$274 Find Cheap Flights from Trinidad to Chicago - 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 to Chicago departing on 9/10. 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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Flight Deals

Cheap Flights from Trinidad to Chicago

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

Fri, Sep 18 - Sat, Sep 26
Air Canada Logo
1:20 am - 1:23 pm
POS
-
ORD
13h 03m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$527Air Canada
Fri, Sep 18 - Sat, Sep 26
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$530Air Canada
Wed, Sep 2 - Sun, Sep 6
Multiple Airlines Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Multiple Airlines Logo
6:00 am - 6:35 pm
ORD
-
POS
11h 35m
1 stop
$568Multiple Airlines
Wed, Aug 19 - Tue, Aug 25
Multiple Airlines Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Multiple Airlines Logo
6:00 am - 6:35 pm
ORD
-
POS
11h 35m
1 stop
$569Multiple Airlines
Wed, Aug 19 - Tue, Aug 25
Multiple Airlines Logo
1:25 am - 8:05 pm
POS
-
ORD
19h 40m
2 stops
Multiple Airlines Logo
6:00 am - 6:35 pm
ORD
-
POS
11h 35m
1 stop
$572Multiple Airlines
Thu, Sep 3 - Sun, Sep 6
JetBlue Logo
8:00 pm - 7:26 pm
POS
-
ORD
24h 26m
2 stops
JetBlue Logo
6:00 am - 6:35 pm
ORD
-
POS
11h 35m
1 stop
$612JetBlue
Fri, Sep 18 - Sat, Sep 26
Air Canada Logo
1:20 am - 1:23 pm
POS
-
ORD
13h 03m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$617Air Canada
Fri, Sep 18 - Sat, Sep 26
Air Canada Logo
1:20 am - 2:52 pm
POS
-
ORD
14h 32m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$621Air Canada
Fri, Sep 18 - Sat, Sep 26
Air Canada Logo
1:20 am - 6:46 pm
POS
-
ORD
18h 26m
2 stops
Air Canada Logo
2:01 pm - 12:15 am
ORD
-
POS
33h 14m
2 stops
$632Air Canada
Thu, Sep 3 - Sun, Sep 6
Multiple Airlines Logo
8:00 pm - 7:26 pm
POS
-
ORD
24h 26m
2 stops
Multiple Airlines Logo
8:40 am - 12:15 am
ORD
-
POS
14h 35m
2 stops
$654Multiple Airlines
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Good to know

Cheapest flight

$274
Flight from Port of Spain to Chicago

FAQs for booking Trinidad to Chicago flights

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

    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 Trinidad to Chicago.

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

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

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

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

    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 Chicago from 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 Chicago

Information on your arrival and departure airports

Chicago (ORD)