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Cheap flights from Illinois to Trinidad and Tobago from $398

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to Trinidad and Tobago departing on 12/17. 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 Illinois to Trinidad and Tobago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
7:15 am - 1:20 amORD-POS
16h 05m2 stops
Air Canada Logo
2:20 am - 1:01 pmPOS-ORD
12h 41m1 stop
$433Air Canada
Find Deal
Fri, Jan 16 - Sun, Jan 18
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$438Air Canada
Find Deal
Sat, Nov 22 - Thu, Nov 27
Multiple Airlines Logo
5:05 am - 8:00 pmORD-POS
12h 55m2 stops
Multiple Airlines Logo
9:10 am - 7:54 amPOS-ORD
24h 44m1 stop
$506Multiple Airlines
Find Deal
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Multiple Airlines Logo
9:10 am - 1:23 pmPOS-ORD
30h 13m3 stops
$516Multiple Airlines
Find Deal
Sun, Nov 30 - Tue, Dec 2
Copa Airlines Logo
3:22 pm - 1:46 amORD-POS
9h 24m1 stop
Copa Airlines Logo
3:46 am - 1:31 pmPOS-ORD
10h 45m1 stop
$527Copa Airlines
Find Deal
Thu, Mar 12 - Tue, Mar 17
United Airlines Logo
10:36 am - 12:23 amORD-POS
11h 47m1 stop
United Airlines Logo
1:30 am - 7:46 pmPOS-ORD
20h 16m1 stop
$549United Airlines
Find Deal
Sun, Nov 30 - Mon, Dec 1
Copa Airlines Logo
8:34 am - 1:46 amORD-POS
16h 12m1 stop
Copa Airlines Logo
3:46 am - 1:31 pmPOS-ORD
10h 45m1 stop
$550Copa Airlines
Find Deal
Fri, Mar 13 - Tue, Mar 17
American Airlines Logo
7:20 pm - 1:51 pmORD-POS
17h 31m2 stops
American Airlines Logo
3:34 pm - 12:14 amPOS-ORD
9h 40m1 stop
$558American Airlines
Find Deal
Thu, Mar 12 - Wed, Mar 18
American Airlines Logo
8:04 pm - 1:51 pmORD-POS
16h 47m2 stops
American Airlines Logo
3:34 pm - 12:14 amPOS-ORD
9h 40m1 stop
$601American Airlines
Find Deal
Fri, Mar 13 - Wed, Mar 18
United Airlines Logo
12:00 pm - 1:05 amORD-POS
11h 05m1 stop
United Airlines Logo
1:30 am - 2:43 pmPOS-ORD
15h 13m1 stop
$624United Airlines
Find Deal
Sun, Feb 8 - Fri, Feb 13

Air Canada flights from Illinois to Trinidad and Tobago

Our best Air Canada deals on Illinois to Trinidad and Tobago flight tickets
Air Canada
Jan 16
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS1:20 amPort of Spain Piarco Intl
Jan 18
POS2:20 amPort of Spain Piarco Intl
12h 41m
1 stop
ORD1:01 pmChicago O'Hare Intl
$433
Find similar
Air Canada
Nov 22
ORD8:15 pmChicago O'Hare Intl
26h 55m
1 stop
POS1:10 amPort of Spain Piarco Intl
Nov 27
POS2:15 amPort of Spain Piarco Intl
18h 40m
2 stops
ORD6:55 pmChicago O'Hare Intl
$438
Find similar
Air Canada
Mar 28
ORD6:04 pmChicago O'Hare Intl
29h 16m
2 stops
POS12:20 amPort of Spain Piarco Intl
Apr 2
POS1:20 amPort of Spain Piarco Intl
14h 50m
1 stop
ORD3:10 pmChicago O'Hare Intl
$443
Find similar

Copa Airlines flights from Illinois to Trinidad and Tobago

Our best Copa Airlines deals on Illinois to Trinidad and Tobago flight tickets
Copa Airlines
Mar 12
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 17
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$527
Find similar
Copa Airlines
Mar 13
ORD8:34 amChicago O'Hare Intl
16h 12m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 17
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$550
Find similar
Copa Airlines
Mar 15
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 20
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$598
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois to Trinidad and Tobago 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 November 10, 2025.
Use the filters below to find and compare flights from Illinois to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/16

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Sun 1/18

2:20 am-1:01 pm

1 stop12h 41m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-6:55 pm

2 stops18h 40m

$438

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/16

5:05 am-8:00 pm

2 stops12h 55m

Port of Spain Piarco Intl

Mon 1/19

9:10 am-7:54 am

1 stop24h 44m

$506

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 11/30

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Tue 12/2

9:10 am-1:23 pm

3 stops30h 13m

$516

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Tue 3/17

3:46 am-1:31 pm

1 stop10h 45m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 11/30

10:36 am-12:23 am

1 stop11h 47m

Port of Spain Piarco Intl

Mon 12/1

1:30 am-7:46 pm

1 stop20h 16m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

8:34 am-1:46 am

1 stop16h 12m

Port of Spain Piarco Intl

Tue 3/17

3:46 am-1:31 pm

1 stop10h 45m

$550

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

7:20 pm-1:51 pm

2 stops17h 31m

Port of Spain Piarco Intl

Wed 3/18

3:34 pm-12:14 am

1 stop9h 40m

$558

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

8:04 pm-1:51 pm

2 stops16h 47m

Port of Spain Piarco Intl

Wed 3/18

3:34 pm-12:14 am

1 stop9h 40m

$601

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 2/8

12:00 pm-1:05 am

1 stop11h 05m

Port of Spain Piarco Intl

Fri 2/13

1:30 am-2:43 pm

1 stop15h 13m

$624

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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See travel insights to Trinidad and Tobago from

How to get the cheapest flight ticket from Illinois to Trinidad and Tobago

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 day to depart on your flight to Trinidad and Tobago?

On average, the least expensive day to fly to Trinidad and Tobago from Illinois is on a Sunday. momondo users have found tickets for Sunday departures for as low as $569. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Trinidad and Tobago is Monday, with ticket prices averaging around $706.

What is the cheapest time of day to depart on your flight to Trinidad and Tobago?

According to our data, the cheapest time of day to fly to Trinidad and Tobago is in the afternoon. momondo users have found flights departing from Illinois to Trinidad and Tobago in the afternoon for as low as $533. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the evening is when there is more demand to fly to Trinidad and Tobago, so prices are often more expensive at around $905 per ticket.

Cheap Illinois to Trinidad and Tobago flight deals and tips

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

Direct flights

None
There are no direct flights from Illinois to Trinidad and Tobago. There are no popular flight routes from Illinois to Trinidad and Tobago.
Search flight deals

  • When did momondo last update prices for flights from Illinois to Trinidad and Tobago?

    Prices for flights from Illinois to Trinidad and Tobago are updated daily.

  • How many operators does momondo search for flights from Illinois to Trinidad and Tobago?

  • How old do you have to be to fly from Illinois to Trinidad and Tobago?

    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 Illinois to Trinidad and Tobago.

  • What documentation or ID do you need to fly to Trinidad and Tobago?

    The required travel and health documents for your Trinidad and Tobago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Trinidad and Tobago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Illinois to Trinidad and Tobago

Compare and see reviews for airlines that fly from Illinois to Trinidad and Tobago with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,429 reviews
Search Air Canada flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights
United AirlinesPriceFrom $560Free CancellationRating
7.4
9,011 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Illinois to Trinidad and Tobago?

It is quick and easy to find Illinois to Trinidad and Tobago 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 Trinidad and Tobago that suits you.

Can I find flights from Illinois to Trinidad and Tobago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Illinois to Trinidad and Tobago flights to just show those with flexible booking policies.

How can momondo help me find flights from Illinois to Trinidad and Tobago?

Once you have performed a search for Illinois to Trinidad and Tobago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Illinois to Trinidad and Tobago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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