Flights from Chicago to Grand Cayman

Selected fares from Chicago to Grand Cayman

Departure
Arrival
Travel dates
Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Thu, Feb 4 - Wed, Feb 10

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Fri, Nov 6 - Sun, Nov 15

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Sun, Apr 3 - Wed, Apr 6

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Sun, Nov 8 - Sun, Nov 15

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Fri, Oct 2 - Fri, Oct 9

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Thu, Feb 4 - Wed, Feb 10

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Thu, Feb 4 - Wed, Feb 10

Round-trip

Departure:

CHI

Arrival:

GCM

Travel dates

Thu, Feb 4 - Wed, Feb 10

Round-trip

September 2015
Sun
Mon
Tue
Wed
Thu
Fri
Sat
1
Tue, Sep 1
2
Wed, Sep 2
3
Thu, Sep 3
4
Fri, Sep 4
5
Sat, Sep 5

Leaving Sat, Sep 5

Returning options:

6
Sun, Sep 6
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Mon, Sep 7
8
Tue, Sep 8
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Wed, Sep 9
10
Thu, Sep 10
11
Fri, Sep 11
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Sat, Sep 12
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Mon, Sep 14
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Tue, Sep 15
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Sat, Sep 19
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Sat, Sep 26
27
Sun, Sep 27
28
Mon, Sep 28
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Tue, Sep 29
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Wed, Sep 30

= Cheapest round-trip flights

* Prices are round trip per person (conditions apply)

Save more with Grand Cayman Flight + Hotel packages

Chicago and Grand Cayman airports and terminals

Airports in Chicago IL, US

Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

    Carriers

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Carriers

Airports in Grand Cayman , KY

Grand Cayman
  • 1

    Owen Roberts Intl (GCM)

    Distance from City Center: 3.5 miles

    Carriers

  

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Featured Grand Cayman Airport Hotels

http://www.tnetnoc.com/hotelphotos/904/346904/2631759-Treasure-Island-Resort-Hotel-Exterior-1-LP.jpg
269 West Bay Road Map
2.7 / 5 73 reviews
  • Special Offer
  • Special Offer
From
$104

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

From
$104
http://www.tnetnoc.com/hotelphotos/751/698751/2631759-Sunset-Cove-Hotel-Exterior-1-LP.jpg
299 West Bay Road Map
3.7 / 5 3 reviews
  • SPECIAL CHECK-IN INSTRUCTIONS
  • SPECIAL CHECK-IN INSTRUCTIONS
From
$250

...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

From
$250
http://www.tnetnoc.com/hotelphotos/798/304798/2241284-Grandview-Condominiums-Guest-Room-1-LP.jpg
95 Snooze Lane Map
4.8 / 5 5 reviews
From
$350

...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

From
$350
http://www.tnetnoc.com/hotelphotos/199/28199/2241284-Comfort-Suites-Cayman-Islands-Lobby-1-LP.jpg
West Bay Road, Map
3.8 / 5 130 reviews
From
$127

...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

From
$127
http://www.tnetnoc.com/hotelphotos/861/34861/2241284-Marriott-Grand-Cayman-Beach-Resort-Hotel-Exterior-1-LP.jpg
389 West Bay Road Map
4.1 / 5 344 reviews
  • SAND DOLLAR 4TH NIGHT FREE
  • SAND DOLLAR 4TH NIGHT FREE
From
$224

...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

From
$224

September

Cheapest weekend flights in September from Chicago to Grand Cayman

Leave
Thu, Sep 3
Chicago
(ORD)
Grand Cayman
(GCM)
US Airways
US Airways
Return
Mon, Sep 7
Grand Cayman
(GCM)
Chicago
(ORD)
US Airways
US Airways
Earn $5.87

Lowest roundtrip airfare in September from Chicago to Grand Cayman

Leave
Sat, Sep 5
Chicago
(ORD)
Grand Cayman
(GCM)
United Airlines
United Airlines
Return
Sat, Sep 12
Grand Cayman
(GCM)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.89

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

Leave
Sat, Sep 5
Chicago
(ORD)
Grand Cayman
(GCM)
United Airlines
United Airlines
Return
Sat, Sep 12
Grand Cayman
(GCM)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.89

October

Cheapest weekend flights in October from Chicago to Grand Cayman

Leave
Thu, Oct 1
Chicago
(ORD)
Grand Cayman
(GCM)
US Airways
US Airways
Return
Mon, Oct 5
Grand Cayman
(GCM)
Chicago
(ORD)
US Airways
US Airways
Earn $5.44

Lowest roundtrip airfare in October from Chicago to Grand Cayman

Leave
Sat, Oct 31
Chicago
(ORD)
Grand Cayman
(GCM)
United Airlines
United Airlines
Return
Sat, Nov 7
Grand Cayman
(GCM)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.85

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

Leave
Sat, Oct 31
Chicago
(ORD)
Grand Cayman
(GCM)
United Airlines
United Airlines
Return
Sat, Nov 7
Grand Cayman
(GCM)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.85

November

Lowest roundtrip airfare in November from Chicago to Grand Cayman

Leave
Fri, Nov 6
Chicago
(ORD)
Grand Cayman
(GCM)
United Airlines
United Airlines
Return
Sun, Nov 15
Grand Cayman
(GCM)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.85

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

Leave
Sun, Nov 8
Chicago
(ORD)
Grand Cayman
(GCM)
United Airlines
United Airlines
Return
Sun, Nov 15
Grand Cayman
(GCM)
Chicago
(ORD)
United Airlines
United Airlines
Earn $4.85

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, Aug 3, 2015

Carrier Flight # Departing   Arriving Flight time Aircraft
American Airlines/American Airlines
AA2458/AA1552

Departing

ORD 5:00 AM

Arriving

GCM 11:47 AM
Flight time 6hr 47min Aircraft 738/319
American Airlines/US Airways
AA2458/US1552

Departing

ORD 5:00 AM

Arriving

GCM 11:47 AM
Flight time 6hr 47min Aircraft 738/319
American Airlines/American Airlines
AA1411/AA1552

Departing

ORD 6:00 AM

Arriving

GCM 11:47 AM
Flight time 5hr 47min Aircraft 738/319
American Airlines/US Airways
AA1411/US1552

Departing

ORD 6:00 AM

Arriving

GCM 11:47 AM
Flight time 5hr 47min Aircraft 738/319
US Airways/US Airways
US2458/US1552

Departing

ORD 5:00 AM

Arriving

GCM 11:47 AM
Flight time 6hr 47min Aircraft 738/319
US Airways/American Airlines
US2458/AA1552

Departing

ORD 5:00 AM

Arriving

GCM 11:47 AM
Flight time 6hr 47min Aircraft 738/319
US Airways/US Airways
US1411/US1552

Departing

ORD 6:00 AM

Arriving

GCM 11:47 AM
Flight time 5hr 47min Aircraft 738/319
US Airways/American Airlines
US1411/AA1552

Departing

ORD 6:00 AM

Arriving

GCM 11:47 AM
Flight time 5hr 47min Aircraft 738/319
American Airlines/Cayman Airways
AA2458/KX103

Departing

ORD 5:00 AM

Arriving

GCM 12:00 PM
Flight time 7hr 0min Aircraft 738/733
US Airways/Cayman Airways
US2458/KX103

Departing

ORD 5:00 AM

Arriving

GCM 12:00 PM
Flight time 7hr 0min Aircraft 738/733
Delta Air Lines/Delta Air Lines
DL2030/DL687

Departing

MDW 6:00 AM

Arriving

GCM 12:40 PM
Flight time 6hr 40min Aircraft 717/M88
Delta Air Lines/Delta Air Lines
DL2031/DL687

Departing

MDW 7:05 AM

Arriving

GCM 12:40 PM
Flight time 5hr 35min Aircraft 717/M88
Delta Air Lines/Delta Air Lines
DL977/DL687

Departing

ORD 6:00 AM

Arriving

GCM 12:40 PM
Flight time 6hr 40min Aircraft 717/M88