Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Chicago to Scarborough from $1,199

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Scarborough departing on 5/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Scarborough

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:20 pm - 9:40 pm
ORD
-
TAB
24h 20m
3 stops
Multiple Airlines Logo
11:45 am - 9:05 am
TAB
-
ORD
22h 20m
2 stops
$1,199Multiple Airlines
Fri, May 22 - Fri, May 29
Multiple Airlines Logo
2:15 pm - 6:10 am
ORD
-
TAB
14h 55m
2 stops
Multiple Airlines Logo
11:45 am - 9:05 am
TAB
-
ORD
22h 20m
2 stops
$1,420Multiple Airlines
Fri, May 22 - Fri, May 29
Multiple Airlines Logo
8:20 pm - 6:10 am
ORD
-
TAB
32h 50m
3 stops
Multiple Airlines Logo
11:00 pm - 7:25 pm
TAB
-
ORD
21h 25m
3 stops
$3,995Multiple Airlines
Fri, May 22 - Fri, May 29

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Scarborough, Eastern 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, momondo users made 832,500 searches. Data last updated March 1, 2026.
Use the filters below to find and compare flights from Chicago to Scarborough, Eastern Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 5/22

8:20 pm-9:40 pm

3 stops24h 20m

Scarborough ANR Robinson Intl

Fri 5/29

11:45 am-9:05 am

2 stops22h 20m

$1,199

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 5/22

2:15 pm-6:10 am

2 stops14h 55m

Scarborough ANR Robinson Intl

Fri 5/29

11:45 am-9:05 am

2 stops22h 20m

$1,420

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Fri 5/22

8:20 pm-6:10 am

3 stops32h 50m

Scarborough ANR Robinson Intl

Fri 5/29

11:00 pm-7:25 pm

3 stops21h 25m

$3,995

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Wed 3/18

7:13 pm-5:10 pm

3 stops44h 57m

$2,990

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Scarborough from

How to get the cheapest flight ticket from Chicago to Scarborough, Eastern Tobago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago to Scarborough ANR Robinson Intl?

British Airways is the most popular carrier operating from Chicago to Scarborough ANR Robinson Intl

What airlines fly to Scarborough, Eastern Tobago?

American Airlines, United Airlines and Air Canada are the top three most popular airlines that fly to Scarborough, Eastern Tobago from Chicago according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Scarborough, Eastern Tobago. Keep in mind that there are 3 different airlines that fly to Scarborough, Eastern Tobago on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago to Scarborough, Eastern Tobago

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Scarborough, Eastern Tobago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Scarborough, Eastern Tobago (CHI to TAB) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Scarborough, Eastern Tobago

Fastest flight time

32h 10m

Direct flights

None
The fastest flight from Chicago to Scarborough, Eastern Tobago takes 32h 10m
There are no direct flights from Chicago to Scarborough, Eastern Tobago. There are no popular flight routes from Chicago to Scarborough, Eastern Tobago.
Search flight deals

  • How far is Chicago to Scarborough ANR Robinson Intl by plane?

    Scarborough ANR Robinson Intl is 2669.0 mi away from Chicago. 32h 10m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago to Scarborough ANR Robinson Intl Airport?

    Prices for flights from Chicago to Scarborough ANR Robinson Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago to Scarborough ANR Robinson Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Scarborough ANR Robinson Intl Airport.

  • What documentation or ID do you need to fly to Scarborough ANR Robinson Intl Airport?

    The travel and health documents required for your trip to Scarborough ANR Robinson Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Scarborough ANR Robinson Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Scarborough?

Book flights to Scarborough if you plan to visit one of these locations
Crown Point

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Scarborough?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Scarborough from Chicago.

Can I find flights from Chicago to Scarborough with flexible booking policies on momondo?

momondo does allow users to show only those flights to Scarborough from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Scarborough?

momondo helps you find the best flight between Chicago and Scarborough by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Scarborough right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Scarborough, momondo offers a useful price alert feature which will track prices for flights to Scarborough from Chicago and alert you when they change.

An easier way to manage your Scarborough, Eastern Tobago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 3/31
Tue 4/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Trinidad and Tobago