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Cheap flights from Trinidad and Tobago to Chicago from $454

This is the cheapest round-trip 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 10/23. 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

Logo
10:10 am - 6:38 pmPOS-ORD
9h 28m1 stop
Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
$454
Find Deal
Thu, Oct 23 - Thu, Oct 30
Logo
10:10 am - 6:38 pmPOS-ORD
9h 28m1 stop
Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
$457
Find Deal
Fri, Oct 24 - Fri, Oct 31
Logo
6:25 pm - 9:22 amPOS-ORD
15h 57m1 stop
Logo
11:55 am - 1:17 pmORD-POS
24h 22m2 stops
$463
Find Deal
Thu, Oct 23 - Thu, Oct 30
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
$562Copa Airlines
Find Deal
Wed, Oct 22 - Thu, Oct 30
Copa Airlines Logo
3:51 am - 12:21 amPOS-ORD
21h 30m1 stop
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
$573Copa Airlines
Find Deal
Mon, Oct 6 - Tue, Oct 14
United Airlines Logo
1:30 am - 10:07 amPOS-ORD
10h 37m1 stop
United Airlines Logo
8:50 am - 12:23 amORD-POS
13h 33m1 stop
$574United Airlines
Find Deal
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
7:00 am - 10:31 pmPOS-ORD
16h 31m1 stop
American Airlines Logo
6:45 am - 9:20 pmORD-POS
13h 35m2 stops
$578American Airlines
Find Deal
Tue, Oct 7 - Tue, Oct 14
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
Air Canada Logo
7:15 am - 1:10 amORD-POS
15h 55m2 stops
$640Air Canada
Find Deal
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
7:00 am - 11:58 pmPOS-ORD
17h 58m1 stop
American Airlines Logo
5:00 am - 9:20 pmORD-POS
15h 20m1 stop
$644American Airlines
Find Deal
Tue, Oct 7 - Tue, Oct 14
United Airlines Logo
1:30 am - 10:02 amPOS-ORD
10h 32m1 stop
United Airlines Logo
2:37 pm - 1:05 amORD-POS
8h 28m1 stop
$1,495United Airlines
Find Deal
Sat, Dec 13 - Sat, Dec 20

United Airlines flights from Trinidad and Tobago to Chicago

Our best United Airlines deals on Trinidad and Tobago to Chicago flight tickets
United Airlines
Feb 26
POS1:30 amPort of Spain Piarco Intl
10h 37m
1 stop
ORD10:07 amChicago O'Hare Intl
Mar 3
ORD8:50 amChicago O'Hare Intl
13h 33m
1 stop
POS12:23 amPort of Spain Piarco Intl
$574
Find similar
United Airlines
Dec 13
POS1:30 amPort of Spain Piarco Intl
10h 32m
1 stop
ORD10:02 amChicago O'Hare Intl
Dec 20
ORD2:37 pmChicago O'Hare Intl
8h 28m
1 stop
POS1:05 amPort of Spain Piarco Intl
$1,495
Find similar

Air Canada flights from Trinidad and Tobago to Chicago

Our best Air Canada deals on Trinidad and Tobago to Chicago flight tickets
Air Canada
Sep 12
POS2:25 amPort of Spain Piarco Intl
18h 46m
2 stops
ORD8:11 pmChicago O'Hare Intl
Sep 19
ORD12:00 pmChicago O'Hare Intl
12h 20m
1 stop
POS1:20 amPort of Spain Piarco Intl
$431
Find similar
Air Canada
Sep 12
POS2:25 amPort of Spain Piarco Intl
11h 49m
1 stop
ORD1:14 pmChicago O'Hare Intl
Sep 19
ORD3:50 pmChicago O'Hare Intl
8h 30m
1 stop
POS1:20 amPort of Spain Piarco Intl
$434
Find similar
Air Canada
Sep 12
POS2:25 amPort of Spain Piarco Intl
13h 30m
2 stops
ORD2:55 pmChicago O'Hare Intl
Sep 19
ORD10:40 amChicago O'Hare Intl
13h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
$495
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 September 10, 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

Thu 10/23

10:10 am-6:38 pm

1 stop9h 28m

Chicago O'Hare Intl

Thu 10/30

5:05 am-8:00 pm

1 stop13h 55m

$454

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/24

10:10 am-6:38 pm

1 stop9h 28m

Chicago O'Hare Intl

Fri 10/31

5:05 am-8:00 pm

1 stop13h 55m

$457

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 10/23

6:25 pm-9:22 am

1 stop15h 57m

Chicago O'Hare Intl

Thu 10/30

11:55 am-1:17 pm

2 stops24h 22m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/22

3:51 am-1:41 pm

1 stop10h 50m

Chicago O'Hare Intl

Thu 10/30

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 10/6

3:51 am-12:21 am

1 stop21h 30m

Chicago O'Hare Intl

Tue 10/14

3:07 pm-1:46 am

1 stop9h 39m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

1:30 am-10:07 am

1 stop10h 37m

Chicago O'Hare Intl

Tue 3/3

8:50 am-12:23 am

1 stop13h 33m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/7

7:00 am-10:31 pm

1 stop16h 31m

Chicago O'Hare Intl

Tue 10/14

6:45 am-9:20 pm

2 stops13h 35m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

Tue 3/3

7:15 am-1:10 am

2 stops15h 55m

$640

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/7

7:00 am-11:58 pm

1 stop17h 58m

Chicago O'Hare Intl

Tue 10/14

5:00 am-9:20 pm

1 stop15h 20m

$644

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/13

1:30 am-10:02 am

1 stop10h 32m

Chicago O'Hare Intl

Sat 12/20

2:37 pm-1:05 am

1 stop8h 28m

$1,495

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

Direct flights

None
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 $304Free CancellationRating
7.6
1,529 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
8,937 reviews
Search United Airlines flights
American AirlinesPriceFrom $561Free CancellationRating
7.2
10,000 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
Lansing
Portage
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