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Cheap flights from Trinidad and Tobago to Chicago from $348

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 8/9. 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
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
$597Multiple Airlines
Mon, Jul 27 - Mon, Aug 3
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Air Canada Logo
6:21 pm - 12:15 am
ORD
-
POS
28h 54m
2 stops
$630Air Canada
Fri, Jul 10 - Sat, Aug 29
Air Canada Logo
1:25 am - 11:20 am
POS
-
ORD
34h 55m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$633Air Canada
Wed, Jul 8 - Sat, Aug 29
Air Canada Logo
1:25 am - 11:20 am
POS
-
ORD
34h 55m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$636Air Canada
Wed, Jul 8 - Fri, Aug 28
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
28h 05m
2 stops
$638Multiple Airlines
Mon, Jul 27 - Mon, Aug 3
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$657Air Canada
Wed, Jul 8 - Sat, Aug 29
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
3:50 pm - 12:15 am
ORD
-
POS
31h 25m
1 stop
$659Air Canada
Wed, Jul 15 - Tue, Jul 21
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
2:08 pm - 12:15 am
ORD
-
POS
33h 07m
2 stops
$663Air Canada
Fri, Jul 3 - Thu, Jul 9
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
$676Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$679Air Canada
Wed, Jul 8 - Wed, Jul 22

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United Airlines flights from Trinidad and Tobago to Chicago O'Hare Intl Airport

Our best United Airlines deals on Trinidad and Tobago to Chicago O'Hare Intl Airport flight tickets
United Airlines
Sep 6
POS2:00 amPort of Spain Piarco Intl
13h 47m
1 stop
ORD2:47 pmChicago O'Hare Intl
Sep 15
ORD8:50 amChicago O'Hare Intl
13h 33m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$690
United Airlines
Jul 9
POS2:00 amPort of Spain Piarco Intl
12h 08m
1 stop
ORD1:08 pmChicago O'Hare Intl
Sep 3
ORD12:16 pmChicago O'Hare Intl
11h 34m
1 stop
POS12:50 amPort of Spain Piarco Intl
$691
United Airlines
Jul 14
POS12:30 amPort of Spain Piarco Intl
25h 15m
1 stop
ORD12:45 amChicago O'Hare Intl
Sep 1
ORD10:40 amChicago O'Hare Intl
11h 43m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$692

American Airlines flights from Trinidad and Tobago to Chicago O'Hare Intl Airport

Our best American Airlines deals on Trinidad and Tobago to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 23
POS7:00 amPort of Spain Piarco Intl
13h 53m
1 stop
ORD7:53 pmChicago O'Hare Intl
Jul 27
ORD8:00 amChicago O'Hare Intl
13h 33m
2 stops
POS10:33 pmPort of Spain Piarco Intl
$697
American Airlines
Jul 12
POS3:18 pmPort of Spain Piarco Intl
18h 50m
1 stop
ORD9:08 amChicago O'Hare Intl
Aug 31
ORD6:49 amChicago O'Hare Intl
15h 29m
2 stops
POS11:18 pmPort of Spain Piarco Intl
$702
American Airlines
Jul 23
POS7:00 amPort of Spain Piarco Intl
16h 00m
2 stops
ORD10:00 pmChicago O'Hare Intl
Jul 27
ORD6:30 amChicago O'Hare Intl
15h 03m
2 stops
POS10:33 pmPort of Spain Piarco Intl
$747

momondo Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Chicago O'Hare Intl Airport 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 June 16, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago O'Hare Intl Airport 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

Mon 7/27

10:10 am-12:15 pm

1 stop27h 05m

Chicago O'Hare Intl

Mon 8/3

8:05 am-8:00 pm

1 stop10h 55m

$597

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 7/10

1:25 am-2:55 pm

1 stop14h 30m

Chicago O'Hare Intl

Sat 8/29

6:21 pm-12:15 am

2 stops28h 54m

$630

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-11:20 am

2 stops34h 55m

Chicago O'Hare Intl

Sat 8/29

8:40 pm-12:15 am

1 stop26h 35m

$633

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-11:20 am

2 stops34h 55m

Chicago O'Hare Intl

Fri 8/28

8:45 am-12:15 am

2 stops14h 30m

$636

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 7/27

10:10 am-12:15 pm

1 stop27h 05m

Chicago O'Hare Intl

Mon 8/3

1:50 pm-6:55 pm

2 stops28h 05m

$638

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Sat 8/29

8:40 pm-12:15 am

1 stop26h 35m

$657

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/15

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Tue 7/21

3:50 pm-12:15 am

1 stop31h 25m

$659

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 7/3

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Thu 7/9

2:08 pm-12:15 am

2 stops33h 07m

$663
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

9:50 am-12:15 am

1 stop13h 25m

$676

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

8:45 am-12:15 am

2 stops14h 30m

$679

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Trinidad and Tobago to Chicago O'Hare Intl Airport

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 month to fly to Chicago O'Hare Intl Airport?

The month of April is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Trinidad and Tobago averaging around $0.

Cheap Trinidad and Tobago to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Trinidad and Tobago to Chicago O'Hare Intl Airport

Fastest flight time

13h 35m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago O'Hare Intl Airport takes 13h 35m
There are no direct flights from Trinidad and Tobago to Chicago O'Hare Intl Airport. There are no popular flight routes from Trinidad and Tobago to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Trinidad and Tobago to Chicago O'Hare Intl Airport

  • When did momondo last update prices for flights from Trinidad and Tobago to Chicago O'Hare Intl Airport?

    Prices for flights from Trinidad and Tobago to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Trinidad and Tobago to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Trinidad and Tobago to Chicago O'Hare Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Trinidad and Tobago to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport

Compare and see reviews for airlines that fly from Trinidad and Tobago to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $572Free CancellationRating
7.4
9,842 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,665 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
Oak Brook
New Buffalo
Joliet
Kenosha
Aurora
Hammond
Racine
Janesville
Evanston
Elgin
South Holland

Why use momondo?

Why should I use momondo to find a flight deal from Trinidad and Tobago to Chicago?

It is quick and easy to find Trinidad and Tobago to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits 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?

momondo helps you find the best flight between Trinidad and Tobago and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Trinidad and Tobago to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Trinidad and Tobago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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