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Cheap flights from Trinidad to Chicago from $252

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 to Chicago departing on 5/8. 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

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Find the cheapest flights from Trinidad to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
8:06 am - 1:40 am
ORD
-
POS
16h 34m
1 stop
$417Copa Airlines
Fri, Apr 17 - Sun, Apr 26
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
9:05 am - 12:20 am
ORD
-
POS
14h 15m
1 stop
$448Air Canada
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
Air Canada Logo
9:05 am - 12:20 am
ORD
-
POS
14h 15m
1 stop
$451Air Canada
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
Air Canada Logo
7:13 am - 12:20 am
ORD
-
POS
16h 07m
2 stops
$455Air Canada
Thu, Apr 16 - Sun, Apr 26
Multiple Airlines Logo
9:10 am - 1:05 pm
POS
-
ORD
28h 55m
1 stop
Multiple Airlines Logo
7:45 pm - 8:00 pm
ORD
-
POS
23h 15m
1 stop
$484Multiple Airlines
Thu, May 7 - Thu, May 14
Multiple Airlines Logo
9:10 am - 9:37 am
POS
-
ORD
25h 27m
1 stop
Multiple Airlines Logo
6:40 am - 6:55 pm
ORD
-
POS
11h 15m
1 stop
$485Multiple Airlines
Sat, May 16 - Sat, May 30
Multiple Airlines Logo
9:10 am - 10:46 am
POS
-
ORD
26h 36m
2 stops
Multiple Airlines Logo
7:45 pm - 8:00 pm
ORD
-
POS
23h 15m
1 stop
$499Multiple Airlines
Thu, May 7 - Thu, May 14
Multiple Airlines Logo
9:10 am - 9:12 pm
POS
-
ORD
13h 02m
2 stops
Multiple Airlines Logo
6:40 am - 6:55 pm
ORD
-
POS
11h 15m
1 stop
$500Multiple Airlines
Sat, May 16 - Sat, May 30
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$505Air Canada
Thu, Apr 16 - Sun, Apr 26
Multiple Airlines Logo
9:10 am - 9:37 am
POS
-
ORD
25h 27m
1 stop
Multiple Airlines Logo
6:40 am - 6:55 pm
ORD
-
POS
11h 15m
1 stop
$514Multiple Airlines
Sat, May 9 - Sat, May 16

JetBlue flights from Trinidad to Chicago

Our best JetBlue deals on Trinidad to Chicago flight tickets
JetBlue
May 16
POS3:00 pmPort of Spain Piarco Intl
18h 59m
2 stops
ORD8:59 amChicago O'Hare Intl
May 30
ORD1:56 pmChicago O'Hare Intl
23h 35m
2 stops
POS2:31 pmPort of Spain Piarco Intl
$572
JetBlue
May 6
POS2:46 pmPort of Spain Piarco Intl
19h 13m
2 stops
ORD8:59 amChicago O'Hare Intl
May 10
ORD6:00 amChicago O'Hare Intl
30h 36m
2 stops
POS1:36 pmPort of Spain Piarco Intl
$658
JetBlue
May 6
POS2:46 pmPort of Spain Piarco Intl
19h 13m
2 stops
ORD8:59 amChicago O'Hare Intl
May 10
ORD6:00 amChicago O'Hare Intl
30h 36m
2 stops
POS1:36 pmPort of Spain Piarco Intl
$671

Air Canada flights from Trinidad to Chicago

Our best Air Canada deals on Trinidad to Chicago flight tickets
Air Canada
Apr 16
POS1:20 amPort of Spain Piarco Intl
12h 45m
1 stop
ORD1:05 pmChicago O'Hare Intl
Apr 26
ORD9:05 amChicago O'Hare Intl
14h 15m
1 stop
POS12:20 amPort of Spain Piarco Intl
$448
Air Canada
Apr 16
POS1:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
Apr 26
ORD9:05 amChicago O'Hare Intl
14h 15m
1 stop
POS12:20 amPort of Spain Piarco Intl
$451
Air Canada
Apr 16
POS1:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
Apr 26
ORD7:13 amChicago O'Hare Intl
16h 07m
2 stops
POS12:20 amPort of Spain Piarco Intl
$455

momondo Fare Finder

 
Customize your flight search to find flights from Trinidad 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 March 28, 2026.
Use the filters below to find and compare flights from Trinidad to Chicago 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 4/17

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

Sun 4/26

8:06 am-1:40 am

1 stop16h 34m

$417

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Sun 4/26

9:05 am-12:20 am

1 stop14h 15m

$448

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-2:55 pm

2 stops14h 35m

Chicago O'Hare Intl

Sun 4/26

9:05 am-12:20 am

1 stop14h 15m

$451

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-2:55 pm

2 stops14h 35m

Chicago O'Hare Intl

Sun 4/26

7:13 am-12:20 am

2 stops16h 07m

$455

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 5/7

9:10 am-1:05 pm

1 stop28h 55m

Chicago O'Hare Intl

Thu 5/14

7:45 pm-8:00 pm

1 stop23h 15m

$484

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/16

9:10 am-9:37 am

1 stop25h 27m

Chicago O'Hare Intl

Sat 5/30

6:40 am-6:55 pm

1 stop11h 15m

$485

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 5/7

9:10 am-10:46 am

2 stops26h 36m

Chicago O'Hare Intl

Thu 5/14

7:45 pm-8:00 pm

1 stop23h 15m

$499
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/16

9:10 am-9:12 pm

2 stops13h 02m

Chicago O'Hare Intl

Sat 5/30

6:40 am-6:55 pm

1 stop11h 15m

$500

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-2:55 pm

2 stops14h 35m

Chicago O'Hare Intl

Sun 4/26

8:40 am-12:20 am

2 stops14h 40m

$505

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/9

9:10 am-9:37 am

1 stop25h 27m

Chicago O'Hare Intl

Sat 5/16

6:40 am-6:55 pm

1 stop11h 15m

$514

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Trinidad 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

Can stopping save me money on Trinidad to Chicago flights?

No. A direct flight is the cheapest option for a flight between Trinidad to Chicago.

Cheap Trinidad to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Trinidad to Chicago

Fastest flight time

11h 53m

Direct flights

None
The fastest flight from Trinidad to Chicago takes 11h 53m
There are no direct flights from Trinidad to Chicago. There are no popular flight routes from Trinidad to Chicago.
Search flight deals

  • When did momondo last update prices for flights from Trinidad to Chicago?

    Prices for flights from Trinidad to Chicago refresh daily.

  • How many operators does momondo search for flights from Trinidad to Chicago?

  • How old do you have to be to fly from Trinidad 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 to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Trinidad to Chicago?

Best airlines flying from Trinidad to Chicago

Compare and see reviews for airlines that fly from Trinidad to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Copa AirlinesPriceFrom $299Free CancellationRating
7.5
1,579 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $322Free CancellationRating
7.1
10,853 reviews
Search Air Canada flights
United AirlinesPriceFrom $559Free CancellationRating
7.4
9,499 reviews
Search United Airlines flights
American AirlinesPriceFrom $562Free CancellationRating
7.1
11,519 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Trinidad.

Can I find flights from Trinidad to Chicago with flexible booking policies on momondo?

All flight searches from Trinidad to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Trinidad 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.

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

If you are not ready to book a flight from Trinidad to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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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