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 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.

$288 Cheap Flights from Trinidad and Tobago to Chicago in 2026/27

Find the cheapest flights from Trinidad and Tobago to Chicago

Round-trip

One-way

Last minute

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

Enter your travel dates to find the best prices.

2:22 pm - 12:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 49m1 stop Panama City Tocumen Intl

12:29 am - 2:01 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

23h 32m1 stop Panama City Tocumen Intl

$712Copa Airlines

Fri, Dec 25 - Tue, Dec 29

10:10 am - 11:34 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 24m1 stop Fort Lauderdale

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

$721Multiple Airlines

Thu, Nov 26 - Fri, Dec 11

10:10 am - 11:18 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

15h 08m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

$726Multiple Airlines

Thu, Nov 26 - Fri, Dec 11

1:25 am - 10:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

10h 46m1 stop Houston George Bush Intcntl

9:25 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 53m1 stop Houston George Bush Intcntl

$749United Airlines

Fri, Nov 20 - Sat, Nov 28

3:47 pm - 10:57 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

20h 10m1 stop Miami

9:01 pm - 2:32 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 31m2 stops Washington, D.C. Reagan-National Miami

$773American Airlines

Sun, Apr 11 - Sun, Apr 18

10:10 am - 12:42 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 32m3 stops Fort Lauderdale Atlanta Hartsfield-Jackson Orlando

10:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 55m1 stop Toronto Pearson Intl

$784Multiple Airlines

Thu, Nov 26 - Fri, Dec 11

2:15 am - 6:30 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

18h 15m2 stops Toronto Pearson Intl Ottawa

8:50 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

26h 10m1 stop Toronto Pearson Intl

$802Air Canada

Thu, Dec 24 - Wed, Dec 30

9:10 am - 11:18 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 08m2 stops Miami Atlanta Hartsfield-Jackson

4:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

30h 20m1 stop Toronto Pearson Intl

$814Multiple Airlines

Sat, Nov 21 - Sat, Nov 28

3:47 pm - 7:20 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 33m2 stops Miami Washington, D.C. Reagan-National

9:01 pm - 2:32 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

16h 31m2 stops Washington, D.C. Reagan-National Miami

$837American Airlines

Sun, Apr 11 - Sun, Apr 18

9:10 am - 11:18 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

16h 08m3 stops Miami Baltimore/Washington Atlanta Hartsfield-Jackson

4:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

30h 20m1 stop Toronto Pearson Intl

$841Multiple Airlines

Sat, Nov 21 - Sat, Nov 28

Recent last minute flight deals from Trinidad and Tobago to Chicago

Enter your travel dates to find the best prices.

10:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 27m1 stop Fort Lauderdale

2:52 pm - 6:55 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

50h 03m2 stops Baltimore/Washington Miami

$711Multiple Airlines

Fri, Oct 30 - Thu, Nov 26

10:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

30h 27m1 stop Fort Lauderdale

4:00 pm - 6:10 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

24h 10m1 stop Fort Lauderdale

$732Multiple Airlines

Fri, Oct 30 - Thu, Nov 26

9:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

31h 27m3 stops Miami Atlanta Hartsfield-Jackson Fort Lauderdale

10:15 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 45m1 stop Toronto Pearson Intl

$750Multiple Airlines

Fri, Oct 30 - Thu, Nov 26

12:25 am - 11:17 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

11h 52m1 stop Houston George Bush Intcntl

2:22 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

31h 56m1 stop Houston George Bush Intcntl

$769United Airlines

Wed, Oct 28 - Thu, Nov 26

9:10 am - 9:17 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

25h 07m2 stops Miami Atlanta Hartsfield-Jackson

8:45 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

14h 15m1 stop Toronto Pearson Intl

$788Multiple Airlines

Thu, Oct 29 - Thu, Nov 26

9:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

31h 27m3 stops Miami Atlanta Hartsfield-Jackson Fort Lauderdale

10:15 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

12h 45m1 stop Toronto Pearson Intl

$804Multiple Airlines

Thu, Oct 29 - Thu, Nov 26

9:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

31h 27m3 stops Miami Atlanta Hartsfield-Jackson Fort Lauderdale

7:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

15h 55m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$816Multiple Airlines

Fri, Oct 30 - Thu, Nov 26

9:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

31h 27m3 stops Miami Atlanta Hartsfield-Jackson Fort Lauderdale

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

21h 00m2 stops Toronto Pearson Intl Bridgetown Grantley Adams Intl

$847Multiple Airlines

Thu, Oct 29 - Thu, Nov 26

3:08 pm - 11:33 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

9h 25m1 stop Miami

6:05 am - 11:45 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

15h 40m1 stop Miami

$866American Airlines

Thu, Oct 29 - Tue, Dec 29

9:10 am - 3:37 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl

31h 27m3 stops Miami Atlanta Hartsfield-Jackson Fort Lauderdale

6:20 am - 5:40 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl

21h 20m3 stops Tampa Washington, D.C. Dulles Intl Toronto Pearson Intl

$869Multiple Airlines

Fri, Oct 30 - Thu, Nov 26

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United Airlines flights from Trinidad and Tobago to Chicago

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

United Airlines

Nov 20

POS1:25 amPort of Spain Piarco Intl

10h 46m

1 stop

ORD10:11 amChicago O'Hare Intl

Nov 28

ORD9:25 amChicago O'Hare Intl

12h 53m

1 stop

POS12:18 amPort of Spain Piarco Intl

$749

United Airlines

Oct 28

POS12:25 amPort of Spain Piarco Intl

11h 52m

1 stop

ORD11:17 amChicago O'Hare Intl

Nov 26

ORD2:22 pmChicago O'Hare Intl

31h 56m

1 stop

POS12:18 amPort of Spain Piarco Intl

$769

United Airlines

Dec 1

POS1:25 amPort of Spain Piarco Intl

15h 18m

1 stop

ORD2:43 pmChicago O'Hare Intl

Dec 11

ORD3:52 pmChicago O'Hare Intl

30h 26m

1 stop

POS12:18 amPort of Spain Piarco Intl

$884

American Airlines flights from Trinidad and Tobago to Chicago

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

American Airlines

Apr 11

POS3:47 pmPort of Spain Piarco Intl

20h 10m

1 stop

ORD10:57 amChicago O'Hare Intl

Apr 18

ORD9:01 pmChicago O'Hare Intl

16h 31m

2 stops

POS2:32 pmPort of Spain Piarco Intl

$773

American Airlines

Apr 11

POS3:47 pmPort of Spain Piarco Intl

16h 33m

2 stops

ORD7:20 amChicago O'Hare Intl

Apr 18

ORD9:01 pmChicago O'Hare Intl

16h 31m

2 stops

POS2:32 pmPort of Spain Piarco Intl

$837

American Airlines

Dec 1

POS4:47 pmPort of Spain Piarco Intl

16h 42m

2 stops

ORD7:29 amChicago O'Hare Intl

Dec 7

ORD7:49 amChicago O'Hare Intl

13h 51m

2 stops

POS11:40 pmPort of Spain Piarco Intl

$866

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 12/25

2:22 pm-12:11 am

1 stop11h 49m

Chicago O'Hare Intl

Tue 12/29

12:29 am-2:01 am

1 stop23h 32m

$712

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Thu 11/26

10:10 am-11:34 pm

1 stop15h 24m

Chicago O'Hare Intl

Fri 12/11

8:45 am-1:00 am

1 stop14h 15m

$721

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Thu 11/26

10:10 am-11:18 pm

2 stops15h 08m

Chicago O'Hare Intl

Fri 12/11

8:45 am-1:00 am

1 stop14h 15m

$726

Quickest round-trip

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Fri 11/20

1:25 am-10:11 am

1 stop10h 46m

Chicago O'Hare Intl

Sat 11/28

9:25 am-12:18 am

1 stop12h 53m

$749

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Sun 4/11

3:47 pm-10:57 am

1 stop20h 10m

Chicago O'Hare Intl

Sun 4/18

9:01 pm-2:32 pm

2 stops16h 31m

$773

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Thu 11/26

10:10 am-12:42 am

3 stops16h 32m

Chicago O'Hare Intl

Fri 12/11

10:05 am-1:00 am

1 stop12h 55m

$784

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Thu 12/24

2:15 am-6:30 pm

2 stops18h 15m

Chicago O'Hare Intl

Wed 12/30

8:50 pm-1:00 am

1 stop26h 10m

$802

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Sat 11/21

9:10 am-11:18 pm

2 stops16h 08m

Chicago O'Hare Intl

Sat 11/28

4:40 pm-1:00 am

1 stop30h 20m

$814

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Sun 4/11

3:47 pm-7:20 am

2 stops16h 33m

Chicago O'Hare Intl

Sun 4/18

9:01 pm-2:32 pm

2 stops16h 31m

$837

Port of SpainChicago

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

POSORD

Port of Spain Piarco Intl

Sat 11/21

9:10 am-11:18 pm

3 stops16h 08m

Chicago O'Hare Intl

Sat 11/28

4:40 pm-1:00 am

1 stop30h 20m

$841

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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?

United Airlines 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	$288
Fastest flight time	11h 49m
Direct flights	None

The best one-way flight to Chicago from Trinidad and Tobago in the past 72 hours is $288. The best round-trip flight deal from Trinidad and Tobago to Chicago found on momondo in the last 72 hours is $712.

The fastest flight from Trinidad and Tobago to Chicago takes 11h 49m

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 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.

Merrillville

New Buffalo

Hammond

Portage

Saint Joseph

Benton Harbor

Lansing

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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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Cheap flights from Trinidad and Tobago to Chicago from $288

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 3/1. 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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Recent last minute flight deals from Trinidad and Tobago to Chicago

Big names and deals

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Filter for what you want

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United Airlines flights from Trinidad and Tobago to Chicago

Our best United 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

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

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

Popular flights according to clicks in the last 7 days on momondo

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