Selected fares from Chicago to Grand Cayman

Flights from Chicago

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.

Flights to Grand Cayman

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.

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Hotels in Grand Cayman

See all 54 Hotels in Grand Cayman
The Westin Grand Cayman Seven Mile Beach Resort & Spa
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Seven Mile Beach, Seven Mile Beach
4.0 out of 5.0
4.0 out of 5 (295 reviews)

The Westin Grand Cayman Seven Mile Beach Resort and Spa is steps from the sand and diving on Governor's Reef. Golfers can drive 5 minutes to play the North Sound ...

$152

$152
Comfort Suites Seven Mile Beach and Resort
Comfort Suites Seven Mile Beach and Resort
West Bay Road, Seven Mile Beach
3.5 out of 5.0
3.8 out of 5 (129 reviews)

This all-suite hotel is 70 yards from Seven Mile Beach, and less than 2 miles from the popular shops of George Town, the capital city of the Cayman Islands.

$111

$111
Grand Cayman Marriott Beach Resort
Grand Cayman Marriott Beach Resort
389 West Bay Road, Seven Mile Beach
4.0 out of 5.0
4.2 out of 5 (359 reviews)

Centrally located on Grand Cayman's famed Seven Mile beach, this oceanfront Marriott Beach Resort is within walking distance of restaurants, shops, and night ...

$199

$199
The Ritz-Carlton, Grand Cayman
The Ritz-Carlton, Grand Cayman
West Bay Road, Seven Mile Beach
5.0 out of 5.0
4.7 out of 5 (83 reviews)

Beautiful Seven Mile Beach, famed for its clear waters and powdery sands, is the setting for this 144-acre luxury resort; Stingray City, a superb snorkeling ...

$379

$379
Compass Point Dive Resort
Compass Point Dive Resort
346 Austin Conolly Drive, East End
3.5 out of 5.0
4.4 out of 5 (14 reviews)

Nestled on the beach, this East End resort is 0.6 mi (0.9 km) from East End Lighthouse and 2.5 mi (4 km) from Grand Cayman Blow Holes. Mastic Trail South Trailhead ...

Sunshine Suites Resort
Sunshine Suites Resort
1465 Esterley Tibbetts, Seven Mile Beach
3.5 out of 5.0
4.1 out of 5 (156 reviews)

Situated across from Seven Mile Beach, this all-suites resort is also next to The North Sound golf course.

$144

$144
Seven Mile Beach Resort & Club
Seven Mile Beach Resort & Club
19 D Piper Way, West Bay Road, Seven Mile Beach
3.0 out of 5.0

Nestled on the beach, this Seven Mile Beach resort is within a 15-minute walk of Galleria Plaza, Camana Bay Shopping Center, and Camana Bay. National Gallery ...

$124

$124
Wyndham Reef Resort
Wyndham Reef Resort
2221 Queens Highway, East End
3.5 out of 5.0
4.2 out of 5 (175 reviews)

Located in Grand Cayman's tranquil East End, 45 minutes from the airport, this resort offers relaxed vacations and cooling ocean breezes.

$125

$125
Britannia Villas
Britannia Villas
169 Britannia Drive, Seven Mile Beach
4.0 out of 5.0

Situated in Seven Mile Beach, this golf condominium resort is within 1 mi (2 km) of Galleria Plaza, Cayman Crazy Golfing Mini Golf, and Camana Bay Shopping Center. ...

Holiday Inn Resort Grand Cayman
Holiday Inn Resort Grand Cayman
278 Crighton Drive, Crystal Harbour
3.5 out of 5.0
3.5 out of 5 (26 reviews)

Located in Crystal Harbour, this beachfront resort is next to a golf course and within 3 mi (5 km) of North Sound Golf Course, Governors Square, and Camana Bay ...

$103

$103

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.