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Cheap flights from Trinidad and Tobago to Chicago from $250

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 9/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Trinidad and Tobago to Chicago

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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:10 am - 9:34 pm
POS
-
ORD
38h 24m
2 stops
Multiple Airlines Logo
7:50 am - 8:00 pm
ORD
-
POS
10h 10m
1 stop
$554Multiple Airlines
Sun, Nov 1 - Thu, Nov 12
Air Canada Logo
1:20 am - 1:23 pm
POS
-
ORD
13h 03m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$556Air Canada
Fri, Sep 18 - Sat, Sep 26
Multiple Airlines Logo
10:10 am - 3:24 pm
POS
-
ORD
31h 14m
1 stop
Multiple Airlines Logo
7:50 am - 8:00 pm
ORD
-
POS
10h 10m
1 stop
$559Multiple Airlines
Sun, Nov 1 - Thu, Nov 12
Copa Airlines Logo
3:50 am - 12:57 am
POS
-
ORD
22h 07m
1 stop
Copa Airlines Logo
3:20 pm - 1:47 am
ORD
-
POS
9h 27m
1 stop
$678Copa Airlines
Thu, Oct 1 - Mon, Oct 5
Copa Airlines Logo
3:23 am - 12:11 am
POS
-
ORD
22h 48m
1 stop
Copa Airlines Logo
12:29 am - 1:27 pm
ORD
-
POS
10h 58m
1 stop
$678Copa Airlines
Sun, Dec 27 - Tue, Dec 29
Copa Airlines Logo
2:23 pm - 12:57 am
POS
-
ORD
11h 34m
1 stop
Copa Airlines Logo
8:01 am - 1:47 am
ORD
-
POS
16h 46m
1 stop
$678Copa Airlines
Fri, Oct 2 - Mon, Oct 5
American Airlines Logo
3:06 pm - 11:30 pm
POS
-
ORD
9h 24m
1 stop
American Airlines Logo
5:00 am - 2:06 pm
ORD
-
POS
8h 06m
1 stop
$689American Airlines
Sat, Sep 26 - Thu, Oct 1
American Airlines Logo
3:06 pm - 9:29 am
POS
-
ORD
19h 23m
1 stop
American Airlines Logo
7:10 pm - 2:07 pm
ORD
-
POS
17h 57m
1 stop
$692American Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
2:00 am - 2:45 pm
POS
-
ORD
13h 45m
1 stop
United Airlines Logo
8:50 am - 11:23 pm
ORD
-
POS
13h 33m
1 stop
$692United Airlines
Sun, Sep 6 - Tue, Sep 15
United Airlines Logo
2:00 am - 12:48 pm
POS
-
ORD
11h 48m
1 stop
United Airlines Logo
10:25 am - 12:50 am
ORD
-
POS
13h 25m
1 stop
$692United Airlines
Tue, Aug 18 - Wed, Aug 26

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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 18
POS1:20 amPort of Spain Piarco Intl
13h 03m
1 stop
ORD1:23 pmChicago O'Hare Intl
Sep 26
ORD8:40 pmChicago O'Hare Intl
26h 35m
1 stop
POS12:15 amPort of Spain Piarco Intl
$556
Air Canada
Sep 18
POS1:20 amPort of Spain Piarco Intl
14h 32m
2 stops
ORD2:52 pmChicago O'Hare Intl
Sep 26
ORD8:40 pmChicago O'Hare Intl
26h 35m
1 stop
POS12:15 amPort of Spain Piarco Intl
$560
Air Canada
Nov 1
POS2:15 amPort of Spain Piarco Intl
15h 23m
1 stop
ORD3:38 pmChicago O'Hare Intl
Nov 12
ORD10:15 amChicago O'Hare Intl
12h 45m
1 stop
POS1:00 amPort of Spain Piarco Intl
$586

American Airlines flights from Trinidad and Tobago to Chicago

Our best American Airlines deals on Trinidad and Tobago to Chicago flight tickets
American Airlines
Sep 26
POS3:06 pmPort of Spain Piarco Intl
9h 24m
1 stop
ORD11:30 pmChicago O'Hare Intl
Oct 1
ORD5:00 amChicago O'Hare Intl
8h 06m
1 stop
POS2:06 pmPort of Spain Piarco Intl
$689
American Airlines
Oct 2
POS3:06 pmPort of Spain Piarco Intl
17h 36m
2 stops
ORD7:42 amChicago O'Hare Intl
Oct 5
ORD8:55 pmChicago O'Hare Intl
16h 12m
2 stops
POS2:07 pmPort of Spain Piarco Intl
$697
American Airlines
Aug 19
POS3:15 pmPort of Spain Piarco Intl
10h 20m
1 stop
ORD12:35 amChicago O'Hare Intl
Aug 26
ORD9:55 amChicago O'Hare Intl
12h 23m
1 stop
POS11:18 pmPort of Spain Piarco Intl
$698

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 July 27, 2026.
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 - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/1

9:10 am-9:34 pm

2 stops38h 24m

Chicago O'Hare Intl

Thu 11/12

7:50 am-8:00 pm

1 stop10h 10m

$554

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 9/18

1:20 am-1:23 pm

1 stop13h 03m

Chicago O'Hare Intl

Sat 9/26

8:40 pm-12:15 am

1 stop26h 35m

$556

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/1

10:10 am-3:24 pm

1 stop31h 14m

Chicago O'Hare Intl

Thu 11/12

7:50 am-8:00 pm

1 stop10h 10m

$559

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 10/1

3:50 am-12:57 am

1 stop22h 07m

Chicago O'Hare Intl

Mon 10/5

3:20 pm-1:47 am

1 stop9h 27m

$678

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 12/27

3:23 am-12:11 am

1 stop22h 48m

Chicago O'Hare Intl

Tue 12/29

12:29 am-1:27 pm

1 stop10h 58m

$678

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/2

2:23 pm-12:57 am

1 stop11h 34m

Chicago O'Hare Intl

Mon 10/5

8:01 am-1:47 am

1 stop16h 46m

$678
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 9/26

3:06 pm-11:30 pm

1 stop9h 24m

Chicago O'Hare Intl

Thu 10/1

5:00 am-2:06 pm

1 stop8h 06m

$689

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/2

3:06 pm-9:29 am

1 stop19h 23m

Chicago O'Hare Intl

Mon 10/5

7:10 pm-2:07 pm

1 stop17h 57m

$692

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/6

2:00 am-2:45 pm

1 stop13h 45m

Chicago O'Hare Intl

Tue 9/15

8:50 am-11:23 pm

1 stop13h 33m

$692

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 8/18

2:00 am-12:48 pm

1 stop11h 48m

Chicago O'Hare Intl

Wed 8/26

10:25 am-12:50 am

1 stop13h 25m

$692

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 airline that flies from Trinidad and Tobago to Chicago?

Air Canada and American Airlines are the most popular carriers operating from Trinidad and Tobago to Chicago

What airlines fly to Chicago?

American Airlines, Copa Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Trinidad and Tobago according to our data. American Airlines is the first choice among our users, with 35% 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.

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

Fastest flight time

11h 34m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago takes 11h 34m
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?

  • 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
1,561 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $572Free CancellationRating
7.4
10,046 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,841 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
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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Wed 8/26
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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