Cheap flights from Chicago to Trinidad and Tobago from $308
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Trinidad and Tobago departing on 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Find the cheapest flights from Chicago to Trinidad and Tobago
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Copa Airlines flights from Chicago to Trinidad and Tobago
Our best Copa Airlines deals on Chicago to Trinidad and Tobago flight tickets
United Airlines flights from Chicago to Trinidad and Tobago
Our best United Airlines deals on Chicago to Trinidad and Tobago flight tickets
momondo Fare Finder
Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 11/7
2:13 pm-1:54 am
1 stop9h 41m
Port of Spain Piarco Intl
Fri 11/13
3:40 am-12:11 am
1 stop22h 31m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 3/27
10:11 pm-2:10 pm
2 stops14h 59m
Port of Spain Piarco Intl
Sat 4/3
3:04 pm-8:16 am
1 stop18h 12m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Fri 3/5
5:00 am-3:10 pm
1 stop8h 10m
Port of Spain Piarco Intl
Sun 3/7
4:04 pm-9:30 am
1 stop19h 26m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 11/7
7:50 pm-3:37 pm
1 stop17h 47m
Port of Spain Piarco Intl
Sat 11/14
4:42 pm-9:00 am
2 stops18h 18m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 3/27
3:13 pm-2:20 am
1 stop10h 07m
Port of Spain Piarco Intl
Fri 4/2
3:39 am-12:44 am
1 stop22h 05m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Thu 4/1
3:13 pm-2:20 am
1 stop10h 07m
Port of Spain Piarco Intl
Sun 4/4
3:39 am-1:34 pm
1 stop10h 55m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Wed 10/28
7:29 am-11:18 pm
1 stop14h 49m
Port of Spain Piarco Intl
Sat 10/31
1:37 am-11:11 am
1 stop10h 34m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Mon 2/15
2:30 pm-1:05 am
1 stop8h 35m
Port of Spain Piarco Intl
Wed 2/17
2:20 am-12:20 pm
1 stop12h 00m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 3/20
8:50 pm-12:01 am
1 stop26h 11m
Port of Spain Piarco Intl
Fri 3/26
1:15 am-1:13 pm
1 stop12h 58m
ChicagoPort of Spain
ORD Chicago O'Hare Intl - POS Port of Spain Piarco Intl
ORDPOS
Chicago O'Hare Intl
Sat 3/20
8:50 pm-12:01 am
1 stop26h 11m
Port of Spain Piarco Intl
Fri 3/26
1:15 am-2:52 pm
2 stops14h 37m
See travel insights to Trinidad and Tobago from
How to get the cheapest flight ticket from Chicago to Trinidad and Tobago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest airline that flies from Chicago to Trinidad and Tobago?
Air Canada is the most popular carrier operating from Chicago to Trinidad and Tobago
What airlines fly to Trinidad and Tobago?
American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Trinidad and Tobago from Chicago according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Trinidad and Tobago. Keep in mind that there are 3 different airlines that fly to Trinidad and Tobago on a routine basis, so you have a few additional options to choose from.
Cheap Chicago to Trinidad and Tobago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Trinidad and Tobago
Frequently asked questions about flying from Chicago to Trinidad and Tobago
When did momondo last update prices for flights from Chicago to Trinidad and Tobago?
Prices for flights from Chicago to Trinidad and Tobago are refreshed on a daily basis.
How many operators does momondo search for flights from Chicago to Trinidad and Tobago?
As of October 2026, there are 3 operators available to choose from for flights from Chicago to Trinidad and Tobago.
How old do you have to be to fly from Chicago to Trinidad and Tobago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Trinidad and Tobago.
What documentation or ID do you need to fly to Trinidad and Tobago?
The required travel and health documents for your Trinidad and Tobago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Trinidad and Tobago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
Best airlines flying from Chicago to Trinidad and Tobago
Compare and see reviews for airlines that fly from Chicago to Trinidad and Tobago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $317 | Free Cancellation | Rating 7.1 11,748 reviews | |||
| PriceFrom $578 | Free Cancellation | Rating 7.4 10,328 reviews | |||
| PriceFrom $623 | Free Cancellation | Rating 7.0 12,147 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Trinidad and Tobago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Trinidad and Tobago from Chicago.
Can I find flights from Chicago to Trinidad and Tobago with flexible booking policies on momondo?
Yes. momondo allows you to filter the results for Chicago to Trinidad and Tobago flights to just show those with flexible booking policies.
How can momondo help me find flights from Chicago to Trinidad and Tobago?
Once all potential Chicago to Trinidad and Tobago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Trinidad and Tobago right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Trinidad and Tobago, momondo offers a useful price alert feature which will track prices for flights to Trinidad and Tobago from Chicago and alert you when they change.