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$402+ Cheap flights from Trinidad and Tobago to Illinois

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Round-trip from

$402
(Kiwi.com)

Popular in

October

Cheapest in

April
From Trinidad and Tobago to Illinois
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($38 potential savings vs. average RT price).
Search Deals

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 February 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/206:01 pmPOS - ORD
2 stops15h 28mMultiple Airlines
Tue 3/253:09 pmORD - POS
1 stop9h 32mMultiple Airlines
Deal found 2/22$402
This Gotogate deal was found by Cheapflights users on 2/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/193:39 amPOS - ORD
1 stop21h 48mCopa Airlines
Tue 3/253:09 pmORD - POS
1 stop9h 32mCopa Airlines
Deal found 2/22$548
This United Airlines deal was found by Cheapflights users on 2/22. 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 3/1712:30 amPOS - ORD
1 stop10h 39mUnited Airlines
Fri 3/2812:45 pmORD - POS
1 stop9h 38mUnited Airlines
Deal found 2/22$572
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Thu 3/203:15 pmPOS - ORD
1 stop18h 50mAmerican Airlines
Tue 3/256:58 pmORD - POS
1 stop18h 07mAmerican Airlines
Deal found 2/22$574
This Air Canada deal was found by Cheapflights users on 2/22. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/292:25 amPOS - ORD
2 stops17h 28mAir Canada
Mon 8/1111:55 amORD - POS
1 stop12h 30mAir Canada
Deal found 2/22$819

Find flights from Trinidad and Tobago to Illinois within your budget

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 February 23, 2025.

Fly from

Trinidad and Tobago

Fly to

Illinois

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 3/20

6:01 pm-8:29 am

2 stops15h 28m

Chicago O'Hare Intl

Tue 3/25

3:09 pm-1:41 am

1 stop9h 32m

$402

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 3/19

3:39 am-12:27 am

1 stop21h 48m

Chicago O'Hare Intl

Tue 3/25

3:09 pm-1:41 am

1 stop9h 32m

$548

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 3/17

12:30 am-10:09 am

1 stop10h 39m

Chicago O'Hare Intl

Fri 3/28

12:45 pm-11:23 pm

1 stop9h 38m

$572

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 3/20

3:15 pm-9:05 am

1 stop18h 50m

Chicago O'Hare Intl

Tue 3/25

6:58 pm-2:05 pm

1 stop18h 07m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/29

2:25 am-6:53 pm

2 stops17h 28m

Chicago O'Hare Intl

Mon 8/11

11:55 am-1:25 am

1 stop12h 30m

$819

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/9

10:10 am-9:07 am

1 stop23h 57m

$566

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Trinidad and Tobago to Illinois

Get recent, data-driven insights about flights from Trinidad and Tobago to Illinois including ideal travel times, pricing trends, and more.

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 $321). 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 February 23, 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 February 23, 2025.
Copa Airlines
7.6
Good
1,500 reviews

Boarding

7.8

Overall

7.6

Food

6.9

Entertainment

6.9

Comfort

7.4

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Copa Airlines
7.6
Good
1,500 reviews
Copa Airlines
7.6
Good
1,500 reviews

Boarding

7.8

Overall

7.6

Food

6.9

Entertainment

6.9

Comfort

7.4

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

United Airlines
7.4
Good
8,754 reviews
Copa Airlines
7.6
Good
1,500 reviews

Boarding

7.8

Overall

7.6

Food

6.9

Entertainment

6.9

Comfort

7.4

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,500 reviews

Boarding

7.8

Overall

7.6

Food

6.9

Entertainment

6.9

Comfort

7.4

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Air Canada
7.0
Good
8,757 reviews
Copa Airlines
7.6
Good
1,500 reviews

Boarding

7.8

Overall

7.6

Food

6.9

Entertainment

6.9

Comfort

7.4

Crew

8.1

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

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.

  • 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 $321). 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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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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$505Average$627FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$556Average$646FlexibilityNo cancel feeOn-time71%
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