1 stop
POS2:00 pmPort of Spain Piarco Intl
$640
Find similar
American Airlines
May 6
POS3:10 pmPort of Spain Piarco Intl
17h 00m
2 stops
ORD7:10 amChicago O'Hare Intl
May 10
ORD8:32 pmChicago O'Hare Intl
16h 28m
2 stops
POS2:00 pmPort of Spain Piarco Intl
$690
Find similar
American Airlines
May 6
POS3:10 pmPort of Spain Piarco Intl
17h 00m
2 stops
ORD7:10 amChicago O'Hare Intl
May 10
ORD8:47 pmChicago O'Hare Intl
16h 13m
2 stops
POS2:00 pmPort of Spain Piarco Intl
$741
Find similar

United Airlines flights from Trinidad and Tobago to Chicago

Our best United Airlines deals on Trinidad and Tobago to Chicago flight tickets
United Airlines
Apr 27
POS12:30 amPort of Spain Piarco Intl
17h 39m
1 stop
ORD5:09 pmChicago O'Hare Intl
May 2
ORD7:30 amChicago O'Hare Intl
14h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$680
Find similar
United Airlines
Dec 13
POS1:30 amPort of Spain Piarco Intl
15h 11m
1 stop
ORD2:41 pmChicago O'Hare Intl
Dec 20
ORD7:35 amChicago O'Hare Intl
14h 48m
1 stop
POS12:23 amPort of Spain Piarco Intl
$1,029
Find similar
United Airlines
Dec 13
POS1:30 amPort of Spain Piarco Intl
17h 33m
1 stop
ORD5:03 pmChicago O'Hare Intl
Dec 20
ORD9:23 pmChicago O'Hare Intl
25h 00m
1 stop
POS12:23 amPort of Spain Piarco Intl
$1,055
Find similar

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 December 11, 2025.
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

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/20

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 1/23

10:00 am-1:20 am

1 stop13h 20m

$440

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 1/23

9:10 am-6:16 pm

1 stop11h 06m

Chicago O'Hare Intl

Fri 1/30

5:15 am-8:00 pm

1 stop12h 45m

$456

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/20

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 1/23

10:00 am-1:20 am

1 stop13h 20m

$461

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/22

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 1/30

2:00 pm-1:20 am

1 stop9h 20m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/20

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 1/23

10:35 am-1:20 am

2 stops12h 45m

$464

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/22

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 1/30

7:15 am-1:20 am

2 stops16h 05m

$466

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/22

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 1/30

2:00 pm-1:20 am

1 stop9h 20m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/8

10:10 am-7:38 pm

1 stop11h 28m

Chicago O'Hare Intl

Thu 1/15

7:20 am-8:00 pm

1 stop10h 40m

$486

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 12/26

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

Wed 1/14

8:45 pm-1:20 am

1 stop26h 35m

$519

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/8

10:10 am-10:39 pm

2 stops14h 29m

Chicago O'Hare Intl

Thu 1/15

7:20 am-8:00 pm

1 stop10h 40m

$527

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $597. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Trinidad and Tobago to Chicago for around $1,058.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Trinidad and Tobago to Chicago during this time can be as low as $716. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $830.

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

9h 50m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago takes 9h 50m
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
7.6
1,558 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.2
11,049 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
Schererville
Valparaiso
Crown Point
Munster
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