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Chicago to Cayman Brac Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Chicago to Cayman Brac

Departure Arrival Travel dates Round-trip
CHI CYB Wed, Dec 31 - Mon, Jan 5 $736

Chicago and Cayman Brac airports and terminals

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

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Airports in Cayman Brac , KY
map of airports in Cayman Brac
  • 1

    Gerrard-Smith (CYB)

    Distance from City Center: 0.7 miles

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Cheap flights from Chicago to Cayman Brac

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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)


Lowest roundtrip airfare in December from Chicago to Cayman Brac

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 31 Chicago (ORD) Cayman Brac (CYB) Cayman Airways $736
Earn $7.36
Return Mon, Jan 5 Cayman Brac (CYB) Chicago (ORD) Cayman Airways
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Flights to Cayman Brac

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.

Chicago Airport Parking

Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.

Chicago Airport Transportation

There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using

Chicago Airport Restaurants

Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using, travelers can quickly and easily find low-fare flights from Chicago.

Gerrard Smith Airport

When you are ready for a Caribbean adventure, search for cheap flights to Cayman Brac on Travelers to Cayman Brac fly into Gerrard Smith Airport, a small airport located 5 miles from West End on the island of Cayman Brac. This airport has daily flights arriving on Cayman Airways from Grand Cayman and Little Cayman.

Transportation on Cayman Brac

Local car rental companies, such as CB Rent-A-Car, are located near the airport and offer low-cost car rentals. There are no international car rental companies with offices on Cayman Brac. You can also rent a scooter or jeep from B&S Motor Ventures. If you prefer to take a taxi, book one before you arrive on Cayman Brac, because there may not be one available at the airport when you arrive.

Cayman Brac Weather

Temperatures in Cayman Brac stay between 68 and 87 degrees all year long. Because it is a tropical island, Cayman Brac does not have separate seasons, although June through October tend to be rainier than other times of the year. Visitors are advised to bring rain coats or umbrellas during the rainy season.

Cayman Brac Attractions

Diving is a huge draw for visitors to Cayman Brac. The island also has a network of caves that can be explored and a picturesque lighthouse that visitors often hike out to see. To learn more about the history of the island, check out the Cayman Brac museum. No matter what activities you choose to pursue, make your lodging arrangements and look for cheap flights to Cayman Brac on before you go.