ORD - POS

$209 Find Cheap Flights from Chicago to Port of Spain - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 8/29. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$471
Typical prices: $581-$706
Multiple Airlines
Mon 9/14Mon 9/21
ORD - POS • 2 stops
Cheapest one-way
$209
JetBlue
Sat 8/29
ORD - POS • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Port of Spain. You'll need at least 1 connection.
Insights
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Top layover airports
Cheapest • Avg $546 (round-trip)
Shortest trip • 9h 02m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Port of Spain!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Port of Spain that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
1:01 pm - 6:55 pm
ORD
-
POS
28h 54m
2 stops
Multiple Airlines Logo
10:10 am - 3:20 pm
POS
-
ORD
30h 10m
1 stop
$471Multiple Airlines
Mon, Sep 14 - Mon, Sep 21
Multiple Airlines Logo
1:01 pm - 6:55 pm
ORD
-
POS
28h 54m
2 stops
Multiple Airlines Logo
10:10 am - 3:20 pm
POS
-
ORD
30h 10m
1 stop
$472Multiple Airlines
Sat, Sep 12 - Fri, Sep 18
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:20 am - 1:23 pm
POS
-
ORD
13h 03m
1 stop
$513Air Canada
Sat, Sep 12 - Fri, Sep 18
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$517Air Canada
Sun, Sep 13 - Sat, Sep 19
Copa Airlines Logo
8:01 am - 1:17 pm
ORD
-
POS
28h 16m
1 stop
Copa Airlines Logo
3:50 am - 1:59 pm
POS
-
ORD
11h 09m
1 stop
$568Copa Airlines
Wed, Sep 23 - Sat, Sep 26
Copa Airlines Logo
8:01 am - 1:47 am
ORD
-
POS
16h 46m
1 stop
Copa Airlines Logo
2:23 pm - 1:59 pm
POS
-
ORD
24h 36m
1 stop
$568Copa Airlines
Sun, Aug 23 - Thu, Aug 27
American Airlines Logo
9:55 am - 11:18 pm
ORD
-
POS
12h 23m
1 stop
American Airlines Logo
7:00 am - 12:35 am
POS
-
ORD
18h 35m
1 stop
$580American Airlines
Sat, Aug 22 - Mon, Aug 31
American Airlines Logo
5:59 pm - 2:14 pm
ORD
-
POS
19h 15m
1 stop
American Airlines Logo
3:15 pm - 7:34 am
POS
-
ORD
17h 19m
1 stop
$580American Airlines
Mon, Oct 19 - Sat, Nov 7
United Airlines Logo
8:45 am - 11:23 pm
ORD
-
POS
13h 38m
1 stop
United Airlines Logo
1:25 am - 11:17 am
POS
-
ORD
11h 52m
1 stop
$750United Airlines
Sat, Oct 24 - Fri, Nov 13
United Airlines Logo
12:45 pm - 11:23 pm
ORD
-
POS
9h 38m
1 stop
United Airlines Logo
1:25 am - 10:11 am
POS
-
ORD
10h 46m
1 stop
$750United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Port of Spain flights

Get data-powered insights and trends into flights from Chicago to Port of Spain to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Port of Spain?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Port of Spain departing in September.

Flight prices are below average for this route right now.

Flights to Port of Spain from Chicago O'Hare Intl Airport usually cost between $548 and $657 in September.
The lowest price found in the past 5 days was $471 on Multiple Airlines (Sep 14-Sep 21).

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Port of Spain, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Port of Spain is November, where tickets cost $443 (return) on average. On the other hand, the most expensive months are February and April, where the average cost of round-trip tickets is $948 and $794 respectively.

Good to know

Low season

January

Cheapest flight

$209
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 37% increase in price.
Flight from Chicago 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Port of Spain flights

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

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Port of Spain was $209 for a one-way ticket and $471 for a round-trip.

  • Do I need a passport to fly between Chicago and Port of Spain?

    Yes

  • Which airports will I be using when flying from Chicago to Port of Spain?

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Port of Spain, also known as Port of Spain Piarco Intl.

  • Which aircraft models fly most regularly from Chicago to Port of Spain?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Port of Spain?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Port of Spain, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Port of Spain, Copa Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Port of Spain are Copa Airlines and United Airlines. With an average price for the route of $654 and an overall rating of 7.6, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $706 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Port of Spain?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Port of Spain.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Port of Spain?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Port of Spain from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Port of Spain?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Port of Spain with an airline and back to Chicago with another airline. Booking your flights between Chicago and POS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Port of Spain?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Port of Spain from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight from Chicago to Port of Spain

Information on your arrival and departure airports