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Cheap flights from Chicago (CHI) to Trinidad and Tobago from $398

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 6/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — POS
May 12 — May 191
From?
To?
Sun 5/12
Sun 5/19
1 adult, Economy
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How far in advance should I book a flight from Chicago to Trinidad and Tobago?

Travelers have found it’s best to book a flight 59 days in advance to save up to 85% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 59 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Trinidad and Tobago 1-2 weeks in advance for as low as $819, or $865 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to Trinidad and Tobago?

Flights from Chicago to Trinidad and Tobago lean towards being more expensive in November. Prices are generally better when you fly from Chicago to Trinidad and Tobago in January, with the cheapest ticket starting at $446.

When is the cheapest time to fly from Chicago to Trinidad and Tobago (CHI - TT)?

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.

Cheap United Airlines flights from Chicago to Trinidad and Tobago

Explore cheap flight options specifically provided by United Airlines for the route between Chicago and Trinidad and Tobago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Take a look at some of the lowest-priced United Airlines flights heading from Chicago to Trinidad and Tobago. Come back soon if you're not finding the exact deal you're looking for.
Wed 6/58:53 amORD - POS
1 stop13h 30mUnited Airlines
Tue 6/1112:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Deal found 5/6$427
Thu 6/278:45 amORD - POS
1 stop13h 38mUnited Airlines
Sun 7/712:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 5/6$544
Mon 6/249:31 pmORD - POS
1 stop24h 52mUnited Airlines
Sun 8/1112:30 amPOS - ORD
1 stop24h 43mUnited Airlines
Deal found 5/6$610
Thu 6/279:15 pmORD - POS
1 stop25h 08mUnited Airlines
Sat 6/2912:30 amPOS - ORD
1 stop10h 38mUnited Airlines
Deal found 5/6$622
Mon 7/86:00 amORD - POS
1 stop16h 23mUnited Airlines
Wed 7/1012:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 5/7$641
Thu 7/116:00 amORD - POS
1 stop16h 23mUnited Airlines
Sat 7/1312:30 amPOS - ORD
1 stop10h 38mUnited Airlines
Deal found 5/7$662
Wed 7/107:35 pmORD - POS
1 stop26h 48mUnited Airlines
Sat 7/1312:30 amPOS - ORD
1 stop10h 38mUnited Airlines
Deal found 5/7$671
Tue 6/259:31 pmORD - POS
1 stop24h 52mUnited Airlines
Thu 6/2712:30 amPOS - ORD
1 stop24h 38mUnited Airlines
Deal found 5/6$728
Sun 5/2610:35 amORD - POS
1 stop11h 48mUnited Airlines
Sat 8/312:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Deal found 5/6$730

Cheap American Airlines flights from Chicago to Trinidad and Tobago

Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Trinidad and Tobago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Some of the lowest-priced American Airlines flights we've found at this time heading from Chicago to Trinidad and Tobago. Deals frequently update to provide users with more options.
Wed 6/56:54 pmORD - POS
1 stop18h 26mAmerican Airlines
Wed 6/123:20 pmPOS - ORD
1 stop18h 40mAmerican Airlines
Deal found 5/6$450
Mon 7/87:10 pmORD - POS
1 stop18h 04mAmerican Airlines
Tue 10/83:18 pmPOS - ORD
1 stop18h 44mAmerican Airlines
Deal found 5/6$517
Tue 6/46:45 pmORD - POS
1 stop18h 35mAmerican Airlines
Tue 6/117:00 amPOS - ORD
2 stops13h 20mAmerican Airlines
Deal found 5/6$521
Tue 6/46:30 amORD - POS
2 stops14h 04mAmerican Airlines
Tue 6/117:00 amPOS - ORD
2 stops13h 20mAmerican Airlines
Deal found 5/6$600
Mon 7/86:45 amORD - POS
2 stops14h 16mAmerican Airlines
Mon 10/143:18 pmPOS - ORD
1 stop18h 44mAmerican Airlines
Deal found 5/7$601
Mon 7/87:10 pmORD - POS
1 stop18h 04mAmerican Airlines
Thu 7/113:22 pmPOS - ORD
1 stop18h 43mAmerican Airlines
Deal found 5/7$627
Mon 7/88:30 amORD - POS
2 stops28h 44mAmerican Airlines
Mon 10/143:18 pmPOS - ORD
2 stops20h 52mAmerican Airlines
Deal found 5/7$663
Fri 7/59:45 amORD - POS
2 stops27h 29mAmerican Airlines
Fri 7/123:22 pmPOS - ORD
2 stops22h 07mAmerican Airlines
Deal found 5/7$691
Fri 7/57:10 pmORD - POS
1 stop25h 51mAmerican Airlines
Thu 7/113:22 pmPOS - ORD
1 stop18h 43mAmerican Airlines
Deal found 5/7$692

Cheap Chicago to Trinidad and Tobago flights in May & June 2024

Find cheap flight options from Chicago to Trinidad and Tobago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Prices were last updated on May 7, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Trinidad and Tobago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Wed 6/55:05 amORD - POS
2 stops19h 37mMultiple Airlines
Wed 6/122:20 pmPOS - ORD
2 stops19h 44mMultiple Airlines
Deal found 5/6$398
Tue 5/149:15 pmORD - POS
1 stop20h 40mMultiple Airlines
Tue 5/214:05 amPOS - ORD
2 stops38h 35mMultiple Airlines
Deal found 5/5$403
Wed 6/57:40 amORD - POS
3 stops17h 02mMultiple Airlines
Wed 6/122:20 pmPOS - ORD
2 stops19h 44mMultiple Airlines
Deal found 5/6$406
Wed 6/58:53 amORD - POS
1 stop13h 30mUnited Airlines
Tue 6/1112:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Deal found 5/6$427
Wed 6/58:50 pmORD - POS
1 stop21h 05mMultiple Airlines
Wed 6/124:05 amPOS - ORD
2 stops19h 48mMultiple Airlines
Deal found 5/6$440
Wed 6/56:54 pmORD - POS
1 stop18h 26mAmerican Airlines
Wed 6/123:20 pmPOS - ORD
1 stop18h 40mAmerican Airlines
Deal found 5/6$450
Wed 6/57:40 amORD - POS
3 stops17h 02mMultiple Airlines
Wed 6/122:20 pmPOS - ORD
3 stops24h 20mMultiple Airlines
Deal found 5/6$478
Tue 6/47:10 amORD - POS
1 stop15h 13mUnited Airlines
Mon 6/1012:30 amPOS - ORD
1 stop10h 38mUnited Airlines
Deal found 5/6$517
Tue 6/46:45 pmORD - POS
1 stop18h 35mAmerican Airlines
Tue 6/117:00 amPOS - ORD
2 stops13h 20mAmerican Airlines
Deal found 5/6$521

Chicago to Trinidad and Tobago 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Trinidad and Tobago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Trinidad and Tobago in 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Wed 6/55:05 amORD - POS
2 stops19h 37mMultiple Airlines
Wed 6/122:20 pmPOS - ORD
2 stops19h 44mMultiple Airlines
Deal found 5/6$398
Tue 5/149:15 pmORD - POS
1 stop20h 40mMultiple Airlines
Tue 5/214:05 amPOS - ORD
2 stops38h 35mMultiple Airlines
Deal found 5/5$403
Wed 6/57:40 amORD - POS
3 stops17h 02mMultiple Airlines
Wed 6/122:20 pmPOS - ORD
2 stops19h 44mMultiple Airlines
Deal found 5/6$406
Wed 10/28:20 amORD - POS
2 stops11h 59mAmerican Airlines
Tue 10/87:58 amPOS - ORD
1 stop9h 08mAmerican Airlines
Deal found 5/5$418
Wed 6/58:53 amORD - POS
1 stop13h 30mUnited Airlines
Tue 6/1112:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Deal found 5/6$427
Tue 10/16:40 amORD - POS
2 stops13h 39mAmerican Airlines
Tue 10/87:58 amPOS - ORD
1 stop16h 36mAmerican Airlines
Deal found 5/5$432
Sat 9/288:20 amORD - POS
2 stops11h 59mAmerican Airlines
Tue 10/87:58 amPOS - ORD
1 stop9h 08mAmerican Airlines
Deal found 5/5$434
Wed 6/58:50 pmORD - POS
1 stop21h 05mMultiple Airlines
Wed 6/124:05 amPOS - ORD
2 stops19h 48mMultiple Airlines
Deal found 5/6$440
Thu 10/311:50 amORD - POS
1 stop8h 29mAmerican Airlines
Tue 10/87:58 amPOS - ORD
1 stop9h 08mAmerican Airlines
Deal found 5/5$441

Chicago to Trinidad and Tobago flights leaving soon

Find last-minute flight options from Chicago to Trinidad and Tobago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Check out these flights departing soon from Chicago to Trinidad and Tobago. Tip: verify your flight details before completing your reservation.
Tue 5/149:15 pmORD - POS
1 stop20h 40mMultiple Airlines
Tue 5/214:05 amPOS - ORD
2 stops38h 35mMultiple Airlines
Deal found 5/5$403
Tue 5/1410:10 amORD - POS
1 stop10h 24mAmerican Airlines
Tue 5/217:00 amPOS - ORD
1 stop13h 39mAmerican Airlines
Deal found 5/5$717
Tue 5/146:30 amORD - POS
2 stops14h 04mAmerican Airlines
Tue 5/217:00 amPOS - ORD
2 stops15h 29mAmerican Airlines
Deal found 5/5$719
Tue 5/148:30 pmORD - POS
1 stop25h 53mUnited Airlines
Mon 5/2012:30 amPOS - ORD
1 stop24h 42mUnited Airlines
Deal found 5/5$798

One-way flights to Trinidad and Tobago from Chicago

Search for one-way flight options from Chicago to Trinidad and Tobago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 7, 2024.
Some of the best available deals we've found on one-way flights from Chicago to Trinidad and Tobago. Users in need of a round-trip flight from Chicago to Trinidad and Tobago instead should update the search form at the top of page.
Fri 5/177:30 amORD - POS
2 stops13h 04mAmerican Airlines
Deal found 5/6$656
Fri 5/177:30 amORD - POS
1 stop14h 53mUnited Airlines
Deal found 5/6$657
Fri 5/177:58 pmORD - POS
3 stops28h 27mMultiple Airlines
Deal found 5/6$3,736

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 2,749,864 searches. Data last updated May 7, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$398 - $768

Route

Depart

Return

Price

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/5

2 stops19h 37m

Port of Spain Piarco Intl

Wed 6/12

2 stops19h 44m

$398

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 5/14

1 stop20h 40m

Port of Spain Piarco Intl

Tue 5/21

2 stops38h 35m

$403

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/5

3 stops17h 02m

Port of Spain Piarco Intl

Wed 6/12

2 stops19h 44m

$406

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/5

1 stop13h 30m

Port of Spain Piarco Intl

Tue 6/11

1 stop11h 23m

$427

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/5

1 stop21h 05m

Port of Spain Piarco Intl

Wed 6/12

2 stops19h 48m

$440

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/5

1 stop18h 26m

Port of Spain Piarco Intl

Wed 6/12

1 stop18h 40m

$450

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/8

1 stop18h 04m

Port of Spain Piarco Intl

Tue 10/8

1 stop18h 44m

$517

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 7/11

1 stop9h 32m

Port of Spain Piarco Intl

Mon 7/15

1 stop10h 09m

$555

Chicago O'Hare IntlPort of Spain Piarco Intl

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 7/9

1 stop9h 40m

Port of Spain Piarco Intl

Fri 7/12

1 stop12h 20m

$768

Flights are sorted by cheapest first

Deals found on 5/6

No data available for this route at this time. Please check back soon.

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 May 7, 2024.
Get a feel of what it's like to fly with United Airlines, American Airlines and Copa 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
8.0
Very good
2,781 reviews
Check prices

Boarding

8.1

Comfort

7.7

Food

7.3

Overall

8.0

Crew

8.3

Entertainment

7.2

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

Copa Airlines
8.0
Very good
2,781 reviews
Copa Airlines
8.0
Very good
2,781 reviews
Check prices

Boarding

8.1

Comfort

7.7

Food

7.3

Overall

8.0

Crew

8.3

Entertainment

7.2

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

JetBlue
7.6
Good
4,530 reviews
Copa Airlines
8.0
Very good
2,781 reviews
Check prices

Boarding

8.1

Comfort

7.7

Food

7.3

Overall

8.0

Crew

8.3

Entertainment

7.2

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

United Airlines
7.4
Good
11,073 reviews
Copa Airlines
8.0
Very good
2,781 reviews
Check prices

Boarding

8.1

Comfort

7.7

Food

7.3

Overall

8.0

Crew

8.3

Entertainment

7.2

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

American Airlines
7.3
Good
14,686 reviews
Copa Airlines
8.0
Very good
2,781 reviews
Check prices

Boarding

8.1

Comfort

7.7

Food

7.3

Overall

8.0

Crew

8.3

Entertainment

7.2

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

British Airways
6.8
Okay
6,870 reviews
Copa Airlines
8.0
Very good
2,781 reviews
Check prices

Boarding

8.1

Comfort

7.7

Food

7.3

Overall

8.0

Crew

8.3

Entertainment

7.2

Reviews

1 / 10

The food is horrible and little, a single meal is served on a 7 hour flight. The movies are old and there are very few options in Portuguese. Regarding the crew, they are not helpful or friendly.

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.

  • Can I find flights from Chicago to Trinidad and Tobago for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago to Trinidad and Tobago for under $400. The cheapest flight booked recently is on Multiple Airlines for just $398, but on average you can expect to pay $530.

  • Are there last-minute flights available from Chicago to Trinidad and Tobago for under $500?

    There are currently 4+ open flights from Chicago to Trinidad and Tobago within the next 7 days for less than $500.

  • What are the most popular airlines that fly from Chicago to Trinidad and Tobago?

    Before booking your flight from Chicago to Trinidad and Tobago check out the most popular airlines for this route: American Airlines, Copa Airlines or United Airlines.

  • What does ORD to POS mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport flight would often be abbreviated as a ORD to POS flight. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Trinidad and Tobago that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Trinidad and Tobago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Trinidad and Tobago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Trinidad and Tobago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Trinidad and Tobago that allow pets onboard?

    Many airlines flying from Chicago to Trinidad and Tobago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Trinidad and Tobago?

    Yes, you can often find last-minute deals on Chicago to Trinidad and Tobago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Trinidad and Tobago flight deals updated?

    The Chicago to Trinidad and Tobago flight deals you see on this page were last updated on 5/6.

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.

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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 2,749,864 searches. Data last updated May 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$430Average$532FlexibilityNo cancel feeOn-time70%
Search Copa Airlines flights
American AirlinesCheapest$437Average$735FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$524Average$664FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
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Search flights from Chicago to Trinidad and Tobago by cabin class

Find flights from Chicago to Trinidad and Tobago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

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How does Cheapflights help users find flights from Chicago to Trinidad and Tobago?

When you search for this flight from Chicago to Trinidad and Tobago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Trinidad and Tobago?

Cheapflights simply makes it quick and affordable to book flights from Chicago to Trinidad and Tobago by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Chicago to Trinidad and Tobago with no change fees?

Certainly. Search results for flights to Trinidad and Tobago from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago to Trinidad and Tobago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Trinidad and Tobago from Chicago today and book when prices fit your budget.

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