Cheap Flights from Chicago to Tobago from $528 Roundtrip

Flight deals from Chicago to Tobago

Looking for cheap flights from Chicago to Tobago, or a last-minute trip? Find the lowest prices on one-way and round-trip flights right here.

Crown Point.$528 per passenger.Departing Wed, Mar 11, returning Wed, Mar 18.Round-trip flight with Spirit Airlines and Caribbean Airlines.Outbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Wed, Mar 11, arriving in A. N. R. Robinson International.Inbound indirect flight with Caribbean Airlines, departing from A. N. R. Robinson International on Wed, Mar 18, arriving in Chicago O'Hare International.Price includes taxes and charges.From $528, select.

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Flying from Chicago to Tobago

Arm yourself with these facts on the fly.

Cheapest flight found	$528
Cheapest month to fly	March
Cheapest airport to fly from	Chicago O'Hare International

How to find cheap flights from Chicago to Tobago

We've compared the best online travel agents and flight providers on the Internet to find the cheapest plane tickets from Chicago to Tobago. Other savvy travelers recently found round-trip flights from $528 and one-way tickets from $219. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into A. N. R. Robinson International

At the moment, the lowest-priced flight tickets to Tobago are from Chicago O'Hare International Airport to A. N. R. Robinson International Airport.

Fly in March

We crunched the flight calendar and found the cheapest time to fly from Chicago to Tobago is currently March.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Tobago.

Watch as flight prices go up and down

With Price Alerts, we'll let you know when flight prices from Chicago to Tobago go up or down so you can book when the time is just right.

Relax – these are fee-free plane tickets

With us, there are no added fees – the Tobago to Tobago flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Tobago flight price?

We looked at all of the upcoming round-trip flights from Chicago to Tobago we could find over the next 12 months. It looks like $528 is the best price. This is good, compared to the average Tobago ticket price of $528.

What is the cheapest month to fly from Chicago to Tobago?

The cheapest month to fly from Chicago to Tobago is currently March.

On which upcoming date is it cheapest to fly from Chicago to Tobago?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Tobago on Wednesday, March 11, 2026.

Are there any direct flights from Chicago to Tobago?

Currently, there aren't any direct flights from Chicago to Tobago, but you can still fly with a stopover.

If I'm flying from Chicago, where in Tobago is cheapest to fly to?

If you're flying from Chicago, the cheapest city in Tobago to fly into is Crown Point. The cheapest airport serving Crown Point at the moment is A. N. R. Robinson International.