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Tobago

$793+ Cheap flights from Chicago (CHI) to Tobago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TAB
Aug 10 — Aug 171
Mon 8/10
Mon 8/17
1 adult, Economy
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Cheap flight deals from Chicago to Tobago

Cheapest flights from Chicago to Tobago
Explore the most affordable flight options available from Chicago to Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 11, 2026.

This Mytrip deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:15 pm
ORD
-
TAB
2 stops15h 35m
Multiple Airlines
Sun 8/3012:30 am
TAB
-
ORD
3 stops33h 30m
Multiple Airlines
Deal found 7/10$956
This Flightnetwork deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:50 pm
ORD
-
TAB
2 stops21h 15m
Multiple Airlines
Sat 8/2912:25 pm
TAB
-
ORD
2 stops21h 35m
Multiple Airlines
Deal found 7/8$1,593

Find flight deals from Chicago to Tobago

Keep the following information in mind while searching for Chicago to Tobago flight deals. Data was last updated July 11, 2026.

Round-trip from

$956
(Mytrip)

One-way from

$793
(Flightnetwork)
From Chicago (CHI) to Tobago
Search Deals
One-way flight from Chicago (CHI) to Tobago
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Tobago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 11, 2026.
Use the filters below to find and compare flights from Chicago to Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Mon 8/24

2:15 pm-8:30 am

2 stops17h 15m

Scarborough ANR Robinson Intl

Sun 8/30

12:30 am-9:00 am

3 stops33h 30m

$976
Quickest round-trip

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sat 8/22

8:50 pm-7:05 pm

2 stops21h 15m

Scarborough ANR Robinson Intl

Sat 8/29

12:25 pm-9:00 am

2 stops21h 35m

$1,593

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 8/21

2:50 pm-11:20 am

2 stops43h 30m

Scarborough ANR Robinson Intl

Fri 8/28

1:10 pm-1:22 pm

2 stops25h 12m

$2,855
Cheapest one-way
Quickest one-way

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Mon 8/24

5:35 pm-8:30 am

2 stops13h 55m

$793

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

Sorted by cheapest first

Best time to book a flight from Chicago to Tobago

Have a flexible travel schedule? Discover the best time to fly to Tobago from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Tobago
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Tobago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Chicago to Tobago that include hotel bookings?

    Yes. In addition to deals on Chicago to Tobago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Tobago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Tobago.

  • Can I find deals for business class flights from Chicago to Tobago?

    Yes. Cheapflights offers flight deals from Chicago to Tobago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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