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Cheap flights from Trinidad and Tobago to Chicago from $346

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 7/22. 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
0 bags

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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
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
1:57 pm - 12:15 am
ORD
-
POS
33h 18m
2 stops
$546Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
9:55 am - 12:15 am
ORD
-
POS
13h 20m
1 stop
$554Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:19 am
POS
-
ORD
26h 09m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
28h 05m
2 stops
$556Multiple Airlines
Mon, Jun 15 - Tue, Jun 23
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
12:59 pm - 6:55 pm
ORD
-
POS
28h 56m
2 stops
$563Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
9:55 am - 12:15 am
ORD
-
POS
13h 20m
1 stop
$569Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
1:49 pm - 6:55 pm
ORD
-
POS
28h 06m
2 stops
$574Multiple Airlines
Fri, Jun 5 - Fri, Jun 12
Multiple Airlines Logo
10:10 am - 12:43 pm
POS
-
ORD
27h 33m
1 stop
Multiple Airlines Logo
6:55 am - 6:55 pm
ORD
-
POS
35h 00m
2 stops
$581Multiple Airlines
Mon, Jun 15 - Mon, Jun 22
Multiple Airlines Logo
10:10 am - 12:43 pm
POS
-
ORD
27h 33m
1 stop
Multiple Airlines Logo
1:50 pm - 9:20 pm
ORD
-
POS
30h 30m
1 stop
$582Multiple Airlines
Mon, Jun 15 - Tue, Jun 23
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
5:35 pm - 12:15 am
ORD
-
POS
29h 40m
1 stop
$585Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
9:10 am - 4:06 pm
POS
-
ORD
31h 56m
2 stops
Multiple Airlines Logo
1:18 pm - 8:00 pm
ORD
-
POS
29h 42m
1 stop
$587Multiple Airlines
Wed, Jun 3 - Wed, Jun 10

Air Canada flights from Trinidad and Tobago to Chicago

Our best Air Canada deals on Trinidad and Tobago to Chicago flight tickets
Air Canada
Jun 15
POS1:25 amPort of Spain Piarco Intl
16h 34m
1 stop
ORD4:59 pmChicago O'Hare Intl
Jun 22
ORD2:15 pmChicago O'Hare Intl
9h 00m
1 stop
POS12:15 amPort of Spain Piarco Intl
$608
Air Canada
May 22
POS1:25 amPort of Spain Piarco Intl
13h 00m
1 stop
ORD1:25 pmChicago O'Hare Intl
Jun 8
ORD9:55 amChicago O'Hare Intl
13h 20m
1 stop
POS12:15 amPort of Spain Piarco Intl
$616
Air Canada
Jun 15
POS1:25 amPort of Spain Piarco Intl
18h 22m
2 stops
ORD6:47 pmChicago O'Hare Intl
Jun 27
ORD5:35 pmChicago O'Hare Intl
29h 40m
1 stop
POS12:15 amPort of Spain Piarco Intl
$642

United Airlines flights from Trinidad and Tobago to Chicago

Our best United Airlines deals on Trinidad and Tobago to Chicago flight tickets
United Airlines
May 5
POS12:30 amPort of Spain Piarco Intl
11h 25m
1 stop
ORD10:55 amChicago O'Hare Intl
May 10
ORD5:30 amChicago O'Hare Intl
16h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$844
United Airlines
May 5
POS12:30 amPort of Spain Piarco Intl
17h 43m
1 stop
ORD5:13 pmChicago O'Hare Intl
May 10
ORD8:46 amChicago O'Hare Intl
13h 37m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$895

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 April 23, 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

Fri 5/22

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Tue 6/30

1:57 pm-12:15 am

2 stops33h 18m

$546
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

9:55 am-12:15 am

1 stop13h 20m

$554

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 6/15

10:10 am-11:19 am

1 stop26h 09m

Chicago O'Hare Intl

Tue 6/23

1:50 pm-6:55 pm

2 stops28h 05m

$556

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

12:59 pm-6:55 pm

2 stops28h 56m

$563

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

9:55 am-12:15 am

1 stop13h 20m

$569

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/12

1:49 pm-6:55 pm

2 stops28h 06m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 6/15

10:10 am-12:43 pm

1 stop27h 33m

Chicago O'Hare Intl

Mon 6/22

6:55 am-6:55 pm

2 stops35h 00m

$581

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 6/15

10:10 am-12:43 pm

1 stop27h 33m

Chicago O'Hare Intl

Tue 6/23

1:50 pm-9:20 pm

1 stop30h 30m

$582

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/22

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Tue 6/30

5:35 pm-12:15 am

1 stop29h 40m

$585

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 6/3

9:10 am-4:06 pm

2 stops31h 56m

Chicago O'Hare Intl

Wed 6/10

1:18 pm-8:00 pm

1 stop29h 42m

$587

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 airlines fly to Chicago?

United Airlines, American Airlines and Air Canada are the top three most popular airlines that fly to Chicago from Trinidad and Tobago according to our data. United Airlines is the first choice among our users, with 30% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 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

10h 42m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago takes 10h 42m
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 $299Free CancellationRating
7.5
1,580 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $322Free CancellationRating
7.1
10,957 reviews
Search Air Canada flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
9,637 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,659 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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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