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Trinidad and Tobago

$220+ Cheap flights from Chicago (CHI) to Trinidad and Tobago

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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Nov 13 — Nov 201
1 adult
Wed 11/13
Wed 11/20
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Find flight deals from Chicago to Trinidad and Tobago

Cheapest flights from Chicago to Trinidad and Tobago
Explore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 8, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
Fri 12/66:07 pmORD - POS
2 stops44h 25mMultiple Airlines
Fri 12/139:10 amPOS - ORD
1 stop11h 57mMultiple Airlines
Deal found 11/6$480
This Copa Airlines deal was found by Cheapflights users on 11/6. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/61:54 pmORD - POS
1 stop9h 49mCopa Airlines
Fri 12/132:27 pmPOS - ORD
1 stop10h 54mCopa Airlines
Deal found 11/6$485
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/510:05 amORD - POS
1 stop10h 40mAmerican Airlines
Tue 12/106:00 amPOS - ORD
1 stop15h 45mAmerican Airlines
Deal found 11/7$487
This United deal was found by Cheapflights users on 11/7. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/55:45 amORD - POS
1 stop16h 38mUnited Airlines
Mon 12/91:30 amPOS - ORD
1 stop20h 25mUnited Airlines
Deal found 11/7$577
This Mytrip deal was found by Cheapflights users on 11/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/66:42 pmORD - TAB
3 stops24h 23mMultiple Airlines
Fri 12/139:00 pmTAB - ORD
2 stops24h 07mMultiple Airlines
Deal found 11/8$657
This JetBlue deal was found by Cheapflights users on 11/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/610:14 amORD - POS
1 stop14h 31mJetBlue
Fri 12/1310:05 pmPOS - ORD
1 stop13h 13mJetBlue
Deal found 11/8$842
This CheapOair deal was found by Cheapflights users on 11/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2010:59 amORD - POS
2 stops49h 10mFrontier
Sun 1/53:29 pmPOS - ORD
2 stops48h 05mFrontier
Deal found 11/7$1,191

Find flights from Chicago to Trinidad and Tobago within your budget

Customize your flight search to find flights from Chicago 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, Cheapflights users made 2,563,714 searches. Data last updated November 8, 2024.

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Any airport

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/30

6:30 am-11:14 pm

2 stops14h 44m

$220

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/30

8:50 am-12:23 am

1 stop13h 33m

$617

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/30

8:30 pm-8:35 pm

3 stops22h 05m

$1,114

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/30

11:55 am-1:33 am

3 stops35h 38m

$1,870

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 12/6

6:07 pm-4:32 pm

2 stops44h 25m

Port of Spain Piarco Intl

Fri 12/13

9:10 am-7:07 pm

1 stop11h 57m

$480

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 12/6

1:54 pm-1:43 am

1 stop9h 49m

Port of Spain Piarco Intl

Fri 12/13

2:27 pm-11:21 pm

1 stop10h 54m

$485

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/25

6:58 am-11:14 pm

1 stop14h 16m

Port of Spain Piarco Intl

Tue 2/4

4:35 pm-12:27 am

1 stop9h 52m

$487

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/25

5:45 am-12:23 am

1 stop16h 38m

Port of Spain Piarco Intl

Mon 2/3

1:30 am-2:50 pm

1 stop15h 20m

$577

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 12/20

10:59 am-2:09 pm

2 stops49h 10m

Port of Spain Piarco Intl

Sun 1/5

3:29 pm-1:34 pm

2 stops48h 05m

$1,191

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 12/6

6:42 pm-9:05 pm

3 stops24h 23m

Scarborough ANR Robinson Intl

Fri 12/13

9:00 pm-7:07 pm

2 stops24h 07m

$657

Flights are sorted by cheapest first

Deals found on 11/7

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

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from Chicago 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 Chicago to Trinidad and Tobago

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $435). Flying from Chicago to Trinidad and Tobago in February is currently the most expensive (average of $621). 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 CHI to TT?

Find hourly flight availability from Chicago to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 8, 2024.

When flying from Chicago to Trinidad and Tobago, 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 Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Trinidad and Tobago ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Trinidad and Tobago when rainfall is around 1.2 in.

Temperature in Trinidad and Tobago by month

Plan your trip to Trinidad and Tobago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Trinidad and Tobago, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. 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 Trinidad and Tobago. Reviews last updated November 8, 2024.
Get a feel of what it's like to fly with American Airlines and United Airlines from Chicago to Trinidad and Tobago by reading reviews from past customers. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.8
Good
1,850 reviews

Comfort

7.6

Food

7.1

Entertainment

7.0

Boarding

7.9

Crew

8.2

Overall

7.8

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Copa Airlines
7.8
Good
1,850 reviews
Copa Airlines
7.8
Good
1,850 reviews

Comfort

7.6

Food

7.1

Entertainment

7.0

Boarding

7.9

Crew

8.2

Overall

7.8

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

JetBlue
7.5
Good
3,477 reviews
Copa Airlines
7.8
Good
1,850 reviews

Comfort

7.6

Food

7.1

Entertainment

7.0

Boarding

7.9

Crew

8.2

Overall

7.8

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Turkish Airlines
7.4
Good
3,898 reviews
Copa Airlines
7.8
Good
1,850 reviews

Comfort

7.6

Food

7.1

Entertainment

7.0

Boarding

7.9

Crew

8.2

Overall

7.8

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

United Airlines
7.4
Good
9,209 reviews
Copa Airlines
7.8
Good
1,850 reviews

Comfort

7.6

Food

7.1

Entertainment

7.0

Boarding

7.9

Crew

8.2

Overall

7.8

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.8
Good
1,850 reviews

Comfort

7.6

Food

7.1

Entertainment

7.0

Boarding

7.9

Crew

8.2

Overall

7.8

Reviews

1 / 10

Nice staff. Delayed flight and delayed parking upon arrival. Copapass didn't work so I could watch movies. Spent extra money to buy a comfortable seat but ended up being seated with a little kid so noisy while there were still many empty seats around.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Trinidad and Tobago. 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 Chicago to Trinidad and Tobago one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $220. Users have also found prices from $617 and $1,870 on United Airlines and Turkish Airlines, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Trinidad and Tobago 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 Chicago to Trinidad and Tobago?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $435). Flying from Chicago to Trinidad and Tobago in February is currently the most expensive (average of $621). 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 Chicago to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
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O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
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Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Castries flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Puerto Plata flights
Midway to Oranjestad flights
Midway to Nassau flights
St. Louis to Punta Cana flights
O'Hare Intl to Bridgetown flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
Midway to George Town flights
Midway to Santo Domingo flights
O'Hare Intl to Kingston flights
St. Louis to Montego Bay flights
Midway to Castries flights
O'Hare Intl to St. John's flights
Midway to Simpson Bay flights
O'Hare Intl to Basseterre flights
St. Louis to Oranjestad flights
O'Hare Intl to Gregory Town flights
St. Louis to George Town flights
St. Louis to Simpson Bay flights
O'Hare Intl to Kralendijk flights
St. Louis to Nassau flights
St. Louis to Christiansted flights
Moline to Montego Bay flights
St. Louis to Providenciales flights
O'Hare Intl to Freeport flights
St. Louis to Willemstad flights
Midway to Kingston flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to Georgetown flights
St. Louis to Santo Domingo flights
St. Louis to St. John's flights
O'Hare Intl to Port of Spain flights

Top 3 airlines flying from Chicago to Trinidad and Tobago

Discover the top 3 airlines that operate flights from Chicago to Trinidad and Tobago. 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 2,563,714 searches. Data last updated November 8, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$426Average$694FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$430Average$555FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$478Average$637FlexibilityNo cancel feeOn-time69%
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