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Chicago to Grand Cayman 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 Grand Cayman

Departure Arrival Travel dates Round-trip
CHI GCM Fri, Dec 12 - Wed, Dec 17 $387
CHI GCM Tue, Dec 9 - Tue, Dec 16 $395
CHI GCM Tue, Dec 9 - Tue, Dec 16 $397
CHI GCM Tue, Dec 9 - Tue, Dec 16 $398
CHI GCM Thu, Mar 5 - Thu, Mar 12 $496
CHI GCM Sat, Dec 6 - Wed, Dec 10 $523
CHI GCM Fri, Apr 10 - Fri, Apr 17 $591
CHI GCM Wed, Feb 4 - Sun, Feb 8 $1,136
CHI GCM Tue, Dec 9 - Tue, Dec 16 $2,213

Chicago and Grand Cayman 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 Grand Cayman , KY
map of airports in Grand Cayman
  • 1

    Owen Roberts Intl (GCM)

    Distance from City Center: 3.5 miles

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Cheap flights from Chicago to Grand Cayman

Sun Mon Tue Wed Thu Fri Sat
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$395
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30

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Grand Cayman Airport Hotels

Hotel only $104

Treasure Island Resort

2 stars
2.7 / 5 73 reviews

269 West Bay Road Map

20% OFF

Beach front Resort conveniently located on 7 Mile Beach. 3 outdoor swimming pools. Treasure Island features 2 restaurants. 1 lobby bar open 7 days a week and a pool sided bar. The guestrooms open... More

Hotel only $240

Sunset Cove

3 stars
3.7 / 5 3 reviews

299 West Bay Road Map

SPECIAL CHECK-IN INSTRUCTIONS

...The condos at Sunset Cove (formerly Treasure Island Condos) are located on the South end of Seven Mile Beach, approximately three miles from Owen Roberts International Airport.... CONTACT Cayman... More

Hotel only $350

Grandview Condominiums

3 stars
4.8 / 5 5 reviews

95 Snooze Lane Map

...Transportation Owen Roberts International Airport (2.6 mi/4.2 km) Nearby attractions George Town (3.1 mi/5 km) Business Free-high speed Internet access Business center... More

Hotel only $145

Comfort Suites Cayman Islands

3 stars
3.8 / 5 128 reviews

West Bay Road, Map

...Comfort Suites welcomes families, individual travelers, and corporate travelers who are looking for an affordable hotel with a great location steps from Seven Mile Beach, close to the... More

Hotel only $185

Marriott Grand Cayman Beach Resort

4 stars
4.1 / 5 343 reviews

389 West Bay Road Map

SAND DOLLAR 4TH NIGHT FREE

...Transportation Owen Roberts International Airport (11.3 mi/18.2 km) Nearby attractions  George Town (10.1 mi/16.3 km) Business Three meeting rooms, with a maximum seating capacity... More

Britannia Villas

4 stars
Not yet reviewed

Britannia Way Map

...Transportation Owen Roberts International Airport (3.8 mi/6.1 km) Nearby attractions George Town (4.3 mi/7 km) Business High-speed Internet access... More

November

Cheapest weekend flights in November from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 20 Chicago (ORD) Grand Cayman (GCM) American Airlines $401
Earn $4.01
Return Mon, Nov 24 Grand Cayman (GCM) Chicago (ORD) American Airlines

Lowest roundtrip airfare in November from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Nov 9 Chicago (ORD) Grand Cayman (GCM) United Airlines $395
Earn $3.95
Return Wed, Nov 12 Grand Cayman (GCM) Chicago (ORD) United Airlines

Best one-week trip in November from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Nov 9 Chicago (ORD) Grand Cayman (GCM) United Airlines $395
Earn $3.95
Return Sun, Nov 16 Grand Cayman (GCM) Chicago (ORD) United Airlines
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December

Lowest roundtrip airfare in December from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Dec 12 Chicago (ORD) Grand Cayman (GCM) United Airlines $387
Earn $3.87
Return Wed, Dec 17 Grand Cayman (GCM) Chicago (ORD) United Airlines

Best one-week trip in December from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Dec 9 Chicago (ORD) Grand Cayman (GCM) US Airways $395
Earn $3.95
Return Tue, Dec 16 Grand Cayman (GCM) Chicago (ORD) US Airways
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January

Lowest roundtrip airfare in January from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Jan 19 Chicago (ORD) Grand Cayman (GCM) US Airways $480
Earn $4.80
Return Mon, Jan 26 Grand Cayman (GCM) Chicago (ORD) US Airways

Best one-week trip in January from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Jan 19 Chicago (ORD) Grand Cayman (GCM) US Airways $480
Earn $4.80
Return Mon, Jan 26 Grand Cayman (GCM) Chicago (ORD) US Airways
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Flights to Grand Cayman

Airports in Chicago

The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com 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 Orbitz.com.

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 Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.

Owen Roberts International Airport

If you're looking for a bargain on flights to Grand Cayman Island, Orbitz.com can help you. The website searches flights from numerous airlines so that you can choose tickets that fit your budget. The Owen Roberts International Airport is the main international airport for the Cayman Islands. It's located on Grand Cayman Island-the largest of the three islands-on Roberts Drive, approximately one mile from the center of George Town. Eleven airlines service the airport, including United Airlines, Delta Air Lines, Cayman Airways and American Airlines.

Transportation From the Airport

Taxicabs are available at the airport on a first-come, first-served basis. Cab fare ranges from $12 to $70, depending on what part of Grand Cayman Island you're visiting. Cab fare into George Town averages between $15 and $18. Limousines and buses also transport passengers from the airport, but they require reservations. If you want access to your own vehicle, you can purchase a vacation package that includes car rental and flight from Orbtiz.com.

Grand Cayman Island Climate

Even though the temperatures in the Grand Cayman Islands range from the low 70s to the low 90s all year long, the weather determines the peak travel season. The off-peak travel season runs from May to November, because the islands have more rainfall during this time. If you use Orbitz.com to book your trip during the off-peak season, you'll save money on your travel expenses.

Highlights and Attractions

The Cayman Motor Museum, Dolphin Cove, Kittiwake Shipwreck & Artificial Reef and Seven Mile Beach are some of the top tourist attractions on Grand Cayman Island. In addition to finding flights to Grand Cayman Island, Orbitz.com can help you purchase tickets to local attractions and arrange guided tours.