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 2 as of July 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.

$447 Cheap Flights from Trinidad to Chicago in 2025

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Find the cheapest flights from Trinidad to Chicago

Round-trip

One-way

Cheap round-trip flights

9:10 am - 9:18 amPOS-ORD

25h 08m1 stop

10:27 am - 6:55 pmORD-POS

31h 28m1 stop

$447

Find Deal

mar., sep. 9 - mar., sep. 16

9:10 am - 9:18 amPOS-ORD

25h 08m1 stop

10:27 am - 6:55 pmORD-POS

31h 28m1 stop

$451

Find Deal

mar., sep. 9 - mar., sep. 16

9:10 am - 9:18 amPOS-ORD

25h 08m1 stop

6:44 pm - 8:00 pmORD-POS

24h 16m1 stop

$463

Find Deal

mié., sep. 10 - mié., sep. 17

2:40 pm - 12:21 amPOS-ORD

10h 41m1 stop

3:07 pm - 1:46 amORD-POS

9h 39m1 stop

$562Copa Airlines

Find Deal

vie., oct. 17 - vie., oct. 24

2:15 am - 1:01 pmPOS-ORD

12h 46m1 stop

8:20 pm - 1:15 amORD-POS

26h 55m1 stop

$565Air Canada

Find Deal

dom., nov. 2 - lun., nov. 10

12:30 am - 7:58 pmPOS-ORD

20h 28m1 stop

6:00 am - 11:23 pmORD-POS

16h 23m1 stop

$573United Airlines

Find Deal

lun., sep. 8 - mar., sep. 16

12:30 am - 12:15 amPOS-ORD

24h 45m1 stop

5:50 pm - 11:23 pmORD-POS

28h 33m1 stop

$574United Airlines

Find Deal

lun., sep. 8 - mar., sep. 16

3:25 pm - 11:49 pmPOS-ORD

9h 24m1 stop

8:47 pm - 2:16 pmORD-POS

16h 29m2 stops

$578American Airlines

Find Deal

mar., sep. 9 - mar., sep. 16

7:01 am - 4:49 pmPOS-ORD

11h 48m2 stops

10:29 am - 11:36 pmORD-POS

11h 07m2 stops

$620American Airlines

Find Deal

lun., nov. 3 - lun., nov. 10

2:15 am - 1:01 pmPOS-ORD

12h 46m1 stop

7:15 am - 1:15 amORD-POS

16h 00m2 stops

$734Air Canada

Find Deal

mar., dic. 23 - vie., ene. 2

Air Canada flights from Trinidad to Chicago

Our best Air Canada deals on Trinidad to Chicago flight tickets

Air Canada

Nov 2

POS2:15 amPort of Spain Piarco Intl

12h 46m

1 stop

ORD1:01 pmChicago O'Hare Intl

Nov 10

ORD8:20 pmChicago O'Hare Intl

26h 55m

1 stop

POS1:15 amPort of Spain Piarco Intl

$565

Find similar

Air Canada

Dec 23

POS2:15 amPort of Spain Piarco Intl

12h 46m

1 stop

ORD1:01 pmChicago O'Hare Intl

Jan 2

ORD7:15 amChicago O'Hare Intl

16h 00m

2 stops

POS1:15 amPort of Spain Piarco Intl

$734

Find similar

Air Canada

Dec 23

POS2:15 amPort of Spain Piarco Intl

14h 40m

2 stops

ORD2:55 pmChicago O'Hare Intl

Jan 2

ORD7:15 amChicago O'Hare Intl

16h 00m

2 stops

POS1:15 amPort of Spain Piarco Intl

$1,187

Find similar

American Airlines flights from Trinidad to Chicago

Our best American Airlines deals on Trinidad to Chicago flight tickets

American Airlines

Sep 9

POS3:25 pmPort of Spain Piarco Intl

9h 24m

1 stop

ORD11:49 pmChicago O'Hare Intl

Sep 16

ORD8:47 pmChicago O'Hare Intl

16h 29m

2 stops

POS2:16 pmPort of Spain Piarco Intl

$578

Find similar

American Airlines

Nov 3

POS7:01 amPort of Spain Piarco Intl

11h 48m

2 stops

ORD4:49 pmChicago O'Hare Intl

Nov 10

ORD10:29 amChicago O'Hare Intl

11h 07m

2 stops

POS11:36 pmPort of Spain Piarco Intl

$620

Find similar

American Airlines

Dec 23

POS4:40 pmPort of Spain Piarco Intl

18h 22m

1 stop

ORD9:02 amChicago O'Hare Intl

Jan 2

ORD6:37 amChicago O'Hare Intl

13h 38m

1 stop

POS10:15 pmPort of Spain Piarco Intl

$829

Find similar

Fly from

Fly to

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 9/9

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

mar. 9/16

10:27 am-6:55 pm

1 stop31h 28m

$447

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 9/9

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

mar. 9/16

10:27 am-6:55 pm

1 stop31h 28m

$451

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mié. 9/10

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

mié. 9/17

6:44 pm-8:00 pm

1 stop24h 16m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

vie. 10/17

2:40 pm-12:21 am

1 stop10h 41m

Chicago O'Hare Intl

vie. 10/24

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

dom. 11/2

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

lun. 11/10

8:20 pm-1:15 am

1 stop26h 55m

$565

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 9/8

12:30 am-7:58 pm

1 stop20h 28m

Chicago O'Hare Intl

mar. 9/16

6:00 am-11:23 pm

1 stop16h 23m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 9/8

12:30 am-12:15 am

1 stop24h 45m

Chicago O'Hare Intl

mar. 9/16

5:50 pm-11:23 pm

1 stop28h 33m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 9/9

3:25 pm-11:49 pm

1 stop9h 24m

Chicago O'Hare Intl

mar. 9/16

8:47 pm-2:16 pm

2 stops16h 29m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 11/3

7:01 am-4:49 pm

2 stops11h 48m

Chicago O'Hare Intl

lun. 11/10

10:29 am-11:36 pm

2 stops11h 07m

$620

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 12/23

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

vie. 1/2

7:15 am-1:15 am

2 stops16h 00m

$734

Flights are sorted by cheapest round-trip flights first.

Sorted 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

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

Best Price Found	$447
Fastest flight time	9h 24m
Direct flights	None
Airports in Chicago	1 airport

The best flight deal from Trinidad to Chicago found on momondo in the last 72 hours is $447

The fastest flight from Trinidad to Chicago takes 9h 24m

There are no direct flights from Trinidad to Chicago. Popular non-direct route for this connection is Port of Spain Piarco Intl Airport - Chicago O'Hare Intl Airport.

There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

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 2 as of July 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 19.98% of all bookings. The subsequent popular models are Airbus A321neo at 10.01%, Boeing 737-900 at 8.26%, and Boeing 737 MAX 8 at 7.77%.

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
United Airlines	PriceFrom $493	Free Cancellation	Rating 7.4 8,900 reviews		Search United Airlines flights
American Airlines	PriceFrom $561	Free Cancellation	Rating 7.2 10,000 reviews		Search American Airlines flights

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Portage

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Schererville

Valparaiso

Crown Point

Munster

Chesterton

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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.