POS - ORD

$404 Find Cheap Flights from Port of Spain to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$712
Typical prices: $574-$824
Copa Airlines
Tue 12/25Sat 12/29
POS - ORD • 1 stop
Cheapest one-way
$404
Typical prices: $298-$573
Air Canada
Mon 2/5
POS - ORD • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Port of Spain and Chicago O'Hare Intl Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
April
Cheapest • 46% price drop
September
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Toronto Pearson Intl (YYZ)
Cheapest • Avg $546 (round-trip)
Newark (EWR)
Shortest trip • 10h 16m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago O'Hare Intl Airport!
Flight Deals
Booking Insights
Flight Deals

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

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

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

Fri, Dec 25 - Tue, Dec 29
Copa Airlines Logo
2:22 pm - 12:11 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 49m1 stop Panama City Tocumen Intl
Copa Airlines Logo
12:29 am - 2:01 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
23h 32m1 stop Panama City Tocumen Intl
$712Copa Airlines
Thu, Dec 3 - Fri, Dec 11
Multiple Airlines Logo
10:10 am - 9:40 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
13h 30m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
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
$719Multiple Airlines
Thu, Nov 26 - Fri, Dec 11
Multiple Airlines Logo
10:10 am - 11:34 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
15h 24m1 stop Fort Lauderdale
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
$721Multiple Airlines
Sun, Dec 20 - Sat, Dec 26
United Airlines Logo
1:25 am - 11:15 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 50m1 stop Houston George Bush Intcntl
United Airlines Logo
7:00 am - 12:18 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
15h 18m1 stop Houston George Bush Intcntl
$724United Airlines
Thu, Nov 26 - Fri, Dec 11
Multiple Airlines Logo
10:10 am - 11:18 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
15h 08m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
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
$726Multiple Airlines
Thu, Dec 17 - Fri, Dec 25
United Airlines Logo
1:25 am - 7:49 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
32h 24m1 stop Houston George Bush Intcntl
United Airlines Logo
4:08 pm - 12:18 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
30h 10m1 stop Houston George Bush Intcntl
$731United Airlines
Mon, Nov 30 - Sat, Dec 5
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
United Airlines Logo
10:30 am - 12:18 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
11h 48m1 stop Houston George Bush Intcntl
$749United Airlines
Fri, Feb 5 - Sat, Feb 6
Air Canada Logo
2:15 am - 6:24 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
18h 09m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
8:50 pm - 1:00 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
26h 10m1 stop Toronto Pearson Intl
$764Air Canada
Thu, Dec 3 - Fri, Dec 11
Multiple Airlines Logo
9:10 am - 7:15 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
24h 05m3 stops Miami Baltimore/Washington Atlanta Hartsfield-Jackson
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
$765Multiple Airlines
Thu, Nov 26 - Fri, Dec 11
Multiple Airlines Logo
10:10 am - 12:42 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
16h 32m3 stops Fort Lauderdale Atlanta Hartsfield-Jackson Orlando
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
$784Multiple Airlines
Booking Insights

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

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Port of Spain to Chicago O'Hare Intl Airport typically range from $574 to $824. The lowest price found in the past 5 days was $712, on Copa Airlines.

Find deals

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

Low season

March

Cheapest flight

$404
Beat the crowds with an average 45% drop in travelers.
The most popular month to fly with an average 26% increase in travelers.
One-way flight from Port of Spain to Chicago O'Hare Intl Airport

When to book flights from Port of Spain to Chicago

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

Your Port of Spain to Chicago O'Hare Intl Airport 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 Port of Spain to Chicago O'Hare Intl Airport?

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

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

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

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

    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 Port of Spain to Chicago O'Hare Intl Airport flight?

    Round-trip flights from Port of Spain to Chicago O'Hare Intl Airport range from $574 to $824, with an average of $698 over the past 12 months. Anything below $574 counts as a good deal.

  • Have flight prices from Port of Spain to Chicago O'Hare Intl Airport 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 $719 to $3,550. That means the highest observed fare was about 5x higher than the lowest one.

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

    One-way fares from Port of Spain to Chicago O'Hare Intl Airport are currently higher than usual. Average one-way flight prices are about $504, which is 21% above the typical average for this route.

  • What car rental options are available at Chicago O'Hare Intl Airport (ORD)?

    Chicago O'Hare Intl Airport (ORD) hosts 5 major car rental companies, with daily rates averaging $64 for economy cars. Top options include:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

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

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

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

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

    • Miami (MIA) - 32% of one-stop connections
    • Panama City Tocumen Intl (PTY) - 19% of one-stop connections
    • Toronto Pearson Intl (YYZ) - 19% of one-stop connections
    • Fort Lauderdale (FLL) - 16% of one-stop connections

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

    Yes. Flexible dates can save you up to 16% on flights from Port of Spain to Chicago O'Hare Intl Airport. Wednesday is the cheapest departure day at $692 round-trip on average, while Thursday is the most expensive at $819, a difference of $127.

    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 Port of Spain to Chicago O'Hare Intl Airport?

    Flying via Newark (EWR) gives the shortest average 1-stop total travel time at 10h 16m, compared with 10h 19m via Miami (MIA) and 10h 27m via Panama City Tocumen Intl (PTY).

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

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

  • What popular places can I visit in Chicago O'Hare Intl Airport?

    Some of the most popular sights in Chicago O'Hare Intl Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago O'Hare Intl Airport on KAYAK.

Your guide to booking Port of Spain to Chicago O'Hare Intl Airport 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 Wednesday departure and avoid flying on Thursday. On this route, Wednesday flights average $692, about $127 less than Thursday fares (16% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Port of Spain to Chicago O'Hare Intl Airport trip for April. Fares historically average $375 round-trip in that month - typically $468 less than the most expensive month, which is May (based on the last 12 months).

More options for your flight from Port of Spain to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago