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$541+ Cheap flights from Chicago (CHI) to Tobago

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — TAB
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This Mytrip deal was found by Cheapflights users on 2/3. 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.
Sun 3/15:15 am
ORD
-
TAB
2 stops24h 15m
Multiple Airlines
Sun 3/88:50 pm
TAB
-
ORD
3 stops28h 50m
Multiple Airlines
Deal found 2/3$541
This Mytrip deal was found by Cheapflights users on 2/2. 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.
Thu 3/125:05 am
ORD
-
TAB
2 stops24h 05m
Multiple Airlines
Tue 3/1710:20 pm
TAB
-
ORD
2 stops21h 11m
Multiple Airlines
Deal found 2/2$578
This Mytrip deal was found by Cheapflights users on 2/5. 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.
Thu 2/196:51 pm
ORD
-
TAB
3 stops33h 19m
Multiple Airlines
Fri 2/2712:30 am
TAB
-
ORD
3 stops33h 24m
Multiple Airlines
Deal found 2/5$866
This Mytrip deal was found by Cheapflights users on 2/4. 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.
Sun 3/227:17 am
ORD
-
TAB
2 stops21h 53m
Multiple Airlines
Sun 3/2910:20 pm
TAB
-
ORD
3 stops27h 02m
Multiple Airlines
Deal found 2/4$933

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$541
(Mytrip)
Provider with most accurate pricing for Chicago (CHI)-Scarborough ANR Robinson Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Scarborough ANR Robinson Intl flights.
Search Deals
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 February 5, 2026.
Use the filters below to find and compare flights from Chicago to Tobago that are best for you.

Fly from

Chicago

Fly to

Tobago

Route

Depart

Return

Price

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sun 3/1

5:15 am-7:30 am

2 stops24h 15m

Scarborough ANR Robinson Intl

Sun 3/8

8:50 pm-12:40 am

3 stops28h 50m

$541

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Thu 3/12

5:05 am-6:10 am

2 stops24h 05m

Scarborough ANR Robinson Intl

Tue 3/17

10:20 pm-6:31 pm

2 stops21h 11m

$578

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Thu 2/19

6:51 pm-6:10 am

3 stops33h 19m

Scarborough ANR Robinson Intl

Fri 2/27

12:30 am-7:54 am

3 stops33h 24m

$866

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Sun 3/22

7:17 am-6:10 am

2 stops21h 53m

Scarborough ANR Robinson Intl

Sun 3/29

10:20 pm-12:22 am

3 stops27h 02m

$933

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

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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