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Cheap flights from Trinidad and Tobago to Chicago (CHI) from $285

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 6/26. 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.
POS — CHI
May 24 — May 311
From?
To?
Fri 5/24
Fri 5/31
1 adult, Economy
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When is the cheapest time to fly from Trinidad and Tobago to Chicago (TT - CHI)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Trinidad and Tobago to Chicago as you normally would.

Cheap United Airlines flights from Trinidad and Tobago to Chicago

Explore cheap flight options specifically provided by United Airlines for the route between Trinidad and Tobago and Chicago. 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 2,634,509 searches. Data last updated May 19, 2024.
Peruse some of the lowest-priced United Airlines flights we've found from Trinidad and Tobago to Chicago. Come back soon if you're not finding the exact deal you're looking for.
Mon 9/2312:30 amPOS - ORD
1 stop20h 22mUnited Airlines
Sun 9/296:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 5/18$464
Tue 6/1812:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Tue 6/258:45 pmORD - POS
1 stop25h 38mUnited Airlines
Deal found 5/18$472
Thu 10/2412:30 amPOS - ORD
1 stop21h 55mUnited Airlines
Tue 10/299:25 pmORD - POS
1 stop24h 58mUnited Airlines
Deal found 5/18$480
Tue 8/1312:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Wed 8/216:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 5/18$504
Mon 8/1212:30 amPOS - ORD
1 stop23h 28mUnited Airlines
Wed 8/216:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 5/18$573
Tue 8/1312:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Tue 8/277:20 amORD - POS
1 stop15h 03mUnited Airlines
Deal found 5/18$601
Tue 8/612:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Wed 8/147:25 amORD - POS
1 stop14h 58mUnited Airlines
Deal found 5/18$605
Tue 8/612:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Tue 8/206:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 5/18$626
Wed 7/3112:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Wed 8/147:25 amORD - POS
1 stop14h 58mUnited Airlines
Deal found 5/18$637

Cheap American Airlines flights from Trinidad and Tobago to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Trinidad and Tobago and Chicago. 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 2,634,509 searches. Data last updated May 19, 2024.
Have a look at some of the cheapest available American Airlines flights departing from Trinidad and Tobago and landing in Chicago. Check back soon if you're not seeing flights that suit your needs.
Tue 9/247:58 amPOS - ORD
2 stops10h 23mAmerican Airlines
Sun 9/298:20 pmORD - POS
1 stop16h 41mAmerican Airlines
Deal found 5/18$467
Tue 9/247:58 amPOS - ORD
2 stops14h 36mAmerican Airlines
Sun 9/296:40 amORD - POS
2 stops13h 39mAmerican Airlines
Deal found 5/18$569
Tue 8/67:05 amPOS - ORD
1 stop14h 48mAmerican Airlines
Tue 8/136:47 amORD - POS
1 stop14h 38mAmerican Airlines
Deal found 5/18$614
Tue 8/67:05 amPOS - ORD
2 stops15h 19mAmerican Airlines
Tue 8/136:47 amORD - POS
1 stop14h 38mAmerican Airlines
Deal found 5/18$617
Tue 8/63:30 pmPOS - ORD
1 stop18h 14mAmerican Airlines
Wed 9/46:40 amORD - POS
2 stops13h 39mAmerican Airlines
Deal found 5/18$618
Fri 10/253:18 pmPOS - ORD
1 stop9h 16mAmerican Airlines
Tue 10/298:21 amORD - POS
2 stops11h 58mAmerican Airlines
Deal found 5/17$633
Tue 8/67:05 amPOS - ORD
1 stop12h 11mAmerican Airlines
Wed 8/1412:15 pmORD - POS
1 stop9h 10mAmerican Airlines
Deal found 5/18$640
Tue 8/67:05 amPOS - ORD
2 stops15h 19mAmerican Airlines
Wed 8/147:25 amORD - POS
2 stops14h 00mAmerican Airlines
Deal found 5/18$641
Tue 8/67:05 amPOS - ORD
2 stops15h 19mAmerican Airlines
Wed 8/146:47 amORD - POS
1 stop14h 38mAmerican Airlines
Deal found 5/18$643

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

Find cheap flight options from Trinidad and Tobago to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,634,509 searches. Prices were last updated on May 19, 2024.
These are some of the most attractive deals on flights from Trinidad and Tobago to Chicago in 2024. For more flight deals, be sure to check back very soon.
Tue 6/1812:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Tue 6/258:45 pmORD - POS
1 stop25h 38mUnited Airlines
Deal found 5/18$472
Wed 6/192:20 pmPOS - ORD
2 stops19h 44mMultiple Airlines
Tue 6/257:36 amORD - POS
1 stop10h 19mMultiple Airlines
Deal found 5/18$559
Wed 6/199:10 amPOS - ORD
1 stop9h 15mMultiple Airlines
Tue 6/257:36 amORD - POS
1 stop10h 19mMultiple Airlines
Deal found 5/18$615
Wed 6/198:40 pmPOS - ORD
3 stops23h 30mMultiple Airlines
Tue 6/257:36 amORD - POS
1 stop10h 19mMultiple Airlines
Deal found 5/18$696
Mon 6/33:14 pmPOS - ORD
1 stop18h 53mAmerican Airlines
Tue 7/97:10 pmORD - POS
1 stop18h 04mAmerican Airlines
Deal found 5/19$706
Fri 6/77:00 amPOS - ORD
2 stops15h 37mAmerican Airlines
Tue 7/97:10 pmORD - POS
1 stop18h 04mAmerican Airlines
Deal found 5/18$735
Mon 6/37:00 amPOS - ORD
2 stops15h 54mAmerican Airlines
Tue 7/97:10 pmORD - POS
1 stop18h 04mAmerican Airlines
Deal found 5/19$737
Sun 6/212:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Tue 7/99:15 pmORD - POS
1 stop25h 08mUnited Airlines
Deal found 5/19$759
Tue 6/1812:10 amPOS - ORD
2 stops19h 56mMultiple Airlines
Tue 6/257:36 amORD - POS
1 stop10h 19mMultiple Airlines
Deal found 5/18$762

Trinidad and Tobago to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Trinidad and Tobago and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 19, 2024.
These are some of the most attractive deals on flights from Trinidad and Tobago to Chicago in 2024. For more flight deals, be sure to check back very soon.
Thu 8/14:41 pmPOS - ORD
2 stops19h 08mFrontier
Wed 8/1411:37 amORD - POS
2 stops25h 25mFrontier
Deal found 5/18$381
Mon 9/2312:30 amPOS - ORD
1 stop20h 22mUnited Airlines
Sun 9/296:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 5/18$464
Tue 9/247:58 amPOS - ORD
2 stops10h 23mAmerican Airlines
Sun 9/298:20 pmORD - POS
1 stop16h 41mAmerican Airlines
Deal found 5/18$467
Tue 6/1812:30 amPOS - ORD
1 stop11h 23mUnited Airlines
Tue 6/258:45 pmORD - POS
1 stop25h 38mUnited Airlines
Deal found 5/18$472
Thu 10/2412:30 amPOS - ORD
1 stop21h 55mUnited Airlines
Tue 10/299:25 pmORD - POS
1 stop24h 58mUnited Airlines
Deal found 5/18$480
Mon 12/231:30 amPOS - ORD
1 stop19h 44mUnited Airlines
Sat 1/49:10 pmORD - POS
1 stop25h 13mUnited Airlines
Deal found 5/18$492
Tue 8/1312:30 amPOS - ORD
1 stop32h 18mUnited Airlines
Wed 8/216:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 5/18$504
Wed 6/192:20 pmPOS - ORD
2 stops19h 44mMultiple Airlines
Tue 6/257:36 amORD - POS
1 stop10h 19mMultiple Airlines
Deal found 5/18$559
Tue 9/247:58 amPOS - ORD
2 stops14h 36mAmerican Airlines
Sun 9/296:40 amORD - POS
2 stops13h 39mAmerican Airlines
Deal found 5/18$569

One-way flights to Chicago from Trinidad and Tobago

Search for one-way flight options from Trinidad and Tobago to Chicago. 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 2,634,509 searches. Data last updated May 19, 2024.
Users in need of a one-way flight from Trinidad and Tobago to Chicago can choose from these deals. Users can also find round-trip Trinidad and Tobago to Chicago flights by using the search form above.
Wed 6/2612:30 amPOS - ORD
1 stop10h 38mUnited Airlines
Deal found 5/18$285
Thu 6/2710:10 amPOS - ORD
1 stop15h 45mMultiple Airlines
Deal found 5/18$365
Thu 6/274:05 amPOS - ORD
3 stops30h 56mMultiple Airlines
Deal found 5/18$402
Thu 6/2710:10 amPOS - ORD
2 stops28h 30mMultiple Airlines
Deal found 5/18$445
Wed 6/2612:30 amPOS - ORD
2 stops15h 20mUnited Airlines
Deal found 5/18$2,496

Find flights from Trinidad and Tobago to Chicago within your budget

Customize your flight search to find flights from Trinidad and Tobago to Chicago 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 2,634,509 searches. Data last updated May 19, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$381 - $625

Route

Depart

Return

Price

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 8/1

2 stops19h 08m

Chicago O'Hare Intl

Wed 8/14

2 stops25h 25m

$381

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/23

1 stop20h 22m

Chicago O'Hare Intl

Sun 9/29

1 stop16h 23m

$464

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/24

2 stops10h 23m

Chicago O'Hare Intl

Sun 9/29

1 stop16h 41m

$467

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 6/18

1 stop11h 23m

Chicago O'Hare Intl

Tue 6/25

1 stop25h 38m

$472

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 10/24

1 stop21h 55m

Chicago O'Hare Intl

Tue 10/29

1 stop24h 58m

$480

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 8/13

1 stop32h 18m

Chicago O'Hare Intl

Wed 8/21

1 stop16h 23m

$504

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 6/19

2 stops19h 44m

Chicago O'Hare Intl

Tue 6/25

1 stop10h 19m

$559

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/24

2 stops14h 36m

Chicago O'Hare Intl

Sun 9/29

2 stops13h 39m

$569

Port of Spain Piarco IntlChicago O'Hare Intl

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 8/7

1 stop10h 51m

Chicago O'Hare Intl

Wed 8/14

1 stop9h 33m

$625

Flights are sorted by cheapest first

Deals found on 5/18

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated May 19, 2024.
Read through reviews of airlines operating flights from Trinidad and Tobago to Chicago, such as United Airlines, American Airlines and Copa Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
8.0
Very good
2,695 reviews
Check prices

Food

7.3

Comfort

7.7

Entertainment

7.2

Overall

8.0

Crew

8.3

Boarding

8.1

Reviews

1 / 10

BYOE (bring your own entertainment). Was not given the seats i had paid for…

Copa Airlines
8.0
Very good
2,695 reviews
Copa Airlines
8.0
Very good
2,695 reviews
Check prices

Food

7.3

Comfort

7.7

Entertainment

7.2

Overall

8.0

Crew

8.3

Boarding

8.1

Reviews

1 / 10

BYOE (bring your own entertainment). Was not given the seats i had paid for…

United Airlines
7.4
Good
10,900 reviews
Copa Airlines
8.0
Very good
2,695 reviews
Check prices

Food

7.3

Comfort

7.7

Entertainment

7.2

Overall

8.0

Crew

8.3

Boarding

8.1

Reviews

1 / 10

BYOE (bring your own entertainment). Was not given the seats i had paid for…

American Airlines
7.3
Good
14,489 reviews
Copa Airlines
8.0
Very good
2,695 reviews
Check prices

Food

7.3

Comfort

7.7

Entertainment

7.2

Overall

8.0

Crew

8.3

Boarding

8.1

Reviews

1 / 10

BYOE (bring your own entertainment). Was not given the seats i had paid for…

Frontier
6.3
Okay
4,055 reviews
Copa Airlines
8.0
Very good
2,695 reviews
Check prices

Food

7.3

Comfort

7.7

Entertainment

7.2

Overall

8.0

Crew

8.3

Boarding

8.1

Reviews

1 / 10

BYOE (bring your own entertainment). Was not given the seats i had paid for…

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Chicago. 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 Trinidad and Tobago to Chicago for under $400 on Cheapflights?

    Yes, there are multiple flights from Trinidad and Tobago to Chicago for under $400. The cheapest flight booked recently is on Frontier for just $381, but on average you can expect to pay $564.

  • What does POS to ORD mean?

    This is defined as Port of Spain Piarco Intl Airport (POS) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

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

    The amount of baggage you can bring on your Trinidad and Tobago to Chicago 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 Trinidad and Tobago to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Trinidad and Tobago to Chicago 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 Trinidad and Tobago to Chicago that include hotel bookings?

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

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

    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 Chicago.

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

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to Chicago 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 Trinidad and Tobago to Chicago that allow pets onboard?

    Many airlines flying from Trinidad and Tobago to Chicago 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 Trinidad and Tobago to Chicago?

    Yes, you can often find last-minute deals on Trinidad and Tobago to Chicago 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 Trinidad and Tobago to Chicago flight deals updated?

    The Trinidad and Tobago to Chicago flight deals you see on this page were last updated on 5/18.

See more FAQs

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Alternative routes for Trinidad and Tobago to Chicago
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 Chicago

Discover the top 2 airlines that operate flights from Trinidad and Tobago to Chicago. 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 2,634,509 searches. Data last updated May 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$512Average$636FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$513Average$719FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
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Search flights from Trinidad and Tobago to Chicago by cabin class

Find flights from Trinidad and Tobago to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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

When you search for this flight from Trinidad and Tobago to Chicago, 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 Trinidad and Tobago to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Trinidad and Tobago to Chicago for you. Better yet — we are completely free to use.

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

Need flexible booking options for your flight to Chicago from Trinidad and Tobago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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