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Cheap flights from Trinidad and Tobago to Chicago from $317

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 5/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
1:29 pm - 6:55 pm
ORD
-
POS
28h 26m
2 stops
$568Multiple Airlines
Fri, May 29 - Fri, Jul 3
Air Canada Logo
1:25 am - 1:25 pm
POS
-
ORD
13h 00m
1 stop
Air Canada Logo
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
$582Air Canada
Fri, Jun 5 - Thu, Jun 11
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
7:52 am - 8:00 pm
ORD
-
POS
11h 08m
1 stop
$601Multiple Airlines
Fri, Jun 12 - Fri, Jun 19
Multiple Airlines Logo
1:25 am - 6:52 pm
POS
-
ORD
18h 27m
2 stops
Multiple Airlines Logo
6:27 pm - 1:26 pm
ORD
-
POS
17h 59m
1 stop
$609Multiple 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
7:52 am - 8:00 pm
ORD
-
POS
11h 08m
1 stop
$614Multiple Airlines
Fri, May 29 - Fri, Jul 3
Air Canada Logo
1:25 am - 1:21 pm
POS
-
ORD
12h 56m
1 stop
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$616Air Canada
Sun, Jun 14 - Mon, Jun 22
Air Canada Logo
1:25 am - 1:21 pm
POS
-
ORD
12h 56m
1 stop
Air Canada Logo
8:35 am - 12:15 am
ORD
-
POS
14h 40m
2 stops
$620Air Canada
Sun, Jun 14 - Mon, Jun 22
Air Canada Logo
1:25 am - 2:50 pm
POS
-
ORD
14h 25m
2 stops
Air Canada Logo
8:35 am - 12:15 am
ORD
-
POS
14h 40m
2 stops
$623Air Canada
Sun, Jun 14 - Mon, Jun 22
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$627Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
10:10 am - 8:22 am
POS
-
ORD
23h 12m
1 stop
Multiple Airlines Logo
1:29 pm - 6:55 pm
ORD
-
POS
28h 26m
2 stops
$636Multiple Airlines
Fri, May 22 - Tue, Jun 30

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

Our best JetBlue deals on Trinidad and Tobago to Chicago O'Hare Intl Airport flight tickets
JetBlue
Jun 19
POS7:45 pmPort of Spain Piarco Intl
14h 00m
1 stop
ORD8:45 amChicago O'Hare Intl
Jun 24
ORD6:27 pmChicago O'Hare Intl
18h 08m
1 stop
POS1:35 pmPort of Spain Piarco Intl
$688
JetBlue
May 22
POS3:46 pmPort of Spain Piarco Intl
23h 30m
1 stop
ORD2:16 pmChicago O'Hare Intl
Jun 23
ORD6:27 pmChicago O'Hare Intl
17h 59m
1 stop
POS1:26 pmPort of Spain Piarco Intl
$719
JetBlue
May 22
POS3:46 pmPort of Spain Piarco Intl
23h 30m
1 stop
ORD2:16 pmChicago O'Hare Intl
Jun 23
ORD6:27 pmChicago O'Hare Intl
17h 59m
1 stop
POS1:26 pmPort of Spain Piarco Intl
$730

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
May 31
POS12:30 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD10:20 amChicago O'Hare Intl
Jun 7
ORD9:36 pmChicago O'Hare Intl
24h 47m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$693
United Airlines
May 21
POS12:30 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD10:20 amChicago O'Hare Intl
Jun 30
ORD2:25 pmChicago O'Hare Intl
9h 25m
1 stop
POS12:50 amPort of Spain Piarco Intl
$729
United Airlines
May 21
POS12:30 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD10:20 amChicago O'Hare Intl
Jun 30
ORD5:30 amChicago O'Hare Intl
16h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$741

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 May 3, 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

Fri 5/29

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 7/3

1:29 pm-6:55 pm

2 stops28h 26m

$568

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

1:25 am-1:25 pm

1 stop13h 00m

Chicago O'Hare Intl

Thu 6/11

8:20 pm-12:15 am

1 stop26h 55m

$582

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/12

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 6/19

7:52 am-8:00 pm

1 stop11h 08m

$601

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 6/15

1:25 am-6:52 pm

2 stops18h 27m

Chicago O'Hare Intl

Tue 6/23

6:27 pm-1:26 pm

1 stop17h 59m

$609

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/29

10:10 am-11:15 pm

1 stop14h 05m

Chicago O'Hare Intl

Fri 7/3

7:52 am-8:00 pm

1 stop11h 08m

$614
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/14

1:25 am-1:21 pm

1 stop12h 56m

Chicago O'Hare Intl

Mon 6/22

2:15 pm-12:15 am

1 stop9h 00m

$616

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/14

1:25 am-1:21 pm

1 stop12h 56m

Chicago O'Hare Intl

Mon 6/22

8:35 am-12:15 am

2 stops14h 40m

$620

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/14

1:25 am-2:50 pm

2 stops14h 25m

Chicago O'Hare Intl

Mon 6/22

8:35 am-12:15 am

2 stops14h 40m

$623

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

8:40 pm-12:15 am

1 stop26h 35m

$627

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/22

10:10 am-8:22 am

1 stop23h 12m

Chicago O'Hare Intl

Tue 6/30

1:29 pm-6:55 pm

2 stops28h 26m

$636

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 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 December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Trinidad and Tobago averaging around $304.

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

11h 53m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago O'Hare Intl Airport takes 11h 53m
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
Copa AirlinesPriceFrom $299Free CancellationRating
7.5
1,578 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $322Free CancellationRating
7.1
10,993 reviews
Search Air Canada flights
United AirlinesPriceFrom $572Free CancellationRating
7.4
9,683 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,674 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
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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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