ORD - POS

$295 Find Cheap Flights from Chicago to Port of Spain - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$625
Typical prices: $595-$779
Air Canada
Mon 12/3Sun 12/9
ORD - POS • 1 stop
Cheapest one-way
$295
Typical prices: $294-$470
Air Canada
Tue 12/11
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 • 33% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Toronto Pearson Intl (YYZ)
Cheapest • Avg $474 (round-trip)
Miami (MIA)
Shortest trip • 9h 31m (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

Thu, Dec 3 - Wed, Dec 9
Multiple Airlines Logo
10:05 am - 1:00 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
12h 55m1 stop Toronto Pearson Intl
Multiple Airlines Logo
9:10 am - 10:00 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
14h 50m2 stops Miami Atlanta Hartsfield-Jackson
$625Multiple Airlines
Thu, Jan 7 - Fri, Jan 15
Multiple Airlines Logo
1:30 pm - 7:30 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
28h 00m2 stops Atlanta Hartsfield-Jackson Orlando
Multiple Airlines Logo
10:10 am - 4:14 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
32h 04m1 stop Fort Lauderdale
$633Multiple Airlines
Sun, Nov 29 - Sun, Dec 6
Multiple Airlines Logo
8:45 am - 1:00 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
14h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
10:10 am - 7:20 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
23h 10m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$635Multiple Airlines
Sun, Jan 17 - Sat, Jan 23
Copa Airlines Logo
2:13 pm - 1:55 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 42m1 stop Panama City Tocumen Intl
Copa Airlines Logo
3:26 am - 12:07 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
22h 41m1 stop Panama City Tocumen Intl
$648Copa Airlines
Sat, Mar 6 - Sat, Mar 13
American Airlines Logo
5:59 pm - 3:13 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
19h 14m1 stop Miami
American Airlines Logo
4:13 pm - 12:47 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
10h 34m1 stop Miami
$660American Airlines
Thu, Jan 7 - Thu, Jan 14
United Airlines Logo
7:25 am - 12:20 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
14h 55m1 stop Houston George Bush Intcntl
United Airlines Logo
1:25 am - 10:10 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
10h 45m1 stop Houston George Bush Intcntl
$660United Airlines
Thu, Dec 3 - Wed, Dec 9
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 - 12:22 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
12h 57m1 stop Houston George Bush Intcntl
$660United Airlines
Sun, Nov 29 - Sat, Dec 5
United Airlines Logo
7:29 am - 12:18 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
14h 49m1 stop Houston George Bush Intcntl
United Airlines Logo
1:25 am - 10:11 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
10h 46m1 stop Houston George Bush Intcntl
$660United Airlines
Sat, Mar 6 - Sat, Mar 13
American Airlines Logo
8:27 pm - 3:13 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 46m2 stops Charlotte Douglas Miami
American Airlines Logo
4:13 pm - 7:10 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
16h 57m1 stop Miami
$664American Airlines
Thu, Apr 15 - Mon, Apr 19
American Airlines Logo
9:01 pm - 2:32 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 31m2 stops Washington, D.C. Reagan-National Miami
American Airlines Logo
3:47 pm - 7:20 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
16h 33m2 stops Miami Washington, D.C. Reagan-National
$664American 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 with more confidence.

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

Based on deals KAYAK users found in the last 12 months, Friday is the cheapest day of the week to fly from Chicago O'Hare Intl Airport to Port of Spain. It’s 10% cheaper than the average day, while Monday is the most expensive, with prices 18% higher.

Find deals

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

Low season

October

Cheapest flight

$295
Beat the crowds with an average 72% drop in travelers.
The most popular month to fly with an average 64% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

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

    Two cabin classes are available on flights from Chicago O'Hare Intl Airport to Port of Spain:

    • Economy Class
    • First Class

  • 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 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.

  • 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 $595 to $779, with an average of $660 over the past 12 months. Anything below $595 counts as a good deal.

  • 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 $625 to $2,350. That means the highest observed fare was about 4x 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 $358, which is 5% below the typical average for this route.

  • 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 averaging $47 for economy cars. Top options include:

    • Classique Car Rentals
    • Hertz
    • Ace
    • Europcar
    • Alamo

  • 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).

  • 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) - 47% of one-stop connections
    • Houston George Bush Intcntl (IAH) - 19% of one-stop connections
    • Toronto Pearson Intl (YYZ) - 19% of one-stop connections
    • Panama City Tocumen Intl (PTY) - 9% of one-stop connections

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

    Yes. Flexible dates can save you up to 24% on flights from Chicago O'Hare Intl Airport to Port of Spain. Friday is the cheapest departure day at $599 round-trip on average, while Monday is the most expensive at $779, a difference of $180.

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

    Flying via Miami (MIA) gives the shortest average 1-stop total travel time at 9h 31m, compared with 9h 39m via Newark (EWR) and 10h 19m 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 2 hours ahead of Chicago O'Hare Intl Airport (Atlantic Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

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 are flexible, aim for a Friday departure and avoid flying on Monday. On this route, Friday flights average $599, about $180 less than Monday fares (23% 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 $377 less than the most expensive month, which is September (based on the last 12 months).

More options for your flight from Chicago to Port of Spain

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