Flights from Chicago to Grand Cayman

Selected fares from Chicago to Grand Cayman

Departure Arrival Travel dates Round-trip
CHI GCM Sat, May 30 - Sat, Jun 6 $463
CHI GCM Thu, Jul 2 - Thu, Jul 9 $481
CHI GCM Thu, Jul 2 - Thu, Jul 9 $487
CHI GCM Thu, Jul 23 - Thu, Jul 30 $518
CHI GCM Thu, Jul 2 - Mon, Jul 6 $554
CHI GCM Sun, Jun 21 - Sat, Jun 27 $612
CHI GCM Sat, Jun 20 - Sat, Jun 27 $747

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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$463
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$463
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Grand Cayman Airport Hotels

Hotel only $19

Treasure Island Resort

2 stars
2.8 / 5 87 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 $250

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 $425

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 $177

Comfort Suites Cayman Islands

3 stars
3.8 / 5 137 reviews

West Bay Road, Map

...Transportation Owen Roberts International Airport (2.1 mi/3.4 km) Nearby attractions George Town (2.6 mi/4.2 km).... Comfort Suites welcomes families, individual travelers, and corporate... More

Hotel only $449

Marriott Grand Cayman Beach Resort

4 stars
4.2 / 5 352 reviews

389 West Bay Road Map

$50 DAILY RESORT CREDIT

...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

June

Cheapest weekend flights in June from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 25 Chicago (ORD) Grand Cayman (GCM) United Airlines $537
Earn $5.37
Return Mon, Jun 29 Grand Cayman (GCM) Chicago (ORD) United Airlines

Lowest roundtrip airfare in June from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Jun 1 Chicago (ORD) Grand Cayman (GCM) United Airlines $463
Earn $4.63
Return Sat, Jun 6 Grand Cayman (GCM) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jun 2 Chicago (ORD) Grand Cayman (GCM) United Airlines $463
Earn $4.63
Return Tue, Jun 9 Grand Cayman (GCM) Chicago (ORD) United Airlines
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July

Cheapest weekend flights in July from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 2 Chicago (ORD) Grand Cayman (GCM) United Airlines $463
Earn $4.63
Return Mon, Jul 6 Grand Cayman (GCM) Chicago (ORD) United Airlines

Lowest roundtrip airfare in July from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 2 Chicago (ORD) Grand Cayman (GCM) United Airlines $463
Earn $4.63
Return Mon, Jul 6 Grand Cayman (GCM) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 2 Chicago (ORD) Grand Cayman (GCM) US Airways $481
Earn $4.81
Return Thu, Jul 9 Grand Cayman (GCM) Chicago (ORD) US Airways
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August

Lowest roundtrip airfare in August from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Aug 13 Chicago (ORD) Grand Cayman (GCM) United Airlines $463
Earn $4.63
Return Sun, Aug 23 Grand Cayman (GCM) Chicago (ORD) United Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Aug 1 Chicago (ORD) Grand Cayman (GCM) United Airlines $483
Earn $4.83
Return Sat, Aug 8 Grand Cayman (GCM) Chicago (ORD) United Airlines
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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.

Flight schedule for flights from Chicago to Grand Cayman on Mon, May 4, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/American Airlines AA1853/AA819 ORD 5:55 AM GCM 11:40 AM 321/319 5hr 45min
American Airlines/US Airways AA1853/US819 ORD 5:55 AM GCM 11:40 AM 321/319 5hr 45min
US Airways/American Airlines US1853/AA819 ORD 5:55 AM GCM 11:40 AM 321/319 5hr 45min
US Airways/US Airways US1853/US819 ORD 5:55 AM GCM 11:40 AM 321/319 5hr 45min
American Airlines/American Airlines AA1411/AA1552 ORD 5:00 AM GCM 11:51 AM 738/319 6hr 51min
American Airlines/US Airways AA1411/US1552 ORD 5:00 AM GCM 11:51 AM 738/319 6hr 51min
American Airlines/American Airlines AA1401/AA1552 ORD 6:10 AM GCM 11:51 AM 738/319 5hr 41min
American Airlines/US Airways AA1401/US1552 ORD 6:10 AM GCM 11:51 AM 738/319 5hr 41min
US Airways/American Airlines US1411/AA1552 ORD 5:00 AM GCM 11:51 AM 738/319 6hr 51min
US Airways/US Airways US1411/US1552 ORD 5:00 AM GCM 11:51 AM 738/319 6hr 51min
US Airways/American Airlines US1401/AA1552 ORD 6:10 AM GCM 11:51 AM 738/319 5hr 41min
US Airways/US Airways US1401/US1552 ORD 6:10 AM GCM 11:51 AM 738/319 5hr 41min
American Airlines/Cayman Airways AA1411/KX103 ORD 5:00 AM GCM 12:00 PM 738/733 7hr 0min