Cheap flights from Trinidad and Tobago to Chicago from $363

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 8/13. 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

 Logo
10:10 am - 10:48 pmPOS-ORD
13h 38m1 stop
 Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
Mon, Sep 15 - Mon, Sep 22
 Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
 Logo
10:27 am - 6:55 pmORD-POS
31h 28m1 stop
Tue, Sep 9 - Tue, Sep 16
 Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
 Logo
10:27 am - 4:15 amORD-POS
16h 48m1 stop
Sun, Sep 14 - Sun, Sep 21
 Logo
9:10 am - 1:09 pmPOS-ORD
28h 59m3 stops
 Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
Mon, Sep 15 - Mon, Sep 22
Copa Airlines Logo
2:40 pm - 12:21 amPOS-ORD
10h 41m1 stop
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
$562Copa Airlines
Find Deal
Fri, Oct 17 - Fri, Oct 24
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
$565Air Canada
Find Deal
Sun, Sep 14 - Mon, Sep 22
United Airlines Logo
12:30 am - 7:58 pmPOS-ORD
20h 28m1 stop
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$573United Airlines
Find Deal
Mon, Sep 8 - Tue, Sep 16
United Airlines Logo
12:30 am - 10:13 amPOS-ORD
10h 43m1 stop
United Airlines Logo
8:45 am - 11:23 pmORD-POS
13h 38m1 stop
$574United Airlines
Find Deal
Sat, Sep 13 - Sun, Sep 21
American Airlines Logo
3:25 pm - 7:24 amPOS-ORD
16h 59m2 stops
American Airlines Logo
5:00 am - 2:16 pmORD-POS
8h 16m1 stop
$578American Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
American Airlines Logo
7:00 am - 6:29 pmPOS-ORD
12h 29m2 stops
American Airlines Logo
5:00 am - 9:36 pmORD-POS
15h 36m1 stop
$716American Airlines
Find Deal
Tue, Aug 19 - Sun, Aug 24

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 8
POS12:30 amPort of Spain Piarco Intl
20h 28m
1 stop
ORD7:58 pmChicago O'Hare Intl
Sep 16
ORD6:00 amChicago O'Hare Intl
16h 23m
1 stop
POS11:23 pmPort of Spain Piarco Intl
United Airlines
Sep 13
POS12:30 amPort of Spain Piarco Intl
10h 43m
1 stop
ORD10:13 amChicago O'Hare Intl
Sep 21
ORD8:45 amChicago O'Hare Intl
13h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
United Airlines
Aug 18
POS12:30 amPort of Spain Piarco Intl
10h 23m
1 stop
ORD9:53 amChicago O'Hare Intl
Aug 24
ORD6:00 amChicago O'Hare Intl
16h 23m
1 stop
POS11:23 pmPort of Spain Piarco Intl

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
Sep 9
POS3:25 pmPort of Spain Piarco Intl
16h 59m
2 stops
ORD7:24 amChicago O'Hare Intl
Sep 16
ORD5:00 amChicago O'Hare Intl
8h 16m
1 stop
POS2:16 pmPort of Spain Piarco Intl
American Airlines
Aug 19
POS7:00 amPort of Spain Piarco Intl
12h 29m
2 stops
ORD6:29 pmChicago O'Hare Intl
Aug 24
ORD5:00 amChicago O'Hare Intl
15h 36m
1 stop
POS9:36 pmPort of Spain Piarco Intl

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 August 2, 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

Mon 9/15

10:10 am-10:48 pm

1 stop13h 38m

Chicago O'Hare Intl

Mon 9/22

5:05 am-8:00 pm

1 stop13h 55m

$429

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/9

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

Tue 9/16

10:27 am-6:55 pm

1 stop31h 28m

$451

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/14

6:25 pm-9:18 am

1 stop15h 53m

Chicago O'Hare Intl

Sun 9/21

10:27 am-4:15 am

1 stop16h 48m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/15

9:10 am-1:09 pm

3 stops28h 59m

Chicago O'Hare Intl

Mon 9/22

5:05 am-8:00 pm

1 stop13h 55m

$498

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/17

2:40 pm-12:21 am

1 stop10h 41m

Chicago O'Hare Intl

Fri 10/24

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/14

2:25 am-6:54 pm

2 stops17h 29m

Chicago O'Hare Intl

Mon 9/22

10:40 am-1:20 am

2 stops13h 40m

$565

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/8

12:30 am-7:58 pm

1 stop20h 28m

Chicago O'Hare Intl

Tue 9/16

6:00 am-11:23 pm

1 stop16h 23m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 9/13

12:30 am-10:13 am

1 stop10h 43m

Chicago O'Hare Intl

Sun 9/21

8:45 am-11:23 pm

1 stop13h 38m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/9

3:25 pm-7:24 am

2 stops16h 59m

Chicago O'Hare Intl

Tue 9/16

5:00 am-2:16 pm

1 stop8h 16m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 8/19

7:00 am-6:29 pm

2 stops12h 29m

Chicago O'Hare Intl

Sun 8/24

5:00 am-9:36 pm

1 stop15h 36m

$716

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Trinidad and Tobago averaging around $561.

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

Best Price Found

$363

Fastest flight time

9h 28m

Direct flights

None
The best one-way flight to Chicago O'Hare Intl Airport from Trinidad and Tobago in the past 72 hours is $363. The best round-trip flight deal from Trinidad and Tobago to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $429.
The fastest flight from Trinidad and Tobago to Chicago O'Hare Intl Airport takes 9h 28m
There are no direct flights from Trinidad and Tobago to Chicago O'Hare Intl Airport. Popular non-direct route for this connection is Port of Spain Piarco Intl Airport - 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 $493Free CancellationRating
7.4
8,904 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
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
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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