Cheap flights from Trinidad and Tobago to Chicago from $286
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Trinidad and Tobago to Chicago departing on 9/11. 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.
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.Find the cheapest flights from Trinidad and Tobago to Chicago
Recent round-trip flight deals from Trinidad and Tobago to Chicago
Recent one-way flight deals from Trinidad and Tobago to Chicago
Recent last minute flight deals from Trinidad and Tobago to Chicago
American Airlines flights from Trinidad and Tobago to Chicago
Our best American Airlines deals on Trinidad and Tobago to Chicago flight tickets
United Airlines flights from Trinidad and Tobago to Chicago
Our best United Airlines deals on Trinidad and Tobago to Chicago flight tickets
See travel insights to Chicago from
How to get the cheapest flight ticket from Trinidad and Tobago to Chicago
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 day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Tuesday when prices can be found for as low as $597. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Trinidad and Tobago to Chicago for around $1,058.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Trinidad and Tobago to Chicago during this time can be as low as $716. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $830.
Cheap Trinidad and Tobago to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Trinidad and Tobago to Chicago
When did momondo last update prices for flights from Trinidad and Tobago to Chicago?
Prices for flights from Trinidad and Tobago to Chicago refresh daily.
How many operators does momondo search for flights from Trinidad and Tobago to Chicago?
There are 2 operators available for flights from Trinidad and Tobago to Chicago as of April 2025.
How old do you have to be to fly from Trinidad and Tobago to Chicago?
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 Trinidad and Tobago to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
Best airlines flying from Trinidad and Tobago to Chicago
Compare and see reviews for airlines that fly from Trinidad and Tobago to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $493 | Free Cancellation | Rating 7.4 8,656 reviews | |||
| PriceFrom $561 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Trinidad and Tobago to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Trinidad and Tobago to Chicago for you.
Can I find flights from Trinidad and Tobago to Chicago with flexible booking policies on momondo?
All flight searches from Trinidad and Tobago to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Trinidad and Tobago to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Trinidad and Tobago.
I’m not ready to book a flight from Trinidad and Tobago to Chicago right now. Can momondo alert me if prices change?
Yes. momondo can track prices for Trinidad and Tobago to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.