ORD - POS

$273 Find Cheap Flights from Chicago to Port of Spain - Compare and Save

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Everything you should know

Cheapest round-trip
$592
Typical prices: $578-$773
Air Canada
Wed 10/3Wed 10/10
ORD - POS • 1 stop
Cheapest one-way
$273
Typical prices: $258-$470
Air Canada
Mon 10/15
ORD - POS • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago O'Hare Intl Airport and Port of Spain. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
November
Cheapest • 32% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Toronto Pearson Intl (YYZ)
Cheapest • Avg $511 (round-trip)
Newark (EWR)
Shortest trip • 9h 39m (one-way)
Insights
Insights
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Flight Deals

Cheap Flights from Chicago to Port of Spain (ORD-POS)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Port of Spain

Sat, Oct 3 - Sat, Oct 10
Multiple Airlines Logo
8:40 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
26h 35m1 stop Toronto Pearson Intl
Multiple Airlines Logo
9:10 am - 9:21 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
25h 11m2 stops Miami Atlanta Hartsfield-Jackson
$592Multiple Airlines
Mon, Oct 19 - Fri, Oct 23
Air Canada Logo
2:15 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 00m1 stop Toronto Pearson Intl
Air Canada Logo
1:20 am - 7:48 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
19h 28m1 stop Toronto Pearson Intl
$593Air Canada
Sat, Oct 3 - Fri, Oct 9
Air Canada Logo
3:45 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
31h 30m1 stop Toronto Pearson Intl
Air Canada Logo
1:20 am - 2:55 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
14h 35m1 stop Toronto Pearson Intl
$593Air Canada
Tue, Oct 13 - Mon, Oct 19
Air Canada Logo
8:40 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
26h 35m1 stop Toronto Pearson Intl
Air Canada Logo
1:20 am - 1:23 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
13h 03m1 stop Toronto Pearson Intl
$595Air Canada
Mon, Feb 22 - Wed, Mar 3
Multiple Airlines Logo
8:25 am - 8:00 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 35m1 stop Fort Lauderdale
Multiple Airlines Logo
9:10 am - 1:36 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
18h 26m2 stops Miami San Juan Luis Munoz Marin Intl
$617Multiple Airlines
Mon, Oct 19 - Sun, Oct 25
Multiple Airlines Logo
8:04 am - 8:00 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
10h 56m1 stop Fort Lauderdale
Multiple Airlines Logo
9:10 am - 9:21 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
25h 11m2 stops Miami Atlanta Hartsfield-Jackson
$620Multiple Airlines
Mon, Feb 22 - Wed, Mar 3
American Airlines Logo
7:10 pm - 1:30 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 20m1 stop Miami
American Airlines Logo
2:30 pm - 12:38 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
12h 08m1 stop Miami
$650American Airlines
Fri, Feb 19 - Wed, Feb 24
American Airlines Logo
4:33 pm - 1:30 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
18h 57m1 stop Miami
American Airlines Logo
2:30 pm - 12:38 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
12h 08m1 stop Miami
$650American Airlines
Mon, Oct 19 - Sat, Oct 24
United Airlines Logo
8:45 am - 11:23 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
13h 38m1 stop Houston George Bush Intcntl
United Airlines Logo
12:30 am - 11:17 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 47m1 stop Houston George Bush Intcntl
$650United Airlines
Fri, Nov 20 - Wed, Nov 25
United Airlines Logo
9:21 am - 12:18 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
12h 57m1 stop Houston George Bush Intcntl
United Airlines Logo
1:25 am - 11:17 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 52m1 stop Houston George Bush Intcntl
$650United Airlines
Booking Insights

Price, demand and travel trends for Chicago O'Hare Intl Airport to Port of Spain flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago O'Hare Intl Airport to Port of Spain with more confidence.

What's the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Port of Spain?

Friday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Port of Spain, it is 7% cheaper than the average day. Monday is the most expensive day with flight prices 19% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Port of Spain?

•November is the cheapest month to fly from Chicago O'Hare Intl Airport to Port of Spain at $443 round-trip.
•December ($767) and February ($724) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 73% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Chicago O'Hare Intl Airport to Port of Spain flights

Low season

October

Cheapest flight

$273
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Intl Airport to Port of Spain

When to book flights from Chicago to Port of Spain

Are your dates flexible? Find out the best times to travel from Chicago to Port of Spain based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago O'Hare Intl Airport to Port of Spain flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Chicago O'Hare Intl Airport to Port of Spain?

    Flights from Chicago O'Hare Intl Airport to Port of Spain usually depart from Chicago O'Hare Intl (ORD) and arrive at Port of Spain Piarco Intl (POS).

  • What cabin classes can I book on flights from Chicago O'Hare Intl Airport to Port of Spain?

    Only Economy Class is available on flights from Chicago O'Hare Intl Airport to Port of Spain.

  • Which airports do connecting flights from Chicago O'Hare Intl Airport to Port of Spain pass through?

    One-stop flights from Chicago O'Hare Intl Airport to Port of Spain most commonly connect through:

    • Miami (MIA) - 48% of one-stop connections
    • Toronto Pearson Intl (YYZ) - 20% of one-stop connections
    • Houston George Bush Intcntl (IAH) - 18% of one-stop connections
    • Panama City Tocumen Intl (PTY) - 10% of one-stop connections

    Miami (MIA) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago O'Hare Intl Airport to Port of Spain?

    Yes. Being flexible with your travel dates can save you up to 23% on the Chicago O'Hare Intl Airport to Port of Spain route. Friday is the cheapest departure day at $607 round-trip on average, while Monday is the most expensive at $779, a difference of $172. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Chicago O'Hare Intl Airport to Port of Spain?

    A nonstop flight from Chicago O'Hare Intl Airport to Port of Spain takes 0h 00m, covering 2,697 miles.

  • Do I need a passport to fly from Chicago O'Hare Intl Airport to Port of Spain?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Chicago O'Hare Intl Airport to Port of Spain changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $592 to $4,170. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Chicago O'Hare Intl Airport to Port of Spain looking right now?

    One-way fares from Chicago O'Hare Intl Airport to Port of Spain are currently lower than usual. Average one-way flight prices are about $317, which is 16% below the typical average for this route.

  • How much time can I save by choosing a different layover airport from Chicago O'Hare Intl Airport to Port of Spain?

    Flying via Newark (EWR) gives the shortest average 1-stop total travel time at 9h 39m, compared with 9h 41m via Miami (MIA) and 10h 21m via Houston George Bush Intcntl (IAH).

  • What is the time difference between Chicago O'Hare Intl Airport and Port of Spain?

    Port of Spain is 1 hour ahead of Chicago O'Hare Intl Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at Port of Spain Piarco Intl Airport (POS)?

    Port of Spain Piarco Intl Airport (POS) hosts 5 major car rental companies, with daily rates starting from around $20 for economy cars. Top options include:
    • Classique Car Rentals
    • Ace
    • Hertz
    • Alamo
    • Europcar

  • How much should I expect to pay for a Chicago O'Hare Intl Airport to Port of Spain flight?

    Round-trip flights from Chicago O'Hare Intl Airport to Port of Spain range from $578 to $773, with an average of $652 over the past 12 months. Anything below $578 counts as a good deal.

Your guide to booking Chicago O'Hare Intl Airport to Port of Spain flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Friday departure instead of Monday. On this route, Friday flights average $607 - about $172 less than Monday (22% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Chicago O'Hare Intl Airport to Port of Spain trip for November. Fares historically average $443 round-trip in that month - typically $324 less than the most expensive month, which is December (based on the last 12 months).

More options for your flight from Chicago to Port of Spain

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