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$299+ Cheap flights from Trinidad and Tobago to Illinois

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Illinois

Keep the following information in mind while searching for Trinidad and Tobago to Illinois flight deals. Data was last updated April 2, 2025.

Round-trip from

$562
(United Airlines)

One-way from

$299
(Air Canada)
From Trinidad and Tobago to Illinois
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One-way flight from Trinidad and Tobago to Illinois
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Find flight deals from Trinidad and Tobago to Illinois

Cheapest flights from Trinidad and Tobago to Illinois
Explore the most affordable flight options available from Trinidad and Tobago to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 2, 2025.

This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1912:30 amPOS - ORD
1 stop19h 45mUnited Airlines
Tue 6/38:10 pmORD - POS
1 stop26h 13mUnited Airlines
Deal found 4/1$562
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/203:05 pmPOS - ORD
1 stop18h 55mAmerican Airlines
Tue 6/35:00 amORD - POS
1 stop8h 05mAmerican Airlines
Deal found 4/1$563
This Priceline deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/222:25 amPOS - ORD
2 stops17h 29mAir Canada
Sun 9/288:25 pmORD - POS
1 stop28h 00mAir Canada
Deal found 4/1$802
This FlightHub deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/192:25 amPOS - ORD
2 stops16h 57mMultiple Airlines
Tue 6/39:14 pmORD - POS
2 stops22h 26mMultiple Airlines
Deal found 4/1$966

Cheapflights Fare Finder

Customize your flight search to find flights from Trinidad and Tobago to Illinois 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, Cheapflights users made 2,558,603 searches. Data last updated April 2, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Illinois that are best for you.

Fly from

Trinidad and Tobago

Fly to

Illinois

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/19

12:30 am-7:15 pm

1 stop19h 45m

Chicago O'Hare Intl

Tue 6/3

8:10 pm-11:23 pm

1 stop26h 13m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 5/20

3:05 pm-9:00 am

1 stop18h 55m

Chicago O'Hare Intl

Tue 6/3

5:00 am-2:05 pm

1 stop8h 05m

$563

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/22

2:25 am-6:54 pm

2 stops17h 29m

Chicago O'Hare Intl

Sun 9/28

8:25 pm-1:25 am

1 stop28h 00m

$802

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/19

2:25 am-6:22 pm

2 stops16h 57m

Chicago O'Hare Intl

Tue 6/3

9:14 pm-8:40 pm

2 stops22h 26m

$966

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/30

2:25 am-8:12 pm

2 stops18h 47m

$299

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 5/29

12:30 am-8:01 am

1 stop32h 31m

$308

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/30

3:05 pm-7:39 am

2 stops17h 34m

$318

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/6

5:53 pm-8:29 am

2 stops39h 36m

$354

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/31

12:44 pm-9:54 pm

1 stop10h 10m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Best time to book a flight from Trinidad and Tobago to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Trinidad and Tobago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Trinidad and Tobago to Illinois

What is the cheapest month to book a flight from Trinidad and Tobago to Illinois?

Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $245). Flying from Trinidad and Tobago to Illinois in March is currently the most expensive (average of $323). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from TT to IL?

Find hourly flight availability from Trinidad and Tobago to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 2, 2025.

When flying from Trinidad and Tobago to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Illinois by month

Plan your trip to Illinois by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

Plan your trip to Illinois by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Illinois, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated April 2, 2025.
United Airlines
7.4
Good
8,615 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.0

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
United Airlines
7.4
Good
8,615 reviews
United Airlines
7.4
Good
8,615 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.0

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
JetBlue
7.3
Good
2,924 reviews
United Airlines
7.4
Good
8,615 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.0

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,615 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.0

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!
Air Canada
7.0
Good
9,022 reviews
United Airlines
7.4
Good
8,615 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Entertainment

7.0

Crew

8.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Illinois. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Trinidad and Tobago to Illinois one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $299. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Trinidad and Tobago to Illinois for a low price.

  • Can I find deals for flights from Trinidad and Tobago to Illinois that include hotel bookings?

    Yes. In addition to deals on Trinidad and Tobago to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Trinidad and Tobago to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad and Tobago to Illinois.

  • Can I find deals for business class flights from Trinidad and Tobago to Illinois?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to Illinois by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Trinidad and Tobago to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $245). Flying from Trinidad and Tobago to Illinois in March is currently the most expensive (average of $323). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Trinidad and Tobago to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Trinidad and Tobago to Illinois

Discover the top 2 airlines that operate flights from Trinidad and Tobago to Illinois. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$493Average$603FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$663FlexibilityNo cancel feeOn-time71%

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