$297 Find Cheap Flights from Trinidad and Tobago to Chicago - Compare and Save

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Cheap Flights from Trinidad and Tobago to Chicago

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

Recent round-trip flight deals from Trinidad and Tobago to Chicago

Fri, Oct 9 - Fri, Oct 23
Multiple Airlines Logo
10:10 am - 3:30 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
30h 20m1 stop Fort Lauderdale
Multiple Airlines Logo
8:04 am - 8:00 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
10h 56m1 stop Fort Lauderdale
$598Multiple Airlines
Wed, Oct 21 - Tue, Oct 27
Air Canada Logo
1:20 am - 6:46 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
18h 26m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
10:15 am - 12:01 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
12h 46m1 stop Toronto Pearson Intl
$613Air Canada
Wed, Oct 21 - Tue, Oct 27
Air Canada Logo
1:20 am - 7:48 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
19h 28m1 stop Toronto Pearson Intl
Air Canada Logo
8:45 am - 12:01 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
14h 16m1 stop Toronto Pearson Intl
$613Air Canada
Mon, Sep 28 - Fri, Oct 9
Air Canada Logo
1:20 am - 1:23 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
13h 03m1 stop Toronto Pearson Intl
Air Canada Logo
2:15 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 00m1 stop Toronto Pearson Intl
$614Air Canada
Mon, Sep 28 - Fri, Oct 9
Air Canada Logo
1:20 am - 6:46 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
18h 26m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
9:55 am - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
13h 20m1 stop Toronto Pearson Intl
$614Air Canada
Mon, Sep 28 - Fri, Oct 9
Air Canada Logo
1:20 am - 6:46 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
18h 26m2 stops Toronto Pearson Intl Ottawa
Air Canada Logo
8:45 am - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
14h 30m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$640Air Canada
Fri, Oct 9 - Fri, Oct 23
Multiple Airlines Logo
10:10 am - 11:32 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
26h 22m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:04 am - 8:00 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
10h 56m1 stop Fort Lauderdale
$656Multiple Airlines
Fri, Oct 2 - Mon, Oct 5
Copa Airlines Logo
2:23 pm - 12:57 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 34m1 stop Panama City Tocumen Intl
Copa Airlines Logo
3:20 pm - 1:47 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 27m1 stop Panama City Tocumen Intl
$669Copa Airlines
Fri, Oct 2 - Mon, Oct 5
American Airlines Logo
3:06 pm - 9:29 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
19h 23m1 stop Miami
American Airlines Logo
7:29 pm - 2:08 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
17h 39m1 stop Miami
$692American Airlines
Fri, Oct 2 - Mon, Oct 5
American Airlines Logo
3:06 pm - 7:53 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
17h 47m2 stops Miami New York LaGuardia
American Airlines Logo
5:00 am - 2:08 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
8h 08m1 stop Miami
$697American Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

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

How long is the flight to Chicago O'Hare Intl Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously, any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Port of Spain, which takes 11h 39m.

How many direct flights to Chicago O'Hare Intl Airport are there each day?

There are around 4,164 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 50% of flights departing in the morning.

Good to know

Cheapest flight

$297
Flight from Port of Spain to Chicago

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The distance between Chicago O'Hare Intl Airport and downtown Chicago is 16 miles.

  • How does KAYAK find such low prices on flights 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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 29,144 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 17% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airline flying from Trinidad and Tobago to Chicago

 
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 12041 reviews
7.5Boarding
7.9Crew
6.4Food
6.8Entertainment
7.2Comfort
Airline reviews

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

2.0 MediocreLora, Sep 2026
Read more American Airlines reviews

Our flight from Chicago to Des Moines was the problem flight due to a dismissive flight attendant. His conduct was unnecessary and unprofessional.. I will avoid using Americam Airlines again because of the situation. Very disappointing.

Mostly excellent. However, many too many gate changes. Connecting flight at ORD changed gate 6 times.

Mechanical issues and delays. I get it but bad experience. Turned my 3 hour airport experience into a 9 hours

The baggage process at the gate was terrible. Stay was not friendly at all

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

We landed slightly early but then sat in holding area waiting for our gate to clear out for about an hour, so technically we arrived one hour late at the gate at ORD. The airport may be partially responsible here, but regardless of who is responsible, it was a bad experience to be so close yet unable to get off the plane.

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

Missed connection from delays and times changing multiple times and then involuntarily booked on another airline next day

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Gurnee
South Haven
Oak Brook
Tinley Park
Hammond
Saint Joseph
Des Plaines
Elk Grove Village
Hoffman Estates
South Holland
Portage
Oakbrook Terrace
Willowbrook
Lansing
Alsip
Delavan
Northbrook
Lisle
Valparaiso

More options for your flight to Chicago