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Cheap flights from Trinidad and Tobago to Chicago from $282

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 4/16. 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
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
4:51 pm - 6:55 pm
ORD
-
POS
25h 04m
1 stop
$468Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
$478Air Canada
Tue, Mar 10 - Wed, Mar 18
Multiple Airlines Logo
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
6:16 pm - 6:55 pm
ORD
-
POS
47h 39m
2 stops
$489Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Air Canada Logo
1:20 am - 8:10 pm
POS
-
ORD
19h 50m
2 stops
Air Canada Logo
6:04 pm - 12:20 am
ORD
-
POS
29h 16m
2 stops
$535Air Canada
Sun, Mar 8 - Mon, Mar 16
Copa Airlines Logo
2:22 pm - 1:15 am
POS
-
ORD
11h 53m
1 stop
Copa Airlines Logo
3:21 pm - 1:46 am
ORD
-
POS
9h 25m
1 stop
$574Copa Airlines
Wed, May 6 - Sun, May 10
Multiple Airlines Logo
9:10 am - 4:55 pm
POS
-
ORD
32h 45m
3 stops
Multiple Airlines Logo
3:55 pm - 12:20 am
ORD
-
POS
31h 25m
1 stop
$581Multiple Airlines
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
1:20 am - 9:10 am
POS
-
ORD
32h 50m
3 stops
Multiple Airlines Logo
6:01 pm - 12:20 am
ORD
-
POS
29h 19m
2 stops
$601Multiple Airlines
Tue, Mar 10 - Wed, Mar 18
Multiple Airlines Logo
1:20 am - 9:10 am
POS
-
ORD
32h 50m
3 stops
Multiple Airlines Logo
6:01 pm - 12:20 am
ORD
-
POS
29h 19m
3 stops
$605Multiple Airlines
Tue, Mar 10 - Wed, Mar 18
United Airlines Logo
12:30 am - 12:37 pm
POS
-
ORD
13h 07m
1 stop
United Airlines Logo
7:30 am - 11:23 pm
ORD
-
POS
14h 53m
1 stop
$636United Airlines
Tue, May 5 - Sun, May 10
American Airlines Logo
3:47 pm - 8:47 am
POS
-
ORD
18h 00m
2 stops
American Airlines Logo
5:00 am - 2:32 pm
ORD
-
POS
8h 32m
1 stop
$663American Airlines
Wed, May 6 - Sun, May 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
Mar 10
POS1:20 amPort of Spain Piarco Intl
12h 41m
1 stop
ORD1:01 pmChicago O'Hare Intl
Mar 18
ORD8:40 pmChicago O'Hare Intl
26h 40m
1 stop
POS12:20 amPort of Spain Piarco Intl
$478
Air Canada
Mar 8
POS1:20 amPort of Spain Piarco Intl
19h 50m
2 stops
ORD8:10 pmChicago O'Hare Intl
Mar 16
ORD6:04 pmChicago O'Hare Intl
29h 16m
2 stops
POS12:20 amPort of Spain Piarco Intl
$535

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
13h 07m
1 stop
ORD12:37 pmChicago O'Hare Intl
May 10
ORD7:30 amChicago O'Hare Intl
14h 53m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$636
United Airlines
Jun 19
POS12:30 amPort of Spain Piarco Intl
9h 55m
1 stop
ORD9:25 amChicago O'Hare Intl
Jun 27
ORD10:42 amChicago O'Hare Intl
11h 41m
1 stop
POS11:23 pmPort of Spain Piarco Intl
$680

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 January 26, 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

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 3/9

9:10 am-9:39 am

1 stop25h 29m

Chicago O'Hare Intl

Mon 3/16

4:51 pm-6:55 pm

1 stop25h 04m

$468

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/10

1:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Wed 3/18

8:40 pm-12:20 am

1 stop26h 40m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 3/9

9:10 am-9:39 am

1 stop25h 29m

Chicago O'Hare Intl

Mon 3/16

6:16 pm-6:55 pm

2 stops47h 39m

$489

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/8

1:20 am-8:10 pm

2 stops19h 50m

Chicago O'Hare Intl

Mon 3/16

6:04 pm-12:20 am

2 stops29h 16m

$535

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

2:22 pm-1:15 am

1 stop11h 53m

Chicago O'Hare Intl

Sun 5/10

3:21 pm-1:46 am

1 stop9h 25m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 3/11

9:10 am-4:55 pm

3 stops32h 45m

Chicago O'Hare Intl

Wed 3/18

3:55 pm-12:20 am

1 stop31h 25m

$581

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/10

1:20 am-9:10 am

3 stops32h 50m

Chicago O'Hare Intl

Wed 3/18

6:01 pm-12:20 am

2 stops29h 19m

$601

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/10

1:20 am-9:10 am

3 stops32h 50m

Chicago O'Hare Intl

Wed 3/18

6:01 pm-12:20 am

3 stops29h 19m

$605

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 5/5

12:30 am-12:37 pm

1 stop13h 07m

Chicago O'Hare Intl

Sun 5/10

7:30 am-11:23 pm

1 stop14h 53m

$636

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

3:47 pm-8:47 am

2 stops18h 00m

Chicago O'Hare Intl

Sun 5/10

5:00 am-2:32 pm

1 stop8h 32m

$663

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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?

American Airlines, United Airlines and Copa Airlines are the top three most popular airlines that fly to Chicago from Trinidad and Tobago according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 3 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 05m

Direct flights

None
The fastest flight from Trinidad and Tobago to Chicago takes 10h 05m
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

  • 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
United AirlinesPriceFrom $290Free CancellationRating
7.4
9,198 reviews
Search United Airlines flights
Copa AirlinesPriceFrom $299Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.2
11,189 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
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