$2,639 Cheap Flights from Tobago (TAB) to Chicago (CHI)

View $2,639 flight on Tue, Feb 24, 2026Opens in a new window

Popular airlines from Tobago (TAB-A.N.R. Robinson Intl.) to Chicago

Cheap Flights from Tobago to Chicago (TAB-CHI)

Prices were available within the past 7 days and start at $2,639 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Flights from Tobago (TAB) to Chicago (CHI)
Origin airport
A.N.R. Robinson Intl.
Destination airport
CHI-All Airports
Distance
2715 mi

Tobago to Chicago Flights

The cheapest times to fly from Tobago to Chicago

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 Tobago to Chicago are during the month of . You can find some of the cheapest flights from Tobago to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Tobago to Chicago

Sunday is one of the best days to book for cheap flights from Tobago to Chicago: 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 Tobago to Chicago

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 Tobago to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $2,639 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 Tobago to Chicago 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 Tobago to Chicago 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.

 

Frequently asked questions

How much is a flight from TAB to Chicago, IL (CHI-All Airports)?
Based on fares listed within the last 7 days on Expedia for flights departing within the next year, round-trip flights from TAB to Chicago, IL (CHI-All Airports) start from . Book ASAP to get the best price for your journey. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from A.N.R. Robinson Intl. Airport to Chicago, IL (CHI-All Airports)?
Most flights can be canceled online, but whether you are charged a fee varies between airlines. If you do need to cancel your trip, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from TAB to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for A.N.R. Robinson Intl. Airport (TAB) to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from TAB to Chicago, IL (CHI-All Airports)?
You'll have 2735 mi to cover on the long-haul Crown Point to Illinois route. Wear comfortable clothes and consider taking earplugs and a sleep mask.
Which airlines fly direct from A.N.R. Robinson Intl. Airport to Chicago, IL (CHI-All Airports)?
Unfortunately, there aren't any airlines that directly fly between A.N.R. Robinson Intl. Airport and Chicago, IL (CHI-All Airports). You'll have to book a flight with at least one stop.
Are A.N.R. Robinson Intl. Airport (TAB) to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from TAB to Chicago, IL (CHI-All Airports) can be hit-or-miss. It is possible to find a bargain, but you could also miss out entirely! If you'd rather play it safe and start planning your trip early on, Expedia compares flight deals up to a year in advance. Just remember that not all airlines publish their prices so far in advance. Our advice? Check back often as updates are made frequently.

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*Available to One Key members.