What airlines fly to Chicago?

United Airlines, American Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from Trinidad according to our data. United Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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

Prices for flights from Trinidad to Chicago refresh daily.

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

The number of operators available for flights from Trinidad to Chicago is 3 as of December 2025.

How old do you have to be to fly from Trinidad 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 to Chicago.

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

The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$440 Cheap Flights from Trinidad to Chicago in 2025/26

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Find the cheapest flights from Trinidad to Chicago

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One-way

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Cheap round-trip flights

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2:20 am - 3:10 pm

POS

ORD

14h 50m1 stop

10:00 am - 1:20 am

ORD

POS

13h 20m1 stop

$440Air Canada

Tue, Jan 20 - Fri, Jan 23

2:20 am - 3:10 pm

POS

ORD

14h 50m1 stop

2:00 pm - 1:20 am

ORD

POS

9h 20m1 stop

$443Air Canada

Tue, Jan 20 - Fri, Jan 23

2:20 am - 6:55 pm

POS

ORD

18h 35m2 stops

10:00 am - 1:20 am

ORD

POS

13h 20m1 stop

$461Air Canada

Tue, Jan 20 - Fri, Jan 23

2:20 am - 6:55 pm

POS

ORD

18h 35m2 stops

2:00 pm - 1:20 am

ORD

POS

9h 20m1 stop

$463Air Canada

Tue, Jan 20 - Fri, Jan 23

2:20 am - 6:55 pm

POS

ORD

18h 35m2 stops

10:35 am - 1:20 am

ORD

POS

12h 45m2 stops

$464Air Canada

Tue, Jan 20 - Fri, Jan 23

2:20 am - 6:55 pm

POS

ORD

18h 35m2 stops

8:40 pm - 1:20 am

ORD

POS

26h 40m1 stop

$483Air Canada

Tue, Jan 27 - Sat, Feb 7

2:20 am - 6:55 pm

POS

ORD

18h 35m2 stops

7:15 am - 1:20 am

ORD

POS

16h 05m2 stops

$486Air Canada

Thu, Jan 22 - Fri, Jan 30

8:20 am - 5:43 pm

POS

ORD

35h 23m2 stops

10:00 am - 1:20 am

ORD

POS

13h 20m1 stop

$499Multiple Airlines

Wed, Jan 28 - Fri, Feb 6

9:10 am - 5:00 pm

POS

ORD

9h 50m1 stop

7:30 am - 8:00 pm

ORD

POS

10h 30m1 stop

$506Multiple Airlines

Wed, Dec 31 - Sun, Jan 11

9:10 am - 5:00 pm

POS

ORD

9h 50m1 stop

6:57 pm - 6:55 pm

ORD

POS

21h 58m1 stop

$509Multiple Airlines

Wed, Dec 31 - Thu, Jan 8

Air Canada flights from Trinidad to Chicago

Our best Air Canada deals on Trinidad to Chicago flight tickets

Air Canada

Jan 20

POS2:20 amPort of Spain Piarco Intl

14h 50m

1 stop

ORD3:10 pmChicago O'Hare Intl

Jan 23

ORD2:00 pmChicago O'Hare Intl

9h 20m

1 stop

POS1:20 amPort of Spain Piarco Intl

$443

Find similar

Air Canada

Jan 20

POS2:20 amPort of Spain Piarco Intl

18h 35m

2 stops

ORD6:55 pmChicago O'Hare Intl

Jan 23

ORD2:00 pmChicago O'Hare Intl

9h 20m

1 stop

POS1:20 amPort of Spain Piarco Intl

$463

Find similar

Air Canada

Jan 27

POS2:20 amPort of Spain Piarco Intl

19h 25m

1 stop

ORD7:45 pmChicago O'Hare Intl

Feb 7

ORD8:40 pmChicago O'Hare Intl

26h 40m

1 stop

POS1:20 amPort of Spain Piarco Intl

$483

Find similar

American Airlines flights from Trinidad to Chicago

Our best American Airlines deals on Trinidad to Chicago flight tickets

American Airlines

May 6

POS3:10 pmPort of Spain Piarco Intl

9h 45m

1 stop

ORD11:55 pmChicago O'Hare Intl

May 10

ORD7:17 pmChicago O'Hare Intl

17h 43m

1 stop

POS2:00 pmPort of Spain Piarco Intl

$635

Find similar

American Airlines

May 6

POS3:10 pmPort of Spain Piarco Intl

18h 39m

2 stops

ORD8:49 amChicago O'Hare Intl

May 10

ORD7:17 pmChicago O'Hare Intl

17h 43m

1 stop

POS2:00 pmPort of Spain Piarco Intl

$640

Find similar

American Airlines

May 6

POS3:10 pmPort of Spain Piarco Intl

16h 14m

2 stops

ORD6:24 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

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

Tue 1/20

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 1/23

2:00 pm-1:20 am

1 stop9h 20m

$443

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

Tue 1/20

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Fri 1/23

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

Tue 1/27

2:20 am-6:55 pm

2 stops18h 35m

Chicago O'Hare Intl

Sat 2/7

8:40 pm-1:20 am

1 stop26h 40m

$483

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

$486

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/28

8:20 am-5:43 pm

2 stops35h 23m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$499

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 12/31

9:10 am-5:00 pm

1 stop9h 50m

Chicago O'Hare Intl

Sun 1/11

7:30 am-8:00 pm

1 stop10h 30m

$506

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 12/31

9:10 am-5:00 pm

1 stop9h 50m

Chicago O'Hare Intl

Thu 1/8

6:57 pm-6:55 pm

1 stop21h 58m

$509

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first

How to get the cheapest flight ticket from Trinidad 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

Prices

Airlines

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 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 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.

Can stopping save me money on Trinidad to Chicago flights?

No. A direct flight is the cheapest option for a flight between Trinidad to Chicago.

Cheap Trinidad to Chicago flight deals and tips

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

Fastest flight time	10h 04m
Direct flights	None

The fastest flight from Trinidad to Chicago takes 10h 04m

There are no direct flights from Trinidad to Chicago. There are no popular flight routes from Trinidad to Chicago.

Search flight deals

When did momondo last update prices for flights from Trinidad to Chicago?
Prices for flights from Trinidad to Chicago refresh daily.
How many operators does momondo search for flights from Trinidad to Chicago?
The number of operators available for flights from Trinidad to Chicago is 3 as of December 2025.
How old do you have to be to fly from Trinidad 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 to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Trinidad to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Trinidad to Chicago is Boeing 737-800, representing 19.56% of all bookings. The subsequent popular models are Airbus A321neo at 12.25%, Boeing 737-900 at 9.38%, and Boeing 737 MAX 8 at 8.69%.

Best airlines flying from Trinidad to Chicago

Compare and see reviews for airlines that fly from Trinidad to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Copa Airlines	PriceFrom $299	Free Cancellation	Rating 7.6 1,557 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $474	Free Cancellation	Rating 7.4 9,094 reviews	Search United Airlines flights
American Airlines	PriceFrom $562	Free Cancellation	Rating 7.2 11,055 reviews	Search American Airlines flights

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 to Chicago?

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 Chicago from Trinidad.

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

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

How can momondo help me find flights from Trinidad 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.

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

If you are not ready to book a flight from Trinidad to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.