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Cheap flights from Trinidad and Tobago to Chicago from $452

This is the cheapest round-trip 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 10/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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

Air Canada Logo
1:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
Air Canada Logo
2:00 pm - 12:10 amORD-POS
9h 10m1 stop
$452Air Canada
Find Deal
Sun, Oct 26 - Thu, Oct 30
Multiple Airlines Logo
6:25 pm - 9:22 amPOS-ORD
15h 57m1 stop
Multiple Airlines Logo
10:27 am - 1:46 amORD-POS
14h 19m2 stops
$458Multiple Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 23
Multiple Airlines Logo
6:25 pm - 9:22 amPOS-ORD
15h 57m1 stop
Multiple Airlines Logo
8:25 pm - 1:20 amORD-POS
27h 55m1 stop
$461Multiple Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 23
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
42h 40m2 stops
Air Canada Logo
6:05 pm - 1:10 amORD-POS
29h 05m2 stops
$471Air Canada
Find Deal
Sun, Nov 16 - Sat, Dec 6
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
$562Copa Airlines
Find Deal
Wed, Oct 15 - Thu, Oct 23
United Airlines Logo
1:30 am - 9:17 pmPOS-ORD
21h 47m1 stop
United Airlines Logo
2:21 pm - 12:23 amORD-POS
32h 02m1 stop
$572United Airlines
Find Deal
Mon, Nov 24 - Thu, Nov 27
United Airlines Logo
1:30 am - 11:09 amPOS-ORD
11h 39m1 stop
United Airlines Logo
12:45 pm - 12:23 amORD-POS
9h 38m1 stop
$574United Airlines
Find Deal
Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
7:19 am - 10:59 pmPOS-ORD
17h 40m1 stop
American Airlines Logo
7:07 pm - 3:33 pmORD-POS
18h 26m1 stop
$616American Airlines
Find Deal
Mon, Nov 17 - Sat, Dec 6
American Airlines Logo
7:19 am - 7:08 pmPOS-ORD
13h 49m2 stops
American Airlines Logo
8:29 am - 11:59 pmORD-POS
13h 30m2 stops
$620American Airlines
Find Deal
Mon, Nov 17 - Sat, Dec 6
Copa Airlines Logo
2:33 pm - 12:04 amPOS-ORD
11h 31m1 stop
Copa Airlines Logo
6:56 am - 1:15 pmORD-POS
28h 19m1 stop
$653Copa Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3

Air Canada flights from Trinidad and Tobago to Chicago O'Hare Intl Airport

Our best Air Canada deals on Trinidad and Tobago to Chicago O'Hare Intl Airport flight tickets
Air Canada
Oct 26
POS1:15 amPort of Spain Piarco Intl
18h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
Oct 30
ORD2:00 pmChicago O'Hare Intl
9h 10m
1 stop
POS12:10 amPort of Spain Piarco Intl
$452
Find similar
Air Canada
Nov 16
POS2:15 amPort of Spain Piarco Intl
42h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
Dec 6
ORD6:05 pmChicago O'Hare Intl
29h 05m
2 stops
POS1:10 amPort of Spain Piarco Intl
$471
Find similar
Air Canada
Feb 26
POS2:15 amPort of Spain Piarco Intl
19h 15m
1 stop
ORD7:30 pmChicago O'Hare Intl
Mar 3
ORD7:15 amChicago O'Hare Intl
15h 55m
2 stops
POS1:10 amPort of Spain Piarco Intl
$651
Find similar

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
Nov 17
POS7:19 amPort of Spain Piarco Intl
17h 40m
1 stop
ORD10:59 pmChicago O'Hare Intl
Dec 6
ORD7:07 pmChicago O'Hare Intl
18h 26m
1 stop
POS3:33 pmPort of Spain Piarco Intl
$616
Find similar
American Airlines
Nov 17
POS7:19 amPort of Spain Piarco Intl
13h 49m
2 stops
ORD7:08 pmChicago O'Hare Intl
Dec 6
ORD8:29 amChicago O'Hare Intl
13h 30m
2 stops
POS11:59 pmPort of Spain Piarco Intl
$620
Find similar
American Airlines
Nov 25
POS4:30 pmPort of Spain Piarco Intl
10h 07m
1 stop
ORD12:37 amChicago O'Hare Intl
Nov 27
ORD8:10 amChicago O'Hare Intl
29h 20m
1 stop
POS3:30 pmPort of Spain Piarco Intl
$632
Find similar

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 September 18, 2025.
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

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 10/26

1:15 am-6:55 pm

2 stops18h 40m

Chicago O'Hare Intl

Thu 10/30

2:00 pm-12:10 am

1 stop9h 10m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 10/16

6:25 pm-9:22 am

1 stop15h 57m

Chicago O'Hare Intl

Thu 10/23

10:27 am-1:46 am

2 stops14h 19m

$458

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 10/16

6:25 pm-9:22 am

1 stop15h 57m

Chicago O'Hare Intl

Thu 10/23

8:25 pm-1:20 am

1 stop27h 55m

$461

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/16

2:15 am-6:55 pm

2 stops42h 40m

Chicago O'Hare Intl

Sat 12/6

6:05 pm-1:10 am

2 stops29h 05m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/15

3:51 am-1:41 pm

1 stop10h 50m

Chicago O'Hare Intl

Thu 10/23

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 11/24

1:30 am-9:17 pm

1 stop21h 47m

Chicago O'Hare Intl

Thu 11/27

2:21 pm-12:23 am

1 stop32h 02m

$572

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

1:30 am-11:09 am

1 stop11h 39m

Chicago O'Hare Intl

Tue 3/3

12:45 pm-12:23 am

1 stop9h 38m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 11/17

7:19 am-10:59 pm

1 stop17h 40m

Chicago O'Hare Intl

Sat 12/6

7:07 pm-3:33 pm

1 stop18h 26m

$616

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 11/17

7:19 am-7:08 pm

2 stops13h 49m

Chicago O'Hare Intl

Sat 12/6

8:29 am-11:59 pm

2 stops13h 30m

$620

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/27

2:33 pm-12:04 am

1 stop11h 31m

Chicago O'Hare Intl

Tue 3/3

6:56 am-1:15 pm

1 stop28h 19m

$653

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Trinidad and Tobago averaging around $542.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $603. This is often the case because there is less demand to fly during this day of the week. On the other hand, Wednesday is the most expensive day to depart from Trinidad and Tobago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $717.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Trinidad and Tobago in the morning is the least expensive time of day to depart. momondo users have found prices as low as $637 when looking at flights departing in the morning. Try not to purchase tickets in the afternoon because they tend to be around $672. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Direct flights

None
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.
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  • 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
Copa AirlinesPriceFrom $304Free CancellationRating
7.5
1,531 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $561Free CancellationRating
7.2
10,000 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
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

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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