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?

There is 1 operator available for flights from Trinidad and Tobago to Chicago as of September 2026.

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.

$313 Cheap Flights from Trinidad and Tobago to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Trinidad and Tobago to Chicago

Round-trip

One-way

Recent round-trip flight deals from Trinidad and Tobago to Chicago

Enter your travel dates to find the best prices.

1:20 am - 1:23 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

13h 03m1 stop Toronto Pearson Intl

8:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 20m1 stop Toronto Pearson Intl

$615Air Canada

Fri, Oct 23 - Sat, Oct 31

1:20 am - 2:52 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 32m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

8:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

27h 20m1 stop Toronto Pearson Intl

$619Air Canada

Fri, Oct 23 - Sat, Oct 31

10:10 am - 3:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 20m1 stop Fort Lauderdale

7:50 pm - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

46h 05m2 stops Atlanta Hartsfield-Jackson Miami

$642Multiple Airlines

Thu, Oct 22 - Thu, Oct 29

10:10 am - 3:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 20m1 stop Fort Lauderdale

8:00 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

11h 00m1 stop Fort Lauderdale

$659Multiple Airlines

Thu, Oct 22 - Thu, Oct 29

10:10 am - 3:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 20m1 stop Fort Lauderdale

8:04 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

10h 56m1 stop Fort Lauderdale

$660Multiple Airlines

Fri, Oct 9 - Fri, Oct 23

10:10 am - 3:20 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 10m1 stop Fort Lauderdale

7:25 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

35h 35m2 stops Houston George Bush Intcntl Fort Lauderdale

$664Multiple Airlines

Fri, Sep 25 - Wed, Sep 30

1:20 am - 2:52 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

14h 32m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

8:40 pm - 7:40 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

22h 00m2 stops Toronto Pearson Intl Bridgetown Grantley Adams Intl

$668Multiple Airlines

Wed, Oct 21 - Thu, Oct 29

3:23 am - 12:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

22h 48m1 stop Panama City Tocumen Intl

2:13 pm - 1:55 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

9h 42m1 stop Panama City Tocumen Intl

$678Copa Airlines

Wed, Dec 23 - Thu, Dec 31

3:06 pm - 12:33 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 27m1 stop Miami

7:29 pm - 2:08 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

17h 39m1 stop Miami

$692American Airlines

Fri, Oct 2 - Mon, Oct 5

3:08 pm - 9:10 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

19h 02m2 stops Miami Charlotte Douglas

5:05 am - 2:08 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

8h 03m1 stop Miami

$697American Airlines

Wed, Oct 21 - Sun, Oct 25

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Copa Airlines flights from Trinidad and Tobago to Chicago

Our best Copa Airlines deals on Trinidad and Tobago to Chicago flight tickets

Copa Airlines

Dec 23

POS3:23 amPort of Spain Piarco Intl

22h 48m

1 stop

ORD12:11 amChicago O'Hare Intl

Dec 31

ORD2:13 pmChicago O'Hare Intl

21h 06m

1 stop

POS1:19 pmPort of Spain Piarco Intl

$678

Copa Airlines

Oct 20

POS3:50 amPort of Spain Piarco Intl

11h 09m

1 stop

ORD1:59 pmChicago O'Hare Intl

Oct 25

ORD3:13 pmChicago O'Hare Intl

21h 04m

1 stop

POS1:17 pmPort of Spain Piarco Intl

$680

American Airlines flights from Trinidad and Tobago to Chicago

Our best American Airlines deals on Trinidad and Tobago to Chicago flight tickets

American Airlines

Oct 2

POS3:06 pmPort of Spain Piarco Intl

10h 27m

1 stop

ORD12:33 amChicago O'Hare Intl

Oct 5

ORD7:29 pmChicago O'Hare Intl

17h 39m

1 stop

POS2:08 pmPort of Spain Piarco Intl

$692

American Airlines

Oct 2

POS3:06 pmPort of Spain Piarco Intl

19h 04m

2 stops

ORD9:10 amChicago O'Hare Intl

Oct 5

ORD9:29 pmChicago O'Hare Intl

15h 39m

2 stops

POS2:08 pmPort of Spain Piarco Intl

$697

American Airlines

Dec 24

POS6:05 amPort of Spain Piarco Intl

15h 39m

2 stops

ORD7:44 pmChicago O'Hare Intl

Dec 31

ORD8:35 amChicago O'Hare Intl

13h 10m

1 stop

POS11:45 pmPort of Spain Piarco Intl

$723

momondo Fare Finder

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

Cheapest round-trip

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Fri 10/23

1:20 am-1:23 pm

1 stop13h 03m

Chicago O'Hare Intl

Sat 10/31

8:40 pm-1:00 am

1 stop27h 20m

$615

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Fri 10/23

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Sat 10/31

8:40 pm-1:00 am

1 stop27h 20m

$619

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Thu 10/22

10:10 am-3:30 pm

1 stop30h 20m

Chicago O'Hare Intl

Thu 10/29

7:50 pm-6:55 pm

2 stops46h 05m

$642

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Thu 10/22

10:10 am-3:30 pm

1 stop30h 20m

Chicago O'Hare Intl

Thu 10/29

8:00 am-8:00 pm

1 stop11h 00m

$659

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Fri 10/9

10:10 am-3:30 pm

1 stop30h 20m

Chicago O'Hare Intl

Fri 10/23

8:04 am-8:00 pm

1 stop10h 56m

$660

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Fri 9/25

10:10 am-3:20 pm

1 stop30h 10m

Chicago O'Hare Intl

Wed 9/30

7:25 am-8:00 pm

2 stops35h 35m

$664

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Wed 10/21

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Thu 10/29

8:40 pm-7:40 pm

2 stops22h 00m

$668

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Wed 12/23

3:23 am-12:11 am

1 stop22h 48m

Chicago O'Hare Intl

Thu 12/31

2:13 pm-1:55 am

1 stop9h 42m

$678

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Fri 10/2

3:06 pm-12:33 am

1 stop10h 27m

Chicago O'Hare Intl

Mon 10/5

7:29 pm-2:08 pm

1 stop17h 39m

$692

Quickest round-trip

Port of SpainChicago

POS Port of Spain Piarco Intl - ORD Chicago O'Hare Intl

POSORD

Port of Spain Piarco Intl

Wed 10/21

3:08 pm-9:10 am

2 stops19h 02m

Chicago O'Hare Intl

Sun 10/25

5:05 am-2:08 pm

1 stop8h 03m

$697

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first

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 airline that flies from Trinidad and Tobago to Chicago?

Air Canada is the most popular carrier operating from Trinidad and Tobago to Chicago

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

Best Price Found	$313
Fastest flight time	11h 39m
Direct flights	None

The best one-way flight to Chicago from Trinidad and Tobago in the past 72 hours is $313. The best round-trip flight deal from Trinidad and Tobago to Chicago found on momondo in the last 72 hours is $615.

The fastest flight from Trinidad and Tobago to Chicago takes 11h 39m

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

Frequently asked questions about flying from Trinidad and Tobago to Chicago

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?
There is 1 operator available for flights from Trinidad and Tobago to Chicago as of September 2026.
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
American Airlines	PriceFrom $574	Free Cancellation	Rating 7.1 12,045 reviews		Search American Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

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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Cheap flights from Trinidad and Tobago to Chicago from $313

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 10/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Trinidad and Tobago to Chicago

Recent round-trip flight deals from Trinidad and Tobago to Chicago

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Filter for what you want

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Copa Airlines flights from Trinidad and Tobago to Chicago

Our best Copa Airlines deals on Trinidad and Tobago to Chicago flight tickets

American Airlines flights from Trinidad and Tobago to Chicago

Our best American Airlines deals on Trinidad and Tobago to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Trinidad and Tobago to Chicago

What is the cheapest airline that flies from Trinidad and Tobago to Chicago?

Cheap Trinidad and Tobago to Chicago flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Trinidad and Tobago to Chicago

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

Traveling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular cities in the United States

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According to popular flight searches on momondo this year

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