$400 Cheap Flights from Chicago (ORD) to Tobago (TAB)

View $400 flight on Sat, Jan 17, 2026Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Tobago (TAB-A.N.R. Robinson Intl.)

Cheap Flights from Chicago to Tobago (ORD-TAB)

Prices were available within the past 7 days and start at $400 for one-way flights and $1,213 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, Jan 3 - Sat, Jan 17
ORD
Chicago
TAB
Tobago
$1,213 Roundtrip, found 2 days ago
$1,213
Roundtrip
found 2 days ago
Select United flight, departing Sat, Jan 3 from Chicago to Tobago, returning Sat, Jan 17, priced at $1,213 found 2 days ago
United
Wed, Oct 15 - Fri, Oct 17
ORD
Chicago
TAB
Tobago
$1,347 Roundtrip, found 3 days ago
$1,347
Roundtrip
found 3 days ago
Select United flight, departing Wed, Oct 15 from Chicago to Tobago, returning Fri, Oct 17, priced at $1,347 found 3 days ago
United
Wed, Oct 15 - Thu, Oct 23
ORD
Chicago
TAB
Tobago
$1,386 Roundtrip, found 3 days ago
$1,386
Roundtrip
found 3 days ago
Select United flight, departing Wed, Oct 15 from Chicago to Tobago, returning Thu, Oct 23, priced at $1,386 found 3 days ago
United
Mon, Oct 13 - Sun, Oct 19
ORD
Chicago
TAB
Tobago
$1,533 Roundtrip, found 3 days ago
$1,533
Roundtrip
found 3 days ago
Select United flight, departing Mon, Oct 13 from Chicago to Tobago, returning Sun, Oct 19, priced at $1,533 found 3 days ago
United
Sat, Jan 31 - Sat, Feb 7
ORD
Chicago
TAB
Tobago
$1,546 Roundtrip, found 2 days ago
$1,546
Roundtrip
found 2 days ago
Select United flight, departing Sat, Jan 31 from Chicago to Tobago, returning Sat, Feb 7, priced at $1,546 found 2 days ago
United
Sun, Oct 19 - Tue, Oct 21
ORD
Chicago
TAB
Tobago
$1,548 Roundtrip, found 1 day ago
$1,548
Roundtrip
found 1 day ago
Select United flight, departing Sun, Oct 19 from Chicago to Tobago, returning Tue, Oct 21, priced at $1,548 found 1 day ago
United
Mon, Oct 13 - Sat, Oct 18
ORD
Chicago
TAB
Tobago
$1,551 Roundtrip, found 3 days ago
$1,551
Roundtrip
found 3 days ago
Select United flight, departing Mon, Oct 13 from Chicago to Tobago, returning Sat, Oct 18, priced at $1,551 found 3 days ago
United
Fri, Oct 10 - Sun, Oct 19
ORD
Chicago
TAB
Tobago
$1,565 Roundtrip, found 3 days ago
$1,565
Roundtrip
found 3 days ago
Select United flight, departing Fri, Oct 10 from Chicago to Tobago, returning Sun, Oct 19, priced at $1,565 found 3 days ago
United
Fri, Oct 10 - Sat, Oct 18
ORD
Chicago
TAB
Tobago
$1,584 Roundtrip, found 3 days ago
$1,584
Roundtrip
found 3 days ago
Select United flight, departing Fri, Oct 10 from Chicago to Tobago, returning Sat, Oct 18, priced at $1,584 found 3 days ago
United
Sat, Nov 29 - Sat, Dec 20
ORD
Chicago
TAB
Tobago
$1,588 Roundtrip, found 3 days ago
$1,588
Roundtrip
found 3 days ago
Select United flight, departing Sat, Nov 29 from Chicago to Tobago, returning Sat, Dec 20, priced at $1,588 found 3 days ago
Iberia
Wed, Feb 25 - Tue, Mar 10
ORD
Chicago
TAB
Tobago
$1,842 Roundtrip, found 6 days ago
$1,842
Roundtrip
found 6 days ago
Select Iberia flight, departing Wed, Feb 25 from Chicago to Tobago, returning Tue, Mar 10, priced at $1,842 found 6 days ago

Alternative airports near Crown Point

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to A.N.R. Robinson Intl. TAB. Cheapest option available. Flights from $2,060
TAB
A.N.R. Robinson Intl.
Cheapest
Flights from $2,060

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB) cost?
Lock in a cheap one-way flight from $400 or cheap return flight from $1,213 from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB)?
Traveling in January is a great way to save, as it's the cheapest month for flights between ORD and TAB. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB)?
Use the filters on Expedia to compare different airlines and find the most affordable carrier that'll fly you from ORD to TAB. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB)?
There are no daily nonstop flights departing from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds before you know it.
What day of the week has the most flights from ORD to TAB?
Typically you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB) route, aim to fly before 3 PM. Flights after this time have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB) last-minute?
Last-minute bookings from ORD to TAB are typically more expensive. For the best prices, start searching for flights ahead of time. That being said, if you can play around with your travel dates, you may find a cheap ticket just before your departure.
Is it cheaper to book an ORD to TAB flight and hotel package?
You'll typically save money by securing an ORD to TAB flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After choosing your preferred accommodations and flights, you can add extras like car rentals, tours and activities.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to A.N.R. Robinson Intl. Airport (TAB)?
In most cases, you can cancel or modify your ORD to TAB flight. However, additional charges may apply, especially if your booking was made more than 24 hours ago. Check your itinerary for the airline's fees and rules on flight changes, or if you'd like further information, head to our Customer Service portal.

Travel information

Travel information

Origin airport
O'Hare Intl.
Destination airport
A.N.R. Robinson Intl.
Roundtrip price
$1,212
Distance
2683 mi

Book with confidence

Book with confidence

Chicago to Tobago Flights

The cheapest times to fly from Chicago to Tobago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Tobago are during the month of January. You can find some of the cheapest flights from Chicago to Tobago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Tobago

Sunday is one of the best days to book for cheap flights from Chicago to Tobago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Tobago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Tobago in 2025. You can also book with separate airlines for your outbound and return journeys, from $400 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Tobago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Tobago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Tobago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.