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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 Tue, Oct 28 - Tue, Nov 4 $445
CHI GCM Wed, Jan 7 - Wed, Jan 21 $466
CHI GCM Wed, Nov 12 - Wed, Nov 19 $483
CHI GCM Sat, Sep 27 - Sat, Oct 4 $498
CHI GCM Sat, Nov 15 - Sat, Nov 22 $500
CHI GCM Sat, May 2 - Sat, May 9 $502
CHI GCM Sat, Sep 20 - Sat, Sep 27 $532
CHI GCM Fri, Sep 26 - Tue, Sep 30 $1,713

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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$482
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

September

Cheapest weekend flights in September from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 25 Chicago (ORD) Grand Cayman (GCM) Delta Air Lines $523
Earn $5.23
Return Mon, Sep 29 Grand Cayman (GCM) Chicago (ORD) Delta Air Lines

Lowest roundtrip airfare in September from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 25 Chicago (ORD) Grand Cayman (GCM) US Airways $482
Earn $4.82
Return Thu, Oct 2 Grand Cayman (GCM) Chicago (ORD) US Airways

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

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 25 Chicago (ORD) Grand Cayman (GCM) US Airways $482
Earn $4.82
Return Thu, Oct 2 Grand Cayman (GCM) Chicago (ORD) US Airways
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October

Lowest roundtrip airfare in October from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 28 Chicago (ORD) Grand Cayman (GCM) US Airways $445
Earn $4.45
Return Tue, Nov 4 Grand Cayman (GCM) Chicago (ORD) US Airways

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 28 Chicago (ORD) Grand Cayman (GCM) US Airways $445
Earn $4.45
Return Tue, Nov 4 Grand Cayman (GCM) Chicago (ORD) US Airways
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November

Cheapest weekend flights in November from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 27 Chicago (ORD) Grand Cayman (GCM) US Airways $616
Earn $6.16
Return Mon, Dec 1 Grand Cayman (GCM) Chicago (ORD) US Airways

Lowest roundtrip airfare in November from Chicago to Grand Cayman

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Nov 20 Chicago (ORD) Grand Cayman (GCM) US Airways $425
Earn $4.25
Return Wed, Dec 3 Grand Cayman (GCM) Chicago (ORD) US Airways

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

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Nov 12 Chicago (ORD) Grand Cayman (GCM) US Airways $480
Earn $4.80
Return Wed, Nov 19 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.