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Cheap flights from Trinidad to Chicago from $383

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 6/12. 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 to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
1:25 am - 6:52 pm
POS
-
ORD
18h 27m
2 stops
Air Canada Logo
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
$573Air Canada
Sun, May 31 - Sat, Jun 6
Air Canada Logo
1:20 am - 6:33 pm
POS
-
ORD
18h 13m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$574Air Canada
Wed, Oct 14 - Tue, Oct 20
Air Canada Logo
1:25 am - 10:18 am
POS
-
ORD
33h 53m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$577Air Canada
Sun, Jun 14 - Sun, Jun 21
Multiple Airlines Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
Multiple Airlines Logo
8:40 pm - 7:40 pm
ORD
-
POS
22h 00m
2 stops
$598Multiple Airlines
Wed, Oct 14 - Tue, Oct 20
Air Canada Logo
1:25 am - 11:20 am
POS
-
ORD
34h 55m
2 stops
Air Canada Logo
6:22 pm - 12:15 am
ORD
-
POS
28h 53m
2 stops
$603Air Canada
Sun, May 31 - Sat, Jun 6
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Air Canada Logo
3:45 pm - 12:15 am
ORD
-
POS
31h 30m
1 stop
$621Air Canada
Sun, May 31 - Tue, Jul 7
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$625Air Canada
Sun, Jun 28 - Mon, Jul 6
Air Canada Logo
1:25 am - 1:21 pm
POS
-
ORD
12h 56m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$642Air Canada
Sun, May 31 - Tue, Jul 7
Air Canada Logo
1:25 am - 6:52 pm
POS
-
ORD
18h 27m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$648Air Canada
Sun, May 31 - Tue, Jul 7
Air Canada Logo
1:25 am - 4:59 pm
POS
-
ORD
16h 34m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$653Air Canada
Sun, May 31 - Tue, Jul 7

American Airlines flights from Trinidad to Chicago

Our best American Airlines deals on Trinidad to Chicago flight tickets
American Airlines
Oct 1
POS3:45 pmPort of Spain Piarco Intl
16h 45m
2 stops
ORD7:30 amChicago O'Hare Intl
Oct 7
ORD7:05 pmChicago O'Hare Intl
17h 55m
1 stop
POS2:00 pmPort of Spain Piarco Intl
$694
American Airlines
Jul 23
POS3:18 pmPort of Spain Piarco Intl
18h 50m
1 stop
ORD9:08 amChicago O'Hare Intl
Jul 27
ORD6:30 amChicago O'Hare Intl
15h 03m
2 stops
POS10:33 pmPort of Spain Piarco Intl
$696
American Airlines
Jun 11
POS7:01 amPort of Spain Piarco Intl
15h 32m
2 stops
ORD9:33 pmChicago O'Hare Intl
Jun 20
ORD8:00 amChicago O'Hare Intl
14h 00m
2 stops
POS11:00 pmPort of Spain Piarco Intl
$719

Copa Airlines flights from Trinidad to Chicago

Our best Copa Airlines deals on Trinidad to Chicago flight tickets
Copa Airlines
Jul 21
POS3:50 amPort of Spain Piarco Intl
11h 07m
1 stop
ORD1:57 pmChicago O'Hare Intl
Jul 25
ORD1:20 amChicago O'Hare Intl
10h 56m
1 stop
POS1:16 pmPort of Spain Piarco Intl
$678
Copa Airlines
Jun 5
POS2:22 pmPort of Spain Piarco Intl
14h 38m
1 stop
ORD4:00 amChicago O'Hare Intl
Jun 10
ORD8:02 amChicago O'Hare Intl
16h 44m
1 stop
POS1:46 amPort of Spain Piarco Intl
$680
Copa Airlines
May 22
POS2:22 pmPort of Spain Piarco Intl
11h 53m
1 stop
ORD1:15 amChicago O'Hare Intl
Jun 30
ORD8:02 amChicago O'Hare Intl
16h 44m
1 stop
POS1:46 amPort of Spain Piarco Intl
$757

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 May 17, 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

Sun 5/31

1:25 am-6:52 pm

2 stops18h 27m

Chicago O'Hare Intl

Sat 6/6

8:20 pm-12:15 am

1 stop26h 55m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/14

1:20 am-6:33 pm

2 stops18h 13m

Chicago O'Hare Intl

Tue 10/20

8:40 pm-12:15 am

1 stop26h 35m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/14

1:25 am-10:18 am

2 stops33h 53m

Chicago O'Hare Intl

Sun 6/21

8:40 pm-12:15 am

1 stop26h 35m

$577

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/14

1:20 am-2:52 pm

2 stops14h 32m

Chicago O'Hare Intl

Tue 10/20

8:40 pm-7:40 pm

2 stops22h 00m

$598

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/31

1:25 am-11:20 am

2 stops34h 55m

Chicago O'Hare Intl

Sat 6/6

6:22 pm-12:15 am

2 stops28h 53m

$603

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/31

1:25 am-2:55 pm

1 stop14h 30m

Chicago O'Hare Intl

Tue 7/7

3:45 pm-12:15 am

1 stop31h 30m

$621
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/28

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Mon 7/6

8:45 am-12:15 am

2 stops14h 30m

$625

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/31

1:25 am-1:21 pm

1 stop12h 56m

Chicago O'Hare Intl

Tue 7/7

8:40 pm-12:15 am

1 stop26h 35m

$642

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/31

1:25 am-6:52 pm

2 stops18h 27m

Chicago O'Hare Intl

Tue 7/7

8:40 pm-12:15 am

1 stop26h 35m

$648

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/31

1:25 am-4:59 pm

1 stop16h 34m

Chicago O'Hare Intl

Tue 7/7

8:40 pm-12:15 am

1 stop26h 35m

$653

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 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 is the cheapest month to fly to Chicago?

The month of April is, on average, the cheapest month to fly to Chicago from Trinidad, with most prices found around $0. If you’re not able to fly to Chicago in April, then June is your next best option. Flight prices from Trinidad to Chicago during June average around $299.

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

14h 07m

Direct flights

None
The fastest flight from Trinidad to Chicago takes 14h 07m
There are no direct flights from Trinidad to Chicago. There are no popular flight routes from Trinidad to Chicago.
Search flight deals

Frequently asked questions about flying from Trinidad to Chicago

  • 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
1,582 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $322Free CancellationRating
7.1
11,050 reviews
Search Air Canada flights
United AirlinesPriceFrom $572Free CancellationRating
7.4
9,730 reviews
Search United Airlines flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,660 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
Munster
Schererville
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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Tue 6/16
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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