$219 Find Cheap Flights from Chicago to Trinidad - 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 Trinidad departing on 9/17. 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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Book Cheap Chicago to Trinidad Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Trinidad 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 Trinidad

Mon, Sep 28 - Fri, Oct 2
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
Air Canada Logo
1:20 am - 4:58 pm
POS
-
ORD
16h 38m
1 stop
$485Air Canada
Mon, Sep 28 - Fri, Oct 2
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$488Air Canada
Mon, Sep 28 - Fri, Oct 2
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
$492Air Canada
Sat, Aug 22 - Mon, Aug 31
JetBlue Logo
6:00 am - 6:20 pm
ORD
-
POS
11h 20m
1 stop
JetBlue Logo
8:00 pm - 8:43 am
POS
-
ORD
13h 43m
1 stop
$497JetBlue
Tue, Aug 11 - Mon, Aug 17
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$533Air Canada
Tue, Aug 11 - Mon, Aug 17
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
Air Canada Logo
1:25 am - 2:44 pm
POS
-
ORD
14h 19m
2 stops
$536Air Canada
Mon, Jan 4 - Sun, Jan 10
Air Canada Logo
8:50 pm - 1:00 am
ORD
-
POS
26h 10m
1 stop
Air Canada Logo
2:15 am - 7:58 pm
POS
-
ORD
19h 43m
1 stop
$550Air Canada
Wed, Sep 16 - Sun, Sep 20
Air Canada Logo
6:21 pm - 12:15 am
ORD
-
POS
52h 54m
2 stops
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
1 stop
$575Air Canada
Mon, Aug 24 - Fri, Aug 28
JetBlue Logo
11:01 am - 6:35 pm
ORD
-
POS
30h 34m
2 stops
JetBlue Logo
8:00 pm - 8:46 am
POS
-
ORD
13h 46m
1 stop
$578JetBlue
Mon, Jan 4 - Sun, Jan 10
Air Canada Logo
3:45 pm - 1:00 am
ORD
-
POS
31h 15m
2 stops
Air Canada Logo
2:15 am - 7:58 pm
POS
-
ORD
19h 43m
1 stop
$598Air Canada
Booking Insights

KAYAK's insights & trends for Chicago to Trinidad flights

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

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Trinidad?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $488, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Trinidad?

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 Trinidad, 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 Trinidad is November, when tickets cost $443 (return) on average. On the other hand, the most expensive months are February and April, when the average cost of round-trip tickets is $948 and $794 respectively.

Find deals

Good to know

Low season

January

Cheapest flight

$219
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

FAQs - booking Trinidad flights

  • How does KAYAK find such low prices on flights from Chicago to Trinidad?

    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 Trinidad.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Trinidad 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 Trinidad?

    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 from Chicago to Trinidad with an airline and back with another airline.

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

    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 from Chicago to Trinidad 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 to Trinidad

Information on your arrival and departure airports

Chicago (ORD)